There’s the writer I am, and there’s the writer that sometimes I wish I was.

Take John Reed, whose epic life Warren Beatty adapted into my favorite movie of all time, Reds.1 Reed and his wife, Louise Bryant, were among the only journalists in Russia during the revolution in 1917. When Reed returned to the U.S., he wrote an influential book called Ten Days That Shook the World.

It was urgent and vivid—a page-turner, as they say. To read it is to feel as if one is in the room with workers and revolutionaries: “Always the methodical muffled boom of cannon through the windows, and the delegates screaming at each other… So, with the crash of artillery, in the dark, with hatred, and fear, and reckless daring, new Russia was being born.”

In the movie, one of the characters says of Reed: “He knew he was on the threshold of history, and wrote it that way.”

Those words have always lingered.

To be on the threshold of history and to write it that way.

I. Interesting times

May you live in interesting times.

I’d always thought that was an ancient Chinese curse, though Perplexity reports that no equivalent Chinese phrase has ever been located. Nevertheless, it’s a useful reminder that “interesting times” doesn’t necessarily mean peaceful or tranquil times—usually, quite the opposite.

It seems as clear as any time in my life that we are at a threshold of history, but thresholds are rarely peaceful affairs. More often, they’re a time of troubles.

My prediction for the near future is that violence will proliferate, and chaos and disinformation will rule. The world will grow more dangerous, and there will be more war. Already, it is reasonable to say that you should not trust video or photo evidence that you see with your own eyes. And what was true a hundred years ago is even more true today: “A lie can travel halfway around the world before the truth can get its boots on.”2

I liken this moment to the period after the invention of the printing press, which spread new ideas and gave us important and fun Summer books but also caused a religious schism that led to the 30 Years’ War. For the history buffs, I offer this unsettling statistic: the 30 Years’ War killed a larger percentage of Europeans than either of the two world wars.

I expect that, barring outright nuclear catastrophe, we will get through this. Humanity always seems to find a way. Maybe we are even headed toward the bright future of eradicated disease and unfettered personal fulfillment that the techno-utopians promise.

But I suggest keeping your loved ones close until it arrives.

II. What one person can do

So, we are standing on a threshold. Shouldn’t I then write about that? Shouldn’t everyone with a pen and a publishing platform be talking about this, the world-historical moment we’re in?

Why write a silly little memoiry newsletter about my Spanish home renovation and painting the new apartment when there are people dying, when the singularity may be near, the world is burning, dictators roam the earth, and a neo-fascist gangster police state is emerging in the land of my birth?

I’ve already answered this question a few times, most recently in Dance harder, dance more (read it if you’re despairing). I quote from Reds and reference several films on the same theme: Dr. Zhivago, The Shawshank Redemption, Jo Jo Rabbit—all movies in which protecting and nurturing the personal is the way to fight a fascist regime:

I can and should write about personal matters in these dark times because to protect the personal is to protect what is most human and individual in each of us. The personal is political—but it is important to insist with our writing and poetry, our music and movies, our painting, sculpture, plays, our stand-up comedy—it is important to insist with all of our heart and souls that it is we individuals who determine the course of politics, and not the other way around.

But how exactly do we resist? What are the concrete actions we should take? I was recently asked: What can one person do in the face of all that is going wrong in the world?

Viktor Frankl writes about this in Man’s Search for Meaning:

We needed to stop asking about the meaning of life, and instead to think of ourselves as those who were being questioned by life - daily and hourly… Life ultimately means taking the responsibility to find the right answer to its problems and to fulfill the tasks which it constantly sets for each individual.

These tasks, and therefore the meaning of life, differ from man to man, and from moment to moment. Thus it is impossible to define the meaning of life in a general way. Questions about the meaning of life can never be answered by sweeping statements. 'Life' does not mean something vague, but something very real and concrete, just as life's tasks are also very real and concrete. They form man's destiny, which is different and unique for each individual. No man and no destiny can be compared with any other man or any other destiny.

I.e., each of us must answer this question for ourselves, in our way.

For one it may be attending a protest; another, painting a mural; a third, starting a business. I can’t say which is the most efficacious, but I do know that, for me, the answer is to write.

When life questions me, I answer with this newsletter.

III. All my discarded writing projects

And yet my writing life is littered with discarded writing projects. It can be surprisingly hard to find motivation on the threshold of history.

Drafts for this newsletter, written, re-written, eventually deleted. Screenplays half-finished. And the books—oh, the books. I believe I’ve finally decided to scrap 70,000 words of my latest and rewrite the story as fiction.

An aside:

When I think about all my romantic notions about being a writer, and how wrong they all are, I think about the typewriter sitting broken on my bookshelf in New Hampshire.

I originally wanted a typewriter because of some notion that I would write my book-length memoir on it, undistracted by internet, email, Instagram, YouTube, porn, politics, drinking—anything else my endorphin-riddle brain might desire.

The romantic notion goes: I would sit alone in my study or in the studio I built for myself on the hillside behind my house and just WRITE.

Except that I haven’t yet built the studio. And in fact, the typewriter is broken. It needs repair. I need to order parts. But also mow the lawn. And fix the stairs. And cook dinner.

Deadlines help. I have recently been working on a new screenplay project, my first in more than six years. The producer gave me a deadline; I met it. A full rewrite of a 60+ page pilot for a new show in about a week.

It’s been nice to flex that creative muscle again. Plus, doing fiction has reminded me that sometimes it’s the better choice for difficult Truths. Maybe the only choice.

IV. Embracing your particular answer to life’s questions

In the opening scene of Reds, Reed is running furiously through what looks like the Sonoran Desert in Mexico, chasing a horse-drawn wagon and trying to outrun gunfire and shelling all around him. Another of the witnesses provides voiceover: “Jack Reed’s life, short as it was, happened at a time—and all of us after all are the victims of our time and place—when he had the opportunity as a reporter to be in some very exciting and dramatic places.”

Alongside Reed, I think of Hemingway or Lee Miller going to cover World War II. Or Michael Herr going to Vietnam. Chris Hedges going to every war zone he could manage in the 1990s. The reporters in the recent movie Civil War.

Of course, it doesn’t always have to be war, but life’s most difficult moral questions are so often revealed by war that it is a time-honored choice among writers.3

I so admire those who recognize they are on a threshold, put themselves into danger, and write it down so that the rest of us may encounter a Truth we might otherwise not. But does this mean I must go to Gaza, or Ukraine? Travel by train or bus, cross the border, see the front lines, and use whatever talents as a journalist and writer to say my version of what is happening there?

In a crucial scene early in Reds, Reed chastises Bryant for writing about an armory show from three years ago, just as Woodrow Wilson seems intent on bringing the U.S. into World War I—she’s feeling sorry for herself, and doesn’t think that his artist friends take her seriously; Reed responds that if she wants to be taken seriously, she should write about serious things.

It’s a scene I’ve pondered a lot over the years.

But Frankl’s dictate that we must all find our own answer to life’s problems applies to writers as well—we must all write about that which we are most called to write. In the manner, on the platform, in the genre that feels appropriate in response to life’s questions.

Just so long as we take that work seriously.

If we do, others will as well.

The other day I sat down next to my friend and walked him through recent use cases for AI from my life, and his mind was blown. Not just at the power of the tools, but the broad scope of things I’m using them for.

Note: this post is an experiment off the beaten path for this newsletter, which is part of why I’m adding a paywall a little ways down. But a lot of people ask me about this stuff—and I’ve been using the tools almost daily since they were released—and after dozens of sit-down conversations with friends and family, I’ve never failed to blow someone’s mind with how I’m using AI. So here goes.

I’m going to explain all the things below, but here’s a preview:

• AI is playing “general contractor assistant” in my Spain renovation. I’ll explain how I’m using Claude’s projects function to do research on materials and building techniques.

• AI is displacing most of my personal Google searches. This is why AI is a mortal threat to Google. I’ll explain how I approach everything from travel and relationship advice to financial planning and health.

• AI has 4x’d productivity in my content marketing business. I’ll explain how my workflows have evolved, including what I do now with ChatGPT, Claude, and Perplexity to deliver content and strategy for marketing clients. (Paid subscribers)

• AI is enabling me to expand my business for the first time in four years. Plus: what it’s like to use ChatGPT’s o1 Pro, including “Deep Research” for client work. (Paid subscribers)

To me, it’s just totally obvious that these tools are game-changers for civilization.

In your own life, if you’re smart about it, you’ll use LLMs for what they are: the most powerful all-purpose personal assistant the world has ever known. And at $20/month (or $200/month for ChatGPT o1 Pro—I’ll get to that), this is the most dramatically underpriced access to a superpower I can imagine.

I’m not trying to be some booster for AI—indeed, I’m the first to be threatened by Large Language Models. I have every incentive to ignore or downplay their significance, as they essentially supplant my core contribution to the economy for the last 20 years. i.e., being able to consistently write clear and compelling copy day in and day out.

Yet maybe it’s exactly because I am a writer that I recognized early just how transformative AI would be. For 15 years, I’d rested easy knowing a machine could never do what I could. Then two and a half years ago, I saw the first version of ChatGPT churn out a decent press release in a few seconds—basically an entry-level copywriting skill. It’s exactly what I got paid to do as Deputy Press Secretary for a U.S. Senate campaign in 2008, only back then it took me 20 minutes to punch them out—and I was (and still am) considered an extremely fast writer.

Anyway, from there the tools only got better and better.

Today, I’d estimate AI can do a better job than perhaps the bottom 80% of writers in the world at nearly all their writing tasks.

And again, it’s only getting better. So this is as real as it gets folks. The disruption is already here. In fact, I’m participating in it.

I. Why I write this newsletter

But before I go further, I want to make one thing clear: I have never used any AI to help write this newsletter, and I don’t think I ever will. I’m not trying to signal or brag or anything—it’s just that using AI to write Post-Nomad would defeat the whole purpose.

I do this for play. I write here to flex the creative muscle. I would do this even if I were retired with millions in the bank. I enjoy getting more subscribers, sure—it means my writing is having more impact. I enjoy even more when people email me in response to posts that have resonated with them.

Telling me you like my writing is my love language.

But this newsletter only generates around 1% of my total income, which is just fine with me. I like that I can continue to play here without regard to whether any of my choices will impact my financial security. This newsletter is where I write for writing’s sake.

So again, using AI would defeat the whole purpose.

One last thing before I jump in: it’s not lost on me that I am exercising a creative muscle that may not be needed at all in the future, and therefore a muscle that will atrophy in the vast majority of humans. “You must learn how to write” has always been great career advice—but I’m not sure it’s relevant now.

In any case, I’ll be happy to be one of the rare few who can still write human-made sentences in the future, whether that skill is economically valued or not.

II. How I’m using AI to assist with the Spain renovation

If you have a long, technical document (or several) that you consult over and over as a reference for anything, there’s a good bet you should create a Project in either ChatGPT or Claude, and upload said document as so-called “project knowledge.”

In the case of the Spain renovation, I found myself doing this over and over with my architect’s “tecnica.” This is a 54-page PDF document that he created as a guide for the builders and as part of the application to the town for the building permit.

The tecnica includes:

• Dimensions & floorplans for the entire 4-story structure

• A step-by-step description of works to be completed

• Addendums of building materials, notably the specific roofing panels to be used

Once I translated this from Catalan into English (using Google Translate’s document upload feature), I uploaded the English version to a new project in Claude and started asking questions.

I have long threads going back and forth with Claude about building techniques, and I’m able to ask specific questions about my project because it already knows everything about my plans.

For example:

1. I engaged Claude in a long discussion about “warm roofs” vs. “cold roofs” as it pertained to my rooftop terrace—a crucial decision that will determine which materials to buy, and how it will be insulated.

2. I used Claude to research specific building materials only available in Spanish supply stores. I did this by downloading the spec sheets from Bauhaus, translating them from Catalan, and then uploading them to Claude. Afterward, we had discussions about whether specific products were appropriate for my use cases.1

3. I use Claude to brainstorm construction techniques or solutions to specific problems. For example, recently the builder asked the architect to provide a solution to replace the floor I’ve demolished on the top level. Currently, it’s all exposed old wood beams:

My architect proposed replacing the beams with dimensional wood joists to ensure they are all exactly level. But I didn’t like the idea of getting rid of the old beams—nor did I want to add to the cost and work for the builder.

I asked Claude what solutions they would recommend to construct a flat OSB subfloor on top of old beams that aren’t level. Here’s how it replied:2

Based on the technical documents provided and your situation, I'll help you create a flat, even surface for the OSB floor installation while working with uneven vigas (wooden beams). Here are the recommended methods:

1. Leveling Strips (Primary Recommendation):

• Install wooden leveling strips (also called shims or battens) perpendicular to the existing vigas

• Use a laser level to determine the highest point of all vigas

• Cut custom-thickness strips to bring all lower areas up to the same height as the highest point

• Secure the strips to the vigas using appropriate screws or fasteners

2. Joist Sister System: Based on the technical project documents, which show the structural importance of these vigas, you could:

• Install "sister" joists alongside the existing vigas where needed

• Cut the sister joists to the proper height to create an even plane

• Secure them firmly to the existing vigas with structural screws

• This method also adds structural reinforcement, which aligns with the project's focus on maintaining structural integrity

3. Self-Leveling Option: Looking at your project documents, particularly the section discussing the terrace area (002.009), you could:

• Install a lightweight concrete leveling layer

• This approach is already being used in parts of your project

• Ensures perfect levelness while adding minimal weight

• Must ensure proper waterproofing and moisture barrier below the OSB

Key Considerations:

• The technical project specifically mentions maintaining the current wooden beams (see demolition specs in EN.100)

• Any solution must not compromise the load-bearing capacity of the structure

• The final floor height must comply with the project's specified dimensions

• Ensure adequate ventilation remains between the vigas to prevent moisture issues

Would you like me to elaborate on any of these methods? Also, what's the maximum height difference between your highest and lowest vigas? This information would help determine the most appropriate approach.

Of course, #1 is what I’d already planned. But it was nice to have other options laid out for me. And the laser level is ready to go.

Obviously, you have to take all construction advice from an LLM with a grain of salt—but in many cases, my use of Claude has given me the language and tools to do deeper better searches elsewhere, such as on YouTube.

AI is good at brainstorming (which I’ll get to more of later), so try asking it for different solutions to problems, and then use those ideas to research elsewhere, or to have a more informed conversation with a contractor.

III. My personal use of AI

AI tools really thrive for a lot of business use cases, but before I get to that long section, I want to list some of the ways I’ve incorporated AI into my daily use:

1. Uploading photos and talking via the apps. Both ChatGPT and Claude are extraordinary at analyzing photos—but that’s only useful in practice if you have the apps on your phone. This has unlimited applications. For starters, I’ve uploaded photos of construction problems in my renovation (“What do you think, should I demolish this cracked concrete, or follow the builder’s recommendation to pour reinforcing concrete over it?”). Or another recent example, when I was trying to change the tire on my Fiat Doblo in Spain. I uploaded this photo to Claude and used the voice feature to ask how to get it off the vehicle:

   

   Here’s the reply:

   I notice this is a close-up image of a spare tire mounting mechanism, likely underneath a vehicle. The image shows what appears to be a tire retaining bracket with a center bolt mechanism and several mounting holes around it. There seems to be some rust or corrosion visible, which might be making removal difficult.

   Most spare tire lowering mechanisms work by:

   1. Inserting the jack handle or special tool through a hole in the bumper or trunk floor

   2. Connecting it to this center bolt mechanism

   3. Turning counterclockwise to lower the spare tire

   However, if you're having trouble, it could be because:

   • The mechanism might be rusted/seized

   • You might need a specific tool that came with the vehicle

   • The release point might be in a different location

   Could you tell me what kind of vehicle this is? That would help me give you more specific instructions for releasing the spare tire. Also, have you located the spare tire removal instructions in your owner's manual? That would be the best place to start.

   The chat went on for quite a while after that. I uploaded more pics as I worked through the process, and asked it more questions. It was like having a mechanic (or my dad) over my shoulder the whole way.

Read more

I would like to live in a spiritually perfect universe. Instead, I am at a dinner just outside Santa Fe.

Those are the opening lines of my grandmother’s memoir, So the Woman Went Her Way. It’s a book that has loomed large in my life. Half the women in my class at College read it. There are copies lining the bookshelf of my home in New Hampshire. And every time I sit down to type words on a page, my grandmother’s brilliant prologue to that book is in some sense still influencing my work.

