Chasing the Taste of Creative Freedom
If you’re new here, welcome! I’m delighted to have you, and super grateful to for featuring Doh this week :) This is a (mostly) paid publication about my travails as a breadwinner and small business owner living in New York City, with lots of embedded links for your perusing pleasure. I hope it brings you as much catharsis as it has for me—you are not alone if you, too, are Rolling in D🤦🏻♀️h.
I don’t remember exactly what the man in the hoodie looked like. It happened so fast. It was a crisp early morning, and hardly anyone was outside. All I know is that he had shifty energy. As I walked with Ryder toward the park, he followed me, crossing the street toward us while filming video on his phone. Why?
When another neighbor approached, he lowered his hands. I looked into his beady eyes as he started speed-walking away. He glanced back over his shoulder once, then twice, monitoring my next moves, as my heart thumped out of my chest.
“Are you okay?” the neighbor walking her creme-colored Labrador asked. “At first, I thought that was your friend, so I didn’t say anything. Otherwise, why would he be filming you?”
I don’t know, I said, and I never would. But was sure of one thing: I wasn’t going to stick around to find out.1
It was April 2021, and I was beyond fried from living in New York City during the pandemic. I called my husband and told him to pack a bag. We would leave that afternoon, a year after the wealthier second-home-owners made their escapes. I couldn’t—wouldn’t—take another second of it. I desperately needed to recharge somewhere, anywhere, away from here.
I called my friend Ann, my New York City Angel. She happened to be out of town for three weeks and graciously offered to let us stay at her place on the Jersey shore, instructing me where to find the spare key.
This was the jangled-nerves, scorched-earth state I was in when I decided to let go of the need to earn money for one year, for the first time in my life.
I would pay for it later. But first, I was free.
Since I was a kid, I have been obsessed with earning and saving money. I saw how tight finances were for the family and how hard my parents worked to provide for me and my younger brother.
In fourth grade, I started selling chocolate bars after school for a sketchy outfit that said if I sold three, I’d get one free. I started babysitting regularly when I was eleven, and always had a side hustle (or three) from then on, even after landing my first full-time job.
Once we arrived at Ann’s, I intentionally gave myself permission not to earn a dollar for the next year. If money came to me through royalties or previous clients or passive-ish income, that was welcome, but I would set myself free from worry for the first time in my life. This would be an investing year, funded by selling my rental property in California. The renters gave notice in November 2020, and I didn’t have the energy to find new ones.
The eye-popping proceeds hit my bank account in March. COVID solidified how untenable so many systems in society were, so instead of chasing the illusion of security, I felt it was time to take some risks by placing a big creative bet.
I would ignore the odds and independently publish my third book, Free Time: Lose the Busywork, Love Your Business.2
After 40 days at Ann’s, I booked two more Airbnbs for six weeks each, in fancy summering locations that I always heard wealthy New Yorkers talking about—indicated by a “the” in front of the region, like the Catskills and the Berkshires (we only skipped the Hamptons).
There is no way I could afford to do this now. But back then, I was exhausted enough to seek my peace at any cost. I was desperate for a break. And (temporarily) rich.
With this permission, the self-appointed freedom to be and create instead of to earn as my primary directive, a latch in me clicked open. Like a genie set free, part of my soul expanded, stretching its cramped wings. For too long, it was tamped down by my inner CFO, who was always making rules and goals, expecting financial deliverables and prudent decisions.
As the city and its stressors receded, I immersed myself in a blissful near-hermetic writing state every day. I let go of the need to chase or cater to clients. I had no emotional bandwidth for them anyway. Speaking engagements trickled to a stop, save for a small virtual gig here and there, as most events were postponed indefinitely.
I became my own angel investor, funding the editing, designing, printing, and marketing of Free Time, unburdened by the need to earn while I did it. The windfall would be on the other side of the book launch, and I harbored delulu fantasies of sales skyrocketing so dramatically that royalties alone would sustain me, as they do for a small handful of my friends.
Would I have done things differently if I had known that wouldn’t happen?
I’m not sure.
Even though things only got harder after the book launched in March 2022—no big net appeared that year or the one after, or even the one after that—the unencumbered joy lives in my memories and in my body.3
Even as I grow increasingly disillusioned by the technofeudalist/late-capitalist cOnTeNt and sOciAl mEdiA grind we creatives operate in, I know that it’s possible to operate differently . . . somehow, someway, someday.4 Perhaps this is why Stefan Sagmeister takes sabbaticals every seven years.
For once, I tasted true freedom—creatively, spiritually, and financially. I can’t untaste it. I know it’s out there. I know that at least I tried my best to sustain it, and that I was fortunate beyond belief to experience it even once, no matter how briefly.5
❤️
I can’t get this “Leaving 2019, Entering 2024” Travolta meme out of my head! As Sari Botton asked a few months back, how many years have you aged in the last four? I’d say ten . . . plus thirty pounds that ensure ninety percent of my closet no longer fits.
If you’re interested in publishing options, check out these episodes of the Free Time podcast: Should you Self Publish? and Let’s Talk Royalties.
See also—the book afterword I never wrote, and my emoji balance sheet:
📊 An Honest Accounting, Part Three
To wrap this series on failures to launch, let’s zoom out to consider the broader business picture. Now if only the IRS would accept this format for official documents 😆
Shout-out and hugs to who shared the news this week about being let go from Vanity Fair, one of her dream jobs, as a “result of wider cuts and union negotiations at Condé Nast.” In a section on, “Me Doing Some Math” I chuckled in solidarity at this line:
There’s more than 19,000 of you reading this right now; if 1,010 of you can support via a paid subscription, I could literally pay for rent and healthcare for the year. The American dream!
If you enjoyed this post, you might also appreciate these Doh greatest hits:
SO much resonance with this one.
You describe so well the feeling of freedom and creative bliss when I decided to not care about money for a year.
And I love your honesty of the experience of financial reality slowly, but very surely, setting in. I feel that in my bones.
They say do what you love and you’ll never work a day in your life! Follow your joy and the universe will pay you for it!
Nice in theory.
Still, I’m so inspired by and proud of you for taking that leap, and placing that bet on yourself. And I feel very confident that a way of working and being that feels aligned is finding it’s way to you.
A reflection: self publishing a book is one of those high risk / high reward swings. I wonder what it would look like to take smaller, cheaper, higher odds types of swings at ways to generate income that feel aligned for you. That’s how I’ve been looking at coaching. And with the bit of income it brings in, it makes me feel safer taking bigger, riskier swings.
Grateful to be on this journey with you.