I've agonized for years about "What I'm doing with my writing" — and now I have an answer

Also, it's 2021: Expect a lot more from me on topics you're not used to

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 for 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.