Rob Pegoraro15 years of evading cubicle capture
April of 2011 presented me with an opportunity disguised as the dismantling of a job I’d had under various titles for more than 17 years: a chance to pick up the work I loved without owing anything to how I’d done it at the Washington Post.
But when I woke up on April 18, my first workday without a desk to my name at 15th and L, and proceeded to file one last uncomplicated tax return, I didn’t realize that I was starting this occupational reboot with a cheat code enabled.
At least then, writing a personal-tech column for a major American newspaper for more than a decade and then getting unexpectedly kicked to the curb proved to be the best #OpenToWork ad I could hope to run.
After getting enough unsolicited inquiries about writing for places on a contract basis instead of as an employee, I decided to try self-employment for at least a while instead of holding out for a full-time job that might return me to cubicle life.
And now I’ve somehow made it 15 years without my work having a single point of failure. No one boss has been able to put me out of business, and no one editor has been able to quash my hopes of writing about any one thing.
That’s left my own decision-making as the one ongoing risk, and I can think of so many ways that has failed me. The worst have been the times, more than once, that I assumed having one anchor client make up the vast majority of my income would be a quasi-permanent situation.
The lesser ones have been my failures to sell stories that should have been easy to land somewhere. It’s weird how I can remember, with painful precision, individual story ideas that I should have turned into money–including the dollar amounts I could have put on each invoice–but instead fumbled away for one stupid reason or another.
My income has varied more than I would have expected; 2012 was my best year, with the help of two clients paying above-market rates that they later thought better of, and then eight years later I finished 2020 with a bit over half that take as the pandemic beat down my fortunes and led me to accept some dismal worst per-word rates.
(It helps, so much, that my wife has a real job with things like a predictable salary and health insurance.)
Battling through 2020 and into 2021 meant more than I realized at the time; one of the best things that self-employment has taught me is resilience.
It’s fair to say that I haven’t optimized my freelance work for personal wealth, not that any journalist makes that choice when they pick this profession. But I think I have optimized it for flexibility, both in the sense of how I’ve been able to write about things outside the mainstream of consumer-tech coverage (space foremost among them) and in how I’ve been able to make money (getting paid to speak remains something I should get better at).
I have definitely optimized my work for taking me to interesting parts of the world.
And because I enjoy my work, I think I’ve done a decent job of optimizing my work for fun. The New York Times’ late, great media reporter David Carr used to describe journalism as a caper that you hope to get away with for as long as you can, and I keep being reminded of how right he was about that.
The past few years have lent one other perspective on my self-employed existence: the sight of so many friends with staff jobs losing those theoretically more secure positions. This February, that happened to about half of the newsroom of the Washington Post–including most of the tech reporters there.
Somehow, despite regular reminders that maybe I don’t quite know what I’m doing, I carry on accumulating clients and 1099 tax forms. And if I can get away with this caper for another two and a half years, I will have spent more time working for myself than for any one company. That will be weird, but maybe not much more stranger than my entire career path so far.
#1099 #caper #cubicle #freelance #freelancing #fullTimeFreelance #independentContractor #journalism #journalist #office #SchedC #ScheduleC #selfEmployed #workFromHome
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