Tax-time thoughts: now with slightly less incompetent accounting!

I have survived, I think, another tax season as a self-employed individual, and I’m increasingly convinced that if I keep doing this I will someday know what I’m doing.

Misc. incomeOnce again, my worst enemy was my inattentive and sloppy accounting. I was still forgetting to tag some expenses as business transactions in Mint until last spring, and It took me until mid-September to lock in the habit of logging every cash expense within minutes of it happening. Memo to Google: This would be easier if the Google Drive app could edit spreadsheets offline.

For cash transactions not properly noted at the time, I had to recreate records months after the fact. That involved the tedious, time-consuming routine of cross-referencing my calendar, e-mail and Foursquare check-ins.

Importing the credit-card purchases that Mint had recorded automatically was the same as ever, which is not good: Intuit’s site still provides no way to limit a transaction search to a date range short of hand-editing a Web address. Intuit, this is idiotic. Try spending some of the money you sink into astroturfed lobbying into adding this most basic of features.

Last year also saw client income (Sulia and WordAds) arrive via PayPal deposits, a first for me. I liked the invoice-free convenience of those payments, but I made two rookie accounting mistakes. The big one was not identifying all of the subsequent PayPal transfers to my bank as freelance income; the little one was using some of a freelancing-inflated PayPal balance to reimburse my share of an Airbnb apartment rented for Mobile World Congress instead of first moving the sum of those freelance payments to my bank, then covering the lodging expense with a separate withdrawal from my bank.

The fact that I realized most of these errors in late March by itself represented my single biggest accounting failure–I spent too much of 2013 in a financial fog, which is stupid. So after cleaning up last year’s records, I set aside a couple of hours last weekend to do the same for those from the first quarter of this year. Like I said: I do learn, just not quickly.

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A love letter to XOXO

PORTLAND–If you write for a living, hope and fear are part of the deal. Hope, because you believe your ability to make words appear on a screen in a pleasing sequence will lead other people to give you money. Fear, because you worry that other people will realize you are not all that good at that work, and that other writers can do it for less anyway.

XOXO badgeI spent three days here last weekend at XOXO, a conference staged to lend hope to independent creativity. That was a fairly abstract concept to me three years ago; I was approaching my 17th year at the same employer and had (fraying) ambitions of retiring there.

Then other things happened, I didn’t get another job as I’d expected, and after two and a half years of freelancing full time, my indie existence no longer feels like a fluke.

But it can still feel lonely. So it was tremendously empowering to commune with smart, talented, hard-working people who had taken a similar course, then see some of them testify about it. I kept finding myself nodding vigorously at things I could have said, or wished somebody would have told me a couple of years ago.

Co-organizer Andy Baio opened the event with an introduction that was part release notes explaining how he and co-conspirator Andy McMillan had designed XOXO to function unlike the average corporate conference, part pep talk for those assembled. “It’s about making new things and putting them out in the world,” he said. “That takes a unique kind of bravery.”

Cartoonist Erika Moen evocatively recalled her own I-think-I’ve-gotten-somewhere moment: “I’m self-employed. I’m creating. I’m in love. I’m happy.” In my notes, those sentences are set off with one all-caps prefix: THIS.

Musician Jack Conte provided a succinct description of the basic business problem for any freelancer–or, for that matter, any newspaper: “You have to make good stuff and convert it into money.”

One of my favorite talks came from musician Jonathan Coulton (longtime readers may recall his guest spot on my Post podcast, the audio of which has apparently gone down the bit bucket). He spoke bluntly about his moments of self-doubt–“there are times when I say to myself, I wonder if I have ever done anything that’s really good?”–but also showed a cheery defiance of standard-issue career advice.

“Don’t let anybody tell you that there’s A Thing you have to do to make this work,” he said before a slide reading “Be a Snuggie,” “You’re doing it right,” and “Fuck ’em.” Instead: “Here is the only metric you need to care about…. Is what you’re doing making you more happy or less happy?”

And Cabel Sasser, co-founder of the Mac software firm Panic, Inc., gave a wonderfully human recounting–who among us has not sometimes thought, “I needed to file a bug report on myself”?–about what it meant to keep his company independent.

What if it fails spectacularly after he’d passed up a lucrative exit? What if it slowly sputters out? I liked his answer: “You won’t know the end until it ends, so let’s fill the middle with as many amazing plot twists as we can.”

The other part of XOXO that lit up my brain was the other people I was able to meet there. Baio and McMillan’s attempts to limit the audience to people who made things, their  exhortations to say hi to whoever’s next to you, and the inevitable random conversations while waiting in line at the food trucks outside the Yale Union building all made this one of the more welcoming spaces I’ve occupied.

Many Internet-famous individuals are jerks, but I did not meet any jerks at XOXO. I was particularly delighted to meet people I hadn’t seen in months or years, or had only known as usernames in Twitter, e-mail addresses in my inbox or a remote voice on the same radio show. You know who you are; hope to see you again soon.