“There are twelve of us in the room,” she continues.

Two men are sitting by the fire. They are in the middle of a seven-day fast and prefer not to sit at the table with the rest of us. A woman who has just begun a sexual liaison with one of them pulls her chair between the men.

Loud enough for all of us to hear, she says, “You know, there are secret manuscripts in a monestery in Llhasa that tell how Jesus really treated women.”

The scene is quintessential Santa Fe. City of my birth, city of holy faith, city where, for more than a century, artists and writers from New York and Los Angeles and Washington D.C. have moved to find a quieter pace of life—and perhaps a more meaningful (or, spiritual) existence.

Someone asked me recently why Santa Fe became such a magnet for artists in the first place, and I replied that I think it had something to do with Georgia O’Keeffe, who first visited New Mexico in 1929, though I’m sure it goes back even further. Most know O’Keeffe as the one who painted flowers that looked like vaginas. Some others know her as the great chronicler of Northern New Mexico’s stark and beautiful desert landscapes. I know O’Keeffe as a woman my grandmother knew and photographed multiple times.

O’Keeffe died in Santa Fe in 1986. I was born in 1981, and so legend has it I actually met her. There, in the dark recesses of my earliest childhood memories, I remember an old woman who my grandmother told me was a famous artist, lying on a bed, quite sick, inside an adobe casita. Maybe that was O’Keeffe.

Anyway, the artists have flocked to Santa Fe ever since. My grandmother among them.

“And how is that?” my grandmother asks the woman who had just mentioned the secret Llhasa documents:

She stares at me as if she didn’t understand.

Thinking perhaps she really doesn’t know how Jesus treated women, I say, “You don’t have to go all the way to Tibet to find that out. It’s in the Bible. I’ve got one here, in my purse, if you want to take a look.”

She looks at me, forehead crinkled, as if to say, “The Bible? Don’t you know better?”

I am surprised. The woman is not interested in information that might be within reach. It is written all over her body, in the darkening of her eyes, the flush rising on her cheeks, the way her shoulders shift and arms wave off a suggestion that knowledge of how Jesus treated women might be at hand.

This book is the record of my grandmother’s own spiritual journey—thus the Bible in her purse. But more than that, it is one of the few books I’ve ever heard of that takes seriously the idea that the Bible contains within it stories of female power. Decades later, women still write to my grandmother to tell her about the influence the book had on them.

It is both a memoir and an exegesis (i.e., an interpretation of scripture). The title, So the Woman Went Her Way, is taken from 1st Samuel and refers to Hannah—the name her daughter, my mom, gave to my sister.

The book was published in 1993. I was 11 years old, going on 12. My sister Hannah was 9. Two years later, she, my grandmother, and my mom would collaborate on a book on how to do art projects for kids on the computer. It was early days and Microsoft Paint was the biggest design tool around. I remember my sister doing a lot of work on the book, and I also remember feeling some slight sense of having been left out.

The three women in my life had published a book together. My sister became a published book author at age 12.

I still haven’t published one.

“What does interest her,” my grandmother continues, “is the gap between how her new love is viewing her and how she wants to be seen:

What obsesses her is her current self. She is draped over a chair crying out for attention and respect that she somehow senses are not really here for her tonight but that she hopes exist in hidden documents in a far-off place guarded by strange men from another culture and a distant past.

If I told her that I was a Celtic princess descended from the Valkyrie and that my sisters, the trees, talked to me about the healing of men and nations, she would believe me. But if I told her the Bible was about her life, she would think I was selling a doctrine.

My grandmother was raised Episcopalian in the suburbs of Chicago and spent summers as a child in Minnesota. She married a man from the big city when she was just 19, and soon after she had my mom. Not long after that, she discerned that the men always coming in and out of the house and speaking in hushed tones were part of the Chicago mob—including her husband. One night she would be laughing and smiling among her husband’s friends at dinner, and the next those men would be “found in the trunk of a car with various body parts removed.”

Two years after she had my mom, she had my uncle, and coming home from the hospital she resolved to find a way out.

Then one evening her husband was in the living room with three men from a small town over a thousand miles away: Deming, New Mexico. They were building houses there with union pension money and offered to give them one of the houses. “I’ll take it,” my grandmother responded.

Her husband was furious, but she drove far away from Chicago with her two kids, eventually settling in Santa Fe.

And oh, does she capture the New Age atmosphere there.

Later, the host of the dinner party says she is “channeling the Magdalene” and my grandmother asks her if she has been writing down any of the messages coming to her “from the only person understood by all four gospels to have been an eyewitness to the Resurrection:

“I don’t have to,” she says. “I have money. I’m spending my time developing television shows on socially conscious investments.”

I hear a small sound, a pop, in my ear. Channeling the Magdalene passed up for socially conscious investments?

The food is served and we all join hands and make the sound of “Om.” There are squeezes on both my hands from people who have never met me before. French phrases are dopped into the conversation, and Velveeta cheese is served melted over the shrimp.

Last Christmas I was in Santa Fe visiting family. It was winter solstice and some friends took me to a dinner party outside of town. The house was owned by an artist, of course, and after the food, we all went outside to where he had built a kind of mini henge. There were gigantic, 8- or 10-foot-tall stone pillars arranged in a semi-circle—he called it a temple.

Our host had hired someone to build up a bonfire, which had now been going for some time. An MC led us through a solstice ceremony. We held hands (and squeezed), sang, chanted, and were encouraged to say our peace to the group.

One man recounted with complete sincerity that he had recently seen our alien overlords’ spaceship through the gaps in two of the stones not too many nights ago, and he was sure that they were interested in the same goals as we all surely were: peace on Earth, etc.

Toward the end, we were asked to go commune with one of the stone pillars. I went up to the tallest and started to feel the texture, picking out hand holds as I went—naturally, my mind turned to whether I could climb it. But I opted not to try and instead wandered back inside to find some hot cider.

In my grandmother’s book, there is also a fire after dinner, but this one is for an Indian sweat:

We walk down the hill, joined by two small children who have been fed in another part of the house, leaving the lights of the house for the light of the fire.

A woman strips to enter the tent where the sweat is taking place. Except for the tent it looks to me like the saunas and Finn baths that I took as a child with my family in Minnesota.

A child starts to cry, and some of the adults tell him to be quiet. I can tell that the four-year-old does not understand why his mother is going with no clothes on into a tent with six other naked men and women.

I have not disrobed and, taking him by the hand, suggest we look for a cookie in the house as I wait my turn for the sweat. We walk up the hill, and he shows me the way to go to find the kitchen. We search through cabinet after cabinet. Wheat germ, noodles, dried tomatoes, nuts. Not an Oreo or a Mallomar, not a Milano in sight.

My grandmother is in the second half of her 8th decade on earth now. She has lived on and off at my house in New Hampshire recently, where she stocked copious amounts of Oreos and some Milano cookies.

She used to occupy my son for hours when he was younger—he would wake up on vacations and go crawl into her bed, where he knew I would let him stay uninterrupted for a few hours every morning watching videos on her iPad. “It’s educational!” my grandmother would say if I came in trying to crack down on screen time.

She is in Santa Fe now, with my sister and her three young kids, the older one, who is six, and the twins, who just turned four. My grandmother has told me that watching those three kids trundle about in all their cuteness, discovering the world in all its complicated glory, is just about her sole joy and purpose nowadays.

So I can very much picture my grandmother in this moment in Santa Fe, taking the little four-year-old by the hand and going in search of cookies. She was probably craving an Oreo herself. That and the naked, self-obsessed New Agers she had been trying to connect with all night were the only excuses she needed to leave the Indian sweat and walk back to the house.

But alas, they can’t find any cookies.

“What kind of house is it,” I say, “without a cookie?”

“Not a very good house,” he says.

Are there no cookies in the New Age?

It’s a great line.

The book is filled with great lines.

A few years ago, I told my grandmother (not for the first time) how much I admired the writing, especially in the prologue. She replied that she had obsessed over it, writing and re-writing until she felt that every single word in those initial pages was exactly the right one.

The writing we most admire can sometimes feel as if it were birthed whole in all its brilliance from someone who is simply much better at the craft than we are. But it’s not true. Most great writers write, rewrite, and do it again and again. We can be masochists that way.

Inevitably, I find that my favorite passages in literature are the product of dozens of rewrites. “The first draft of anything is shit,” Hemingway once declared.

I had been dispairing about the quality of my own writerly output at the time, so knowing more about my grandmother’s process on the prologue made me feel better. It meant I wasn’t necessarily a worse writer than her—I just hadn’t put in the same effort.

Still. This is the example I have been chasing for almost as long as I can remember.

Not just her. It was all great writers and all great writing. My childhood homes were stuffed with books. On the wall above a doorway in one house, my mom once painted the words of Cicero: “A room without books is like a body without a soul.” Imagine growing up and walking under those words daily.

In high school and college I accumulated used books from thrift stores at such a rate that by the time I moved back to Santa Fe to go to grad school, I loaded no fewer than 12 boxes of books into the moving truck, and did so with pride. I was 23 years old.

To me, books were the pinnacle of civilization—not the only way, but the best way to leave a creative legacy. Books were what we write when we have something to say. It thus followed: if you have not written a book, you must not have had anything important to say.

It’s taken me a lifetime to unwind some of that thinking. Today, I regard a book as one medium among many, just one tool. Art and influence can come in many forms, and important things to say can be said in a whole host of mediums. Although: I still can’t shake the thought that a book is just a bit more special than all the rest.

My grandmother, no doubt, is still waiting for me to publish one. And to be fair, it still might come. The draft is sitting there, in my files, awaiting the day when I have the motivation to do the rewrites necessary to transform it from the aforementioned first draft “shit,” to something that I would actually like to put into the world.

I’m not sure if or when that day will ever come—and I’m trying not to feel like a failure about that. Legacy, influence, and impact can come in many forms if those are indeed things you seek. That might seem obvious, but for me, it has been a lesson slowly, sometimes painfully learned.

At the end of the dinner party, my grandmother drives home:

A glance at the odometer tells me I live forty-two and a half miles from the intersection of Trinity and Oppenheimer Drive. Checking the mailbox, I walk down the drive to the house fully aware that I live at the intersection of the mystical and the individual and one man’s finger away from total annihilation.

And then there’s this:

My grandson Russell’s bike is on the walk, and I remind myself to tell him tomorrow that bikes get parked, not dropped.

The words mattered to her. And indeed they do.

I’ve always loved reading about other writers—biographies, explanations of process, how they make sense of what they do. Much of my early professional life was spent romanticizing the whole thing. It’s all too easy to picture the solitary, tortured soul, punching away at the typewriter, cigarette burning down to the stump, glass of whiskey at the ready.

One thinks of Bukowski’s “so you want to be a writer,” the prose “bursting out of you,” coming “unasked out of your heart and your mind and your mouth and your gut.”

Later, I had to spend quite a bit of time de-programming myself from such romantic nonsense.

Nowadays, I mostly think about writing in terms of a craft I’ve spent decades improving upon. Writing earns me a living, and it also satisfies a creative itch.

I wrote about this almost three years ago:

In my own life, there have been several stretches, usually a matter of a few weeks, when I didn’t write a word. That may seem of small significance to a lot of people, but for someone whose identity is so tied up in being a writer, not to write for that stretch of time feels like a profound failure. Or dare I say, an existential crisis.

But what happens — what has always happened — is that I come back to writing. I miss it. I re-discover that, even if there is no one out there expecting to give me money in exchange for my writing, I still desire to write. I’ve asked myself the question a hundred times in my life: would I simply give up writing if I were able to make my living in some other way? And the answer is always the same: no.

I would still write. I’d write even into the void. For posterity. For myself. To help me understand what I think about what’s going on. Or just to exercise that part of my brain.

Writing is not easy for me, and I usually want to smack anyone who claims it’s easy for them, or if they try to give me advice on how to make it easier, maybe punch them in the face. All those “writing is easy” people can keep that crap to themselves, as far as I’m concerned.

Anyway, it’s still a fraught relationship, me and writing, even after so many years doing it.

Thus, I tend to bookmark, save, and sometimes obsess over things others have written on the subject, using them to help refine and inform what place writing should hold in my life. Below, I share some of those musings.

I. Valuing status over income

Possibly an obvious point, but Michael Makowsky writes that the status of writers is “grossly out of proportion to the wages they are earning in the market.”

Yes, writers prefer status over money, and I’m no different, though I’ve never thought of it as status so much as influence.

I really got off, for example, on speechwriting in politics and campaigns. There was a powerful politician person, and they were saying my words! When I was a reporter, it was incredibly gratifying to know my stories were being read by more than a hundred thousand people all across New Mexico every morning—and also I didn’t really care that that job didn’t pay well.

II. Being alert to audience capture

Being clear about my motivations I think makes me more alert to audience capture than perhaps others are.

“Write something people want to read,” wrote Zawn Villines a while back, in the middle of a long piece about finding success on Substack. Yes, sure, but also this is exactly the kind of advice to be weary of, whether you want a large audience or not, whether you want to make money or not.

Good writing that people want to read is kind of like inventing a new business—obsessive market research is only going to get you so far. (Why do you think most books never make back the advance publishers paid to the writer?)

I always think of the famous Henry Ford quote: “If I had asked people what they wanted, they would have said faster horses.”

Similarly, truly great writing isn’t crowd-sourced, poll-tested, or imitative. One has to actually invent in order to write well, which is partly why ChatGPT is not such a good writer.

And good writing is writing that people want to read. It’s kind of a paradox—you want people to read your writing, but in order to write stuff people want to read I advise you largely ignore the part of your brain that continually asks, “What do I think people want to read?”

III. Beware money

Related to above: earnings do not mean you’re good. Money does not equal quality.

Mastering capitalism is not the same as living a good life. In fact, the two are not particularly correlated as far as I can tell.

Still, money as an indicator of success is pretty much the water we swim in as a society. When people say you’re “winning,” at life, what they usually mean is you’ve made a lot of money: you sold your book, IPO’d your company, achieved FIRE (Financial Independence, Retire Early), or what have you.

So, while I’m often jealous of writers who seem to be raking in that sweet sweet Substack subscription moolah, I remind myself that my end goal here is not wealth in itself, but rather all the other goals I set in my life, according to the values I hold.

There’s an old Atlantic article I think about, published just as people were re-evaluating their relationship to work post-pandemic. Authors Charlie Warzel and Anne Helen Petersen advised:

Think back on a time in your life before you regularly worked for pay. Recall, if you can, an expanse of unscheduled time that was, in whatever manner, yours. What did you actually like to do? Not what your parents said you should do, not what you felt as if you should do to fit in, not what you knew would look good on your application for college or a job.

That, in a sense, is how I think about topics for this newsletter. I’m writing about the things I do with my unscheduled me time: namely climbing, travel, and building stuff (i.e., my renovation projects).

The rest I largely try to ignore.

IV. Writing about yourself

Another temptation in writing: making every story into another chapter in your own personal hero’s journey.

Most talk about life as a path—I think it’s a wilderness.

The problem with a life path, I wrote a few years ago, is the suggestion that life has paths at all:

Most of us are trained from a young age to look for our purpose, to search it out, to find our path, as if we are wandering in the wilderness and need only to wander until we find the road, and when we find it, the way forward will be clear. But what if there are no paths and no roads? What if life isn’t some forest with futures laid out that we only need to search for and find in order to move forward? What if there is only… life?

I suggested that a large wilderness is a more apt metaphor for life. We kind of wander through it aimlessly, not knowing how large it is where each direction might lead.

So, how should one write if, like me, you are writing about yourself? The philosopher Kieran Setiya captured it well:

What makes the narrator’s life worth living is not some grand narrative, running from conception or birth to inevitable death; it is the countless little thoughts and deeds and gentle, joking interactions that occupy day after day after day. If you pay attention, Baker intimates, there’s enough in a single lunch hour to fill a book.

The more you appreciate the sheer abundance of incident, the more you’ll see any life as an assortment of small successes and small failures, and the less prone you will be to say, despairingly, “I’m a loser”—or with misplaced bravado, “I’m a winner!” Don’t let the lure of the dramatic arc distract you from the digressive amplitude of being alive.

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Everything works out in the end. If it hasn't worked out yet, then it's not the end.

Nothing else so crystallizes how utterly intent we humans are at making sense of our existence by telling a story about it.

