(1) Create a digital jpg of your signature and save it so you can insert it into any invoices/contracts. Saves the annoyance of printing, signing, then scanning! Keep track of stories and projects you’ve pitched and gotten assigned in a Google spreadsheet so you know where you pitched and if you got paid. Too much to keep in your own head, and e-mails get lost! But do label those e-mails, so you can find them easily.
(2) Use Boomerang for Gmail (free for up to 10 e-mails a month, you likely won’t need more) to send follow up e-mails so people get them at the right times instead of at 2am when you thought of an idea or remembered you never got paid. Gives off the aura that you are less crazy than you are, even though everyone, including you, knows that you are crazy. Why else would you be a “freelance” “writer” “slash copywriter” “inserting scare quotes into everything you do”?
(3) The Affordable Care Act is not perfect, and it may not have been created for us freelancers, but it does make it possible for us to continue this lifestyle in a manner that offers a feeling of stability and security without paying a $600 COBRA until we die of natural causes. It is important and it’s worth signing up for.
(4) Give yourself permission to write the things that matter to you. If you have a freelance desk job that isn’t your whole heartsoullifeblood, that’s okay. That’s preferred, actually! Because it means you won’t have to write about crap you don’t care about, just to survive. If you’re not getting published in all the “fancy” places, that’s okay. If people ten years younger than you are who are effortlessly beautiful and effortlessly successful and have that effortlessly shiny, Ivy League hair are getting featured on cool podcasts about the writer’s life and humblebragging about their latest New Yorker/Harper’s/New York 4k word feature, that’s okay. (Actually, it’s not okay, that’s fucking infuriating and you hate them, but sometimes good work comes from seething jealousy, once it converts into inspiration.)
Occasionally, it has been said and thought, the writing that matters most (to the person writing the writing and the people who may read it, or not) takes longer than a tweet, 20 minute phone interview, or even week-long pitch-then-frantically-write-to-meet-deadline binge to complete.
It has been said that the “industry” is changing. That “content” is king. That “longform” is kinda cool, again, nostalgic, even, and why not, people will save it to that app that lets them read 10k words on the subway. That there are new ways and angles to do what you do because it’s all that you know how to do, without feeling like your life, as a writer, is kinda meaningless. It has been said, it has been discovered, by some, that the trick is to write for you. To write what you want, because you want to. Not because it pays. That’s why you have that desk job, remember? That’s why you decided not to pitch stuff that you don’t care about, so that you have the time to do what you do care about, even if you keep inventing reasons not to have the time, still, even if you do.
(5) So work on that. Work on finding the patience to allow the words to come to you and let them spill out, sometimes terrible and sometimes not half bad, maybe. Work on working on finding “a time to write every day” or at least every week. Work on ways to forgive yourself for typing the worst sentence ever written in the history of words, until the next sentence, lol, that was even worse, let’s watch an episode of The Bachelorette because you are a farce so you should watch a farce and root for the farce to become a real thing with all the “right reasons.” Work on working on it. Even talking about it casually, occasionally, means you’re at least thinking about it, which is better than not thinking or working on it at all. But work on not talking about your “process” whenever someone says “What’s it about?” and continue to fine-tune a polite answer that expresses a combined thanks that they’re asking and seem interested with a vague description of what it is, without going into detail, followed a seamless change of subject, because what the fuck are you supposed to say about your WORD DOCUMENT that is the embodiment of every atom of your being, all your hopes and dreams, the compulsion that sickens and enlivens you at once, etc., you can’t talk about this in public without sounding insane, so stop! But be cool about it. This isn’t the time or the place. You’re just out having some frozen yogurt. You wish it was ice-cream. You wish you were home finishing that book you’re addicted to reading that you wish you wrote, but at least it’s in you now, and somehow, you have faith that its influence will reach the part of yourself that you bury along with the stuff that scares you the most, which is why you’re trying to write about it, which is what you know is the story that you want to tell and that eventually you will.