I’m a writer—what are you?

September 8, 2023

Midjourney/prompt: "man looking out over a giant chasm that needs to be crossed, vertigo, watercolor"

Ignoring what is obvious incurs a huge cost.

It requires you to go about your day numbing yourself to the reality of who you are and what you want—which is a waste of time for you and everyone around you.

By contrast, admitting what is obvious is freeing and motivating. But it’s terrifying to do it. Sometimes the most obvious truths about ourselves are hard to see because the consequences of those truths seem so dire.

This happened to me recently. I admitted a truth that was probably obvious to everyone around me, but not to myself: I’m a writer. This sounds so obvious that it feels like it is a joke. I write a weekly column at a newsletter that I started—of course I’m a writer

But this is one of those truths for me. And I’m glad I can admit it.

If there are obvious truths like this for you, you should find them, and admit them, too.

Why you can’t admit the obvious

The poet Robert Bly wrote that we all lug an invisible bag around with us everywhere we go. We’ve been filling it since childhood with the parts of ourselves that are true to us—to how we feel and what we want—but that aren’t acceptable to the people around us.

It starts with our parents: “don’t make noise during dinner,” or “in this family, we play baseball.” It continues with our teachers: “you’d be good at math if you only applied yourself.” Finally, it starts to come from peers in high school: “that’s nerdy,” or “you’ll never have a career doing that.

Each of these interactions causes us to put parts of ourselves in the bag. And the things we put in the bag are the obvious truths that we can’t admit, and that we try to ignore.

Being a writer is one of the things I tried to put in my invisible bag. For a long time, admitting that I am a writer and that I want to be a writer felt like it would force me to shed my identity as a founder, eliminate the possibility of building a consequential company, and seriously cap my potential career earnings.

So, I pretended to be a founder who also liked to write.

The first clue that I wanted to be a writer was that, after I sold my last business—a B2B software business—instead of going back into software, I started Every.

Every is a startup, so it lets me call myself founder. But on the inside, it also secretly lets me do the thing that I really wanted to do but couldn’t admit to myself or anyone else: be a writer.

While I deeply enjoy almost every part of running a startup—coding, sales, marketing, managing, fundraising, etc.—writing is the thing that I’ve always loved the most.

I knew this back in third grade when I wrote a 100-page novel in longhand on loose-leaf sheets of paper. But after writing that novel, I decided I needed more life experience to be a real writer, so I “retired.”

In fifth grade I read a biography of Bill Gates and became enamored with entrepreneurship, so I decided to start a Microsoft competitor. I called it Megasoft. I learned to code so I could build an operating system to compete with Bill—and even though the operating system never saw the light of day, it set me off on a path building software businesses.

Both of these parts of myself have always been intertwined in a braid. But now, I’ve decided to shift the emphasis. I’m not a founder who also likes to write. I’m a writer who also likes to build businesses.

Living in this truth—the truth of what is obvious—is freeing. It will make me the best writer I can be. And, I think—paradoxically—it will help me build better businesses.

When you admit what is obvious, you start to improve

Billions of dollars in value are wasted every year by people doing the high-status thing they wish they felt compelled to do instead of the weird, low-status thing they actually want to do. Why is this value wasted?

You’re never going to be great at something you want to want. It’s always going to be a half-in, half-out kind of thing—instead of the all-in endeavor that greatness requires. Doing what you want to do, by contrast, lets you go all in.

As soon as I admitted to myself that I am a writer, it was easy for me to throw myself into it with wild abandon. Suddenly, I was sucking down great writing and furiously scribbling in my notebook. I made a list of skills I wanted to build and topics I wanted to cover. I realized how important it is for me to go deep on the future of AI and scientific discovery, AI’s power as a tool for creative expression, and its importance as a method for understanding ourselves. I recommitted to publishing this column every week. It felt like I didn’t have enough time in five lifetimes to do everything I wanted to do—and I feel like my writing is significantly better than it has ever been.

