Thoughts on a year of self-employment

After 17 years of working for the same company, I’ve now clocked a year working for myself–by which I mean I’ve been busy writing for and then invoicing a changing selection of companies.

When I started this journey last April, I figured I’d sign on with one new employer or another after a sojourn on the bench. Freelancing found me instead. As a few full-time possibilities either evaporated or didn’t seem right for me, I signed on to write for Discovery, then CEA, then USA Today.

Separately and combined, these gigs met most of my requirements. And now it’s been a year and counting of this lifestyle.

What I like:

  • My income no longer has a single point of failure. If one client gets sick of me, I have others. If one shifts into high-maintenance mode, I can at least hope that the rest don’t require as many processor cycles. Related: I’m no longer handcuffed to the newspaper industry’s business-model problems.
  • Without getting into the numbers, I’m making a good living–even a little above my expectations.
  • The journalistic palette is wider this way: I’ve written everything from 400-word posts to 2,000-word features, depending on the client, a flexibility I did not have as a columnist.
  • I can exercise whatever entrepreneurial instincts I have to chase new business. Making an infinitesimal amount of extra money from speaking fees has been pleasant; writing for sites and publications I’ve admired as a reader and cited as a writer–Ars Technica, Boing Boing, Washingtonian, and ReadWriteWeb, to name four–has been better.
  • As long as I don’t sound like a complete jerk, I can say what I think online instead of living in fear of some pin-headed social-media policy.
  • I’ve escaped the frequently-awful software many print publications seem compelled to inflict upon themselves. Most of my clients only ask that I paste the text of a story into an e-mail or as an .rtf attachment; two use standard blogging platforms.
  • If there’s an interesting event happening out of town, the only person who needs to approve my travel is my wife. After having to grovel for permission to go somewhere for a story or a conference, I appreciate this freedom. (Airlines, Amtrak: You’re welcome.)
  • I have more time to spend with our almost two-year-old. Wait, why didn’t I list this one first?
  • If I’m tired in the afternoon and don’t have an immediate obligation, I can take a nap.

There are also less-enjoyable parts of this business model:

  • I can’t invoke an employer’s name in “do you know who I am?” mode to get access and instead have to hope that an elevator-speech listing of clients works. Sometimes it doesn’t. Since one of my bigger fears about freelancing was falling off the map entirely, this bothers me more than it should.
  • My contracts don’t have page-view clauses, but I worry about how much traffic my work gets anyway. I don’t see how I can’t: As a freelancer, I’m more expendable than an employee.
  • I can opt out of stories I find useless, but I still don’t have every pitch accepted. In particular, I’m not writing as much about tech policy as I’d like–or, at least, enough to justify the amount of speaking I do on the subject.
  • I’ve descended to a new level of tax-prep hell, in part because of my own disorganization. On the dubious upside, having to write a large check to the U.S. Treasury every quarter makes me more aware of my tax burden than the average taxpayer. (I can live with the total outlay; just simplify the math involved.)
  • Staying in touch with multiple editors and on top of multiple deadlines, then invoicing everybody somewhat on time, also taxes my weak organizational skills. I’m slowly becoming a better juggler of these things, but I still have to rank myself in the “conscious incompetence” phase.
  • The health-insurance system is no friend to the self-employed. Fortunately, my wife has good insurance through her work, and if all goes well I can shop for health care on a more equal basis in 2014.
  • I don’t sign on in the morning with the sense of collective purpose I had walking into the Post newsroom. This didn’t really hit me until I stopped by the Newseum last fall and lingered at its exhibits about how newspaper reporters battled to report about 9/11 and Katrina. That’s no longer part of my world, and I do miss it.

This last item may be a feature or a bug, but I’m not sure: Now that I’ve gotten well-accustomed to working from home on my own clock and with my own dress code, I may be rendering myself unemployable for any future day job.

Updated 6/20/2012 with a couple of issues I realized I’d out of the 1.0 version of the post–software and scheduling. 

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12 thoughts on “Thoughts on a year of self-employment

  1. Rob–Heard it said once you succeed working for yourself, you’re not worth a D___ working for anyone else–Congratulations on your progress–

  2. Rob: Re the “ET” Once you get organized and can make reasonable projections for a whole year, just be reasonably close with the payments. If you miss it won’t be by much, and the penalty rate isn’t all that bad!

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