A Completely Subjective Do’s and Don’ts Guide to Freelancing
On October 15, 2011, I moved back to my adolescent bedroom with $300 to my name; on October 1, 2012, I moved into a Bushwick apartment I’d recently signed a lease for, once more a proud, productive member of the American economy. In between, I freelanced extensively for a number of publications, usually on a daily basis — my math is very 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. Over the last year several people have burnished my ego by telling me I’m the only one amongst our age group whom they know to be making a full-time go of the freelance thing, which is sort of hilarious/terrifying because I fell into it accidentally and had never taken the time to think about how I’d gotten to this position. Here is my stab at some of that thought process, 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. I am wrong a lot, and 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, and thus I will share it with you.)
Do: Wake up early
Even on days when I don’t have any immediate deadlines to worry about, I get up no later than 9 o’clock to surf the Internet, read magazines/books, make breakfast, shower, listen to music, sit in bed staring at the ceiling and contemplating the fragility of existence, etc. It’s good professional practice to be available just as everyone is getting into their offices, in case there’s something that needs doing; you never know whose mind you’re on, and when you’ll be needed. A story I share a lot, because it continues to horrify me: One time I broke my rule and woke up at 10, not 9, which happened to be the day an editor from Rolling Stone emailed me and a handful of other freelancers who were 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 0.2 seconds; instead, I was left feeling especially stupid and lazy and broke and so forth. I have literally never woken up later than 9 since this incident, and it’s served as good training for when I actually do have things to wake up early for. (CAVEAT: You may be one of those freakish night people who work best at 3 AM, 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 time for you to wake up so that you don’t spend the day in a zombie-like fugue state.)
Do: Cultivate multiple interests
This is the most subjective part of this list, since different approaches work for different people. I write about a lot of different things, but other people have found more success in sticking to one specific subject. However, I can personally tell that I’ve benefitted from paying attention to different fields — sports, music, politics, movies, whatever — and chasing those interests down the appropriate professional roads so that I might have my cake and eat it too. (Things I have been paid/published to attend: Lollapalooza, a Katy Perry concert, a Billy Corgan-promoted wrestling show.) It depends on your personality type, whether you get off by burrowing termite-deep into one area, or whether you’re more fulfilled by spreading your mental energy around. Everyone is different, but I think it’s important to be honest in where your strengths lie; I’ve never been the type to sit for 12 hours a day listening to new music 100% of the time, so I made a concerned effort to pitch outside of music publications.
Don’t: Force things
There was a horrid, torrid month where I published eight things in four weeks for The Atlantic’s website, which involved waking up every day, thinking “What can I pitch?” and forcing myself to trawl for any idea worth developing. I’m proud of some of the writing but all of it required a lot of massaging by my very gracious editor, and the original drafts/pitches definitely reflect the desperation of someone worrying about paying his rent. Obviously, the luxury of taking your time isn’t afforded to everyone but if you’ve got the means to exist comfortably, then it’s worthwhile to slow down and wait for your opportunity to strike, when you’re capable of confidently pitching something in your expertise. In 2011, I was pitching think pieces on Kelly Rowland that would’ve surely turned out to be unreadable; please, don’t pitch think pieces on Kelly Rowland if you didn’t hear “Motivation” until like two months after it came out.
Do: Find your people, stick by them
One of my more ignoble claims to Tumblr fame was a slightly defensive post I wrote about a lamentable situation I observed, in which people my age were too quick to be friendly with writers/editors older than them so that they might create a more advantageous professional reality. It got a lot of responses, some of them fair and some of them bullshit; in retrospect I was salty about a dozen other things, which led to being less articulate than I could’ve been. My stance on this is now somewhere in the middle, as usually turns out to be the case: I stand by the assertion that you shouldn’t fake being nice to people you genuinely find distasteful for whatever reason, though that doesn’t mean you should be mean to them. (Just… try to avoid them? Or learn how to interact in a neutral, cordial way without being an asshole? Whatever works.)
A good idea, though, is to find other writers, ideally in your age range/experience level who are similarly down with getting shit done, and whom you can hopefully hang out with IRL. (IRL > URL, always.) I won’t pump up their worthless egos by mentioning them specifically, but the best personal/professional development of my life over the last year has been offline vibing with a circle of other young Internet Illuminati writer types; it’s nice to be surrounded by people into similar stuff as you, for when you fear minute discussion of the latest Azealia Banks Twitter feud might be alienating your friends who work in law firms, and you will find that the people closest to your level are the most likely to share your same hopes, fears, etc., about how stuff is going. As you’re going to end up freaked to death at least 20% of the time, it helps to have someone you can grab post-work craft brews with and commiserate over your follow/follower ratio. Plus, some of them will also keep unconventional work hours, too, which means you can get long lunches in the middle of the day and laugh at your friends stuck in offices/cry over your lack of vacation days. It’s a balancing act.