Looked at one way, the quote speaks to our willingness to self-delude. We’ll stop at nothing to construct a personal narrative that makes us the hero of our own story. We’ll even delude ourselves about the nature of time and space.

Looked at another way, nothing is more natural. We tell ourselves stories and always have. It’s part of what makes us human. Our capacity for making up grand narratives is in some sense part of our superpower as a species—we make sense of things, we are meaning-making machines. It’s what we do, and it’s gotten us this far.

I’ve written before about how life is not a path, there are no forks in the road—in actuality, life is a wilderness. We choose direction based on imperfect information. There are no campsites, no trails, no way to even know which way is forward.

And yet, these metaphors about paths and journeys are kind of the water we swim in. It’s hard to even have a conversation about a significant life decision without using the language.

Even this newsletter can’t escape it. I have nothing to offer but stories—

And in that spirit:

I. Why I write memoir

Substack has this great chart that they published as part of a series on how to find and engage your audience, which they in turn borrowed from People & Company’s Get Together resources.

It shows eight reasons people might decide to subscribe to or follow your stuff:

I’ve often looked at this chart and wondered which one I am—it’s important to me, after all, that people actually read my writing, but it can be a struggle to understand one’s own positioning. Why do you people subscribe? (Feel free to write me and let me know!)

It’s difficult to know ahead of time which pieces will resonate and which won’t. Sometimes my favorites wallow in obscurity, while casual, off-hand passages end up having a deep impact.

Occasionally, the two overlap—what I personally think is good writing is also what resonates. But it’s never a sure thing. I usually have to wait and see. I have to wait for people to email me, or send me a voice memo, or tell me in person the next time we get together.

For a while, I looked at that chart and thought I was “Guidance.” I thought maybe I was helping people navigate complex topics or challenges. Specifically, I was helping location-independent digital nomads (or those who aspired to location independence) navigate the complex decision-making around where to live, what to invest in, and how to create meaning and legacy in their lives.

Except, when I told this to a close reader of this newsletter, she said no, you’re not Guidance—you’re Inspiration.

The thought had honestly not occurred to me, especially since I tend to be highly suspicious of inspirational content.

And yet, I could see what she meant. I have very deliberately crafted the life I want, according to values that are important to me. I spend a huge amount of my time doing the things I love and that are important to me: climbing, kitesurfing, traveling, and spending time with friends and family. I have been location independent for a decade now, having built my own consulting business that I can run from anywhere. In February, I purchased an old fixer-upper in a climbing town in Spain. This Summer, I will move with my son to Barcelona.

All these things can serve as inspiration to others who might share similar aspirations.

But one thing I don’t do (or, do very rarely), is give advice. I don’t give advice because I don’t think my own life is necessarily instructive of anything.

I am a data point of one.

It would be the height of hubris to suggest that because I did something some way, therefore now you should do something the same way. I am but a single example of how to do something, and probably a not particularly applicable one. That is why I write memoir.

It comes down to this: I can only speak for myself. Anything else feels dishonest.

But it’s a constant pull to try to make myself into some kind of guru. To suppose that I have some profound wisdom or method to impart to the masses. To essentially say to the world: look what I’ve done with my life, AND THEREFORE here’s what you should do with yours.

I say this, despite the fact that I have derived a huge amount of personal and professional inspiration from others who do give advice, who have written books, published YouTube videos, and inspired me to dig deeper and live better. I owe a lot to those people, and I think they should keep doing it.

It’s just not for me. I have to stick to what I know, and the only thing I know for sure is my own experience. So, that is what I write about. Memoir.

II. When I quit a job I hated, started my own business, and rose like a Phoenix from the ashes

You know the entrepreneurial hero’s journey? It goes like this:

I was laid off; I didn’t know what to do; I felt like my life was in crisis; then I searched within myself, I found the answers I had been looking for, and now I’m a successful online consultant with a growing roster of clients that I’m passionate about and a glorious life working from a beach in Thailand. Or Bali. Or take your pick.

I have my own entrepreneurial hero’s journey, but it’s a story I’ve always resisted telling for precisely the reasons stated above.

It is a classic, click-bait tale of when I reached a low point, quit a job I hated, started my own business, and rose from the ashes like a Phoenix, now location-independent and able to pursue my dreams—and it is instructive of next to nothing.

But maybe, just maybe, it is a little inspiring.

Anyway, it’s time I got it off my chest.

It was September 2020, six months into the pandemic, and I’d been unemployed for more than a year.

After I was first laid off in 2019, my partner and I went to Mexico to work on our Spanish. When covid hit, we came back to my house in New Hampshire. I spent the time renovating the garage, rock climbing, and writing. I’d started two Substacks, this one and another built around everything I knew about the business of healthcare.

But eventually, the severance package, savings, and unemployment insurance were all running out, and I still had no clear idea of which “path” I wanted to take next.

This is the context for why, in September 2020, I decided to take a job.

It was a normal, traditional, full-time job at a marketing agency. They were headquartered in Northern Virginia and at one point expected me to come into the office—but the pandemic was still on, and allowances were still being made. For now, I could continue to work from New Hampshire.

It felt good to have a team again, some structure to the days. It especially felt good to have money just flow into my bank account each month.

The agency had a bunch of healthcare clients, and I’d been in healthcare for more than a decade, at times managing my own clients. It all seemed well suited to me, a good fit as they say, and more importantly, the job fixed all my financial anxiety.

I jumped in head first—ready to be a team player, ready to manage whatever clients they threw at me, and ready to help grow the business however I could.

This all lasted about a month.

By November, I felt overworked and was glad to have a few days off for Thanksgiving. By Christmas, I’d begun to sense that everything about the place was pretty toxic. I won’t dwell on the gory details, but I was having trouble understanding how anyone could run a business this way. In December, school was back in-person and we’d come back to the DC area. I’d never had a particularly stressful work environment—but by January, after the holiday break, just over two months into the job, my stress levels were through the roof.

I took walks each day during lunch just to cool my head. By 5 pm or 6 pm, when the work day was over, I would be so frustrated that I’d walk out of my office, march straight to the kitchen, and pour a large glass of wine so I could chug it.

My stress overflowed into the entire household, to my partner, to the kids. I couldn’t hide it, and they’d never seen me this way.

I won’t belabor the entire saga—it gets into the nature of work and time itself. Suffice it to say that in 20 years of healthy participation in the market economy, neither I nor my labor had ever been treated with such disregard. Never in two decades had I experienced such a disconnect between the quality of the work I was doing and how that work was being judged. Never before had I clashed this seriously with an employer.

By February, I knew there were irreconcilable, fundamental philosophical differences.

After a particularly fraught call with the CEO, I hung up, walked into the other room, and told my partner, who had been half-listening in on my side of the conversation, “I think I need to quit.”

It was not a good time to quit a well-paying job. We’d just signed a lease on the house in Bethesda. Inflation was starting to rear its head. I had already exhausted much of my savings during the previous year.

Without this job, my income would plummet. I had a side client at the time that was paying me $775/month to do content marketing. Another, larger client I had brought to the agency, but wasn’t sure I’d be able to leave with now due to a non-compete.

I had bills to pay, a family to support, and absolutely no guarantees of anything.

This was the low point.

Still, I knew I had to leave. The job was taking an extreme toll on my mental health, which impacted my physical health, and it was overflowing into everything else.

The next day I submitted my resignation.

And what happened next was… kind of incredible.

The very next day I received an email out of the blue from an old colleague. He wanted to introduce me to a doctor friend of his who had started a new physicians group and needed “a content guy.” Within a few weeks, I’d pitched and won the business and had a sizeable new client.

Other things also fell into place. I retained my existing client, and meanwhile the agency and I mutually agreed I could leave with the one I’d brought in. That relationship was mine and it was clear they still wanted to work with just me. A few days later, that client in turn sent me a referral—business I pitched and won and which turned into my fourth client.

Within a month of quitting, I was actually billing more in client revenue than I had been making at the agency—and I still am to this day.

Those few weeks after leaving, when everything clicked, felt almost as if the fates were smiling down. It had taken some bravery, some guts, to do what I did. And it had taken faith. And it seemed I was being rewarded for it.

Fortune favors the bold, I thought. Everything works out in the end.

The clichés came hard and fast, and more than a few times I thought about how everything I’d done, the professional risk I’d taken, seemed to have all been validated. I was telling myself a story with me as the hero, and this one had a familiar arc—in the end, I’d won, if indeed this was the end.

Still, I knew that my success hadn’t come from luck, or from being brave, or from having faith. The answers were more mundane.

My referrals had come because I asked for them, and also because I’d been in the industry for ten years and had a large network of colleagues who knew and trusted my work. My first two clients had come through the newsletter, the one I’d been writing about the business of healthcare. Former colleagues were reading it and ultimately reached out when they needed help (the full tale is on my company’s About page).

That’s really all the secret sauce there is to impart, and it’s certainly not enough to get all presumptuous doling out advice. I’m not gonna write a book about it or anything.

Because the truth is all of this could collapse tomorrow. ChatGPT or some other fancy new platform could come along and destroy my business. The industry could change. My clients could get bought by other companies. A recession could finally come. Anything could happen.

And whatever does, I’m sure it’ll be tempting to tell myself some story about why it happened that way. To place everything within a narrative, with me at the center.

Just take it with a grain of salt. I’m a data point of one.

III. Work and life aren’t a balance—they’re a matrix

There is at least one thing that the owners of the marketing agency I agreed on: the concept of work-life balance is kind of bullshit.

There is no HR policy that will ever solve for a toxic work environment, no amount of rah, rah mission, vision, and values preaching that will make up for a genuine lack of purpose. No amount of vacation time will negate a culture of workism (workism being the idea that to work is to be virtuous, and that to work more, harder, or longer, begets yet more virtue.

But success in business is not the same as success in life, and by now it should be rather obvious to everyone that the number of hours one spends at one’s desk has little bearing on your value to an organization, even less bearing on your value to society, and virtually no bearing whatsoever on whether you are living a good and meaningful life.

Anyway.

Your work is part of your life. You should do what you can to make the work itself sustainable. Not set up some dichotomy where one must balance the other.

wrote about this last year:

When we describe work and life as things to be balanced, we are suggesting that work and life are at odds with each other. More time or energy allocated to work means less time and energy allocated to life. 

This is obviously absurd, though. Work is just another part of life like family, community, food, fitness, creativity, travel, fun, spirituality, etc. 

The question isn’t how do you balance work and life, but how do you create a healthy relationship among work and the various other important areas of life?

Work, life, spirituality, travel, fitness, fun, and all the rest of it aren’t a balance—they’re a matrix.

Each has its own weight and importance. And everything is interconnected, intertwined, and mutually dependent.

We crave validation, or to serve. We want to be good partners, good parents. We seek novelty but also safety and comfort. We pursue wealth, status, freedom. Maybe we want to travel to all the places, do all the things, live multiple lives if we have to. We try to balance the expectations of society against what is innate to our being, if we can even figure out which is which.

Yet there is no one rule for how to sort through this matrix—it’s just too complicated—and whatever conventions once existed for solving, or at least navigating (surviving?) it are no longer up to the task.

This is why we fall back on aphorisms and proverbs. We share pithy quotations, and we tell stories. Maybe it’s the only thing we can do. I’ve done it myself. I’m doing it now.

It was my first job in marketing, at an agency, so there was a process. The client needed a rebrand, and I was to come up with at least 50 options for names. My boss was going to come up with another 50, and so would his boss, the owner of the agency. Next, we’d look at each other’s lists, and whittle it down to a few dozen. Then we’d perform due diligence, ensuring the names were available in the market and that a suitable URL was free. Then we’d whittle down some more, until finally, we presented the client with 3-5 finalists, and, if we felt strongly, a single recommendation.

When you are doing this for hire, for someone else, you need the process. You trust the process because the process protects you. In business, no one wants to acknowledge that process is often designed to CYA (Cover Your Ass), and yet—CYA it does. Process can get you many good and useful things, but it also cannot guarantee a good outcome. Not in hiring, not in planning, and certainly not in naming or branding.

The job is made even harder once you turn it on yourself. It’s hard to be objective, difficult to look inward, especially from a far enough distance to see the forest for the trees. There’s good reason people hire outside consultants: they can look dispassionately from the outside in.

Still, this weekend, after a process not at all like the one above, I rebranded. What was once What Really Matters is now Post-Nomad.

This is about why I made the change, and how.

Are you a business?

Conventional wisdom tells you to treat your own brand as a business. Yet there are difficulties in doing so.

This Substack, which I have been writing now for three years, is as close to representing me as there is on the Internet. The URL is my name, the writing is my voice, and the content is entirely my choice.

But if there’s one thing I deeply believe, it’s that I am not a business.

For three years, I have actively resisted doing the businessy-type things with this newsletter that one might do if they were trying to make it into an income-generating activity. I rarely look at the analytics. I did zero keyword planning. No content calendar. No positioning. And certainly no brainstorming of a list of names.

Because I have other income (from consulting and real estate), I have allowed this space to be my playground, free from the profit motive, and from all attendant distortions that come from choosing what to say or how to say it based on whether I think someone will pay me.

And yet…

People are still paying me. At first, it was a friend or two. Then a former colleague here and there. But then… a complete stranger signed up to pay me $5/month. Then another. And another.

These subscriptions cause endorphins to momentarily coarse through my body. If an email from someone who writes to say how one of my posts resonated with them satisfies a deep longing in my soul (to be influential, to have my writing be impactful), then a new paid subscription satisfies a deeply competitive instinct in my American capitalist beating heart.

But how to combine these two desires into one, the satisfaction to my soul and to my capitalist heart? Should I combine them?

What I’m doing with my writing

About a year and a half ago, I confessed that I really didn’t know what I was doing with my writing. Which is another way of saying: I didn’t think there was necessarily any unifying brand, idea, argument, or worldview that I was writing about (or if there was, I couldn’t see it).

Yet I still had to name it something. Three years ago when I moved my blog from Wordpress to Substack, the space at the top of the page couldn’t just be left blank.

How did I handle this? Here’s what I wrote last year:

First, I named the newsletter What Really Matters. It was a generalist’s name, meant to provide broad latitude in topic selection and a lot of freedom to take the newsletter in different directions. Having just lost a full-time marketing job and in no mood to over-analyze my newsletter’s brand positioning, I didn’t think too long or deep about it. I just wanted to convey that I was writing about important life things, since that’s what I like to talk and think about.

The second decision, in some ways more important, because it’s much more difficult to undo, was to put the content at russellmaxsimon.com. In other words, my own name. As anyone in marketing knows full well, changing your domain is a hell of a lot more difficult than changing your site’s name. Changing your domain risks breaking links for readers, tanking your Google domain authority, and surrendering hard-earned SEO karma.

So why did I choose my name as the URL but What Really Matters as a title? The short answer is that I knew one was easily changed and the other wasn’t, so I decided to experiment with the flexible thing and play it safe with the inflexible thing.

Well, today the experiment ends, and also I’ve changed my mind: I do think my writing is expressing a particular worldview. I do think I am advancing a certain thesis.

It just took three years of writing to figure out what it was.

Summing up a subject, thesis, or worldview

The first lesson of naming is exactly this: you have to know what the thing is about.

If you don’t know, then you need to go with something generic and simple. Stick with your name. But if you’re writing about something, then you have your starting point.

One of the best names for a Substack I’ve seen is Matt Yglesias’ Slow Boring. The name comes from Max Weber: “Politics is a strong and slow boring of hard boards.”

That’s an entire worldview summed up in a sentence. The worldview is that politics is a slow and painful process. It takes time and endless, diligent effort, and the result is a small hole on a hard board that is just a little deeper than it was before. In other words, a lot of work for an unsatisfying result. Weber’s sentence perfectly illustrates Matt’s approach to politics: take the small wins, do the compromises, choose the popular issues, use them to win elections, win more elections to gain power, and then use that power to make whatever slow, hard, painful, small progress can be made.

Weber’s philosophy sums it up, and Matt took the operating metaphor of that sentence and made it the name. Slow Boring. (Side benefit: as a stand-alone name, “Slow Boring” sounds kind of funny—also in perfect keeping with Matt’s irreverent humor and light-hearted style).

After three years of writing, I finally had, if not a worldview, at least a subject and loose thesis. The thesis is that, in a world of remote work and location independence, many of us are over-indexing on freedom, and under-investing in substantive legacies that are rooted in place. We are placing too high a priority on “traveling the world,” and too little on “investing in a place.” There is too much emphasis on goals and bucket lists; not enough on discovering ways of life: how you want to live, and where, and with whom.

