Self-employment is easier if you’re not at the mercy of health-insurance companies

I am thankful every day that my wife has a good job that includes affordable health insurance for our family. But seeing the Republican Party attempt to demolish the Affordable Care Act over the past few months has made me even more appreciative of being a kept man.

For as long as I’ve been self-employed, I’ve been able to tell myself that if my wife’s job ever went away, the ACA would give us a fair shot at keeping health insurance for the three of us–even today, the rates I see quoted at HealthCare.gov remain reasonable. Meanwhile, not having to worry about exceeding lifetime coverage caps (my friend Kate Washington’s testimony about the costs of her husband Brad’s treatments for cancer are essential reading) or being judged to have a pre-existing condition takes a lot of anxiety off my mind.

Most of the GOP’s proposed replacements for the ACA would have taken a hammer to some if not all of those protections. It’s possible that my wife’s premiums would have dropped as a result. But we don’t want to trim that bill at the cost of screwing over other people.

Like, for example, self-employed friends who get their coverages on ACA exchanges. Tom Bridge and his wife Tiffany each run tech consultancies in D.C., and without the law’s protection they’d be looking at vastly higher coverage for themselves and their son. He’s tweeted often and well about how this product of the Democratic Party has allowed him to build a business.

Friday morning’s Senate defeat (thanks, Senators Collins, McCain and Murkowski and all 48 of their Democratic colleagues) against the latest in a long line of ACA-gutting bills drafted in secret and in haste should ease the existential dread they and many others have been feeling.

(President Trump being President Trump, he won’t shut up on Twitter about how the GOP should keep trying to kill “Obamacare” despite its unbroken record of failure so far. He’s the Black Knight of American politics on this subject.)

It does not, however, end the need to fix what’s wrong with the ACA in some markets. Another freelancer friend, Seattle-based tech writer Glenn Fleishman, has seen his costs climb to “ridiculous” levels–as in $20,000 this year. He’s now seeking full-time employment to escape that.

Now would be a great time for the Republican Party to accept that Americans have decided health insurance shouldn’t be left as a privilege, then bring some business smarts towards crafting the most efficient, choice-driven way to meet that goal. Since most other industrialized countries achieved universal coverage long ago, there’s a huge variety of ideas for them to steal, and which Republicans could have learned from over the past seven years instead of repeatedly staging stunt votes against the ACA.

The party that constantly says it speaks for entrepreneurs should be able to sell this as making it easier for people to start a business and create jobs. Or the GOP can continue to try to tear down this part of President Obama’s legacy, all so the self-employed can once again be “free” to run into the embrace of a large corporation if they don’t want to have to worry about getting sick.

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Five years of not having a real job

Monday marked five years since I’d last been on the clock for an employer. The continued absence of a salary still doesn’t bother me.

Five years of 1099sA lot has changed since the day that started with my failing to sleep in, then involved the hilarity of filing our taxes and ended with a few retellings of my what-happened story at an Online News Association meetup.

My top sources of income have changed almost every year, so I’ve gotten used to answering such vaguely existential questions as “where are you at?”

I’m no longer incompetent at accounting and have even gone back to doing our taxes, Schedule C and all.

I’ve traveled to places I might have never seen on the Post’s dime. I did enjoy marking the fifth anniversary of my independence in Hong Kong, although I can’t say the same about spending the preceding 16 hours in seat 21K. One contributing factor to all that travel: Sufficient practice at public speaking has begun to pay off with more invitations to moderate a panel or give a talk, and accepting them doesn’t require multiple layers of newsroom approval.

I’ve been able to say what I think on Twitter and Facebook without worrying about running afoul of some newsroom social-media policy intended to fool readers into thinking we have no opinions about what we cover.

And I don’t know if I can call myself a hustler, but I’m definitely a more aggressive capitalist than I was in 2011.

In an alternate universe flipped to a different page in this Choose Your Own Occupational Adventure book, I might have landed another full-time job. I half-expected that to happen within a few months of leaving the Post, but instead a variety of interesting freelance opportunities appeared and I chose to follow them. (Lesson learned that most people unfortunately can’t apply: It’s not that hard to start as a freelancer if you first hold down a column for a major newspaper for over a decade.)

I may yet regret going this route–yes, I have been following the news about Yahoo. But every new round of newsroom layoffs and every job-destroying pivot at a new-media startup reinforces my sense that having a full-time employer provides little more security than cultivating a good set of regular clients that can’t constitute a single point of income failure.

Check back in another five years, and I should be able to report if I was right about that.

Post-travel to-dos

Cards and card

I’m through the worst of what I’m not-so-fondly calling Conference Month, and all of this travel is reminding me of the tasks that await each time I come home and finish unpacking.

Let’s see:

  • Do laundry.
  • Catch up on other household chores: sweep the floors, do the dishes, bake bread, reaffirm my earlier decision that the late-summer lawn is a lost cause.
  • Go over my e-mail to see which messages I should have answered three to five days ago.
  • Tag and categorize business expenses in Mint, then verify that I didn’t forget to record any cash transactions in the Google Docs spreadsheet I use for that purpose.
  • Send LinkedIn invitations to people I met on the trip, assuming their profiles show signs of recent life. (Go ahead, call me a tool now.)
  • Throw the latest set of press-kit USB flash drives onto the pile.
  • Scan business cards into Evernote.
  • Download, edit, geotag and caption photos, then post them to Flickr (for public viewing) or Facebook (for friends).
  • Make sure I got the proper frequent-flyer credit for the last round of flights.
  • There’s probably some other chore that should be on this list but that I will only remember when I’m on my way to National or Dulles.

As I write this, there’s a stack of business cards on my desk and several dozen pictures in iPhoto that have not been edited, geotagged, captioned or shared. And I only have five days before my next work trip, the Online News Association’s conference in Los Angeles, so you can imagine how well this is going.

Conference organizers, maybe you could find other months to host your events?

 

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.

Things a freelance writer can be thankful for

Clients who say yes to your pitches–or at least politely say no and explain why they didn’t work for them.

Thanks

Clients who offer you unexpected assignments, preferably near a dollar a word.

Clients you don’t have to invoice twice–better yet, who pay before you can get around to sending an invoice.

Contracts that don’t have work-for-hire or indemnification clauses. (How often does the latter form of legalese save any company from legal trouble?)

That moment when a crafty lede pops into your head, fully formed.

The state of flow in which words seem to fly onto the screen by themselves, and you only need to keep your fingers over the keyboard.

Having your reporting lead you in an unexpected direction, in the process reminding you that this profession should be roughly equal parts learning and teaching.

Catching a stupid error that you were thisclose to sharing with the world.

Discovering that you’ve written a phrase in a headline that Google has never seen before.

Editors who ask good questions that reveal flaws in your argument, or at a minimum don’t edit in mistakes.

Anybody on a copy desk who quickly fixes the mistake you discover after publication or posting.

Readers who appreciate what you do.

Happy Thanksgiving, all!

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.