A friend of mine started freelancing at the end of last year, so I decided to give him a boring but useful present: a blank copy of the Google Docs spreadsheet I use to track my expenses.
A systematic, easily smartphone-accessible way to record the costs of doing business–organized so you can copy the year-end totals into your Schedule C tax form–is exactly the thing I needed when I started freelancing almost eight years ago. Instead, I had to survive some excruciatingly stupid accounting practices and eventually thumb-wrestle my way to marginal competence.
I was glad to give my friend a boost past that phase, and now I want to do the same for any self-employed types reading this. Here you go: Make a copy of this template (go to the File menu and select “Make a copy…”) to your Google account and get to work.
This template is organized by types of expense, with the biggest categories in my case–travel and meals and entertainment–getting their own sheets. When possible, I’ve aligned types of costs with TurboTax’s vocabulary to reduce springtime tax-prep confusion. In addition, you’ll see a box in which you can plug in the relevant numbers for a home-office deduction, but I recognize that not every 1099-income type will claim that.
I’ve also left comments throughout the spreadsheet (look for the orange triangle at the upper-right corner of a cell) explaining what goes where. If you see ways to simplify this or if you think the spreadsheet is missing an important angle, please let me know in an e-mail or a comment below this post.
I spent more time writing about information-security issues in 2018 than in any prior year, which is only fair when I think about the security angles I and many of other people missed in prior years.
Exploring these issues made me realize how fascinating infosec is as a field of study–interface design, business models, human psychology and human villainy all intersect in this area. Plus, there’s real market demand for writing on this topic.
I did much of this writing for Yahoo, but I also picked up a new client that let me get into the weeds on security issues. Well after two friends had separately suggested I start writing for The Parallax–and after an e-mail or two to founder Seth Rosenblatt had gone unanswered–I spotted Seth at the Google I/O press lounge, introduced myself, and came home with a couple of story assignments.
(Lesson re-learned: Sometimes, the biggest ROI from going to conference consists of the business-development conversations you have there.)
Having this extra outlet helped diversify my income, especially during a few months when too many story pitches elsewhere suffered from poor product-market fit. My top priority for 2019 is further diversification: The Parallax is funded by a single sponsor, the Avast security-software firm, which on one hand frees it from the frailty of conventional online advertising but on the other leaves it somewhat brittle.
I’d also like to speak more often at conferences. Despite being half-terrified of public speaking in high school, I’ve become pretty good at what think of as the performance art of journalism. This took me some fun places in 2018, including my overdue introduction to Toronto. (See after the jump for a map of my business travel.)
At Yahoo, it’s now been more than five years since my first byline there–and with David Pogue’s November departure to return to the New York Times, I’m the last original Yahoo Tech columnist still writing for Yahoo. My streak is even longer at USA Today, where I just hit my seventh anniversary of writing for the site (and sometimes the paper). Permanence of any sort is not a given in freelance journalism, and I appreciate that these two places have not gotten bored with me.
I also appreciate or at least hope that you reading this haven’t gotten bored with me. I’d like to think this short list of my favorite work of 2018 had something to do with that.
My alarm at seeing some sketchy Facebook pages in a relative’s News Feed led me to find a bug in Facebook’s iPad app and led Facebook to boot two of the worst offenders, with a combined 3.4 million Likes.
My work for this year isn’t done, but my income almost is. One client’s payment arrived today (having that happen less than three weeks after invoicing ranks as a Christmas miracle), another has told me to expect a direct deposit next week, and that’s all the positive cash flow I’m expecting for 2018.
Nearing that taxation-and-accounting finish line has me thinking once again of how I try to keep track of what I’m making throughout the year. I have three different models for this, and each can be wrong in their own ways.
• What I file in a month: This approach has has the advantage of focusing on the one thing I can control the most. But a lot can happen after I file my copy, by which I mean it can go through a prolonged edit that pushes back completion of the work by weeks.
Or by months: An editor’s departure at one site earlier this year left a post collecting dust for several weeks until one of his now-overworked colleagues could tend to it between other tasks.
• What I invoice in a month: Sending in the form itemizing your work and requesting payment has a pleasing finality, but not everybody sends the direct deposit or the check on the same timetable. Thirty days is typical, but USA Today and Wirecutter usually beat that number by at least a couple of weeks (having two of America’s largest newspapers turn around a payment that quickly continues to amaze me). Sometimes the same client’s payments arrive on wildly varying schedules for no apparent reason.
Last year, I also had a client reject an invoice because of a glitch with the bank deposit information I’d provided, and because the parent firm of this site picked an invoicing system for its fundamental meanness, I had to start the invoicing process for that story from scratch. Fortunately, I’ve not yet had to send more than a few nagging e-mails to get a invoice paid out, which is not a given in this line of work.
• What I get paid in a month: There’s no arguing with the numbers on a bank statement, but this can often be a fake metric because it reflects work done months later. And for every month where a round of overdue payments finally land and make me look like a business genius, there’s going to be another where a couple of invoices get processed just late enough to have that money hit my account not on the 29th or the 30th but on the 1st or the 2nd of the following month.
As it happens, it looks like I’ll get a reasonably large deposit from one site early next month. I’ll try not to let that cash flow get to my head… because I really thought I would have seen a chunk of that change by now.