Even for those whose work is rooted in place, often the dream is to cut it all loose and go vagabonding, to move, to travel, to sail around the world, or embark on #vanlife or some such rootless existence—but to what end? Even those of us who feel stuck in place can benefit from a better framework for thinking through where they would go and why.

In other words: what comes after all this location independence? What comes after you have the time, money, and freedom to travel? What comes after knowing that you want to pursue what Hunter S. Thompson called the Ninth Path—defining what way of life you want, and resolving to make your living within that way of life?

As I looked back on my writing from the past three years, I realized I had been thinking through these questions from the start, even back to the very first podcast I recorded in August, 2019. I had just visited Cabarete in the Dominican Republic for the fourth time in seven years. When I got back, I talked about how my relationship to the place had changed over time, and how it no longer felt like home in the way it had, and also how so few of us are willing to revise our relationship to a place, even in the face of changes on the ground, or changes in ourselves.

Since then, I’ve written post after post on finding home, searching for meaning, and building a legacy that is rooted in place. To cite just a few:

• Rumney, NH vs. Washington, DC

• A pandemic letter from Prague

• House hunting in Italy

• The nostalgia of fixing my first home

• Kitesurfing in La Ventana

• Ways of life and returning from Mexico

• Things in real life (and how we choose what to work on)

• Finding home in New Zealand

• A climbing legacy, bolted in place

Even in the few podcasts I recorded, I searched out and spoke to people who had moved their families to a new place (Frederique Irwin to New Zealand; Devon Reehl to Costa Rica) in search of a better way of life.

In other words, I haven’t changed anything; didn’t revise any past posts; just named the thing I’ve been doing.

The process that wasn’t a process

At first, I thought I’d rename the newsletter Finding Home.

I didn’t brainstorm 50 names and write them down in a notepad. After more than a decade in marketing and branding, I still can’t quite bring myself to treat this newsletter in the same ways I would treat a business client. The two are just not the same.

Besides, I don’t need to cover my ass with process here.

I did, however, spend around three weeks in silent brainstorming mode. Finding Home seemed to fit a lot of what I was doing. The only problem is that it did kind of sound like a name for a real estate blog, and I am definitely not writing a real estate blog. I may be ostensibly writing about house-hunting in Italy, but the true subject of that piece was the process of imagining other lives lived, and deciding whether to upend one current life for another.

Another direction I’d been mulling was something about digital nomads. As someone whose work has been more or less location independent for 10 years, I’d often had a loose afinity for the digital nomad community. But the relationship was an uneasy one.

On the one hand, I could work from anywhere, and had. I’d sent blast emails from the top of a bus in London, kitesurfed and worked from the beach in the DR, and held countless zoom calls from an apartment in Prague. I’ve traveled to more than 40 countries, but in the last decade it’s been what people are now calling “slow travel.” No trip was less than three weeks, with my preference always to stay in place, and keep going back to places I liked. I generally don’t do a lot of typical tourist things; I find a local climbing gym, and I stay in shape. I find one or two local restaurants that I like, and then I keep going back. I find a neighborhood pub. Mostly, I cook at home. I try to find the unique things about living in that place (often a kitesurfing or a climbing destination) and then ask whether this is something I want to keep coming back to, or do for longer, or do permanently. What am I doing in these places? Searching for a way of life.

So on the one hand, I am a digital nomad. But on the other, I’m not trying to tick off a bucket list of countries or spend my life in perpetual movement. I’m a father to a 12-year-old boy, and I’ve just turned 40. I’ve had not just one career, but by some measures I’ve had three. I’ve already traveled extensively, and money is good. I am of the digital nomad community, but also separate from it in important ways.

You can see where all this is going…

Post-Nomad

Eventually, I opened Notepad on my laptop and typed out the following:

Post-Nomad: Legacy, meaning, and finding home in an age of infinite choice

I was in New Zealand at my sister’s house, and she and I had been going back and forth on the themes in my newsletter for a few days. My sister is a professional semiotician, which means she studies cultural symbols for a living, usually on behalf of big consumer companies that are in the initial stages of new product development, or trying to figure out whether to enter a new market.

It’s heady stuff, and I asked if she could look at the headlines and images in some of my recent posts and come up with various “codes” to explain their meaning, as she would for a client.

We spent about an hour in her kitchen going over the various posts, and eventually, she handed me a piece of paper on which she’d scrawled a bunch of codes—two- or three-word summaries of meaning.

None of them felt like good names, but I did appreciate one of her core observations: Hunter S. Thompson’s “Ninth Path” letter is occupying a lot of space in my worldview. Not only have I hosted an Interintellect salon by doing a deep read of the letter, but various passages from it show up in probably a dozen of my posts, and the ideas expressed show up throughout.

Armed with my sister’s paper and my own notes, I started working on a revised draft of the Substack welcome email for free subscribers. If you’re considering a rebrand, or just starting new, this is probably a good place to begin working out how to put thoughts to paper. The free subscriber welcome email is often the first place where you deliver your raison d’etre for readers. It’s like the email equivalent of your About page.

Mine essentially has five parts:

1. At the top is the Hunter S. Thompson quote about finding a way of life. Similar to how Yglesias puts the Max Weber quote at the top of his About page.

2. Then, a summary of what I’m doing, and what the newsletter is about. This is the core explanation of your brand, where you distill into a few sentences the point of the newsletter, its themes and/or worldview.

3. An ask for readers, in this case to write me with feedback, story ideas, or examples of people who are working through the same questions I’m exploring. My most important metric is when people email me in response to posts that resonate, so it was important for me to say that I am very open to this!

4. Next, a short list of what they’ll find in the newsletter, including links to representative posts that explore and unpack the core themes.

5. Finally, reasons to become a paid subscriber. I really like what Susbtack founder Hamish McKenzie had to say on this subject, so I link to that, and I also link to my post on the different models of writing online and what they say about your values.

And speaking of #5:

Subscribe now

Finally, I drafted some bullet points and questions on what I mean by “legacy,” “meaning,” and “home,” the three words from my tagline that have anchored a lot of recent posts, and which I knew would inform a lot of what comes next:

1. Legacy—How do we build a lasting legacy when everything is so ephemeral—disappearing posts, algorithmic feeds, everything bits and data—and at a time when the greatest aspirations of our elite class are to build apps or write software?

2. Meaning—How do we create meaning out of a world seemingly intent on nihilism, or at least the post-modern, relativistic conclusion that lol, nothing matters?

3. Home—If you can go anywhere, be anyone, and do anything, then where do you go? When digital nomadism gets old or becomes lonely: where do you find home, and with whom?

No one can do this for you

I have enough experience over the past 15 years of positioning companies to know that naming a thing is incredibly hard. To name is to define what was undefined, to distill an entire argument, or a set of ideas down to their essence, and to do so in as few words as possible.

For years, I’ve asked those around me who I trust, loyal readers all, to see if they couldn’t help me narrow in on a better focus for the newsletter other than the previous name, What Really Matters. And though many offered their helpful suggestions, in the end, it was me who had to make the decision.

For me, Post-Nomad does everything I want it to do: places my writing in the context of recognizable audiences and movements, suggests what kind of readers may be interested in, and get value from what I’m writing here, as well as hint at larger themes.

The name sparks interest in what lies beneath, in part because it does something a lot of good names do: it gives a novel twist to a known idea.

My last step was doing the due diligence: I typed it into Google.

Nothing.

Crickets…

Even the URL was available (though not any more… ‘cause I bought it, suckers!).

It meant I’d hit the sweet spot, and I was very happy indeed. No companies, no newsletters, and no competition. No one else naming their things what I wanted to name my thing. I get to own the space; it’s mine if I grab it.

I may not want to think of myself as a business, but even I know that is a great place to be in. I finished the draft welcome email, wrote the equivalent version for the About page, and changed the name and tagline in settings. Finally, I switched out the image: same colors, same underlying photo, but zoomed in, cleaner, and with the new name overlayed on top.

I’m very happy with the result, and, as is the case with many things in life, by committing to a direction, it has actually expanded the space for creativity. Now that I know the themes, I’ve got what feel like unlimited ideas for how to explore them in greater depth.

And so, without further delay, I introduce:

Post-Nomad

Legacy, meaning, and finding home in an age of infinite choice

That time between Christmas and the New Year has always been fraught.

Somewhere in there is my birthday. Exactly which day I do not often divulge, because I do not like getting birthday messages. Could be today, could be another—who is to say? Besides, time is but a human measurement, so said the late founder of the religion of my birth.

I agree with her on that much: time is a human measurement. To Mary Baker Eddy, that meant that time, along with matter, is an illusion, and thus not to be taken too seriously. For me, though, it means time is everything.

Maybe time is the only thing.

We only have one swirl around on this rock, that is true, and however you want to measure it—in birthdays, in minutes, or in moon cycles—it dwindles away for you as it does for me, never to come back.

This year, my birthday marks forty years on Earth. In the first twenty, I was barely conscious of time as a resource. I floated with the tide, as Thompson would put it.

In the next ten, those halcyon years of growth they call your 20s, I felt I lived many lifetimes. Each new career, each move to a new city, each time I formed a sense of self and was then forced to revise, each new relationship where I fell in love and then out and then back again—all of these felt like I had been given more time on this Earth in more variations than anyone had any right to expect.

Then, six months before the end of that decade, when I was 29, I became a father, and everything started all over again. It was a role I had always wanted, and I am glad it happened then, and not, as many of my friends and peers have experienced it, toward the end of the next decade.

In year 30, my son’s mom and I split up, and life was pain for quite some time. I rebuilt, made a new home, made money. I took myself to the DR. I learned to kitesurf. I fought for shared custody and got it. I learned that I was me again: reasonably intelligent, charming when I wanted to be, and yes confident in my own judgment.

And then, once the bottom part of the hierarchy was fulfilled, I began a tear into the thing on top: self-fulfillment. I went on a creative tear: wrote a story, wrote a screenplay, wrote another. Started producing and directing them, went to film festivals, met other filmmakers, grew, created.

In my 30s I made plans and wrote down goals and reached them, most of them, though there was one—is still one—that hangs out there. Write a book.

In my life, my identity has always been as a writer. I wrote as a journalist, then I wrote as a marketing professional. I wrote for politicians, wrote for campaigns, wrote for nonprofits, and still write for companies and clients. I wrote screenplays, and even for that brief time when I started calling myself “a filmmaker,” really I was a screenwriter who had learned a bit of how to direct and produce.

A few years ago, I started writing this newsletter. It is my playground, and needs no producer or director, or agent to realize its final form. There is no point or goal, and few earnings. Readership: hundreds, not thousands. Stakes: low. I wish for this particular creative activity to be more or less disconnected from profit. Which is what I also wish for my life: to have it be about time and not money.

What will I do in the next decade? How will it feel? It seems the answer will have a lot to do with what I decide is still left to do, and what I decide it is time to give up on doing.

I once told a group of people during a retreat in Medellín—digital nomads most, thinkers some—that I felt my legacy was to be inextricably bound up in whether I could write, how well I could write, and what that writing could or would do in relation to the world. We were workshopping the idea of Ikigai at the time, a concept I have since come to revile, but which some may find mildly helpful in a childish sort of way to think through different life options.

It was a little while after this conversation that one of the women who had been listening to me wax on in my self-serious way about how important my writing was to me turned around from the front seat of a car and just blurted it out: what if you were to give that up?

I think I must have looked at her kind of funny.

“Give up what?” I asked.

“Give up this need you have. To write all the time.”

“No, I can’t. I won’t.”

And yet, her words have stayed as a kind of shadow in the back of my mind, calling to me. There are times when writing becomes so difficult and miserable and pointless that I think to myself: you know, there is an option here. Just stop… Stop thinking of yourself as a writer. Stop thinking you must write. Do something else. Dig ditches. Build homes. Teach kids how to kitesurf or climb. You can become an electrician and install mini splits or solar panels. After all, if there’s one thing I know for sure, Russell, it’s that the world needs more solar panels.

It’s roughly five years since I had that conversation.

And what remains, as I turn forty, feels mainly like a choice: what is left to be done vs. what is left to give up.

Sometimes, when I feel as if I should write or publish but do not have a particular topic in mind, I go to my Substack and look at the list of drafts started but not finished. The list grows longer and longer. Here’s a partial view — all of these have drafts and notes waiting for my attention one day:

David Hume and living in the matrix

The choices we make for our kids

I was wrong about my depression

Fox thinkers and hedgehog thinkers

Euphemisms for money

On commoditizing your time

Marketing is dead; long live marketing

Fear and waiting

How to write about yourself

Making decisions amid uncertainty

Our relationship to government

The anti-life coach

The superpower every man should learn

Effortless adventure

The brave face

Substitutes for religion

I am not your writing coach

The Ninth Path

What will be your “legacy”?

Can you be yourself when you’re around other people?

How NOT to write a personal mission statement

Yes but should you make money writing online?

Growing up in the 90s didn’t prepare me for this

Idolizing Hemingway (TBD in aforementioned book)

It’s an attention economy and I don’t care about your attention

Paying attention to women

Why I’m not taking vacations anymore

Rock climbing in Paklenica

Notes on Anna

On losing guy friends

Do not go gentle

As I said, this is a partial list. There are thousands of words still unpublished waiting in those drafts. Ideas to be developed. Or abandoned.

And there are other life goals (the phrase is beginning to seem quaint), as I turn 40, that I think I am ready to give up. And others I’m not. Some countries still to visit, mountains still to climb, and others I’ll never see. Business enterprises to embark on, and others to cut loose. Languages to learn, or give up on learning. People to go see or give up on seeing.

Perhaps in your 40s, you begin to triage time.

Or perhaps I will find some kind of grace so that it doesn’t feel like a triage. Wouldn’t that be nice.

Sometimes when I was starting a new story and I could not get it going, I would sit in front of the fire and squeeze the peel of the little oranges into the edge of the flame and watch the sputter of blue that they made. I would stand and look out over the roofs of Paris and think, “Do not worry. You have always written before and you will write now. All you have to do is write one true sentence. Write the truest sentence that you know.” So finally I would write one true sentence, and then go on from there. It was easy then because there was always one true sentence that I knew or had seen or had heard someone say. If I started to write elaborately, or like someone introducing or presenting something, I found that I could cut that scroll-work or ornament out and throw it away and start with the first true simple declarative sentence I had written.

Some people seem to think this method of writing one true sentence and avoiding anything elaborate is some kind of sage, Papa-delivered advice on overcoming writer’s block.

I happen to think it’s the opposite. It’s Hemingway’s little competitive way of saying to future generations of writers: don’t even try. No one will write truer sentences than me.

I’ve been working on a memoir the past few months. It’s about unfulfilled creative ambition, how we think about legacy, and the ways in which certain writers have been an essential guide for me in my own struggle for legacy and creative fulfillment.

It’s called Idolizing Hemingway. And I want to give up.

How it’s going

A few people have asked me how far along I am in this memoir. The answer depends. The words I currently have down on the page generally fall into three categories:

1. Total words: 45,000+

2. Words I’d actually show to a friendly editor: ~15,000

3. Words I personally think are good: not that many

Or, there is another metric: how many words are true in the sense that Hemingway meant it? How many words are my most honest, truest accounting? So true that they feel more real even than the reality I lived.

The answer is probably none, or close to none.

As I sit in my chaise in the evenings or afternoons or whenever I can drag myself to the keyboard, I increasingly stare at the draft I am producing and think to myself: I’m not good enough. My writing just isn’t good enough.

I am supposed to be writing about how past writers like Hemingway have shaped my feelings about legacy and the creative life, and here I am paralyzed by the exact subject about which I’m supposed to be writing, paralyzed because the bar I’ve got in my head—one true sentence—is apparently too high a bar for me to cross.

Where we get validation

I’ve thought a lot about creative validation. In fact, I made a whole movie about it, run time one hour and fifteen minutes (recently posted to YouTube if you’re interested).

I think sources of creative validation can be separated into a few categories:

1. Validation from one or a small handful of trusted sources (spouse, friends)

2. Validation from elites (good reviews)

3. Validation from audience size (more sales/readership/likes, etc.)

4. Validation from within

In my film, the main character, an aspiring theatre director named Evelina, is intensely preoccupied with creative validation, especially from audiences and critics. She wants to make “great art,” and her definition of great art is a theatre production that critics and audiences love.