Who’s going to win in that scenario? Will it be me, or someone who wants to write but can’t seem to bring themselves to sit down at the keyboard?

Of course, doing this required me to grapple with a problem: how to square wanting to be a writer with wanting to build businesses. It was scary to want to be a writer because it meant giving up on being a founder. But as soon as I admitted the obvious, something else happened:

I started to find heroes who had done exactly that.

When you admit what is obvious, you can find examples to look up to

Once I admitted what was obvious, I realized there are a lot of people who have done something like what I want to do.

Bill Simmons is one such example. He built The Ringer, a sports and pop culture website and podcast network, which he sold to Spotify for $250 million. Simmons was both the CEO of The Ringer and one of its main stars—The Bill Simmons Show was the marquee podcast on the network.

How’d he manage to square the circle between creative output and running the business? As far as I can tell, he stuck to what he’s good at: creating content, and spotting and developing talent. Then he recruited and maintained a core group of trusted operators around him who handled the rest of the business. He sets the vision, and they execute.

Once I found Bill Simmons I saw this dynamic at play in a thousand other places. Neuroscientist and philosopher Sam Harris mostly spends his time writing and recording podcasts, but he also founded Waking Up, a meditation app that helps his audience apply and practice the mindfulness skills he writes about. Sam doesn’t run the business day-to-day, though—he has a trusted general manager to handle that, so he can focus on thinking and creating. Other examples abound: Nate Silver, who started data journalism site FiveThirtyEight and is one of its main voices; Shane Parrish, who founded the popular blog Farnam Street; and Hank and John Green, the brothers, writers, and YouTubers who started both VidCon and creator merchandise company DFTBA; Gwyneth Paltrow who founded Goop.

I had previously been blind to this way of operating because it’s so anathema to the usual tech ethos, which is to hire other people to do the creative work, rather than continue to do it yourself.

But it makes a lot of sense for a creator-run business to be structured in this way. The best thing a founder of any business can do is focus on what they are uniquely suited for—and hire people better than them to do the rest. In a creator-run business, the founder should focus on making the product.

Once I found this way of operating, I started to bend my world that way. I made a few key hires (to be announced soon!) and began to hand off some of my day-to-day operational responsibilities. I’m still intimately involved in every aspect of the business, but my day is significantly more focused around doing the best creative work I can for Every—and I expect that to pay significant dividends for the business over time.

It’s truly the most satisfied, excited, and aligned I’ve ever felt running Every. Which brings me to my last point:

How could I have done this sooner?

How to admit what is obvious

Admitting the obvious is to take a scary leap. It is to make decisions that bring your life into alignment with what you truly want—rather than what you think you should want or what others want from you. It is to risk taking the low-status meandering path, instead of the high-status linear one.

It can be easy, in retrospect, for me to wish I had done this earlier. To think that it might be possible to white-knuckle my way through future admissions of this kind, to give up all of my internalized shoulds, and any temptation to be affected by the desires and pressures of the people around me. To want to leap that gap in a single bound, and to believe that I could if I tried hard enough.

But I’m not sure that’s possible. Sometimes the obvious truth is hidden from you for a reason, and it takes great care and lots of time to see it.

Spiders weave webs across gaps that cannot be crossed by crawling or jumping. Instead, when a tiny spider wants to weave a web across a large distance, it produces a fine adhesive thread that it allows to catch and drift along the wind. It can feel by the sensitive vibrations passed along the thread when it catches and adheres on the other side of the gap. Then, it carefully walks across that first strand like a tightrope walker, laying another thread down as it goes.

It weaves back and forth like this—carefully, one step at a time—until a web is formed out of thin air.

I think this is the way to admit the obvious. Loose a single thread in the direction of what you want. When it catches—follow it, and strengthen it. Eventually, you’ll be ready to cross the gap with confidence and spin a web of your own.