Freelancer Interview: Brady Gerber

Brady Gerber recently left a career in music PR to reinvent himself as a full-stack software engineer. But the one thing that’s been consistent throughout his career transition has been freelance writing. With bylines at New York Magazine, Rolling Stone, Pitchfork, and many more, Brady has amassed an impressive body of work on his own terms, always on a freelance basis. To get a better understanding of what life as a freelancer is like, I asked Brady a few questions about the industry, and his biggest challenges as a self-employed writer.

How long have you been freelancing?

I made my first blog over a decade ago while I was in high school. My earliest freelance stories came out of writing those daily blog posts and wanting to flesh out those ideas on the other blogs and outlets I liked. From there, I gradually started pitching bigger outlets and magazines, and now I mostly freelance for New York Magazine.

What was it that drew you to freelancing in the first place?

There’s great clout and exposure from being a staff writer at a well-known publication, but I’ve always loved the freedom and flexibility of freelancing. I love being able to work with different outlets and editors and being pickier about the features I write. As a freelancer with a day job, I get to work as hard as I want since I’m not depending on freelance checks to pay the bills, and I can stop writing for a moment if I need to take care of more important things in life. I don’t publish too many stories throughout the year, but I care very much about everything I write, and that’s more valuable to me.

What is your strategy for pitching editors?

When pitching a new editor, I try to do the heavy lifting early on by researching, writing, and editing a strong pitch, and then (respectfully) following up as needed. By researching a lot and taking the time to write a solid pitch, I’ve established a foundation and have a better idea of a story, instead of “This band has a new album out next month.” If an editor likes the pitch, the work turns into us working together to build upon that foundation.

What is your worst freelancing experience?

I once pitched an outlet that would have been an impressive-sounding byline but was notorious for dropping stories and not paying writers. The pitch was accepted, I filed my draft, and I never heard from them again. When your friends and colleagues tell you that an outlet isn’t worth their byline, they’re probably telling the truth.

What is your best/most seamless freelancing experience?

Over the recent years of freelancing for New York Magazine, my editors and I have developed a kind of professional trust. It started slow and didn’t develop overnight, but from consistently pitching and filing on time, and being respectful when receiving edits, feedback, and rejections, we’ve gotten to know each other and have found a groove of how to work together. Establishing that trust not only gains you more work, it also gives you the opportunity to work on bigger and more challenging ideas, since an editor is more willing to take a chance on a writer they already know.

Do you track invoices and outstanding payments? If so, how? If not, why not?

I have my own private excel spreadsheet where I keep track of my invoices and payments, and I update new and outstanding payments as I go. I try to stay on top of updates as they happen in real-time so that when tax season comes, I have all my info ready to go and don’t have to frantically try to remember an entire year’s work.

How much time do you spend tracking down payments or following up with assigning editors?

I’ve been lucky to work mostly with editors who are transparent and communicative about payments and edits, and who are not bothered by the occasional follow-up; even if payments are slightly delayed, it tends to work out in the end. I also realize that because I have a day job, I don’t feel as urgent to aggressively track down payments. If I was a full-time freelancer, that would be different.

How long does it typically take for cash to hit your bank account after you file a story?

There are always exceptions, but for my interviews and features, when there is a clear timeline, an invoice is usually taken care of within 30 or so days after a story’s run date.

What tools would make your life easier as a freelancer?

I’ve recently embraced using Google Calendar to remind myself when to follow up on pitches, and to keep track of the different stages of writing a feature. I now try to establish clear due dates for outlining a feature, writing a first draft, editing that first draft, and then polishing and grammar-checking everything before filing. Any tools that would help make the scheduling of the actual writing would make life easier.

Anything else?

You can only benefit from taking the time to learn about personal finance and write out a plan for how to be financially OK, in good and bad times. Freelancing is such volatile work, you’ll want some kind of consistency to keep you grounded. We all have access to different tools, networks, and sources of income; what works for me might not work for you, and that’s OK. The most important thing is to have clear goals and make a plan that works for you.

Also, a great bit of non-finance advice that I received when I was starting out as a freelancer: read more than you write. Good writers are good readers. Read as much as you can, especially about subjects you’ve never written about or don’t know much about, to learn the kinds of writing that grab your attention.

Brady is lucky that his experience has a freelancer has been mostly issue-free and payments typically come on time. If you’ve been keeping up with our blog, you know that there are some cases in which freelancers never receive payment at all. It’s these issues that served as the spark for building OutVoice. 

Want to know more? Click here to schedule a demo with our founder, and learn how to save your freelancers once and for all by paying while you publish, and putting out calls for specific content, as needed — all on one platform.