I used to hate that I wasn’t a “real” writer. The definition of a “real” writer, of course, was a deeply elusive one, a goalpost that I constantly moved for myself depending on how insecure I wanted to feel on any given day. And it was all ridiculous—by the most crudely tangible definition, I was certainly a “real” writer. From the age of about 23, I was employed as a full-time writer, writing articles for a variety of outlets in addition to my main staff writer gig, publishing a book that appeared in real bookstores (and real Urban Outfitters, which perhaps contributed to the overall sense of literary inadequacy — “Urban Outfitters Book” is something of a slur among those who care about this sort of thing).
There could have been no stronger indications that my work was “real,” at least insofar as the market dictated. But as anyone who has ever felt a sense of creative or professional inadequacy knows, the details of your CV have almost no bearing on how you feel about yourself. If you want to feel like a loser and an impostor, your brain will find a way to make it happen. And for me, the idea of what a “real” writer looked like was incredibly well-defined. The best shorthand I can find, both in terms of her overall aesthetic and untouchable career chops, would be Zadie Smith, but it didn’t have to be her. It just had to be a dewy, understated woman who stayed off the internet (the prestigeless swamp in which most of my writing lived, and continues to live), put out a few Serious Books or Well-Chosen Essays per year, and generally lived a life of measure and thoughtfulness.
The kind of writing I did — lists, lowbrow personal essays, the occasional thinkpiece — felt like a direct insult to this kind of writing, offensive to be included in the same sentence. Combined with my lack of a college degree and generally shallow cultural tastes, I was never at a loss for ways to feel inadequate as a writer (and, subsequently, as a person).
Several years later, as the CEO of a profitable niche media company whose day-to-day work life contains relatively little writing (though we are releasing a book in January, which I shamelessly encourage you to order), I can sincerely say that it’s been longer than I can remember since I’ve felt that same flush of professional inadequacy. I write much less, I write about a topic that is about as unliterary as they come (personal finance), and my future looks more and more full of that nebulous business-adjacent work of “creative direction,” rather than any Real Writing. And while at first this transition bothered me — I will never forget a particularly condescending exchange with a Real Writer Friend who smugly asked me if I’m “not really a writer anymore” — I now feel deeply comfortable in who I am and the work I do. And it’s not just because the lane I have carved for myself is wildly underpopulated (not that many people are doing narrative work about money these days), but because I’ve become ruthless about deciding what work is and isn’t worth it to me.
You see, for the longest time, my metrics of an hour or a year well spent professionally were entirely external. I hoarded “prestige” bylines like a doomsday prepper. I relished the occasional crumb of approval from the people I considered to be “important.” I considered myself only as successful as my most recent accolade. But in starting a business, with its constant flux of tasks and schedules and roles you are forced to play, I quickly gave up on waiting for the same kind of approval. Most of the work in business-building goes inherently unseen—work put in on the backend, and administrative tasks and projects you cannot discuss until six months into working on them. It’s a humbling experience, one that forces you to immediately confront what you do and do not value in your limited available time.
My partners and I have had deep, sometimes-tearful conversations about what we are truly good at and where we feel like we are frankly wasting the company’s time. We’ve had to move people off projects, accept that we may not be the right lead for things, and give up parts of our professional identities to make room for what works.
My partner Lauren, for example, who is a career designer, has grown to understand that she is better off focusing entirely on design work and largely moving away from business. There is just such a high demand for visual work across our brand, and she is the only one who can do it competently, so stepping away from things like sales calls or ideating on RFPs was a natural transition.
But for me, as a career writer, I quickly learned that sales was simply easier for me, and having worked in creative direction before starting our company, I largely embraced working with our third partner, who is more exclusively focused on business.
In both cases, there are insecurities attached: I’m doing less of the purely creative work that used to define me, and Lauren is not always as in the loop on our development of big business projects. But this is the way we work best, the way we have grown astronomically in a year, the way we get the most value from our days.
And ultimately I’ve learned that the most important work is the work that makes the best use of you and forces you to confront what it is you do well. On the level of the work, I will never be the kind of writer I used to desperately envy, and the skills I possess in business are only hurting me if I put them on the back burner because they are not “prestigious enough.” My desire to self-identify as a Real Writer put me at a huge disadvantage, using only a small percent of what I’m really good at. At the end of the day, I am most fulfilled when I have done good work, and I am less fundamentally concerned with what that work must look like. My partner happens to be a creative who is more classically skilled at what she does and whose true value lies in creating and expanding a visual identity for what we do. But my writing is simply not as essential — between our team and our hundreds of freelancers and contributors, there are many writers who can do it just as well, if not better.
I am not creatively envious of Lauren because she is more of a Real Designer, because I have accepted that I do not need such a title to define my work. Ultimately, as long as your locus of validation is external, you are never going to be satisfied. You are always going to be measuring yourself against a person who has more financial means, more access, more connections, more privilege in choosing the work we do. (Because we have to remember, particularly in creative work, getting to be selective about the work we do or only doing a certain “level” of work is, above all, a question of having the financial freedom to do so.)
I have largely ditched my desire to be a certain kind of writer, because it’s simply not an option for me, and I have leaned into the creative direction (even though that basically means—gasp!—advertising) that creates the most value. My less-glamorous work funds not just the work we do as a media company, but also my ability to live a balanced life when I shut my computer at the end of the day.
Because chasing after a perpetually moving North Star of professional validation guarantees only one thing: You are always going to be obsessed with work, and therefore always forgetting to just live.