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.)
DO: WAKE UP EARLY
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 Z extra.)
DO: CULTIVATE MULTIPLE INTERESTS
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.
DON'T: FORCE THINGS
There was a horrible month where I published eight things in four weeks on 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 that work, 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 your roll and wait for inspiration to strike, which gets easier the more culturally literate you become. Remember, getting accepted is just half the battle; you've actually got to write about something after that, and if you've overstepped your bounds everyone will be able to tell.
DO: FIND YOUR PEOPLE AND STICK BY THEM
One of my more ignoble claims to Tumblr fame was a slightly defensive post I wrote about people my age who were too quick to be friendly with writers/editors older than them so that they might bootstrap their professional stature. It got a lot of responses, some of them fair and some of them not; in retrospect, I was salty about a dozen other things, which led to being less articulate than I could have 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 stuff done, and whom you can hopefully hang out with IRL. (IRL > URL, always.) The best personal/professional development of my life over the last year has been offline vibing with a circle of other young Internet writer types; it’s nice to be surrounded by people who are 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 working similar gigs to you are the most likely to share your same hopes, fears, etc., about how stuff is going.
As you’re going to end up irrationally insecure and paranoid at least 20 percent 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 anyway, is that once you’ve found the people you get along with, you should stick by them 100 percent of the time. No subtweeting, shade-throwing, reputation undermining, or any of that. It’s not cool, and believe me, people will absolutely notice your capacity for loyalty or lack thereof; in fact, it's one of the first things they will notice.
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. As a result, I think I have relatively tough skin when it comes to the kind of anonymous hatred you’re likely to experience by putting your name out there.
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. Here, repeat with me: Anyone who hurls vitriol from behind the facade of anonymity isn't worth paying attention to. If they use their name, then just respond if whatever they've said really gets your goat. (And please, learn how to pick your battles.) Exposing yourself to this is 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 care.
(BUT ALSO) DON'T: READ COMMENTS
What is wrong with you? Why would you do this? Build your confidence and then get away, forever.
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 baby who needs his binkie. 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. (If they think that adverb should go, then let it go.)
DON'T: FORGET TO STAND UP FOR YOURSELF
But also, screw 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 on time-sensitive things, don’t pay on time, 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 I don't pay contributors at Brooklyn's Finest. (Originally, I was planning on just doing everything myself until multiple people pointed out that would be insane.) But 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, The Classical doesn’t pay—not the website, at least—but it's a ton of fun and great association.)
Learn to tell the difference between a labor of love—like this website!—and an established business. Websites vary, but somebody working at a publication with a print edition can absolutely pay you and is just slow to say so because of the budget he would like to maintain. Please, do everyone in our profession a favor and stand up for yourself by at least asking for something for the time you’re putting in. 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, 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 a bigger deal than money, as The-Dream sang, and don’t stress if something doesn’t work out for totally valid reasons.
DO: BUY BUSINESS CARDS
You don’t really need to do this. But I have felt like a human God every time I hand one out, which has happened more than I'd have expected, usually to non-media types who might not know how or want to follow you on Twitter.
DO: GET USED TO BEING ALONE
I have a few friends who I swear haven't been single for more than a few weeks since their first pubescent breath. Fortunately, I am the complete opposite and have gotten pretty well acquainted with being alone (hey ladies!), which is a constant of writing. You can't concentrate with someone jawing in your ear, can you? You're inevitably going to spend a lot 0f isolated time if you work at home and have roommates with conventional work hours (or no roommates at all, but if you're making that kind of bank off freelancing you must be Michael Lewis).
It's important to know how to stay focused without human contact, which means saying no some of the time when people want to hang out and also acknowledging when you just need to be by yourself for some much needed mental detoxing. But also don't forget to interact with people so you remember what it's like to be smiled at; roommates you like can help with this, but going to the coffee shop can substitute for that in a jiffy.
