The first time someone asked me to name a company, my instructions were to take a pen and a notepad and spend the afternoon brainstorming in solitude.

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:

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:

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

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?
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?
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

Post-Nomad

How to name your Substack