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.

Storytelling about story selling

Earlier this week, I did a foolish thing: I wrote an article without even trying to get paid for it. The piece in question–a 313-word listicle relating ten thoughts about Facebook on the day of its tenth birthday–only took a few minutes to write, and in the moment my Facebook page seemed like an apt spot for it.

Tumblr post buttonMost of the time, however, I’m not in such a rush and I do want to make some kind of money for writing something longer than a few paragraphs. (For about a year, this blog generated no income, but since the spring of 2012 WordPress.com’s ads have been paying me an exceedingly low per-word rate.) But if I have an idea that’s not an obvious fit for one of my regular clients, where do I try to sell it?

For me, the answer is not always the obvious “whoever will pay the most money.” Assuming the options are all offering about the same range, other considerations come into play:

Audience: If I’m writing something that I hope will change people’s minds, then I’d rather a site be able to get my words before more people. If it’s more of a personal essay or some specialized topic that won’t get a large readership anyway, that’s not such a concern, and I’ll even write behind a paywall.

Old or new client? I don’t want to let my connections with editors go stale–when an editor knows you and your work well enough, you can pitch a story and get it assigned to you in a minute’s worth of Twitter direct messages. But if I’m not getting my byline to show up in different places, it feels like I’m not trying hard enough.

Contract: Most freelance contracts are written to reserve as much of the post-publication upside as possible for the client. Ones that instead let me keep copyright to my work and resell it later on (thanks, The Atlantic Cities and The Magazine) easily get my attention.

CMS: Being an outside contributor generally insulates me from whatever horrible content-management system a newsroom uses, but if a site uses a good CMS it gets a little extra credit. For example, it doesn’t hurt that Yahoo Tech uses Tumblr, and one big reason I want to write something for The Magazine’s venture on Medium is to spend some quality time in that CMS without writing for free.

Comments: Because I’m one of those weirdos who actually enjoys reading and responding to reader comments, I appreciate writing for sites that make it easy to do so–and have commenters who generally know what they’re talking about. (Yes, Yahoo Tech doesn’t have comments yet. A custom system that, per, David Pogue, will “attempt to eliminate awful anonymous drive-by potshots that add nothing meaningful to the discussion” is on the way; when it launches, you will see me on it.)

Ease of payment: I usually don’t think to ask about this until after I’ve filed, but if I don’t even have to invoice the client to get paid, that’s great. Having the payment deposited directly in my business account or sent via PayPal helps too, but my bank’s nearest branch is only a 10-minute walk away, and I could always use its app to scan in a check. Really, just don’t make me have to invoice twice and I’ll be happy enough.