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.

2021 in review: return to flight

The course of this year abounded in bumps–from the horrifying sight of an attempted coup at the Capitol six days into January to the stubborn, vaccine-refusal-fueled persistence of the pandemic. But 2021 was still not 2020, and I refuse to brush that aside.

The most important dates on my calendar this year had no equivalent on last year’s: my first, second and booster shots of a coronavirus vaccine. Those Moderna doses helped give me so much of my life back, and I’ve tried to repay that continuing to volunteer at vaccination clinics.

They also allowed my writing to feature something last seen in January of 2020: datelines. My first travel for an assignment came in July, when I set out on a 1,000-plus mile road trip for PCMag’s Fastest Mobile Networks report. That was followed in August by a transatlantic jaunt to Estonia and back, a quick September visit to Miami Beach to moderate my first in-person panels since February of 2020, an October reunion with Online News Association friends, and November trips to Lisbon for Web Summit and to the Big Island of Hawaii for Qualcomm’s Snapdragon Tech Summit (note that organizers paid my travel costs for all of those events except the ONA gathering).

The long days I spent drive testing wireless networks for PCMag paid off a second time when the editors asked if I’d be interested in doing more work there. That solved a problem I had when I ended my experiment in writing for Forbes–where to cover tech-policy developments–but this gig has since allowed me to write about such non-political subjects as a test drive of a $120,000+ battery-electric Mercedes.

This year also saw me write for several new places–always a good thing for a freelancer, also a key factor in 2021’s income exceeding 2020’s by a welcome margin–while last week marked my 10th anniversary as a USA Today tech columnist. That’s approaching the length of my tenure as a Washington Post tech columnist, which is crazy to consider.

Among all of this year’s work, these stories stand out in my mind:

  • In February, I wrote about App Store ratings fraud for Forbes, because a company as self-righteous about its control of a mobile-apps marketplace as Apple should do a better job of policing it.
  • I teed off on exploding prices at Internet providers in a May column for USA Today after being inspired and irked by the poor disclosure I saw during the research for a U.S. News guide to ISPs.
  • In my debut at the Verge in early June, I explained how data-broker sites function as a self-licking ice-cream cone and offered practical advice about how to limit the visibility of your personal details.
  • Family tech support awakened me to the inadequacy of Gmail’s message-storage management, leading to a USA Today column teeing off on Google for that neglected user experience.
  • Who better to quote as a hype-puncturing source about SpaceX’s Starlink satellite broadband than Elon Musk himself? The reality-check video keynote he did at MWC in late June yielded a Fast Company post that helped inform my subsequent coverage of rural broadband.
  • I combined my notes from the Estonia trip with interviews of U.S. experts afterwards for a Fast Company story explaining that Baltic state’s e-government journey–including why it would be such a heavy lift here.
  • I used my PCMag perch to unpack Apple executive Craig Federighi’s disingenuous Web Summit talk about App Store security.

Having mentioned my business travel here–see after the jump for a map of where I flew for work in 2021–I have to note that the most important flights I took were the ones that reunited me with family members for the first time in well over a year. I hope your 2021 included the same.

Continue reading

An update on my Forbes experiment

It’s now been a year and change I started writing about the intersection of media, policy, and technology at Forbes. It’s also been two months and change since I last published anything there.

That might look like a conclusive verdict against the experiment I started last June, but the reality is a little more nuanced. On one hand, I’ve very much enjoyed the ability to “write and publish as I see fit instead of waiting for an editor to okay a pitch and then edit my copy” (as I wrote last summer). On the other hand, I’ve yet to clock enough page views in a month to earn above the minimum rate.

So when I had a bunch of new work come my way starting in April, I had to decide at the start of May if I would commit to writing my monthly minimum of five posts–my arrangement doesn’t provide partial pay for posting less than that–or take a break to focus on this new business. And since I had gone months without seeing any Forbes post crack a five-digit number of page views, that was an unavoidable call for me.

My most-read story at Forbes, a post I wrote at the end of November about the strange lifeline AT&T and, to a lesser extent, Verizon provide to the hoax-soaked One America News Network, has drawn a total of 35,747 views as of today. But most have done much worse than that unspectacular total, with many failing to crack a thousand views. That’s frustrated me to no end–not least since I’ve seen pieces at other outlets do great in the same time–but at a certain point, I had to stop banging my head against that wall and direct my attention to work that didn’t have Web-traffic stats between me and my payment. 

It’s possible that the subscription paywall Forbes put in place late last year (you should see the dialog above after reading five stories at the site in a month) has made it much harder for a post to go viral there. But I’ve seen at least one friend who writes at Forbes continue to hit numbers that should earn a decent bonus. Maybe I’m just page-view Kryptonite at this client in particular?

If I am, and if I decide to call it a day for this experiment, I will have no regrets. I’ve been able to address important topics–for example, Apple’s retelling of app-distribution history, the self-owns of some senators trying to interrogate tech CEOs, Google’s abusive conduct of its display-advertising business, President Trump’s clumsy and illegal attempts to regulate social media–as I saw fit. (Thinking about that, it would have been nice to toss up a post Thursday about the lawsuit by 36 states and D.C. against Google over its control of the Play Store instead of limiting my commentary to a Twitter thread that made me no money at all.) And the effort I put into focusing on media-policy issues also made me a sharper, better-sourced reporter in that area.

