Not That Kind Of Mentor: What I “Learned” In My Second Year As A Freelance Writer

freelance writer advice

In 2014, my second full year as a full-time freelance writer, I had two interactions that underscored how weird and nebulous the industry I’ve chosen is. The first was with a four-year-old child who was avoiding his nap and telling me all about his plan to become a racecar driver.

“I have to listen to my teachers because I have to be a racecar driver and you have to go to college to be a racecar driver and you go to college when you listen to your teachers.”

“Okay, sounds great. Go to sleep.”

“What are YOU going to be? A racecar driver?”

“I’m a writer. Seriously, it’s time to close your eyes now.”

“So did you went to college and you said I want to be a writer and they said okay you be a writer and now you’re a writer? Because I’m going to be a racecar driver.”

“…That’s actually pretty accurate.”

The second exchange was with a very sweet young woman who’s currently in her sophomore year at the college where I did my undergraduate work. She’d read some of my writing, which is primarily about television and pop culture, and wanted to know what she should be doing to pursue a similar line of work. I suggested books and websites to read, encouraged her to take in as much pop culture as she could and argue about it with smart people, and explained why she might want to consider graduate school at some point.

“Right,” she said, “But what do I, like, do?”

I knew what she wanted: concrete, practical, infallible advice about pitching, finances, and making it work. But the trouble is that writing is an industry with few set qualifications and rules, and my career has broken the few that there are. I was in the right place at the right time with the right skill set, and I stayed in that right place and worked my ass off. And so I can’t present a clear career path for others to emulate because I didn’t have one. That frustrates me, because I’d like to be a help to young writers, and especially young women, who (perhaps against their better judgment!) want a career like mine. I’m short on practical advice, but here’s what I’ve learned so far.

Do not work for free.

Stop for a second and say those words out loud to yourself. You will be asked to work for free when you’re starting out as a writer. Depressingly, you’ll continue to be asked to work for free after you’re already “established.” And you’re probably going to be tempted to do it – after all, it’s good exposure, right?

Sure, it’s important to get your work “out there,” but there are ways to do so without letting someone else profit off your work. Write for college publications if you’re still in school, start a blog, or look for chances to publish with non-profit sites or literary magazines.  Frankly, anytime you work for free, you contribute to breaking the industry you’re trying to break into. The more writers work for free, the more employers publishers will decide that writing is a job that’s not worthy of fair compensation. Don’t ruin it for yourself or for the rest of us.

Don’t quit your day job (until you can).

I freelanced in one capacity or another for over five years before I quit my day job. I had a respectable amount of money socked away when I finally resigned, but was unprepared for how long I’d have to wait between freelance checks sometimes. Even though I thought I’d responsibly prepared for whatever financial setbacks came my way, I wasn’t ready for how quickly my reserve would drain while I frantically re-invoiced clients.

Put money aside, stay at your day job until it’s driving you absolutely mad, and then stay another 90 days and save, save, save (you can do anything for 90 days). And don’t get bogged down by the idea of not having a “real writing job” in the meantime. There’s nothing wrong with having a not-all-that-awesome day job for awhile if it’s paying your bills and allowing you time to write on the side. Keep your head up, bartenders and baristas.

Don’t go it alone.

I don’t have traditional co-workers anymore, which was a huge transition after leaving an office where I liked (and played board games and brainstormed with) the people I worked with. In the years since I’ve been in a traditional workplace, I’ve had to do things differently.

Fortunately, one of my oldest friends is a writer whose work is not so very different from mine, and we’re able to spend a lot of time working alongside each other. Sometimes we meet up in person, but most of the time, we chat online and swap ideas, jokes, and commiseration. (Even as I’m writing this, I’m semi-grumpily waiting for her to come back to Google Chat so I have someone in the trenches with me while I work.)

Chances are you already have a friend in your social network who’s a writer, too – reach out and see if they’d like to be writing pals. Ask for their feedback. Say “yes” when they ask for yours. Read the same things and nerd out (or passionately disagree) about them. Complain about how tired you are.

Always, always be on time.

The best compliment I received this year came out of the worst professional mistake I made. Because I review a lot of television, I often file work late at night and then immediately go to bed. And because sometimes the freelance life is awesome, I often go to bed without setting an alarm and sleep late.

On October 31 – I remember the date clearly because I later joked on Facebook that I was apparently going as someone CAVALIER ABOUT HER CAREER for Halloween – I woke up to a couple of emails and a Twitter DM from my editor asking where the piece I’d submitted for that day was. I panicked and quickly realized I’d forgotten to actually send the piece in. I apologized profusely, and my editor was very understanding, saying, “I was worried about you, not the piece! You’re literally never late.”

There are a lot of things you can’t control as a writer. You can’t decide which editors accept your pitches or ensure that a piece turns out the way you’d planned it to be. But you are in control of how and when you turn your work in, and editors see and remember that. Be the person who is literally never late.

You are not out of time.

I laugh hysterically at how overwrought I was as a 24-year-old because I felt like I “hadn’t accomplished anything yet.” I’d read 30 Under 30 lists and think about how my time was running out (spoiler: it ran out, I was never on one, and everything’s fine), and I wound up wasting a lot of energy on the idea that my life was a mess and career was a shambles.

You’re not out of time. You’re never out of time. You can say you’d like to do something before 25, or 30, or 40, but you don’t get extra credit or a prize for sneaking an accomplishment in before a milestone age. (The New Yorker ran a “3 Under 3” list earlier this year that I read when I need to regain perspective about this.) Some of the writers you admire did their greatest work when they were very young; some did it later in life. Relax. Don’t let worry over the fact that you haven’t done something yet keep you from actually doing it.


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Lauren Hoffman lives and writes in Seattle, Washington. By day, she's a freelance writer and editor; by night, she's at work completing a book-length non-fiction project, Up High Down Low.