How Ann Friedman Found Freedom in Freelancing

How Ann Friedman Found Freedom in Freelancing - Ann Friedman Interview
Photo: Jorge Rivas

If you think building a multimedia brand is strictly reserved for venture capital-backed power-players, it’s time to think again. Cast your eye to Ann Friedman, a one-woman army whose personal brand includes a popular podcast (Call Your Girlfriend, co-hosted with Aminatou Sow), a weekly newsletter (The Ann Friedman Weekly), a regular column at New York magazine’s The Cut, and features for Elle, The Gentlewoman, and The Los Angeles Times, among others.

Ahead, Friedman shares the highs and lows of building her own media company, her daily routine, and what success means to her now. (Spoiler alert: It isn’t about the fancy title.)

Can you tell me a bit about what you’re currently working on?

Ann Friedman: I just wrapped a few interview-based magazine covers, including Allison Janney for the latest issue of The Gentlewoman and one I can’t tell you about yet for Glamour. I’m still writing for The Cut, where I was a columnist for four years, though I’m more focused on reporting these days. And I’m almost at the five-year anniversary of my newsletter, so I’m writing a “What I’ve Learned” post about it. I’m also scheduling interviews with authors for our spring books episode of Call Your Girlfriend and also trying to stay on top of some annoying tax stuff.

Right now, you run your own digital multimedia company. But when you think back to the early days of your career, when you were just out of college, did you have a different idea of what you’d end up doing? Did you have, say, a 5- or 10-year plan?

AF: I’ve never had a five-year plan. I’m just not very good at thinking several steps ahead. I like focusing on the next goal, and then when I achieve it, deciding what to do next. When I graduated college I could not have predicted that almost my entire career would be in digital media – I just sort of assumed that eventually, I’d ease into print prestige or something. But very quickly, it became apparent that digital was not only where the jobs were, but where I was most excited to be working. And I never, ever could have predicted the self-employed set-up I have now.

“I’ve never had a five-year plan.”

I read that you started out as a freelancer by chance because you were fired. Looking back, do you think you would have ended up going freelance by choice, at some point?

AF: I’m not sure. I tried to go freelance in early 2011, but that only lasted a few months because I got an editing job offer. Which was lucky because I think I would have run through my savings pretty quickly. After I was fired from that editing job in mid-2012, I thought about getting another staff job, but I didn’t want to leave Los Angeles. So even though I was forced into it, I really did choose to stay in self-employment. Now it’s hard to imagine going back to a staff job.

What was your first year of freelancing like? Was it nerve-wracking?

AF: It was very, very hard, but I’m proud to say that I made it through without asking my parents for money. I had lots of connections to editors, but when you’re just starting out and have yet to make a name for yourself as a writer, rates are low. You have to produce so many pieces just to make rent, and there’s the guilt that crops up whenever you step away from your laptop. As I’ve worked hard and built some of the things I do into micro-businesses, that’s taken the pressure off of writing. Now I make money from my newsletter and the podcast, in addition to pushing my writing rate up, which means my life is still busy but feels very sustainable.

After you had been freelancing for a while, you started your podcast (with co-host Aminatou Sow) and your newsletter. Did you have plans to sort of branch out into new types of content and expand your business or did you think of these more as hobbies at the beginning?

AF: They weren’t hobbies, but “experiments” might be the right word. When you’re self-employed and not applying for staff jobs, you have to pursue ways of expanding your professional skill set on your own terms. I wasn’t interested in the newsletter or the podcast because I thought they’d be businesses of their own, but I did think that learning those skills would serve me in the long term. And it seemed fun to play around with both email and podcasting.

“You have to pursue ways of expanding your professional skill set on your own terms.”

Once you had your various writing projects, your newsletter, your podcast – all the components of a multimedia company – how did you figure out how to structure your days? Especially because, as it was just you, you had to also deal with the admin side of being a business?

AF: Years of paying attention to when and how I work best has led to a rough daily schedule of doing my writing (or most intellectually taxing) work first-thing in the day, then doing interviews, email, that sort of thing in the afternoons. With both the newsletter and the podcast, there was a period of extreme growing pains while I figured out the business/admin side. When I was figuring out the recurring-payment software for the newsletter or when we were trying to figure out which ad reps to work with for the podcast, it felt like all I did was admin work. But now that I’m over the hurdle with both, I can honestly say that the business side is a relatively manageable part of what I do.

Was there a moment where you felt like you switched from being a self-employed writer to a business – or was it one long progression for you?

AF: It was a gradual progression. But when I incorporated in 2015 it felt like a milestone. Incorporating really helped me take myself more seriously as a business, even though it was technically just a tax-designation change and I wasn’t doing anything new.

And has there been a change in what success looks like for you?

AF: At the very beginning of my career I think I defined success in terms of title or role, like “Senior Staff Writer at Very Important Magazine.” Now I’d say success is having a lot of appealing options, enjoying the freedom to explore new things that interest me or take time off when I need it, and being secure enough (financially, professionally, emotionally) to say no to the things that don’t align with my values.

“Success is … enjoying the freedom to explore new things that interest me.”

Traditional media companies such as the New York Times wield a lot of power – and in this “fake news” era, it seems that credibility and influence are more important than ever. As your business has grown, have you found yourself being more mindful of what you say and write? Do you think you have a responsibility to do so?

AF: I do feel a responsibility to be accurate and thoughtful and considerate in what I write and say, but that is not necessarily a new thing. I think that if you want a platform, you have to accept responsibility for how you use it.

Do you see yourself ever going back into the workforce and taking on a 9-to-5 job?

AF: It’s hard to imagine right now, but like I said, I don’t really make 5- or 10-year plans. So, who knows?

Lastly, just for fun, which product gets you through the day?

AF: I have to say my laptop. But also: water (is that a product?), my Vornado space heater (this time of year) and Intelligentsia El Gallo Breakfast Blend coffee (every morning).

Which podcast do you listen to most (besides CYG)?

AF: I jump around and listen to a lot of different things, but I’m a reliable This American Life listener. (Yes, I know everyone’s heard of it already and you were probably expecting a new rec here. Sorry!)

What do you do to relax?

AF: Read fiction. Walk in the park near my house. Cook dinner. Lay flat on my back on the floor of my office.

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By |2018-10-14T17:37:16+00:00April 3, 2018|Cover Story, Entrepreneurship, Work|

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