Meanwhile, management at Forbes has made some smart moves–in particular, bringing on the Houston Chronicle’s former tech columnist Dwight Silverman to cover the computing industry was a great call on their part. And nobody there has told me that time’s up on my contributor gig. But I do know that July already looks shot in terms of writing bandwidth that would let me return to it.

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.

2019 in review: rerouting through adversity

I spent much of this year dealing with two issues that I haven’t talked much about here until now.

One was the quiet end of my work at The Parallax after the sole sponsor of that information-security site, the security-software vendor Avast, ended this relationship in January. I knew that was a risk factor going in–as I admitted in last December’s year-in-review post–but I also thought The Parallax would find new sponsors quickly enough. Unfortunately, that has yet to happen.

2019 calendarThe other was the shrinking of my role at Yahoo Finance. Starting in the spring, I went from regularly writing six or more posts a month to just two or one… the most recent being in October.

Why that’s happened isn’t totally clear to me, but I know that the folks at Yahoo Finance have increasingly emphasized live video coverage from their NYC studios while leaning more on such other Verizon Media properties as Engadget for tech coverage. Meanwhile, my own story pitches this year didn’t feature any topics quite as captivating as self-driving Cadillacs or giant rocket launches.

Whatever the causes, seeing a high-paying gig expire and a high-profile gig diminish–after USA Today cut my column back to a twice-monthly frequency–made this my first year of full-time freelancing without real anchor clients. Meaning, I’ve started most months of the year without being able to count on the same set of companies for the majority of my income. And then I took too long to work the problem instead of hoping that my batting average at Yahoo would improve.

In that context, it ranks as a minor miracle that my income for 2019 only fell by about 15 percent compared to 2018. 

I made up the difference by writing for a batch of new places–the Columbia Journalism Review, Fast Company, TechCrunch, The Atlantic, and Tom’s Guide–and becoming more of a regular at some of these new clients as well as some older ones, in particular Fast Company and the trade publication FierceVideo.

Among all those stories that ran in all of those places, these stand out months later:

I also launched a Patreon page that’s contributed a modest amount of income and might do more were I less apathetic about promoting it. And I had more of my travel this year covered by conference organizers in return for my moderating panels at their events; see after the jump for a map of where I flew for work in 2019.

The series of sponsored (read: well-compensated) feature-length explainers about 5G that I did for Ars Technica in December have me ending 2019 in better shape than I’d thought possible a few months earlier. I can also feel a grim sort of pride at remaining in this profession at all after a brutal decade for the journalism industry.

But I know what I need to do in 2020: Find more ways to make money that don’t rest on the brittle business of online programmatic advertising.

Continue reading

An unpersuasive PR follow-up: “any interest?”

I’m terrible at answering e-mail on a timely basis, so I don’t complain when PR types follow up on their pitches. But I do wish they could be a little more creative in how they try to regain my attention.

Instead, the typical follow-up consists of the body of the first e-mail topped by a two-word query: “Any interest?”

That’s it. There’s no attempt to expand on the prior pitch, no hint of new developments with the PR firm’s client, no suggestion that anything the world has changed to make the subject more interesting. Maybe the service picked up another 80,000 users, maybe the app just got a round of bug fixes, maybe the CEO beat the charges–but “any interest?” tells me none of those things.

(Even worse: When the sender chooses to prefix the follow-up e-mail’s subject with the unfortunate abbreviation “F/U”.)

Meanwhile, freelancing has taught me that “any interest?” is the weakest possible follow-up with an editor. If my first e-mail didn’t get catch that person’s eye, I have to provide something more–a data point or two that suggests this story is moving and the editor would be well-served to have me chase it.

I’ve been making this point over and over when I talk to PR professionals, and yet I keep getting any-interest-ed in e-mail. There must be some outside factors to explain the persistence of this habit, and I should really try to sell a more in-depth story about it somewhere. Assignment editors reading this: Any interest?

Playing hooky for home openers

I watched the Nationals lose a winnable baseball game Thursday. I’ve done that a lot since 2005, but this 8-2 defeat wasn’t just any home game. It was the Nats’ home opener–as far as I can figure out, the 13th that I’ve seen in person, starting with our team’s debut at RFK in 2005.

(The exception was 2007. According to an e-mail I sent to my wife, I listened to the game on the radio from home.)

That also makes this spring pastime one of the few consistent examples of me taking advantage of the flexible scheduling that I should theoretically enjoy as a work-from-home freelancer.

As in: When I wandered into this lifestyle, I had delusions of being able to devote the occasional morning or afternoon to a movie or a museum. Nope!

The reality has been one of compressed chores. My schedule affords enough idle time to let me get in some gardening or expedite a Costco run, but tearing myself away from other obligations for a few hours in a row seems impossible… except for this one rite of spring. I should not complain about that, even when the game in question has us getting lit up by the Mets.

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.

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?