How to Sail Out of Paycheck Harbor
What life is like after spending a career in journalism, higher education and nonprofits, then making the leap into creative entrepreneurism.
Recently, I’ve enjoyed lunch or Zoom happy hour with friends, former colleagues, who sit in executive-level positions in nonprofit and universities—positions similar to what I once held. After a while, the conversation turns to what I am doing now and what life is like on the other side of the institutional structure, and I love this question. I get to gush about how cool my schedule is now, how I feel creative and alive in my work, and how, for the first time in a long time, I have a voice again and can speak my truth. My “truth” isn’t all that profound. It’s a familiar story to anyone who has sailed from the harbor of a steady paycheck for the seas of something like entrepreneurship.
Then—this has happened several times—as I am rambling on over our salads and wine, my friends say, “you are making me nervous.”
I don’t believe they’re feeling nervous for me, or not exactly. I think they’re catching my sense of personal freedom and independence, this new vibe, which is completely antithetical to operating with your head down like a cog in the hierarchical machine of large, lumbering institutions. Yes, and, thankfully, it’s not up to me to say whether large institutions are good or bad. People build complex systems. It’s just what we do. Within them, we ensure that each person serves a purpose or a function, and these functions synch up with precision, and this precision creates predictability. Then we outfit the whole with control mechanisms—including mowers that cut tall poppies down to size.
Not everyone is seeking professional or creative freedom. Not everyone wants to be an entrepreneur, or a creative professional, or some other kind of tall poppy. After all, it comes with a price.
When I was earning an MFA in creative writing, one of my professors used to say, “If you can do anything with your time other than write, you should. Go skiing. Throw dinner parties. Travel to Greece. Whatever.” At the time, I was truly ambivalent about this lecture. I wanted to write, and a writer was what I’d become, but could I just as easily be something else? Her conviction that this path may be regrettable was totally lost on me, and what a strange question, I thought. Who wouldn’t want to write if they could, like what’s the harm? Also what’s a “dinner party.”
Years later, of course, I understood. Writing can be a lonely and rugged road, and I am reminded of this every time a non-writer asks me about my weekend plans. In fact, just the other evening—it was a Saturday—I got a phone call.
“Guess what I’m doing?!” I said, so excited to have a fun answer.
“Working.” Zero hesitation. Ouch.
“Wrong! I’m making enchiladas.”
No doubt, working, which often means writing in my world, was a solid guess. The thing about being invested in one’s creativity is that outwardly, our lives can appear a little dull, a little predictable and confined. But inwardly, it can feel like living at the base of a waterfall. Forceful, loud, beautiful.
I tried, for many years, to give up being a writer because of the perceived dullness. I determined to make something else of myself, as if it were as simple as joining the Y or dying my hair a different shade blonde. (Studying coaching was initially a move within this plan, actually.) But I’ve since come to realize that I’m never quite as alive as I am when I’m engaged with ideas on the proverbial page. I love so much about language and the challenge of using it to capture a particular vision or idea. I love how letters look, how they combine and weave, the imprint they leave on paper from the force of the typeset. How books smell. The personalities of fonts.
Looking back, I can see all the ways I gravitated toward artistic ritual and practice from the get-go. When I was a kid, for example, the first thing I wanted to do in the morning was practice the piano. Eventually, for the sake of the household, my parents set a rule: No playing before 6:30 a.m. Writing is like this for me now. It’s what I wake up to do. (Luckily for late sleepers it is a quiet activity.)
As many an entrepreneur-friend will tell you, I flirted with leaving the philanthropy-slash-nonprofit sector long before I made the leap. I coveted the entrepreneur’s life, sought mentors, listened to podcasts, enrolled in classes—and all of it helped. But my hang-up has always been that I’m wired to make a difference over a profit, to prioritize excellence and artistry over quantity of output, meaning-making over selling, and discerning the “right” thing over other interests. (It’s also true that the work I enjoy is time- and resource-intensive, which makes it expensive, which means it’s accessible only to some, which chaffs against my conviction that self-actualization is a right, not a privilege.)
What I finally came to realize is that I didn’t need to make an either/or choice. Instead, I had to find a way to unite my desire for collaboration and community-building with autonomy and creative freedom. The missing piece in my understanding was that I didn’t want to be a lone tall poppy—I want to water and nurture a field of them.
You may not be a writer (and I am not only a writer, either) but you might feel as though you’re also squirreling away secret dreams or ambitions. You might feel, as I did, a bit incomplete in your work, that your true talents are unseen or misunderstood, and that you have so much more to offer. Or, maybe you feel your values shifting, like you’ve completed one career and are ready to launch another. (And you might believe, for valid reasons, that this longing needs to stay quiet for now, too. You might have responsibilities. You might have more to learn in your present circumstance.)
Don’t wait too long, though. Human beings are resilient and tenacious to a fault, and we can deny or work against our nature, living outside of who we truly are, for a very long time. But it can result in an even greater dullness. I promise you.