Meanwhile, another character named John, one of the actors in Evelina’s production, is equally preoccupied with validation. Only, he is one hundred percent motivated from within. The only opinion that matters about his performance as an actor is his own.

In one of the film’s pivotal scenes, John has realized he isn’t living up to his own standard for a good performance, launching him into a crisis in which he freezes up, unable to remember any of his lines. He is unsure of whether continuing with the production—or even trying to be an actor—is worth it.

Maybe you’ve guessed, but I’m the John character.

The flaw within

Of course, it’s always nice when you, dear readers, email me a kind reply about how good this or that piece of writing was, and it’s also nice to see new subscribers come in. It makes me feel good that my writing is of some greater resonance, and not just a kind of masturbatory self-help session I carry out in public from time to time.

Still, I already know what is good before I hit the “Publish” button, and a large percentage of the satisfaction I get from writing is already received before my writing ever reaches an audience. This only reinforces my identity as someone who gets their validation from within (because true artists do the art for its own sake, not for the validation of others; their only guide is their own internal muse.)

But there’s a flaw with this line of thinking, and I’ve been aware of it for a while.

I may think I am almost entirely motivated by my own sense of what is or is not good writing. But where did that sense originally come from?

In my head, I have an idea of what is good writing, but that idea was formed by multiple influences from multiple time periods in my past. So, in some sense, I have incorporated those influences into my own internal guide. But in another sense I am actually in the first category of the different kinds of people I mentioned above: I get my validation from a small handful of trusted sources, those sources being the other literary influences from my past.

Of course, this is a horrible place to be in as a writer, comparing myself to the best work of other world-historical writers. No wonder I’m paralyzed.

An alternative way of thinking, equally paralyzing

Hemingway wrote the first draft of his first masterpiece, The Sun Also Rises, in about six weeks of fevered typing. But then the real work began. He went through dozens of drafts before sending it to his publisher. Even then, after getting back the galleys, he went through more than a dozen additional revisions.

When I read about Hemingway’s editing process for that book, a book which I revere, I felt both better and worse about my own writing. Better because I am only on what could be considered my third or fourth revision of certain sections (with others still to be written at all).

But it also made me feel worse because I don’t know if I have it in me to do that much work on a manuscript. If Hemingway went through 30 or 40 drafts, and I’m already getting burned out after three or four, what does that say about me the writer? How much do I really care about the things I’m telling you I care about if I’m not willing to put in the work?

There, now I have said the thing in the plainest way I know how: I want to quit because I am scared I simply don’t have the work ethic to be as good as I want to be.

So where does that leave me?

If you’ve been reading this newsletter for long enough, you may be used to the fact that I don’t always offer prescriptions. No need to wrap things up with a pretty, optimistic bow at the end. Sometimes it’s just a question I have, and this one is unresolved.

I am here in my office at my desk, with the 45,000+ not very good words safely closed away in its file so that I don’t have to stare at writing I am not happy with, and don’t have to do the hard work of making it more true.

And meanwhile, time ticks away, never to come back.

When I started this newsletter I made two important brand decisions — and for anyone interested in the topic, you might have noticed the two were in conflict.

First, I named the newsletter What Really Matters. It was a generalist’s name, meant to provide broad latitude in topic selection and a lot of freedom to take the newsletter in different directions. Having just lost a full-time marketing job and in no mood to over-analyze my newsletter’s brand positioning, I didn’t think too long or deep about it. I just wanted to convey that I was writing about important life things, since that’s what I like to talk and think about.

The second decision, in some ways more important, because it’s much more difficult to undo, was to put the content at russellmaxsimon.com. In other words, my own name. As anyone in marketing knows full well, changing your domain is a hell of a lot more difficult than changing your site’s name. Changing your domain risks breaking links for readers, tanking your Google domain authority, and surrendering hard-earned SEO karma.

So why did I choose my name as the URL but What Really Matters as a title? The short answer is that I knew one was easily changed and the other wasn’t, so I decided to experiment with the flexible thing and play it safe with the inflexible thing.

But there’s a longer answer, and for anyone who has often wondered to themselves what am I doing with my writing, the longer answer is worth reading.

What it means to be a writer

To be a writer is to be in a state of continual existential crisis. Obviously.

Ok, but seriously. How you define what it means to be a writer has a lot to do with how you choose to brand your writing, whether it’s here on Substack or somewhere else. Just as your choice of technology platform is reflective of your values and identity, so is choosing a brand.

Saying you’re a writer, walking around telling people hi, I’m a writer, implies that you do it professionally, no matter how much you may want to count your private journaling, or maybe those un-read screenplays sitting in your drawer. For me, though my career titles on my LinkedIn page all have the words marketing or communications in them, I have long told myself I was a writer mostly on the basis that most marketing pretty much is writing.

But I could never simply say I’m a writer to new people at a party and leave it at that, at least not with a straight face. In fact, most often I didn’t say that at all, instead swallowing my pride and copping to being in marketing. It was only deep down I maintained the identity for my own self-worth: Writer.

Sure, I did the journaling. And yes I’ve got un-read screenplays in a Google Drive folder somewhere. I’ve even got screenplays which I produced into films. But I never made my living off that writing. I made my living writing for others, writing what they wanted, writing for companies, writing to sell products or services or to attract job candidates, or earn media attention, or — this was fun, but seedy in its own way — writing to win elections.

So, going around saying you’re a writer implies to some extent that it is your professional livelihood. But there is another sense in which being a writer has little to do with money, and everything to do with desire.

Writing out of desire

In my own life, there have been several stretches, usually a matter of a few weeks, when I didn’t write a word. That may seem of small significance to a lot of people, but for someone whose identity is so tied up in being a writer, not to write for that stretch of time feels like a profound failure. Or dare I say, an existential crisis.

But what happens — what has always happened — is that I come back to writing. I miss it. I re-discover that, even if there is no one out there expecting to give me money in exchange for my writing, I still desire to write. I’ve asked myself the question a hundred times in my life: would I simply give up writing if I were able to make my living in some other way? And the answer is always the same: no.

I would still write. I’d write even into the void. For posterity. For myself. To help me understand what I think about what’s going on. Or just to exercise that part of my brain.

If you are like me then, you may feel just fine calling yourself a writer even though you never earn a penny from your writing. If it’s something you feel you must do, and would do even with no outside motivation, well then you deserve the title.

This, it turns out, has profound implications for something so seemingly small as naming a newsletter.

Some newsletter naming examples

When I was just starting out on Substack, I looked to writers like Ben Thompson, who I knew of through his technology blog Stratechery. I also looked to Azeem Azhar, whose newsletter about future tech trends is called Exponential View. Both these writers chose a URL that was also the name of their publication (stratechery.com and exponentialview.co).

On the other hand, I was also looking to writers like David Perell, who went with the height of personal brevity and hosted everything on perell.com, or Nat Eliason, who also went the personal route with nateliason.com. Neither of these young writers chose to create some other brand to house their writing: they wrote as their own brand.

So, what distinguishes Perell and Eliason from Thompson and Azhar?

I think it’s a few things. For one, Thompson and Azhar both had very clear domain expertise. They both also use their writing as the way of earning itself. The writing is the product. Thompson earns a living directly from subscriptions to Stratechery.

Perell and Eliason on the other hand each write about a broader set of topics, and neither seems to think of their writing as the way they earn their living, at least not directly. Rather, their writing essentially serves as lead gen for something else, whether it’s Perell’s Write of Passage workshop or Eliason’s marketing agency Growth Machine. Notice that when either of them wanted to start selling, they did create a brand, if only just as a landing page, separate and distinct from the personal writing.

When the professional is personal

I’m not some culture critic here, but I do think the example above is illustrative of something I’ve noticed among younger creators, say those under 30, which is that, for them, there is little difference between the professional and the personal. It’s not lost on me that Perell and Eliason are of a younger generation than Thompson and Azhar, which I think leads to different thinking about how one builds a career (more of which in a future post). Eliason’s personal interests, as he’s said a few times on his YouTube channel, include entrepreneurship, for example, which is about as professional sounding a personal interest as I can imagine.

The point is, there is no separation for these young creators between who they are as people and where they plan to take their careers. They could be fooling me, of course. But whether it’s just the appearance of inseparability or the reality is kind of beside the point: they are using their own personal brand, and URL, as a kind of content hub for building out their career.

That may seem like an obvious thing to do for a lot of people. But for me, an aging 30-something (ok, I admit it: one year away from turning 40), it’s actually quite —how shall I put this — unprofessional to let so much of your so-called personal life into the professional realm.

Related but crucially different, the cliché I had growing up was to follow your dreams, to find your passion, and the like. The idea I was taught was to find that thing that I was so passionate about that it didn’t feel like work.

Lots of ink has been spilled on why that’s terrible advice, so I won’t repeat all that here, but the point is that I was told to find a way to fit my work to my passions. But for the younger generation, creators like Nat and David, there really appears to be no separation between the two.

The cool thing for them is: they are way better than me at figuring out how to make that work. In fact, much as I kind of want to pour out resentment over the whole state of affairs, I must admit that Eliason in particular has been (gag) inspirational for me. In fact, he got me thinking the other day about the very problem I put into the title of this post, the problem of what I’m doing with my writing.

And the thinking led to a breakthrough.

All the topics you want to write about

What got me thinking was a video Nat put out from early December with the cheesy title, “How I never stop writing.”

It’s not normally something I would click on, since I don’t really have a problem getting words out on the page, or coming up with ideas about what to write. In fact, one day over the holiday I thought to count up all the drafts I had in my Substack of post ideas I’d captured but had not yet written. There were fifty-four.

And so it wasn’t Nat’s advice on keeping more than one draft going at a time that resonated with me. No, it was when he suggested I write down five to ten topic areas that I’d like to write about. He recommends this, he says, because brainstorming with a constraint can actually result in more ideas than if the field were wide open, just as thinking of a joke is kind of hard, but thinking of a knock knock joke is much easier.

But as I said, I don’t have trouble coming up with ideas on what to write. What I have trouble with is categorizing those ideas. In other words, branding them. Basically, I don’t like being tied down, don’t like pigeon-holing myself, and have never been able to commit to focusing on just one thing. It’s played hell with my attempts at self branding, but, as Michelle Obama said, it is what it is.

For whatever reason, perhaps it was my slight holiday hangover, I decided to actually follow Nat’s advice. And notice that he didn’t suggest writing down 5-10 topics which all merge together into a cohesive brand, or which are all part of a strategic business plan to reach target audiences, or even 5-10 topics which are at all related. What he said was to write down 5-10 topics that you might like to write about.

So I did. I ended up with seven topics, then realized some of them were pretty similar, so consolidated them to five. Some of them I’ve already clearly been writing about here. Others, not so much. Here’s what they are:

• Personal narrative (Or, memoir generally) (examples here, here, here, here)

• Life planning & goal setting (examples here, here, here)

• Writing & marketing (examples here, here)

• Climate havens & community (example here)

• Rock climbing & kitesurfing (example here, here)

Writing these out like this was, oddly, something I’d never tried to do before. Maybe I’d resisted doing it. I mean, I had the interests in my head — I knew all the different things I wanted to write about — but I’d never thought of them as categories on a website. Which is strange, since I’ve been leading content marketing programs for quite a long time now, and categories on websites is kind of a thing when you do content marketing.

Whatever, it’s hard to turn the lens inward. But as I wrote them out, finally, that’s when something I’ve been stuck on for a long while, agonized over, you might even say, suddenly become unstuck.

And this is the long answer to why I used my name as the URL here but chose something else as the title: because I’d been stuck.

The answer to what I’m doing with my writing

The insight Nat helped me with was simple, but in fact it’s taken me years to accept. What I realized was precisely that my many disparate interests need not hold together in a unified brand or whole because that’s me.

I think this is something the young folk like Nat have an easy time with, but the older geezers like me have trouble with. Or maybe it’s just my over-analytical mind, trying to plan out the end game before I’ve even gotten started. Maybe my strategic marketing brain was actually getting in the way, insisting that I do branding before I choose what to write about.

Whatever it was, I suddenly understood that lack of separation between the personal and professional that comes so naturally for Nat and David. I think they realize something important: not just that it’s ok to have a lot of disparate interests, but also that it’s ok to project that into the world, even to those with whom you want to have a professional business relationship.

Nat is interested in entrepreneurship and also productivity and sleep and marketing, but also he’s getting into real estate and YouTube-ing. I’m interested in writing and memoir and how we craft personal narrative and also climate change, especially climate havens, and also community and rock climbing and kitesurfing — and a great many other things (though I’m less interested in writing about those other things).

That may seem like a bunch of disconnected interests but guess what: A., that’s fine, because I’m a person who has a lot of different interests, and B., they’re actually more connected than you think, and I’m looking forward to writing about that.

I’m here in New Hampshire because I love climbing, but also because much of New England is a climate haven, and also I like to think about how climbing and kitesurfing play in to identity in a culture where identity is so wrapped up in work, and also why are there so few memoirs by straight men talking about the kinds of choices unique to manhood (although here’s a male memoir about a surfer, so that’s a start,) meanwhile why are there are so many amazing memoirs by women talking about the choices unique to womanhood, and also, speaking of narrative and life stories, how do we plan our lives and set goals such that time doesn’t pass us by accidentally, so that we may live with intention and do the things we want to do (like kitesurf and climb)?

The self contains multitudes. We’re all, most of us, multi-faceted beings with a lot on our minds. Or if not, if since the moment you were born you entered the world with a single over-riding passion, an interest so consuming and pure that you are well on your way to becoming the leading voice in your field for a generation, well that’s fine. You do you.

As for me, I’ve come to a kind of new comfort with expanding the scope of what I plan to write about here. And I finally have an answer to the question of what I’m doing with my writing. The answer is: I’m gonna do me.

As a writer and former journalist, it’s been hard to miss this year’s steady drumbeat of other writers and journalists departing their institutional publications for Substack.

I started this newsletter thinking I was late to the Substack party. Turns out I was kind of early. In one of my first posts I grappled with how closely I identified with the term itself, writer. Would I blog just for me? Would I keep a journal? Would I try to make money with my writing, and if so, how? The most fundamental question I faced was this: was I serious about my own professionalism?

Ultimately, I decided I was, and I wrote a post about it titled Why I moved from Wordpress to Substack (And what it all means). The piece was as much about my values as a writer as it was about the platforms themselves. Indeed, it was really about what the decision on platforms says about your values.

Why journalists are joining Substack

The answer begins with Hamish McKenzie, one of Substack’s co-founders and a former journalist himself. In a post from May 18th, What’s next for journalists, McKenzie talks about his past as a freelance writer. He came to the U.S. in 2010, 29 years old, and hustled and scraped to make $35,000 his first year. That’s a princely sum for a freelance journalist at any age, especially one newly arrived to the U.S.

For as long as I’ve been following McKenzie’s posts, I’ve been impressed with his grasp of the major forces impacting journalism, and his attention to building a platform which works for journalists. Take, for example, Substack’s announcement in July that they would begin providing legal support for their writers. Only a journalist can truly appreciate how significant that was. The line between freedom of the press and censorship, or between defamation and truthful reporting, can sometimes only be defended (and sometimes must be defended) by a lawyer who knows what they’re doing, and the presence of that support gives journalists the crucial confidence they need to do their jobs well without fear of being sued into oblivion.

McKenzie’s attention to journalism has resulted in a kind of slow drip of prominent writers who have abandoned their institutional comfort blankets in favor of Substack’s direct-to-reader, subscription-based model. In fact, so many prominent reporters have joined Substack this year that the shift itself has become its own story. Here’s just a partial list of big names from this year:

• April 6th: Matt Taibbi, formerly of Rolling Stone (his announcement)

• July 17th: Andrew Sullivan, formerly NY Magazine (resignation letter)

• Aug. 17th: Anne Helen Peterson, formerly BuzzFeed (her announcement)

• Sept. 23rd: Casey Newton, formerly The Verge (his announcement)

• October 29th: Glenn Greenwald, formerly The Intercept (his announcement)

• November 13th: Matthew Yglesias, formerly Vox (his announcement)

Scott Alexander of Slate Star Codex has also written that he’s considering a move to Substack.

The common thread

Shortly after Glenn Greenwald announced his departure from The Intercept in October, I saw a Twitter commentator who fancied themselves particularly woke chime in on the exodus. She had seen all these white men bringing their audiences to Substack and concluded that the platform must therefore be yet another tool for perpetuating the white patriarchy and boosting existing power structures.

