Ten years without a real job

I have now somehow clocked a decade of self-employment, and I won’t even pretend that was the plan when my status as a Washington Post employee officially expired on April 29, 2011. At the time, I assumed I would spend not too many weeks as a gentleman of leisure, then find a place where I could resume covering the things I cared about in the world of technology.

(By which I mean, not rewriting Apple rumors.)

Photo shows a 1 and a 0 from a toddler's alphabet set, as seen resting on graph paper.

Instead, multiple places found me, offering freelance rates that were good enough to convince me to try self-employment. It seems that my sudden and surprising appearance on the market represented unintentional, effective positioning on my part; my least-useful advice to new freelancers is “have a column at a major American newspaper, then have the paper kick you to the curb when nobody expects it.”

I also didn’t realize at the time how lucky I was to start freelancing by having two different clients commit to pay for a set amount of work each month at an above-market rate. My gigs at Discovery News and the Consumer Electronics Association eventually went away–there’s no such thing as a permanent freelance client–but they allowed me to figure out the basics of indie existence without stressing over each month’s income.

They also let me start seeing what I’d missed at the events that had never been in the cards for me at the Post–like SXSW, MWC and the Online News Association’s annual gathering–and begin to develop my own sideline as a conference speaker.

I have learned an enormous amount about the self-employed existence since then–battering my way to marginal competence at accounting, struggling with parallel editor-relationship management, booking travel on my own criteria and then optimizing it, time-slicing workdays to get chores like a Costco run done faster than salaried folks can manage, and bringing a certain equanimity to fluctuating cash flow. (My actually-useful advice to new freelancers is “have a spouse with a real job.”) Some years have been much better than others, while last year was much worse than the rest. Marching on as a freelance writer through a global pandemic even as friends have fled the business is one of the harder things I’ve had to do in my career–but the important thing is that I persisted, and now business is picking up and I can even look forward to once again traveling for work.

Ten years and 87 1099 tax forms later (I may be missing a few in that count), I still think I’ve been pretty lucky in this ongoing chapter of my professional life. I’ve never had a client fail to pay me; while I have had to nag a few for several months for a payment, my single longest wait happened because I forgot to invoice the client. I have covered stories and gone to parts of the world that probably would have remained daydream material had I somehow stayed on my old path. And since April of 2011, no one company has ever been in a position to put me out of business. That means a lot.