The Freelance Life
I love being a freelance editor; I also kind of hate it. If you’ve ever been a freelancer yourself, I’m sure you’re familiar with the ambivalence. Case in point: Nothing beats the comfort of sitting in a café, sipping a cocktail on a Wednesday afternoon, knowing you have a month of work lined up starting next week. Meanwhile, the rest of the world is locked away in tall buildings, and you feel like you’ve somehow gamed the system. But the same situation with nothing on the books? Well, that’s an invitation to a panic attack.
In 2017, I left a job I’d held for nearly a dozen years for a permalance gig with a large newspaper. I had hoped it would turn into a full-time gig. When it didn’t, I was suddenly adrift and, like so many others, turned to freelance out of necessity.
What I learned in the ensuing months can mostly be reduced to two interweaving dynamics. First, your network is your life. It sustains you with opportunities. Second, if you’re not careful about choosing the right work, you can quickly become very busy at being unfulfilled.
As a practicing introvert, I found nothing scared me more than the proposition of networking. In hindsight, I think I didn’t understand the true nature of the endeavor. Networking is an act of imagination. It’s an attempt to create a future with people you admire. Yes, it takes vulnerability and has the potential to leave you feeling rejected, but so does any other project worth your time. Talking to people, reaching out for advice, assistance, or the possibility of collaboration, are all part of the process. They are just as essential to making stuff as a camera or a fast computer. I’ve learned to practice these skills the way I would learn a new piece of software: At first, it feels clunky and awkward, but with enough research, reading, and firsthand experience, it becomes much easier.
My friend and fellow freelancer Meredith Hogan adds, “It feels weird to ask for work. But do it anyway. Also, while the steady drumbeat of layoffs in our industry is a morale-buster, the silver lining is that all of those people — as they spread out to new jobs and new organizations — just widened your potential pool of clients.”
A metaphor that’s helped me along the way is to think of my network as a garden: I plant seeds without expectation. A friend of mine works at a famous film company. I contacted her as soon as I left my job. It took another eight months before work finally showed up. That’s not unusual. Freelancers are often the last people picked for the team. While you wait, it helps to become friends with uncertainty. To hone that skill, I recommend The Places That Scare You by Buddhist nun Pema Chödrön. I also use the free software Trello to keep track of whom I’ve contacted and when. That way, I can be reminded to follow up every month or so and not become a nuisance along the way.
Decades ago, when I worked in television, I helped a colleague find a job. He never thanked me. Worse, I never heard from him — until he came looking for work again. I learned then not just to ask people for things. You have to check in with people even when you’re busy. Ask how they are. Buy them a drink. Send a thank-you note. People appreciate kindness. A network is a living thing. It must be nurtured.
Beyond just finding work, though, it’s crucial to find the work that feels right. In many ways, this can be the most stressful part of freelancing, as it requires one to say no to otherwise viable opportunities. For me, this presents the most challenging question: what to do when a solid money-making gig is offered but there’s the possibility of a more interesting, less definitive one that might happen at the same time. There’s no easy solution to this problem. It’s like trying to play poker with cards missing.
Money is on the table, so you should take it, right? Well, maybe. But if you consistently make that decision, you can find yourself swamped with work
that you don’t necessarily want and isn’t particularly meaningful. And as writer Annie Dillard rightly says, “How we spend our days is, of course, how we spend our lives.” Sure, you have to pay the bills, but you also have to curate your own career. No one else is going to do that for you. In hindsight, I feel like I spent 18 months successfully hunting for work, found good opportunities, but nevertheless forgot to stay focused on my primary career goals. A helpful guide to maintaining the right focus in that area is Essentialism by Greg McKeown. He writes, “As hard as it can be to say no to someone, failing to do so can cause us to miss out on something far more important.”
I’ve spent considerable time thinking about this problem in the last two years. In doing so, I created a flow chart. I’m not certain it presents the best answer, but it’s the best I have right now.
Freelancing just might be the best/worst thing that’s happened in my career. Meredith again echoes my own experience: “I’ve been able to collaborate with people whom I’ve admired from afar but couldn’t work with directly until now, and I’ve reunited with favorite former colleagues to do work too.”
But freelancing can be a lonely life, working at home alone for weeks at
a time. And come bill time, it can be frightening, too. But for photographers and filmmakers, the best opportunities are often measured in months, not years. It’s a scary proposition to be sure. Bruce Springsteen put it best: “Mama always told me not to look into the sights of the sun/ Oh, but Mama, that’s where the fun is.” ■
This essay was originally published in the September/October 2019 issue of National Press Photographers Association News Photographer. Reprinted with permission.