She’s since deleted the tweet, perhaps because she realized in retrospect how wrong she got it. But the online debate I saw about the kinds of writers who were leaving their previous institutional homes got me thinking what those writers might share, which got me back to thinking about values.

Fact is, the Substack model is the exact opposite of a tool for perpetuating established power structures, much less white or male ones. To begin with, it’s free. So there should be no confusion about needing a lot of money or access to capital to get started. Secondly, our subscribers are our own. We can upload an email list to the platform, or export our email list from it. There is no algorithm designed by any Silicon Valley frat boy intermediating my content from you the reader, and I hope there never will be.

Of course, writers like Matt Taibbi, Andrew Sullivan, and Matthew Yglesias are able to bring their existing audiences to Substack, but there’s hardly anything nefarious there, and in order to do so, they had to use other platforms, namely Twitter. It’s not like Taibbi was able to export some email subscriber list from The Rolling Stone, or Yglesias from Vox.

In fact, I think Sullivan said it best:

Well, yes. The Substack model does kind of lends itself to that.

What kind of writers join Substack

If Substack does become a kind of identity marker, let it not be a marker of political ideology. Let it instead be a marker of independence, of freedom.

Newspapers have been in a death spiral for a long time now. I could feel the beginnings of it when I was newspaper reporter, from 2004 to 2007. I covered politics for the Albuquerque Journal, then, as now, New Mexico’s largest daily newspaper.

Yet I could see the threats to circulation and to ad revenue, and thus to our ability to do good work. Craigslist was taking over the classifieds. Facebook and YouTube were just at the start of their path toward global domination. “Information wants to be free” was still a kind of mantra among certain idealistic Internet purists. Whenever a reporter left our newsroom, the powers that be declined to fill the position, and the rest of us made do, trying to cover the same areas with an ever-dwindling staff.

I remember a debate one day in the newsroom. The publishers had come to talk about the strategic future of the newspaper, specifically how they would adapt to more and more readers going online, cancelling their paper subscriptions. A few of the younger staff writers argued that the web version of the site should be totally free, because that’s what people wanted — make it free, draw the audience, and then make up the lost revenue from paper subscriptions on online ad revenue.

I’m embarrassed to say I was one of those young staff writers. Oh how naive and wrong I was.

Today, count me among those who whose most fervently held beliefs include the idea that chasing eyeballs for the purpose of selling ads is leading to the wholesale degradation of our media, our public discourse, and indeed our souls.

The Substack model matters

In journalism, it used to not matter much who your advertisers were. As a reporter, I never saw the ad sales people and they never saw me. They worked in some other part of the building I never went in to.

Fifteen years later, who your advertisers are matters a great deal. Journalists with podcasts read the ads themselves. In their own voice. My old-school, old media sensibilities are still kind of aghast at how definitively the old wall between the reporters and the advertisers has collapsed. Now, journalists tell me on their podcasts how much they love the products or services they are paid to shill in between segments. Now, companies are political. You can’t not be. To do business in America is to more and more often take sides in a culture war.

Substack stands in opposition to this trend. If a writer is to be financially accountable to someone, so Substack has declared, let it be their readers. Let that relationship take precedence, Substack has said. And furthermore: let the platform which enables that subscription model tie its financial incentives to the writers who use it. When I make money, Substack makes money, and not before then. As my revenue goes up, so does theirs. No advertisers and no algorithms.

So, what does it mean to have chosen this model? Simply that we value our independence — and we want a technology partner who defends it.

My guess is a lot of you found me via this post on why I moved from Wordpress to Substack, which, starting about six weeks ago, the Google Gods were kind enough to smile down on with attendant blessings. Suddenly, I began ranking quite high on searches related to “Wordpress vs. Substack” and the like, which has led to a pretty dramatic acceleration in subscriber growth:

Perhaps that post struck a nerve not just because I described the various models of writing online (I also covered my thoughts on writing for Medium), but also because I talked about what those platform choices meant for my identity as a writer, and how your choice of revenue model isn’t just a business decision — it’s a values decision. It’s a matter which should be deeply personal.

That post is now the most-read article I’ve written, by far.

And this has got me wondering: how should I respond to this turn? Should I respond?

“Define this newsletter”

Last week, Pranav Mutatkar’s Embrace Your Lazy newsletter hit my inbox.

I met Pranav on an Interintellect salon. (If you haven’t heard of Anna Gát and the Interintellect yet — you’re welcome). I liked what Pranav had to say about movies and directors and more broadly about how artists relate to their work, so I started reading some of his stuff, and subscribed to his newsletter.

Anyway, in Pranav’s most recent post, he wrote about how to grow old. Here’s the part that stuck out to me:

As we get older, we are slotted into these boundaries. It makes it easier for others to define us.

I never felt comfortable with boundaries. When somebody defines me, I feel the need to do the opposite to rebel against the definition. I think I have a bit of the Krishna trickster blood in me.

But for marketing purposes, defining what this newsletter is about... is... probably important. Currently, when somebody asks me to define this newsletter I just go 🤷.

(Ah, the shoulder shrug emoji. An emoji for these times.)

Pranav was touching on a subject near and dear to my heart, which is how we define ourselves in relationship to the people who are watching — or in this case reading. In fact, I made a whole movie about how artists get validation and what it means. Now that I’m writing this newsletter, I still feel that tension, between making this a space just for me and responding to readership.

Give the people what they want to hear is never a mantra I’ve been particularly interested in following, perhaps to my detriment. But that’s not to say I don’t still feel the pull. When one of my Tweets takes off, goes viral, of course there’s this little voice inside saying well, how do I more of THAT?

Honestly, I hate that voice.

What sets newsletters apart

When Pranav asked his readers to “define this newsletter,” I decided to write him back. I told him I felt the same pull he did, but at the same time I tried to remember that I set up What Really Matters as a space just for me.

But also:

…I get a bunch of subscribers, and I’m like, “Ok, how can I get more subscribers,” and then I’m like, “Wait, Russell, why do you want more subscribers? What are you trying to achieve here — audience for audience’ sake? What does that have to do with living your life on your terms?

These are the conversations I have with myself.

But the exchange with Pranav is worth recounting, because I think newsletters, especially those in the Substack mold, set themselves apart from much of what is online through their simplicity, their direct connection with the reader, and their limited feedback loops:

1. Simplicity: this is a space for writing, period. Sure, you can embed stuff from elsewhere on the Interwebs, but I’m a writer. I don’t want to have to compete on photography, videography, fancy programming, graphic design, infographics, UX, UI, all that jazz. A newsletter is a letter, simple as that. And I can write those.

2. Direct Connection: in other words, email. This isn’t some new, algorithmically superior model of delivery that Donald Trump will try to force the sale of for political advantage in some global game of faux privacy protection. It’s good old-fashioned email, delivered to your inbox whenever I hit send. You can either read it, or not. You can hit reply, or not. And this really matters, because, relatedly…

3. Limited Feedback Loops: The worst thing about social media, IMO, is its endorphin-chasing feedback loops. Those little hearts on the Instagram posts, that little red notification at the top of the Facebook page, those little bits of “they love me! something new!” that we don’t think of as chasing but are driven to chase nevertheless. They are bad for you, bad for me, bad for our kids, bad for everyone. In contrast, I don’t really have a lot of metrics for Substack: I can see open rates, who opens, and a rough approximation of where new readers come from, although even that is pretty limited.

All of these characteristics — as well as the financial model itself — make newsletters a special kind of breed when it comes to online content (if you haven’t already, read The different ways to make money with online content, and what the decision says about your values).

But even with its strengths as a medium, even newsletters risk leading you astray from the things which are most meaningful. If you are writing for an audience, ask yourself why? To what end? For most of you the answer is probably something like, “So I can get some percentage of them to sign for the paid version, so I can make money.”

Fair enough. We all gotta eat. But perhaps it’s worth noting that I make about 98% of my money from marketing consulting; the other 2% from newsletter subscriptions. Do I wish the 2% were a higher number? Yea. But, as we’ve been saying a lot around this house: it is what it is.

And yet, here I am, on a weekend, punching out nearly two thousand words for you dear readers. Clearly, I’m writing for some internally motivated reason — which I think is that I honestly wish people would focus more on what really matters to them, and if more people did that perhaps I wouldn’t feel so lonely all the time. I, personally, would feel more connected with y’all if we stopped chasing money and adulation and brought it back to the basics: the human connections, the time with family, time spent learning, time spent outdoors, or on creative fulfillment, time spent following your loves, your passions, or at least: finding out what those are.

Because as it stands, I more often see those things being harnessed as a means to make money or build businesses, rather than being pursued as ends in themselves. Which is sad of course, but also the world we live in.

All of which is to say this: more subscribers isn’t the point. The point is how you wish to spend your time on this Earth. Because, as we can all at least agree, the Google Gods are fickle. Your proud SEO ranking will one day vanish. And then where will you be?

In 2016, I took a solo trip to a tiny island in Belize, Caye Caulker. It was a stretch of sand with some tiki bars and sailboats. There were no cars, and one dirt road. I flew in on a 4-seater operated by Tropic Air.

For the next 12 days I had only two goals: kitesurf when windy, and write a feature-length screenplay. As it turned out, I finished the screenplay in eight days.

I also didn’t write another script for more than a year.

Working in spurts

I’ve always worked well in spurts.

Research papers in College took me one, long 36-hour stretch, when I would go to the library, put my head down and get it done. The writing itself rarely took me more than a few hours. When I became a reporter the lifestyle fit me well: wait, wait, wait, NEWS! Now write the piece on deadline! Now! And then go back to waiting.

(I never miss deadlines, incidentally)

Make your living as a writer for long enough and you’ll come to understand that writing fits this style naturally. You think, you ponder, you procrastinate — and then you WRITE.

For several years I made independent films, and being a filmmaker has a similar workflow: lots of waiting and planning, waiting and planning, followed by an intense few days or weeks of PRODUCTION.

The script I wrote in Belize was 85 pages. A few months later, I shot it over the course of seven days. A couple weeks later I had a finished feature film. And then, I didn’t make another movie for more than a year.

31 Days to Climb 5.12

The point is, I’ve found a mode of production that works for me.

Last week, I started a new experiment: I would give myself one month to reach a goal of climbing 5.12. It’s a hard grade that many climbers never break in to. I’ve been climbing roughly 15 years, but it’s only in the past year, after moving to Rumney and having the cliffs so close by, that climbing 5.12 has felt achievable to me.

The question was, how would I actually get there? What strategy would I use? I came up with a plan, one that I felt might match well my penchant for periods of calm, rest, and idleness, followed by intense stretches of work.

I’ve written about the plan on a separate Substack. There, I track daily about progress, and the content is heavily focused on climbing and a related goal of eating uber-local, so if you’re interested in those subjects do check it out.

Whether I achieve it or not (so far a shoulder injury is threatening to derail the entire thing), I have fortunately earned enough self-knowledge at the ripe age of 38 to know the limits of my discipline. I know that a month-long project of intense work is appropriate for me, although it may not be appropriate for everyone.

Other models (For ex., “Write every day”)

There are some people who I admire greatly, but who are likely terrible models for me to emulate. Take the economist Tyler Cowen. I honestly can’t understand how he writes so much, so consistently, day in and day out, on his Marginal Revolution blog, weekends included, plus manages to publish so many books of material not on the blog, plus manages a full course load of teaching. Not to mention all the other non-work activities which make up a life.

Cowen has a podcast where he often asks guests about their “production function.” That is, how they get stuff done. For Cowen himself, he writes every day. Writer David Perell had Cowen on his own podcast to do an entire episode about Tyler’s production function, and I must confess I haven’t yet listened. Because I just don’t think Cowen is a good model for me.

He writes every day. I write in spurts. He gets far more writing done than me. I do other things. That’s just the way it is, and I try not to beat myself up about it.

(Incidentally, Cowen has also said he believes that he is preternaturally even-keeled. Never too excited, never too depressed, Cowen simply works through news & events which would probably throw most other people off their game).

Society is terrible at this

The thing is, society is absolutely terrible about matching people to their proper production function, much less encouraging them to find it for themselves.

Take the 9 to 5 work day, which is more or less a historical accident — the result of a compromise between management and labor over the latter’s previously bone-crushing factory hours. Working 9 to 5 doesn’t have any relevance, as far as I can tell, to getting anything done in a setting where the main work is office work.

Nor, as far as I can tell, does it have any relevance to hourly wage labor. If I were digging ditches for a living, I may just decide it made more sense for me to work 12 hours a day for 4 days a week. Or, if I didn’t need that much money, only 2 days a week. Or perhaps I would take advantage of long daylight hours in the Summer to work 7 days a week, then work not at all from November through March, when the ground here in New Hampshire is too frozen to dig anyway. If I’m getting paid by the hour, what does it matter which hours? The employer of ditch diggers could hire as many as he or she wishes, entirely on their own schedules, so long as ditches get dug.

In office settings, it’s been clear for years, decades perhaps, that most of the actual important work, or production, gets done in a small amount of time. Thus we “discover” things like the Pareto Principle, in which 80% of effects come from 20% of causes. If you want something to get done, so the office saying goes, give it to the busiest person.

Old models made new

I’ve been thinking a lot about a long piece by writer Aaron Jacob, published in July in Palladium Magazine: “How work became a job.” Jacob traces some of the history of wage labor, which is more or less a post-industrial invention (I highly recommend it as a long read on a lazy Sunday).

The gist is that prior to the industrial revolution, most workers were artisans, which is to say they made things, then sold the things for money. But the rise of big factories required a lot of workers to operate the new machinery. None of these workers owned the factory, so the owners began paying wages. You give me your time, I give you money.

As Jacob recounts:

As the late historian and social critic Christopher Lasch notes in The True and Only Heaven, opposition to wage labor was widespread in the first half of the 19th century: “the general uneasiness about the new economic order found its most striking expression in the nearly universal condemnation of wage labor.” Lasch recounts how prominent American voices explicitly linked wage labor to the institution of slavery.

Catch that? Wage labor was considered akin to slavery.

Oh, how far we’ve come. Or, maybe not so far at all.

One proposal at reform was that workers had to at some point gain ownership over the means of production. I get that this sounds Marxist with our 20/20 hindsight, but the reality is that workers who worked to produce things for other people — workers who didn’t own their own tools, their own means — was a totally alien concept. It was more appropriate to think of factory work as being like serfdom than as being an indication of a modern economy.

With this perspective, the way our modern economy functions simply feels asinine. Don’t we have anything better to offer?

The future of work

There are far better prognosticators on what the future of work might hold than me. I recommend checking out some of Paul Millerd’s writing, to start (he’s the one that led me to discover the Jacob piece).

But it does seem to me that a two things are clear:

1. Finding your own production function is about more than personal goals or achievement; it’s about recapturing a very human, indeed ancient, relationship to work.

2. Any way we can recapture personal ownership over one’s time and labor, and ideally real artisanship, wherein we make something people need and then sell it, is something I’d be interested in supporting. It’s not some nostalgic pining for the past which makes me say that, but rather a new and deeper understanding of the course of human history.

Finally: if the coronavirus pandemic and its attendant economic upheaval have any positive follow-on effects, I hope one of them is that we may begin to move toward a healthier relationship with work, labor, and the oh-so-capitalistic term, productivity.

And maybe, just maybe, we realize that the way we’ve been doing things just isn’t working any more.

I’d had a nagging feeling for a long time — for as long as I’d held my previous job — that I had not been writing honestly. Jobs can do that to you. When your income (and therefore your family’s wellbeing) becomes dependent on someone else’s good graces, you begin to make compromises. We all do.

My compromise was this: I withheld, obfuscated, and omitted. I was not writing honestly.

So what?, you might ask. That’s civilization. As soon as we are around other people we bend ourselves to be agreeable. We preserve our relationships above all else because we are social animals. If that relationship is with our boss, we bend all the more. And, perhaps, protecting relationships at the expense of full truth is good and right. What is it that we live for if not strong relationships?

But there is a perversion that goes on when money is involved, and it will always be there so long as we remain financially dependent on others. That’s what I’m concerned with here. When you become financially independent, you can, quite literally, do whatever the hell you want. Say what you want, write what you want, and be as disagreeable as you’ve always dreamed. It’s not called “fuck you” money for nothing.