The other side of this, and it’s so obvious I shouldn’t even have to say it but I will anyways, is that once you’ve found the people you get along with, you should stick by them 100% of the time: No subtweeting, shade-throwing, reputation undermining, or any of that shit. It’s not cool, and believe me, people will notice your loyalist tendencies or lack thereof.
Do: Read comments
Another story I love to repeat: I was honest-to-blog e-stalked by a dude at Northwestern over my sophomore/junior year, which turned into a story for the Daily Northwestern that ended up paying for my Playstation 3. (Some of the writing in this piece is truly lamentable, so bear with me, but I think it remains a gripping read in parts.) As a result, I sort of have freakishly tough skin when it comes to the kind of anonymous hatred you’re likely to experience by putting your name out there in any form; things I have been called over the last six months include “fratty as fuck,” “discursive past the point of any logic,” “feminine with a faggy smile,” etc. By exposing yourself to this and steeling yourself to the logic that anyone distasteful enough to hate from the safety of an Internet screen is definitely not worth fucking with is, I think, an important part of confidence-building, sort of like walking over hot coals. Learn to take the pain, and you’ll realize you don’t even give a shit.
(But also) Don’t: Read comments
What the fuck is wrong with you? Why would you do this? Get over the confidence-building portion, and never do it again.
Do: Respect your editor
You’re not the only person he/she has to deal with, and there’s a fine line between patiently checking up on something and being the flea-ridden freelancer who can’t handle his shit. Don’t worry about following up immediately on every pitch, and don’t inundate him/her with a lot of tiny, irrelevant corrections/requests about how you think things should be; they don’t care, don’t have the time to care, and will almost certainly hate you the second you show some attitude about a dumb thing.
Don’t: Forget to stand up for yourself
But also, fuck your editor some of the time. I have the tremendous luck of mostly working with awesome, capable, professional people, which has given me a sixth sense about recognizing the rotten apples. Those include people who are terrible about getting back to you re: important things, don’t pay on time, grotesquely chop up your sentences without telling you, don’t offer to pay, act unnecessarily aggressive in your correspondence, and so forth. I have the bad habit of developing Stockholm Syndrome with all my editors, which gives me the hives any time I actually have to protest at an unfair request. But it’s important to find a non-confrontational tone with which to voice your beefs, and to acknowledge when you’re being taken advantage of.
Do: Ask for money
This is a sticky subject, since the ESPN site I’m cultivating won’t really afford me the type of budget where I can pay my writers anything worth a damn. (Originally, I was planning on just doing everything myself until multiple people pointed out that would be insane.) Exposure can be worthwhile, and not just a HuffPost buzz word, and it’s important to recognize when you can be a good person/personally benefit by doing something pro bono. (For example, writing for The Classical doesn’t pay but it’s a lot of fun to do, good exposure, working with good people, good times all around, no regrets, FIDLAR.) Some publications, however, can absolutely pay you and are just slow to say so because of the budget they’d like to maintain; please, do everyone in our profession a favor and stand up for yourself to at least demand something for the time you’re putting in, if you accurately gauge them to be capable of paying. This is a good resource about who pays, and you will figure out the rest by asking your friends/contacts.
Don’t: Make it weird for your friends
Eventually, you’ll be lucky enough to become personal friends with editors your own age range, which may embolden you to pitch them on stories you think they might like to publish. Sometimes they will, and sometimes they won’t; remember that love is more important than money, as the-Dream sort of declared, and don’t stress it if something doesn’t work out for totally valid reasons. I’m waiting to see if a pitch will get accepted at a publication where one of my good friends works; if it doesn’t, we’re still going to get drunk and play videogames this weekend.
Do: Buy business cards
You don’t really need to do this. But you will feel awesomely professional every time you hand one out, which actually happens more than you’d expect. (Here’s a good site for templates and such.)
Don’t: Be jealous
I used to get a ferocious case of the blahs every time I heard someone I knew had been hired by somewhere impressive, but I quickly realized this was mostly my ego talking because I didn’t really want to work for those publications; I just wanted to be wanted, you know? It’s hard, but you’ve got to get over it and spend more time chasing the type of things you’d like to do rather than worry about where everyone else is; this is a marathon, not a rat race, and you’ll benefit by keeping the big picture in sight rather than anxiously wondering why you haven’t been approached by BuzzFeed. (Maybe no one else feels like this, in which case I’ve just given myself away as a prideful psychopath.) I recommend familiarizing yourself with the tenets of Buddhism and/or the music of Lil B.
Do: Keep it positive, and spread it around
The corollary to the last step is being open with handing work you can’t do to friends who can, because paying it forward pays for itself in the form of good karma, positive vibes, and all the ooey-gooey liberal values that I will always swear by. In the eternal words of Ash Ketchum in the first Pokemon movie, “Stick together! It’s the only chance we’ve got!” Or, as Morrissey sang, “It’s so easy to laugh, it’s so easy to hate / It takes strength to be gentle and kind.” That’s the last, maybe most important thing I have to impart.