The bureaucratic burden of telling clients “pay me”

It’s the first day of a new month, and that can only mean one thing for my e-mail: more .pdf attachments than usual in my outgoing messages, in the form of invoices for one freelance client or another.

Close-up of the 4 / $ key on a Mac keyboard, without which I would struggle to invoice anybody.

Instructing these companies to pay me for work done over the previous month should be easy after 11-plus years of not having a real job, but there’s still some struggle attached to this chore during and after the invoicing process.

The easiest part of it involves longer-running clients, where I just need to open the invoice document from the previous month, change the invoice number and the date, update the work done and the sum due, and attach the new file to an email.

But with less-frequent clients, I need to remember if there’s some wonkiness with a P.O. number or payment instructions that I may or may not have remembered to save in a previous version of the invoice file.

Others require their own format, usually a Google document or form or an Excel spreadsheet. Not knowing what kind of file a company will want me to produce before it will send me money is one of the things that’s kept me from following advice to use a professional accounting app like QuickBooks… another thing being my own apathy.

This routine can get more complicated if I’m away from home, since all of these invoice templates live on my Mac and since my Windows laptop doesn’t have a PDF-editing app equivalent to Apple’s Preview (sorry, Drawboard PDF). But keeping these financial documents in one folder on one computer allows for a simple accounting system: Right before I e-mail an invoice, I save it to an “Invoices – owed” folder, and once it gets paid I move it to an “Invoices – paid” folder.

It’s not the most sophisticated system, but it still seems to work after 11 years and change. At least when I remember to prepare and send the invoice in the first place. Which reminds me that I still have one invoice to finish for one client and a second to create for another, and of course they’re not in the same format.


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.

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.

Between-meetings workspace options in downtown D.C.

One of the weirder aspects about freelance life, beyond being able to work without pants, is the feeling of statelessness I have when I’m between appointments in D.C. The only desk, power outlet and room that I can call mine are across the Potomac at my home; in the city, I have no one place to be.

But when I’ve got time to spare in the District, I need some place with a chair, wireless Internet, a power outlet, air conditioning and heating and, usually, access to caffeine. Here are my usual options; maybe they should be yours too?

Kogod Courtyard

Kogod CourtyardThis beautiful atrium between the National Portrait Gallery and the Museum of American Art is near perfect–it looks fantastic, it’s centrally located at Eighth and F Streets downtown, it’s got a good little cafe off to the side, the sound of children playing can keep you grounded–but for two irritating defects. One is what appears to be a complete lack of outlets. The other is the bizarre way the WiFi blocks IMAP and SMTP ports, meaning my laptop’s e-mail client can’t get or send any messages.

Coffee shops: This would be a “duh” option, but it can’t be just any coffee place. Everywhere chains like Starbucks and Cosi seem just too obvious–if I’m going to spring for a latte, I might as well get something I can’t replicate in any other city in America. I don’t have any one go-to spot in this category, but if there were a downtown D.C. equivalent of Arlington’s Northside Social or Adams Morgan’s Tryst, that might change.

Libraries: If you don’t need coffee on the spot, the District’s library system is an underrated resource. The branch locations are all in much better shape than the MLK Library (901 G St. NW): I love the Mies van der Rohe architecture there, but it’s uncomfortably overheated in the winter and, like it or not, will reacquaint you with the state of homelessness in D.C.

Dedicated coworking spaces: I don’t need a separate office often enough to pay for one, but every now and then places like Canvas (1203 19th St. NW) will have free days. And I’ve had a couple stops in the last month at the Regus business center at 1200 G St. NW (one of nine in the District), courtesy of the free membership United Airlines handed out to me and other people who spend too much time on its airplanes. This is a great place to nap–its tiny, windowless “business lounge” was empty both times–but for the same reason is also seriously deadening.

What options am I missing? Enlighten me in the comments.

Update, 3/29/2014: A couple of days ago, I finally got around to following up on a suggestion a reader left on my Facebook page after this post first went up. Hence the following addition…

Main Reading Room, Library of Congress: You can’t even get in without first obtaining a “Reader Card” at the Madison Building across the street (don’t worry, it’s only a five-minute process), and then you have to check your bag and coat before taking a roundabout route through the Jefferson Building’s basement. But then, wow: You’re typing away in one of the most beautiful spaces in Washington, a regular basilica of books. And the WiFi is fast and reliable.

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.