How exactly I was being dishonest

The writing I did on behalf of my company and the clients I had is one thing: marketing people are used to, shall we say, writing around the ugly parts of the story. Marketers must be anchored to the truth in the content they put out, but they don’t exactly write the content with that intention. They write to support business goals.

That’s not what I’m talking about here. I’m talking about the ways in which I was distorting even my non-business writing. I would publish occasional stories on my personal blog, but I was always careful to avoid certain topics.

I didn’t, for example, write about how often I traveled. Though I worked remotely as a supposed full time employee, I often switched states, traveled on work days, even left the country a few times without telling anyone at work. My travel never impacted the quality of my work, or my output - but still, I felt that I was hiding a certain part of myself, simply by not being able to talk openly about the travel experiences which I valued so much.

I also avoided talking too deeply about healthcare — the business I was in. As a marketing person, I had to be a cheerleader for my industry. In marketing, you can be honest in your personal life, but not too honest. Everyone working in every industry maintains willful blindspots about the nature of the business they’re in. In my case, it was the business of emergency medicine. The people I worked with took care of patients when they needed taking care of the most — and that was good. But I never thought too hard or too deeply about the ugly implications of what it really means to make emergency care into a for-profit business. (I have started to do that in another healthcare-oriented newsletter.)

Mostly, though, I avoided writing about my profound discomfort with the nature of work itself. For example, many people I worked with liked to refer to us all as a family. At least, a “work family.” That phrase always offended me, but I could never say that, at least not in public. I already have a family, thank you very much. My work is my work. I do it to support my family, not because they are like a family.

“Work as family” is just one of the ways in which companies - not just the one I worked for, but many others around me - create a sort of myth to convince its employees of half-truths in order to get them to devote more of themselves than they otherwise would in service of profit. But your labor is one of the most sacred things you can give. It should not be given lightly.

I also have a profound discomfort with the nature of the U.S.’s brutalistic form of capitalist striving, and with the idea that my company should own my time. Once I was at a meeting of company leadership — about three hundred people were there — where I was asked to donate money out of my paycheck into the company’s Political Action Committee. You see, legislation was currently being debated in Congress which threatened the business, and my money was needed to make sure the company’s view of the situation prevailed.

Now that I’m out and have had a chance to dive deep on the issue in question [click this link if you are a healthcare wonk], I am glad I decided not to give.

Does it even matter to be able to speak honestly in public?

So I wasn’t writing honestly on my personal blog. So I wasn’t saying all the things I really wanted to say about the world. Did it even matter? It’s not like I was suffering under some semi-despotic regime that was monitoring my every communications, looking for apostasy.

Honestly, I could have said everything I wanted to in public, on my blog, on social media, wherever. But I did risk damaging my work security by doing so. Anyway, I could always talk with my family and my friends. My free speech was not being impinged. I didn’t live in a totalitarian regime. So who cares if I was self-censoring?

Well. I suppose I cared.

To write honestly is to strive toward truth

I care about being a writer, and writers have to be read, and if I’m going to care about that, I better damn well care about writing honestly and publicly.

It’s not clear to me that every writer feels this way. Many, including myself, write for money, and perhaps it’s better for all of our income earning potential to write dishonestly. I can think of more than a few political opinion writers who would rather be sensational than honest because it will get them more attention, and more attention will get them more advertising dollars. Give the people what they want, I suppose.

There are plenty of incentives floating around the world which would lead writers to write dishonestly. I’m just not interested in making myself beholden to them, and maybe that means my writing won’t get as much attention, and maybe that means I won’t make enough money to keep devoting all this time to it, and maybe that means there will be less honest writing out there in the world.

That would be fairly tragic. In my humble opinion.

Maybe I’m being too hard on myself. It wouldn’t be the first time, and it won’t be the last. Or, perhaps it’s time to turn to fiction. There, one can be as honest as one likes, because hey: the character said it, not me.

Yes indeed.

Like this writing? Please consider subscribing for $5/month. Yes — I am aware of how odd it is to solicit money for my writing directly after the above article. But hey: it’s a nuanced, complex world out there.

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Where the soft, pastel (only with filters) light of the sunset silhouettes my stylish linen pants (don’t own any) and casual-chic button-down (haven’t bought new clothes in a while)…

Where I record effortless (deciding what I’m going to say takes work), inspirational (picture me looking into the camera and saying, “all you have to do is believe in yourself!), and pithy (I like to write long sentences) thoughts of the day (thoughts you just had that day are probably best kept to yourself)…

You can probably see where I’m going with this.

I want no part of it.

It’s true, I could be missing out on the big bucks by choosing to largely ignore photos and video. But I have my reasons.

I don’t want to go through life thinking about which parts of it would look good on camera

For all the screeds against going through life with your smartphone in your hands, not looking at beautiful vistas with your eyes, but through your camera lens, I actually think the bigger problem with living your life on Instagram is the mental bandwidth.

Everywhere you go, every moment you live, every piece of avocado toast you order, in the back of your mind, you are thinking: Instagram? (Or, take your pick of social media broadcast platforms).

I’ve been there. For a long while I was there. I would walk through the streets of a new city, gazing up at the architecture, smelling the smells, listening to the sounds, looking at the people, but all the while in the back of my mind, even if in my subconscious, I would be thinking: is this good enough to photograph? Do I want to project this time and moment and image out to the world?

Eventually, I decided I would much rather simply leave the phone at home. Or, if I needed it for directions or to coordinate logistics, leave it in a bag somewhere. Delete the apps from your phone. Break the habit in whatever way you can.

But haven’t we always taken photos when we travel?

Yes, we have. But the Internet and social media and digital cameras have fundamentally changed that experience.

We have unlimited space to record. Once we were constrained by the amount of film we had, or by the number of those disposable travel cameras we’d buy before the trip. Now, we have unlimited storage. Even if our phones fill up, there’s the cloud. We can film all day, every day, to our heart’s content.

More impactful, are the feedback mechanisms of social media (the likes, the comments, the followers) that are designed to deliver little dopamine hits to our brain and keep us coming back.

Social media has fundamentally altered our relationship to documenting our lives. We don’t do it anymore so that we can show our friends the photo album when we get back home and develop the film. Now, we do it for the dopamine hit. That’s not healthy.

Do you want the experience, or do you want to document the experience?

And no, you can’t do both at once without compromising the experience itself.

I was in Medellín, Colombia once with a group of people, and some of us decided to take a salsa lesson. Not five minutes into the hour-long class, literally in the middle of practicing a step, one of the women in the group took out her phone and started recording the lesson. She pointed the camera at me, at the salsa instructor, and then at herself.

She never did learn how to salsa dance that day. But I’m sure her thousands of followers on Instagram appreciated that she was pretending to learn, right?

My kid’s school has a policy against parents recording school plays. And thank God, because there’s nothing worse than looking at a little one giving it their all and simultaneously trying to ignore the twenty smartphone screens on your periphery from all the parents holding them up in the air for the best shot. I’m sorry, but if grandma couldn’t make it to see the school play, then she couldn’t make it.

At the last wedding I went to, the first thing the officiant did was ask everyone to put away their phones. At least a dozen guests had seriously planned to look at the couple saying their wedding vows through screens rather than actually look at the couple saying the vows.

The tide is turning. People are realizing that it’s better to focus on the experience than on documenting the experience. Do you lose some photographic record of something when you may wish you had one? Yeah, sometimes. But your experience - and your memory of it - is all the richer for it. Your memories are always with you. The photographic record is somewhere up in the cloud.

I don’t want to produce the thing while I’m doing the thing

When I write or when I record a podcast, I’ve had time to think about my experience and to process it. Training a camera on my life is the opposite. That’s producing the content as I’m living it.

I simply don’t want to live that way. When I’m climbing, I don’t want to take a break to rig up another rope or get out my drone (drones are damn noisy to have at a cliff when belayers and climbers need to clearly communicate with each other) and start filming. When I’m kitesurfing, I don’t want to bring my camera in a water-proof bag out on the water with me and hit record. Part of the great joy of kiting is the ability to focus only on what’s in front of you: the wind, the waves, the sun. Not the GoPro in your lines pointed at your face.

In contrast, writing and podcasting are asynchronous to the experience. I can live my life and then later produce content about it. I can focus on doing the things I love and connecting with the people in front of me, without doing the work at the exact same moment.

I’m not that good a photographer, nor do I want to press others into service on my behalf

They say behind every gorgeous Instagram photo of a sexy woman on a beach are a hundred mediocre photos taken by her boyfriend or husband or girlfriend. I’ve seen these productions in action.

When I went to Mexico in April to kitesurf, my friend and I were walking down the nearly abandoned beach on the ocean side of Isla Blanca, waves crashing, beautiful white sand in either direction, palm trees, and the only other people we came across were a topless girl in the sand, kneeling in the waves, artfully throwing her hair this way and that into the wind, and two guys with smartphones trying to capture her from every angle. It was a long beach - as we approached, saw what was happening, and walked by, the photography continued the entire time, unabated.

I am not a great photographer, nor do I want to spend the time taking the photos necessary to become one, nor do I want to press friends and significant others into taking the photos necessary to make it all look good. So I’m not going to.

More importantly: I’m not going to start a newsletter that relies on content that I know I’m not committed to making the best I can. Which brings me to:

I want to be challenged in my writing

If I’m not going to be showing you a constant stream of photos of the things I did, the places I went, the people I was with, that means I’m going to have to describe it for you. And that means stretching myself with my writing.

A few weeks ago, I wrote my first Weekly Update from Cabarete in the Dominican Republic where I was kitesurfing. I had only taken one picture of the kites spread out on the beach. But I wanted to tell people what it was like to kitesurf. You can watch all the kitesurfing videos ever made and go follow some professional kiters on Instagram, but I’m not sure any of that will actually communicate what it’s like.

Here’s what I wrote:

You fly the kite, tapping deep into childhood memories of directing something high up in the air, watching it luff and dive and move to your whimsy, and then you direct it to pull you across the ocean on a wakeboard, or a surf board if it pleases you, wind blowing in your hair, the ocean under your feet, pulling in the bar for more and more speed, leaning back against the harness connecting you to the kite, and then - you bear upwind, create tension in the lines, give a yank to the bar, run the kite overhead, and then UP.

You fly.

The kite pulls you into the air, ten feet, fifteen feet, as if a benevolent hand was lifting you up by the waist, the sounds falling away, the feeling of weightlessness, and you, feathering the kite back and forth before you start to fall. And then you look down, the waves of the ocean approaching, pointing your board downwind as you pull down on the bar, powering up the kite, slowing your descent, until you glide back on to the water, dipping the kite further to pick up speed until you are again whisking over the waves with not a care in the world.

Like I said: pure joy.

That’s what kitesurfing feels like.

There’s a reason people read novels even though they don’t have any pictures in them. The words create the picture in your mind, and that picture in your mind can be far more vivid and powerful than the equivalent photo or video.

A big part of what this newsletter is about is experience. I’m finding more and more that the best way I can truthfully communicate experience is not through photos or videos, but through words.

Deciding to start a newsletter on Substack was more than a technology decision, and it was more than a business decision. It was a values decision.

In order to explain, we’ll need to do a brief survey of the different models of making money with online content. I’ll give examples of each, and point out the direct line that can be drawn from the choice of platform and its attendant business model, back to the values of the creator, and how those can often be mismatched.

If you choose to make content online (as opposed to using the internet to sell products - that’s a whole different discussion), beware of the mismatch. Online media ecosystems are plagued by model mismatch: the people who are creating content on them care about one thing - but the model forces them into caring about a different thing.

For example:

• A video creator cares about having personal connection to a highly niche audience - but YouTube rewards him or her with ad revenue based reaching as big an audience as possible.

• A writer cares about explaining complex issues of public interest in a nuanced and detailed way - but the ad model of newspapers pushes him or her toward mass market, click-bait headlines that punish nuance.

• A podcaster cares about independence, both real and perceived - but the podcast platform matches their content to advertisers on their behalf, with little regard to whether those advertiser create a real or perceived conflict of interest.

Of course, making money online isn’t only about deciding what you value and then choosing the right combination of technology and platforms to get you there. Making money online is primarily about quality: did you create something that other people want to read, watch, or listen to?

But among all the myriad online guides to monetizing content, what is consistently left out of the conversation is values. So, let’s step back for a moment and go to first principles.

Do you want to make money from your content?

For many people, this is the first decision. If you don’t need to make money or don’t care about making money, then you need not concern yourself with which platforms enable which models - or what that says about your values.

All you need to decide is whether you care more about maximum control or about being discovered and growing your audience. This has been the historical tradeoff that most online content creators have had to grapple with, and there are basically only two choices:

1. Maximum Control: get your own URL, build your own website, and use open source tools to the extent possible. Basically, use Wordpress.

2. Being Discovered: trade control by choosing a platform that aids in content discovery. E.g., YouTube for video creators, Medium for writers, etc.

Most of the content creators you’ve ever heard of picked number two and figured out how to create enough quality content and game the platform well enough to be discovered. They succeeded by the platform’s rules, although the rules often changed.

The real drawback of choosing option two from a values perspective is that these creators were pawns in an aggregation theory play by big tech companies.

A brief history of Google & Facebook dominance

Facebook and Google have roughly the same business model - and for the past half decade the two companies combined have captured the overwhelming majority of new online ad dollars spent. They did it by aggregating audience and then forcing advertisers to pay dearly to reach that audience. In both cases, the losers were content creators.

Facebook did it by getting 2.4 billion users on its platform and, because it was a social network in which users voluntarily handed over everything about their personal lives, Facebook was then able to sell that personal data to advertisers at an increasing premium.

Google did it by building the best search engine the world, so that in 2018, 90 percent of all searches online went to Google. Since searches were often markers of intent to buy (i.e., “best vacuum cleaner”), advertisers eventually needed Google if they wanted any kind of discoverability for their products.

In both cases, it was content creators left in the dust - the fruit of their creation depended on either Google or Facebook for discovery. For the past five years, headlines like this one have been the norm: Digital Ad Market Soars To $88 Billion, Facebook And Google Contribute 90% Of Growth.

Online ad revenue has grown steadily. In fact, 2019 will be the year that spending on digital advertising finally outpaces print and television. The only problem is that nearly all that growth online - we’re talking 80-90% of it - has gone to two companies alone: Facebook and Google.

The models of making money from online content

The clear losers in all this, again, were content creators. Specifically, newspapers. But we’ll get to that.

As it became more and more clear that Facebook and Google were making most of the money that there was to be made from online content, the Internet began casting about for alternative models of making money online.

So far, those models can be boiled down into five buckets:

1. Advertising (Google & Facebook): depends on scale and audience size.

2. Subscriptions: depends on earning loyal, niche audiences.

3. Donations: depends on audience size, loyalty, and goodwill.

4. Affiliate marketing: depends on credibility, trust, & quality content.

5. Cross-promotion: similar to affiliate marketing, but rather than using credibility to sell other people’s products, use credibility to sell your own products.

In the next section, I will go through all of these, give examples of thriving businesses using each one, and connect the models to the values of the people in charge of creating content for each.

1. Advertising

Google, Facebook, & newspapers

I won’t dwell on advertising too much because I’ve already described how it works above, and pointed out that Facebook and Google own the space. But I will say a little something about newspapers, because I used to work for one. In fact, I covered politics for The Albuquerque Journal from 2004 - 2006 just as the biggest revenue-destroying changes were beginning to hollow out the industry.

In the old days, newspapers derived most of their revenue from advertising, and supplemented that with subscriptions and classifieds. The Internet, then, destroyed newspaper revenue in three steps.

First, Craigslist all but destroyed the approximately 10 percent of newspaper revenue that came from classifieds, and it did it in approximately seven years, from 2000 to 2007. Second, during those same years, Facebook and Google began to siphon advertising revenue because newspapers no longer had a monopoly on reaching readers within their particular geographic area. Third, because readers no longer needed a newspaper to get their news (now they had the whole Internet), subscriptions also declined.

Today, the only newspapers really thriving are the very large ones with very strong brands. The New York Times and the Wall Street Journal, both of which are more than a hundred years old, are the poster children for successful newspapering in the age of the Internet.

Advertising-based television

There is one other example of successful advertising-based online content: television.

It’s easy to draw a line in the TV and film industry between traditional and online, broadcast and streaming, but I prefer a different distinction: advertising vs. subscription.