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.

Respect the vacation

I did something a little crazy two Tuesdays ago, which was board a plane without a laptop. That strange behavior–the last time it had happened might have been Christmas of 2010–was the result of something almost as out of character, my taking a vacation.

iPad not at work

If you define that term as meaning a trip out of town that runs at least a week, which does not involve more than a tiny fraction of your usual workload and which is not listed on your taxes as a business expense, our last one had been a pre-parenthood jaunt in Montana in 2009.

The next summer saw entire weeks of time off, courtesy of our daughter’s birth–but that period  lacked the essential vacation ingredient of sleeping in. In 2011 and 2012, we had some great long weekends, but nothing matching the traditional definition.

(Some of my work trips have had vacation-like qualities–SXSW absolutely comes to mind–but if you’re on e-mail and Twitter all the time, your laptop is in use every day and all of the expenses will wind up on your Schedule C, the obnoxious term “workcation” is unavoidable.)

This year, however, things finally lined up. Our tenth wedding anniversary was approaching; we could leave our kid with her parents then; we both had enough time freed up in our respective work schedules. I even committed to avoid booking any business meetings in the tech-friendly cities we visited–that’s Portland in the above shot–even though that could have easily converted my airfare into a Sched C line item and allowed me to sell a story or two from the road. But I still had to force myself to unplug from my usual online outlets.

I used to be a hard-liner about not checking any work-related communication on vacation. That got harder to do as the pace of tech journalism accelerated, but many of our vacation destinations still enforced some disconnection. (Have you ever tried checking your e-mail in the middle of Glacier National Park? Would you be excited about doing that from the shared computer in the lobby of a hotel in China?)

This time, however, I figured I couldn’t skip telling people about just-published posts I’d written in advance (the last ones filed at around 3 a.m. the morning of our flight out of D.C.) or answering tweets mentioning me. And not checking my work e-mail at all also seemed like a freelance foul. It didn’t help that major tech-news events happened while I was out: Apple’s Worldwide Developer Conference and the revelation of massive phone and online surveillance by the National Security Agency. But even so, I found myself checking Twitter less and less after the first few days, to the point that I spent at least 48 hours without tweeting anything, and I felt zero guilt about letting unread e-mails and RSS items pile up.

There’s probably something to be learned from that experience. And yet: Here I am typing this on a Saturday evening.

What next?

To judge from the different paths that my fellow ex-Posties have taken, the newspaper is the equivalent of a liberal-arts college without a strong career center: There’s no one obvious next step, so people get to make up their own.

Some have moved on to news services, Web-only news organizations, TV networks, magazines or other non-newspaper outlets; several research and write about the issues they covered for think tanks or universities; a few have written books; a few have become spokespeople for politicians or do public relations for companies or PR agencies; and one or two have struck out on their own. Not that many have signed up with other papers.

What’s next for me? I don’t entirely know. But since I’ve been getting that question so often–and because, who knows, a potential employer or client might see this–I thought I’d set down what I would like in my next line of work.

  • It has to involve writing. Even on crummy days at the Post, playing with the English language could cause a smile to break out on my scowling face. Why else have I been doing so much writing–for free–on Twitter and Facebook? Why, even though my wife and I e-mail each other about once every workday, do I still try to come up with new subject lines when I write her? Writing is what I do.
  • It has to involve learning. At its best, journalism brings back the rewarding parts of college–you discover new things that get the gears turning in your head–but doesn’t require you to write about them in academese or pay for the privilege.
  • It should be related to technology. I’ve spent a long time immersed in this field, still find it deeply fascinating and want to see what the companies, organizations and people I’ve grown to know will do next. In other words: Don’t tell me I’ve sat through dozens of Windows installations for nothing!
  • It should be in the D.C. area. I’ve now spent more than half of my life here; while the city’s knocked me down a few times, it’s picked me up far more often. It would take an exceptional opportunity to pry me away.
  • It doesn’t have to involve a newspaper. If anything, the prospect of a job that isn’t saturated with angst over the paper’s mission, transition to the Web or adaption of traditional journalistic standards to social media would be a relief. My next job might not have to involve a newsroom as such either: Some analysts and tech-policy types I know blog more often than Post writers.
  • I wouldn’t mind the option of working from home, at least during prime front-porch season. That makes freelancing an option as well. (It helps that my wife’s health-care options aren’t bad, and that we have the prospect from 2014 on of not getting shafted by insurance companies should we shop on our own.)
  • Please, oh please, no more crummy software. Thanks, but I’ve spent enough time as collateral damage of a news organization’s abusive relationship with groupware and content-management-system vendors.

I suppose that doesn’t narrow things down all that much. But if you have any suggestions for places I should seek out, or ones I should avoid, I welcome them in the comments.