DO: TAKE CARE OF YOURSELF
A scenario that repeats itself all too often involves me waking up, sitting in bed as I begin working, and getting so into my task at hand that I forget to eat until the afternoon when I've been up since nine. It's a terrible habit, and leads to feeling lethargic and clammy given too many missed breakfasts; I recommend keeping a variety of quick meals on hand, whether it's cereal or a bucketful of hard-boiled eggs (don't laugh, one or two will give you turbo fuel for a few hours) so that you can satisfy the gremlin in your belly without spending too much time off-topic.
Take vitamins—if you're not worried about the correlation to gallstone incidence—and try to go for walks if you're too lazy to join the gym. I mean, I don't know shit about "keeping healthy" but it seems like it takes little effort to avoid processed foods, get sunlight/mild exercise, get a good amount of sleep from time to time, etc. It's not really that appealing to be one of those manic man-boys/girl-women who proudly, precociously trumpet their inability to take care of themselves. Basically, just don't try to be how I've imagined Josh Radnor's character in Liberal Arts (a movie I have never seen).
DO: SAVE YOUR RECEIPTS
I don’t have much to say about this because 2013 is the first year I’ve done so, but I assume that at the end of the year I’ll be able to hand this packed binder to a tax guy who can figure out how to write off the tickets for movies I ended up writing about. Just get one of those file folders and save everything.
DON'T: STRESS YOUR 'BRAND'
Up until late 2011, my Twitter was private and useless; it's only a little less useless now, but I've opened it up and attempted some veneer of what I might call "professional" as a way to keep in touch with people in the business, so to speak, although I did spend the entirety of Pitchfork Music Festival weekend tweeting just the most inane bullshit, so who knows.
Social media is an important way to network with folks you might not know and get new work, but your work will always speak for itself more than whatever image you're able to project via the many, many ways we project our image in the digital age, so don't worry about followers and notes and retweets or whatever. Just focus on being good, which is a function of time and effort, not how many digital strangers want to make out with you.
DO: MAKE YOURSELF COMFORTABLE
Since you’ll probably be working from home, make sure you enjoy doing so. Invest in a new computer if you have the money, or a new desk. (It’s tax deductible!) Listen to music, bounce a ball against the wall, take small naps; do whatever you need to do in order to be in a right frame of mind so that you don’t end up going stir crazy every day. Working from home means you don’t have to pretend to be alert, so treat yourself to that massage every once in awhile.
DO: SET LITTLE GOALS
Alright, I’m veering dangerously into some self-help stuff, but bear with me. Obviously you should set goals for yourself in every area of life, whether it’s moving out of your mom’s house (check!) or learning how to drive (nope, city living forever). In this sense I mean you should pick specific writing things you’d like to do within a set time period, whether it’s getting a pitch accepted somewhere you haven’t written before, writing something that’s more than 2,000 words, getting something in a magazine instead of a website, or whatever. The more specific you can be in terms of topic/publication, the more motivated you may be to get it together. But manage your ego and expectations: nine out of 10 times, all your story is going to amount to is a paycheck, appreciation from your colleagues and friends, and a meaty clip for the resume. Still, that should be enough.
DO: READ A LOT
It’s worth stating. Read novels, short stories, poetry, long-form articles, short-form articles, essays, think pieces, investigative pieces, history, philosophy, anything and everything, especially if you find yourself unable to write at the moment; it all ends up being valuable if you’re paying attention.
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.
Writing is a marathon, not a sprint, and you’ll benefit by keeping the big picture in sight rather than anxiously wondering why you haven’t been approached by MySpace. (Maybe no one else feels like this, in which case I’ve just given myself away as a prideful psychopath.) Read Buddhism! Listen to Lil B! Start taking psychedelics! Stay happy, friends.
DO: KEEP IT POSITIVE, AND SPREAD IT AROUND
The corollary to the last step is 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 until death or whenever I start appreciating Phil Mickelson, whichever happens first. 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.