December 30, 2016

A December of doing nothing

From the moment I went freelance on August 1, I knew in the back of my mind that I'd be taking December easy—I'd earmarked a check-in with myself around the six month-ish mark and the holidays are usually a quiet time in digital media anyway. I told myself I was going to work as hard as I could the first few months of freelancing, establish a roster of regular clients, and pare down from there—that's the strategy with which I approach pretty much any situation in my life when both ultimate goals and clear pathways to success aren't immediately obvious (especially when it comes to work). My theory is that you can't meticulously plan and control process, details, and outcomes if you're (1) not sure what you want, in concrete terms, and (2) if you don't really know what you're getting into, so you might as well go all-in, then figure out what you can do without after a 90-day trial run. In my case, the "great unknown" is the current state of the industry—we've seen plenty of legacy magazines and media brands fold or drastically scale back over the past few years, and the past five months have been no different. So, while the market is strong for freelancers right now (the more staff jobs are lost, the more contract an freelance work is available), doing the work is like throwing spaghetti against the wall: you can type until your little fingers fall off, but if your commissioning editor gets the boot, your outlet folds, or there's a holdup at payroll because of corporate changes, as an outsider, besides sending strings of strongly-worded-but-polite emails into the ether, you're kinda out of luck.

I've been really lucky: freelancing has been really good to me. After working in the industry for 15 years, I have lots of good friends in assigning positions at big publishing houses. So over the past few months I've been working consistently—and have gotten some really plum assignments that included lots of once-in-a-lifetime travel (see: What to do on the Rocky Mountaineer in Conde Nast Traveler, and my week at Versailles Behind the scenes with Brad Kilgore at A Taste of Waldorf for Food & Wine). For anyone who's thinking of going freelance and wondering about how the finances stack up, I can only speak from my experience, but I made way more money as a freelancer than I did as a director at a major media company—and while it's not a regular paycheck that's direct-deposited into your account every two weeks (and sometimes you do find yourself badgering editors to approve your invoices), freelancing can be very financially rewarding.

There's also the lifestyle, which is pretty much unbeatable. Over the past five months of saying yes to nearly every assignment editors threw my way, I'd estimate that, on average, I probably worked really hard two days every week—and by really hard, I mean I'd start writing at 6 or 7 a.m. and would churn through the day writing, doing phone interviews, transcribing, and writing more, until 11 p.m. or midnight. OK, that sounds like a crazy day, but keep in mind that the rest of the week—for five days!—I'd probably work about two hours each morning, then be free the rest of the day. Plus, no commute. And NO MEETINGS, which is a huge boon to productivity. To be honest, I can't really think of many downsides to freelance life, besides the obvious: drastic reduction in human contact, no brainstorming sessions with your colleagues, no funny Slack convos, reduced exposure to shared cat GIFs. The only thing that really bothers me, that I'll never get over, is surrendering control of your work. As someone who works outside of an office and isn't part of a core decision-making editorial team, you completely lose control over your story once it's filed—you have no real say over how it's illustrated, very little say in the editing process, no control over publication time or date, and zero influence over how your story is positioned in the larger framework of digital editorial strategy. That's been my only frustration over the past few months. Freelancing has taught me to be way more zen about this, though, and I've definitely learned to let go (a little bit).

So yeah, back to December. It's been such a luxury to do very little this month. I've really been laying low since Thanksgiving, getting lots of sleep, eating enormous holiday meals, watching way too much YouTube, and traveling. There have been a few stories here and there—my trip to France, a story for GQ on ugly Christmas sweaters, and some news reblogging here and there. But otherwise, zilch. It's probably the longest break I've taken since I started working full-time after grad school and it's been glorious. Like, today for instance, I woke up at 7 a.m. and went back to sleep after realizing I didn't have anything pressing to accomplish this morning, now it's noon and I'm thinking I'll spend my afternoon at the Natural History Museum and maybe go for a drink at one of my favorite places in town, a deconsecrated church where my friend Alex and I threw our joint 22nd birthday party. I feel like a lady of leisure.

That said, I've recently made the decision to step back into an office job, so it's T-10 'til I'm back on staff somewhere! I'll let you guys know when that announcement is official in the new year. Giving up my introvert/recluse lifestyle wasn't the easiest decision to make, but it's the opportunity of a lifetime—and I'm super excited to get back into the strategic side of digital editorial. You know what they say about the pendulum swinging both ways—I guess after months of stepping completely away from the managerial side of things and focusing on writing (which I love), there's something inside of me that won't feel fulfilled unless I'm hitting goals on a bigger corporate scale. So yeah, I'm very excited.

OK, let's go see some Dodo birds.