Transitions

To be responsible is to take your life in your hands and own your own power and purpose. It is to say “yes” to what you truly are, even though you do not yet know who you are. This is why it is a gamble that many avoid, preferring to instead live the safety of what is known and defined. To live oneself is always to step into the unknown: this is the adventure and the challenge. In the words of the Sufi master Abû Sa’îd: “What you have in your mind, forget it. What you have in your hand, give it. And that which is to be your fate, face it.” —Llewellyn Vaughan-Lee, The Signs of God

I’ve received many requests for time lately, a call for office hours of sorts, primarily revolving around the same question: How did I transition from a full-time job to working for myself? What’s my best advice for those who want to do something else? Particularly when the “something else” is in a creative field like writing.

I was speaking to a friend-of-a-friend recently about this very concept, and I realized my advice is pretty simple: You just have to do it. Small, iterative steps toward what you hope to achieve. Small, iterative steps down as many paths as possible. In my experience, there are no shortcuts. Or, if there are, I can’t offer much advice because I apparently missed them!

So first, those small steps: You have to do the thing—writing, podcasting, making content for social—even when very few people will see it, read it, or listen to it. You have to start where you are. Email lists are built one subscriber at a time. There’s no known way to market podcasts outside of guesting on other shows and hoping you can generate some word-of-mouth virality. I started Pulling the Thread at close to zero and have slowly grown from there. Instagram is less transparent to me, but I can tell you that I had a few thousand followers in 2019, to the point where I was told I didn’t look like a real person with a real job. I rarely-to-never posted. I didn’t get fully organized on Instagram until this year. Honestly, I enjoy making Instagram videos now, but it took me a long time to face my ambivalence (I wrote about “influencers,” “followers,” et al in this post).

Having worked in media for a long, long time, I promise there are no audience development hacks (again, if there are, I don’t know them). The only way to build something meaningfully big is to build something meaningful—and then put in the time. I wish I had better news! I can say the intimacy of connection is powerful regardless of the size of your audience: To be read or listened to by anyone is an honor. I believe we’ve all been deluded by scale plays that more is better, that what you’re doing doesn’t have value if it doesn’t reach millions: But chasing audience is a race to the bottom. One look at our pockmarked media landscape, entirely predicated on getting as many eyeballs as possible, is a testament to that: Make things that matter, otherwise there’s no point. And worse: there’s the potential to cause harm.

This is where it gets tricky, because when it comes to making money, audience and its size does matter. Particularly if you want to monetize directly: When it comes to something like writing, you can charge for subscriptions (Substack, Patreon), there are brand partnerships (selling ad integrations on your mailing list, or Instagram), you can sell courses and workshops, or you can sell the thing directly (book deals, either via publishers or publishing yourself, writing for magazines and sites that still pay, etc.). You can also write for trade (copywriting).

I make money through writing books—my own, as well as for other people. I've been ghostwriting and co-writing since I was 25. It has been essential extra income throughout my career. But even now, 12 books later, it is not enough. I supplement through consulting and board work as well. Some writers can wing it on writing alone, but it’s a hard craft—doing it well is one thing, but then getting people to pay you for it (both in advance and for the actual, finished book) is another thing entirely. And don’t forget that advances from publishers are amortized over years—typically you get ¼ on signing, ¼ on manuscript acceptance (which can take years), ¼ on publication of hardcover, ¼ on publication of paperback. Ghost-writing is a slightly different pay-out, but you have even less control over delivery. If you earn out your advance, you can make money on the back end, though this is hard to do, and even harder to plan. So my best advice for anyone who wants to make it as a writer or other creative is to walk many paths at once: It’s not romantic, but it is a way to quell anxiety if you need to make a living. It’s too much pressure (in my humble opinion) to rely on a single stream of potentially inconsistent income.

This is not to say that you shouldn’t do it: I heartily recommend following your heart, particularly if you’ve built a career helping other people follow theirs. I also believe that you can only know what you want to do with your life through a process of elimination—most of us didn’t pick exactly right out of school. And even if we landed in the relative ballpark—I started as a magazine editor and have not deviated far—chances are that we’ve iterated our way to some new version. Recently I was with some college students who reminded me that the jobs they’ll have when they’re 25 or 30 might not yet even exist. So that’s my other best advice: Assume you won’t be doing what you’re doing now in 7 years. Stay nimble, stay open. Inch your way toward something that might feel better bit by bit—make it a tangential move rather than a complete reinvention. (Or do that, too, I’m just not that brave—my best friend bailed on a career as a bankruptcy lawyer to start a makeup line called Reina Rebelde, so ask her for advice on complete career turnarounds!)

Most people ask me for advice about writing and podcasting, though, so I can also offer this: The barrier to entry on both of these is very, very low. (Unlike, say, starting a makeup line.) Anyone can launch a podcast and achieve reasonable sound quality. Anyone can buy a domain and throw up a website with a blog, or kick-off a Substack email. If that appeals to your heart, you have no excuse not to try. Do what you can to take the pressure off, and give yourself time to figure out what you’re all about. Don’t try to monetize out of the gate. Don’t assume you’ll have a massive audience in months, and then judge yourself when it doesn’t emerge. To quote my friend Jen: Start small—and then smaller still. And to go to Llewellyn Vaughan-Lee’s words at the top of this email, “To live oneself is always to step into the unknown: this is the adventure and the challenge.” Go for it. One step at a time.