I don’t think I would have had the courage to become a freelancer if I hadn’t been laid off.
The year was 2014. I was 27, living in a tiny studio on the Upper West Side, conveniently located next to not one, not two, but three frozen yogurt shops. I had just lost my job, and my ego was crushed.
Once the initial humiliation wore off, the layoff started to feel like a nudge toward something I’d wanted to try for a long time: Could I actually make it as a freelance writer?
I gave myself six months. My definition of “making it” was modest. I needed to earn enough money to pay the rent on that tiny apartment and support myself without going completely broke.
Somehow, I did — though just barely. There was, for instance, the afternoon I had a meltdown in Westside Market after discovering that the money I had diligently set aside for estimated quarterly taxes — look at me, being responsible! — was not even close to enough.
Still, I kept going. In the 12 years since, I’ve had a few full-time jobs but spent most of my career working for myself. I’ve been a journalist, author, editor, writing teacher, and even cheese consultant. Before AI, I sometimes got paid to transcribe interviews. I once demonstrated very fancy olive oil to shoppers in grocery stores.
With plenty of caveats, I love freelancing. I’ve traveled around the world for stories and met wonderfully weird, brilliant people I never would have encountered otherwise. I can meet a friend for lunch at 1 p.m. on a Tuesday without asking anyone’s permission and stay all afternoon. When my kids have a school event, I can usually be there.
I built a career by saying yes to almost everything
But somewhere along the way, I also got very good at saying yes to work.
Some of that work was deeply satisfying. Some of it paid well. And some of it was writing digital shelf copy — the product descriptions and specifications you see on sites like Amazon and Walmart, down to dimensions and other decidedly unpoetic details.
There was nothing wrong with that work. It paid me reliably and well, which is not a small thing. But over time, I accumulated more and more work that felt farther from the reason I had wanted to become a writer in the first place.
My life kept changing, too. I’m now 39, married, with two young kids, one fluffy dog, a mortgage, and the assorted responsibilities of an adult woman approaching 40. Until recently, both of my children were in eye-wateringly expensive preschool. My husband has a great job, including, praise the Lord, great health insurance, but my income still matters to our family, and it matters to me.
For nearly two years, I also had what felt like the freelance holy grail: a client on a substantial monthly retainer. The work was steady, the income predictable, the relationship long-running. Freelancers know how rare that combination can be.
Losing a major client made me rethink what ‘success’ means
Then, this summer, it ended. I found out by email while I was in England, at a family gathering filled with cousins and children screaming in a sprinkler during a brutal heat wave. One minute, I had this dependable chunk of monthly income. The next minute, I didn’t.
My immediate response was panic. I started doing the familiar freelancer math: How big is the hole? What can I pitch? Who can I email? What new client can I land? How quickly can I make the number go back to what it was before?
For years, that reflex has served me well. Freelancing requires a certain amount of hustle. One assignment ends, so you find the next one. A client disappears, so you replace them.
But after the first wave of anxiety passed, I noticed something else. I wasn’t entirely devastated.
The work had provided real financial security, but it had also occupied a lot of my time and brain space. Meanwhile, the parts of my career I care about most — journalism, editing, teaching writers, building a writing community, and, I hope, writing another book, had been squeezed around its edges.
Suddenly, there were edges again!
My instinct was still to fill them immediately. Instead, I’m trying something that feels much harder: leaving some of that space open.
That doesn’t mean I’ve decided money is unimportant or that I’ll never take another well-paying copywriting client. I like earning money. I like contributing significantly to my family. I like the security of knowing what will come into my bank account each month.
I’m also beginning to wonder whether maximizing my income at every moment is the same thing as building the career I want.
At 27, losing my job pushed me toward a working life I was too scared to choose for myself.
At 39, losing a big client may be asking me a different question: Now that I’ve proven I can make a living this way, what do I actually want to make?
For the moment, I’m trying not to answer too quickly.
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