A Completely Subjective Dos and Don’ts Guide to Freelancing

And now, for all us freelancers, some words on how to handle the freelance life, from a writer so entertaining that we’re sure he’ll be snatched up to a high-dollar gig in no time. (Don’t forget about us little folks, Jeremy! Puh-leez!)

freelancingby Jeremy Gordon

On October 15, 2011, I moved back into my mom’s house with $300 to my name; on October 1, 2012, I moved into a Brooklyn apartment, lease signed and bags bulging, once more a proud, productive member of the American economy.

In those 11 1/2 months I freelanced extensively for a number of publications, usually on a daily basis; my math is shaky, but I estimate I published somewhere between 200,000 and 400,000 words in that time span, some of them terrible, some of them not-terrible, but all of them paid for. (I’ve written more and been paid more since then.)

Since moving here, enough people have burnished my ego by telling me I’m the only one our age they know who is making a full-time go of the freelance game, which is both hilarious and terrifying because I fell into it entirely by chance and had never taken the time to think about how I’d gotten here. Here’s my stab at working out some of it, though I’m sure I’m forgetting plenty.

(Disclaimer: Things I have been wrong about include the long-term viability of Kreayshawn, the candidacy of Francois Hollande, the importance of chemistry between the 2012-13 Los Angeles Lakers, the subversiveness of Odd Future, etc. If anyone reading this has found a better way to do the things I’m writing about, great! Please chase that. But this has generally worked for me.)

Even on days when I don’t have any immediate deadlines to worry about, I try to get up no later than 9 a.m.—and it’s usually much earlier—to surf the Internet, read a magazine or book, make breakfast, shower, listen to music, sit in bed staring at the ceiling and contemplating the true way of all death, etc.

It’s good professional practice to be available as the people you work with—for me, that’s mostly New Yorkers—are getting into their offices, because you never know what needs doing and whose mind you’ll be on. (Also, it’s just good practice for when you need to be up stupidly early for something important.)

A story I share a lot because it continues to horrify me: In my more deeply unemployed days, I was up late and decided to wake up at 10 a.m. instead of nine, which of course was the day a Rolling Stone editor emailed me and a handful of other freelancers who had been working on a non-writing thing to see if one of us could come into the office for a few days, since they were shorthanded. Had I been awake at my usual time, I would’ve replied in half a second and soon been on my way; instead, I was left feeling like the world’s laziest idiot. Since then I’ve never woken up later than nine, aside from the brutal hangover every now and then.

(Caveat: You may be one of those freakish night people who work best at 3 a.m., which means you’ve just got to find a sleep routine that works for you. I recommend this site, which does a good job of approximating a reasonable sleep cycle so you don’t wake up feeling like a World War Zextra.)

This is the most subjective part of this list, since different approaches work for different people. I’ve known freelancers who burrow termite-deep and get rewarded with a full-time job in that field, but for those of us who got into this to avoid the job, there’s plenty of benefit in paying attention to multiple areas of interest.

I balance the bulk of my time evenly between sports and culture, which lets me bounce around from topic to topic depending on where my curiosity is led that month and has enabled flexibility for when new opportunities arise. Everyone is different, but it’s important to be honest about where your strengths lie; I’ve never been the type to sit for 12 hours a day listening to new music, so I made a concerted effort to pitch outside music publications.

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