I’m not a millennial and I don’t have any tattoos or piercings, so I would appear to be wildly ineligible for Patreon.
Yet I’m still curious about using that crowdfunding site to give people a chance to underwrite my work if they feel so inspired. I can’t tell if that is me being entrepreneurial or vain, so I’m writing this post to try to untangle my thoughts.
I first encountered Patreon when founder Jack Conte gave an exuberant presentation on the site’s backstory at 2013’s XOXO conference. (His talk rambles a bit–which is fine if you enjoy dancing robots–but overall merits 24 minutes of your time.) I decided that letting fans pledge as little as a dollar or two a month to indie creatives was a smart response to declining ad rates and the overall horribleness of the content industry. And then I thought little more about that concept until I started seeing more people and sites I know pop up on Patreon.
You can sum up the Patreon proposition as “Kickstarter over time.” Instead of asking for support for a particular project, creators invite fans to kick in a defined sum each month to support their ongoing efforts–and can also offer extra rewards for contributions above a certain level.
For example, my friend Glenn Fleishman‘s typographic-centric pitch includes exclusive or early access to his articles, science-minded podcaster Rose Eveleth offers a patrons-only newsletter, and the Arlington news site ARLNow.com touts a private Facebook group for more-generous contributors.
After conversations with a few Patreon fans at XOXO this September, I e-mailed Glenn to ask how that was working for him.
His two bits of advice: Find something you can provide to Patreon contributors that they couldn’t get elsewhere, and show what their support lets you do that you couldn’t accomplish otherwise.
I think I have a good answer for that first item: my time. As most people who have e-mailed me can attest, getting my attention when I’m constantly changing channels between stories and clients is… problematic. If I could offer something like a private Slack group or some other closed forum, I’d like to think that would appeal to people who miss the Web chats I did at the Post. (I miss them too.)
My other concerns: I wouldn’t have enough time to tend a Patreon page (note that I’m typing this near 10 p.m. on a Saturday); nobody would support it; worst of all, nobody would support it, and outsiders would then point and laugh.
At the same time, I like the idea of generating another stream of income, even if it only underwrites one trip a year. Getting acquainted with the inside of a crowdfunding platform seems like an overdue to-do item for me. And the last few months have made me increasingly uneasy about relying on my Facebook page for occupational banter with readers.
Having spent this much time musing about crowdfunding, I might as well crowdsource part of this decision. Please take the poll below, and if you have suggestions for what you’d want me to do at Patreon or another crowdfunding platform, please share them in the comments.
Yesterday, I forgot to invoice Yahoo for the last month’s worth of stories, and my stupid oversight may save me a little money next year.
That’s because the odds of payment for November’s work at Yahoo Finance arriving by Dec. 31 just got two days’ worse. And if I don’t get paid by then, I don’t owe taxes on the money until 2017.
The downside of this scenario is that my 2016 income, already assured to fall below 2015’s because I wrote less than usual in early summer, will drop even more. That potential embarrassment bugs me, but apparently not enough that I remembered to get the payment machinery in gear by Friday.
Deferring income isn’t exactly an advanced financial hack, but it is something I couldn’t do when I worked on a salary.
Tax calculations should also drive me to go on a moderate hardware-spending binge this month. My laptop and my desktop are both ancient, and replacing either now would put a nice big expense on my Schedule C.
More important, CES is now only a month away. And I can’t possibly make any big electronics purchases before using that event to see what the gadget industry has in store for this year–its no accident that electronics rarely land on my Christmas list.
That leaves me another way to lower my tax burden: a late-December spree of charitable donations. You may have read a lot on Twitter about #GivingTuesday this week, but for me that day comes on the last Tuesday of this month–when I know the donation will count for my 2016 taxes but won’t come due on on my credit-card bill until sometime in February. Please do the same if you’re financially able.
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.
A 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’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.
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.)
Over the last few weeks, I did the one thing I was sure I’d never do after leaving the Post: prepare my own taxes instead of paying a tax professional to do the work.
I’d outsourced my tax prep over the last three years with generally satisfactory results. But this time around my tax guy had raised his rates while my own financial situation had not gotten more complex; I felt like I had finally disciplined my once moronic, then merely slovenly accounting; it seemed wrong to go four years without even looking at a category of software millions of Americans do battle with every spring.
And so I renewed my acquaintance with Intuit’s TurboTax for the first time since 2011–not as a reviewer, but as a paying customer. It went better than I’d feared.
The biggest upgrade from my earlier agonies was effective record-keeping: I’d entered every cash expense last year into a Google spreadsheet on my phone within hours or, at worst, days, then imported business credit-card transactions into the same sheet every quarter. Between that and being able to consult last year’s return for guidance on what should go where, I had the outlines of my Schedule C knocked out in shockingly little time.
That’s a great reason to go to a tax pro in the first place: If you don’t know to do this stuff, you need somebody who can coach you. The results don’t just help at tax time, but throughout the year.
I was relieved to see that the stupid date-validation bugs I’d complained about in 2011 were gone–well, in most of the app.
Did I play this unnecessary game of tax-code-optimization as well as I could? I believe I did, but I won’t know for sure until after we actually file. Yes, although the 1040 and our assorted alphabetical schedules are done, I opted to file an extension. I will be dropping a sizable chunk of money into my SEP IRA to chisel down our tax bill, and I’d rather not completely clean out my account in the process.