So: traditional broadcast television for years operated on a pure advertising model. The idea, just like Google and Facebook, was to get as many viewers as possible in order to charge the highest possible fees to advertisers. This model is still alive and kicking: major sports events, big reality television shows, and the CSI franchise all fall into this model.

In contrast, you have cable television and streaming - both of which are subscription models (and thus covered below).

The values associated with an advertising model

By now it should be crystal clear that if you go with an advertising-based model, you care about audience size. You want to reach the largest number of people possible.

In my humble opinion, making especially unique or transformative content is extremely difficult in this model. Disney its epitome: all their movies adhere to a formula, and all their brands are proven to have mass-audience appeal. Disney is a juggernaut. They own Star Wars, Marvel, and Pixar, besides having their own extremely large catalogue of home-grown formulaic fairytales.

With Disney +, the company is finally jumping in to a new, subscription-based model, in order to compete with Netflix, HBO, and the like. But they are doing so having built an empire on mass market appeal and the advertising dollars that come with that.

Since ad-based models depend on audience size, they also, by extension, depend on number of views and time spent on platform. Those two types of engagement metrics are what drive YouTube and Facebook. They are, arguably, bad for your health and bad for society at large.

The longer you watch, the more you watch, or the longer you scroll, the more minutes of advertising content they can sell. The business models of broadcast television, Facebook, and Google, all depend on your eyes being glued to their platform for as long as possible, as often as possible.

What does that mean for content creators? It means that if this is your model - if you are a YouTuber who is dependent on the meager revenue splits that Google deems you worthy of receiving, at its complete discretion and subject to change at its whim and without notice - than you are signing up to produce content designed to get users/watchers/readers glued to your content as often as possible for as long as possible.

It’s not a good way to go for society as a whole, and rarely for you as an individual.

2. Subscriptions

Cable & Streaming

Cable TV is a subscription model: one flat monthly fee gets you the premium channels. But cable companies were developed pre-Internet, so they flexed their market power in the same way that newspapers did - by aggregating users in a particular geographic area. In order for a content creator, for example AMC, to reach the cable company’s customers, it had to accept the conditions of the cable company as far as revenue split.

Eventually, channels like AMC learned they could extract higher revenue splits from cable companies if they could demonstrate an incredibly loyal audience. That’s why shows like Breaking Bad, The Walking Dead, and Mad Men made AMC so much money, and why shows like The Sopranos made HBO so much money. Audiences loved the shows so much that they would subscribe to an entire cable bundle just to get those shows. Thus, AMC or HBO could extract higher prices from cable companies for being included in the bundle.

Netflix, Hulu, HBO Now (and recently Disney+) all have the same essential model as AMC does: build loyal audiences willing to pay the monthly subscription fees just for their content. The only difference is that the streaming networks use the Internet to stand alone from cable bundling, instead building a direct relationship with their respective audiences.

Patreon & Substack

Patreon and Substack (which powers this newsletter) are two newer examples of the subscription model applied to individuals who create content online. Creators on Patreon charge a fee per thing created, whether it’s a video, a podcast, or an article. Substack - and a host of other relatively new entrants - allows its users to charge monthly subscriptions.

Some individual content creators are using the subscription model independently of particular platforms. The epitome of this is Ben Thompson’s Stratechery, which releases free, weekly long-form analysis of the technology industry, but charges a monthly subscription for additional daily posts.

As Thompson has repeatedly said: the model scales very well. In the beginning, he worked a lot and only had a handful subscribers. Now, he works the same amount, still hard, but he has thousands of subscribers.

The values associated with a subscription model

Like the creators of Breaking Bad, who earned money from the intense loyalty of fans who subscribed to cable just so they could get the next episode of Walter White building his meth empire, content creators who rely on a subscription model are aiming to build a loyal audience in a particular niche.

Even at the height of its popularity, Breaking Bad viewership was dwarfed by the latest bland iteration of CSI. Ben Thompson and Stratechery will likely never earn a paid subscriber base as high as the readership of a free, ad-based tech website. But then, maximizing eyeballs is not the point. Promoting a unique, individual voice is.

If you pay for something, you value it. If you get something free, you inherently devalue it. This is why so many people have argued that the early decision of newspapers to put their content online for free was a tragic strategic error, because it conditioned readers to expect that they should get the news for free. In fact, many an argument was had in the newsroom of The Albuquerque Journal circa 2006 about whether the newspaper’s website should be totally free or have a paywall (the paper’s farsighted publishers, to their credit, always maintained a paywall).

Thus, making money from content online via a subscription model continually forces the content creator to think: how do I deliver real value to the subscribers? Not how do I get as many people glued to this as possible, but how do I get the people who value this to continue valuing it.

The subscription model drives content creators toward niche, and away from mass market. This is why most of the “brave,” or subversive, or risky shows are on a handful of channels: HBO, Netflix, etc. It’s because those channels thrive on loyal niche audiences who pay, not casual viewers to tune in in order to tune out.

As you may have noticed, I like this model. It’s the one I have chosen for myself, not just with this publication, but with Healthpolity, in which I cover healthcare & policy. That said, there are still a few other models to cover, each of which is interesting in its own right.

3. Donations

Maria Popova’s Brian Pickings & Sam Harris’ Making Sense

Maria Popova and Sam Harris (I wonder if those two have ever been mentioned in one sentence together?) both produce content that is free for all. All of it. They make money by asking people to donate.

Popova has a weekly newsletter called Brain Pickings. Her website has a prominent sidebar that says “donating = loving,” and allows readers to donate on a monthly or one-time basis. Harris, meanwhile hosts a podcast called Making Sense (formerly called Waking Up).

The values associated with a donation model

Harris has expounded at length about he chose the donation model. For him it all comes down to two things: independence and reaching as wide an audience as possible.

Harris is out to change culture. That’s his goal, his mission, and the reason he picked the particular medium and model that he did. That’s why he redirected his primary effort from writing books to hosting a podcast. Because a new book, even a bestselling one, is likely to only reach tens of thousands of people or for the really successful ones hundreds of thousands, over a few months. Meanwhile, last year Harris noted that each one of his podcasts is downloaded by more than two million people.

In terms of reach and influence, it’s not even a close competition.

Secondly, Harris values being independent. He routinely delves into topics that are highly politically charged, and Harris speaks often about his unwillingness to be beholden to advertisers - any advertisers.

On the other hand, Harris does welcome donations from his listeners. For a time, Harris used Patreon to solicit donations, but even being associated with Patreon’s content policies eventually led Harris to quit the platform and develop his own system to accept payments.

Content creators who follow the example of Popova and Harris value reaching as many people as possible, but not in order to sell them ads. They value this because they value influence as an end in itself.

This kind of scale is necessary to make the donation model work - Harris says only about 1 percent of listeners ever donate. So unless you’re among the very few who can reach that scale, a donation model is unlikely to pay the bills. On top of that, you have the problem mentioned above that when content is free, users inherently devalue it. Popova’s supposition that “donating = loving” is a tenuous assertion on which to base your business.

4. Affiliate Marketing

Personal Blogs, Amazon, & The Wirecutter

Many personal bloggers have taken to using a “Recommendations” page in order to monetize their content. My favorite personal finance blogger, Mr. Money Mustache, does this with a Mr. Money Mustache Recommends page. The idea is to use your website to link to other products with a special kind of affiliate link that tracks whether the reader buys or not. Then a percentage of that sale goes back to you the original referrer.

Amazon likely has the largest affiliate marketing program in the world, so that if you have a large enough audience and you want to start recommending products to them, Amazon will pay you for confirmed purchases. My favorite website that does this is The Wirecutter, which was acquired in 2016 by The New York Times.

The values associated with an affiliate marketing model

Because The Wirecutter’s entire business model is recommendations of products, their most valuable asset is authority. That’s why each product recommendation they have begins with a long section on why the reader should trust the recommendation, and from whence their authority on that particular product derives.

Mr. Money Mustache’s authority to recommend financial products such as credit cards and books on personal finance derives from the articles he wrote over years that birthed the FIRE (Financial Independence, Retire Early) movement. His readers trusted his authority and opinion of the products, so affiliate marketing was a natural fit.

Content creators who choose this model value their independence - but affiliate marketing is still a tricky balance. Content creators make money from their recommendations, but readers must still trust that those recommendations are not financially motivated. That takes a size-able store of accumulated expertise and goodwill to pull off.

Examine.com, for example, has made a business off providing objective, science-based reviews of nutritional supplements. But unlike Mr. Money and The Wirecutter, they take pains to disconnect their financial incentive from the recommendations itself. Instead, Examine.com makes money by selling additional in-depth products of research. Which brings us to the final, last way to make money from content online.

5. Cross-promotion

Examine.com, Scriptnotes & David Perell

The final way to make money online is to use the content to sell something else. This is a classic “top of the funnel” marketing technique: your content draws people in, builds a relationship and builds trust, so that when you have something to sell you now have a captive audience of potential buyers.

This method is championed by David Perell, whose writing I really admire. I’ve mentioned his “Ultimate Guide to Writing Online” in the past. In it, Perell writes:

Each article is a sales pitch for your knowledge on that topic. It’s an always-on broadcast of who you are, and an open invitation for other people to create personal and career opportunities for you.

Accordingly, Perell has been selling an online course called Write of Passage on how to get started writing online.

As already mentioned, Examine.com uses this model to sell additional research. Another personal shoutout should go to the Scriptnotes podcast, which is hosted by screenwriters John August and Craig Mazin. August and Mazin like to joke that their podcast doesn’t make money and never has - still, they make some money. Enough to pay their costs as well as a producer. They do this in two ways: selling scriptnotes t-shirts (I have one), and selling USB sticks with the entire back catalogue of podcasts.

The values associated with the cross-selling model

This final category is tricky because while cross-selling is one way to make money using online content, it can just as well be described as a marketing strategy for selling anything. In other words: Content Marketing.

The most visible proponent of this strategy is probably Gary Vaynerchuk. He is, quite simply, a content machine. He does long Instagram posts, Tweets relentlessly, distributes a prolific Podcast (The GaryVee Audio Experience), records every talk he’s ever given for YouTube, and has a team of content creators following him around seemingly 24/7 to transform what he says and does into audio, video, and written content. All this on top of actually running a creative marketing agency.

Every piece of business advice I’ve ever heard Vaynerchuk give boils down to the following: create great content about the thing you’re selling.

Gary’s values are hustle, hard work, passion. He has a particular gift for merging concise, insightful straight-talk about business goals with aspirational, made-for-social-media soundbites about how to capture your passion, stay motivated, and succeed in life (I had my fill after the first ten hours or so of listening).

Still, if you plan to use online content to cross-sell, go listen to Vaynerchuk for a while. The values you embrace will be as diverse as the products or services that content marketers are selling. In fact - it’s most likely that the product or service came first, and the content to help sell it second.

Choosing your model is about choosing your values

All these examples and all of this background is ultimately to make a simple point: deciding where to host your blog or your podcast or your videos isn’t just a technology decision: it’s a values decision.

When I moved my personal blog to Substack, I first had to do some pretty serious thinking about the purpose of writing in my life. Was I writing just for my personal edification, or did I want to do it professionally? Was I seeking to influence people, or did I want to prioritize making a living?

But the questions apply to anyone making anything online. I’ve seen too many people look at the models out there and begin creating content to fit the model. I say, rather than conforming your content to the values of platforms already in existence, decide what you value first, and then find the platform and the financial model that matches those values.

Wait. Let me explain.

A few days ago, Bluehost kindly informed me that renewing my hosting account for the next three years would cost $395. If I wanted to keep Wordpress, I needed to keep Bluehost. If you work that out, it means hosting my personal blog at russellmaxsimon.com was costing me around $11/month. Not too bad at all.

But it did raise the question: what exactly was I doing on that site? I hadn’t published anything since my alarmist, cautionary climate announcement back in January. (For the record, I am still alarmed, and everyone should still take caution. It’s only getting worse.)

But readers have not exactly been knocking down my door. Google analytics tells me so. Now, that may have something to do with my complete lack of self-promotion, exemplified by my decision to digital detox and stop telling everyone online what I’m doing and writing all the time.

It may also have to do with my lack of output. For months, I have been reassessing why I write, what I want to write about, and what measures of success in writing matter to me, if any. No matter how I pose this question to myself, it’s always a tough one to think through.

“I just write for myself”

If you are the kind of person who goes around telling people, “Oh, I just write for myself,” I can only assume that means that you write a diary. Offline. Where no one can read it.

Good on ya.

I am not that kind of person. I started as a journalist. But even before that, as long as I can remember, I have written to be read. If no one reads it, what’s the point? If a tree falls in the woods… a poet should be there to paint the picture for the rest of us.

But what kind of readership was I looking for? Did I just want my grandmother (hi Lynne!) and my family and friends to read me? In that case, perhaps I should keep doing what I was doing and pay the $395.

Or, did I want to try to make some kind of income off my personal writing? Or - and this was the real choice - did I want to simply reach as wide a readership as possible, money be damned? Was I looking for fame and influence, or to make a living?

David Perell, whose work I’ve been following for a while, has grappled with this question too.

What About Medium?

Basically, I was trying to decide whether I should move my writing to Medium. On Medium, after all, they give you readers. They put your stuff in front of other people. If it’s good, it gets in front of more people.

Here’s what Perell had to say about that in a great post called The Ultimate Guide to Writing Online:

But David, what about Medium?

Don’t write on Medium.

Look, I get it. Writing on Medium is an easy way to pick up readers and increases your chances of going viral. But the costs exceed the benefits. Medium is terrible for SEO. You don’t own your content and the platform makes it difficult to turn one-time readers into loyal ones.

The more you can use platforms you own, the better. Rather than writing on Medium, do the work to build a personal blog. That way, you can have a central place to point people to.

So I took part of his advice and disregarded the other part. I decided not to post on Medium. Medium is where you go to get readers to the exclusion of all other goals. That’s why politicians post their big ideas there. They want the most possible number of people to read it.

But I was also sick of building a personal blog. Not much building was going on in any case, and now I had a $395 bill coming up for my trouble.

The model that appealed to me most was a combination of what Ben Thompson does at Stratechery and what Azeem Azhar does with his Exponential View newsletter. And, for that matter, what David Perell does with his his newsletter, called Monday Musings. The model is some free content plus paid subscriptions for readers who want more, focusing on email for distribution.

Substack

I wondered what technology Azhar and Perell were using for their newsletters, and before long I found the answer: Substack. I started researching their shtick, and here’s the passage the won me over, from one of Substack’s recent blog posts:

We started Substack because we wanted to build a better future for readers and writers. Today’s media environment is built on warped incentives, with writers and publishers forced to compete for people’s attention. Many who succeed under the current model are the ones willing to hunt for clicks by fomenting outrage or catering to the lowest common denominator. Many writers and outlets have become convinced that the only path to success is through reaching an audience of millions. It can be hard to see a way out. 

I do not want to foment outrage, nor do I want to cater to the lowest common denominator. That way lies the hallowing out of your soul, not to mention our democracy and our world order.

Substack is keeping it simple, and aligning its business model with the interests of its writers. Rather than my paying $395 and then making a go of it for the next three years, I could pay nothing, and then Substack makes money if and when I make money. I like that kind of alignment.

The only question I had left to answer was: did I believe in myself?

Do you believe in yourself?

Haha, jk lol.

People who know me know that I think everything about that question and that advice is bullshit. Americans seem to be particularly inured to the idea that if you only believe in yourself, you will gain all your wildest dreams. Maybe it’s something about our capacity for optimism or magical thinking, or just our capacity for refusing to accept our own shortcomings, or maybe it’s our capacity for sticking our head in the sand, or maybe it’s our naive belief in our own exceptionalism or maybe it’s…. I could go on.

But in all seriousness, I needed to ask myself a pretty serious question about my writing: did I want to professionalize it, or just keep it casual and low-stakes? And if I wanted to professionalize it, what was I willing to do to make that work, and what was my metric for success?

I had to answer those questions before I could decided what to do about that $395. They are big questions. Are you just writing for yourself? Then go buy a Moleskin and grab a pen.

For me, once I decided what my purpose and goals were, the choice of technology became clear. I was going to shut down the Wordpress blog. I was not going to Medium. I was going to write more regularly, and use Substack to set up a subscription service, a la Perell and Azhar.

And I was going to write about the thing I always think about anyway: what really matters. What really matters in life, in work, in politics, in everything. I had my purpose. I had my goals. And so I had my technology platform.