The first difficult part about introducing Ann Friedman is that you’ve most likely read (or heard) her work and have your own personal sentiment about her, which I’ll likely disappoint. The second difficult part is that she is a (great) writer, which means that in an effort to pick your words carefully you’ll end up scrolling endlessly through her blog in procrastination. A Los Angeles-based journalist, Ann Friedman writes a weekly column for NYmag.com and contributes to a range of publications including The Guardian and ELLE—addressing topics of gender, politics and culture with the rarely equal balance of intellect and approachability. She co-hosts the podcast Call Your Girlfriend with Aminatou Sow, which will make you want to step up your own BFF conversation game. She also slices and serves up funny truths in hand-drawn pie charts with nice ink pens. Ann might not be the girlfriend you can call (or maybe you can, if you’re lucky), but at least she’s one you can listen to.

“It’s three years into the freelance phase of my career, and lately I’ve been re-evaluating a bit and wondering, ‘Is all of this working for me? How can I step it up?’ I go through periods where I’ll take on a lot of new assignments and really push myself. Then there are other times when I recognize that’s not sustainable for a long period of time and I’ll scale back. Balancing between those two modes of working is where I try to be, and generally it’s pretty intuitive, although not always something I can control. As a freelancer, assignments will collide and the world does not always work perfectly with your calendar. There are periods of deadline-packed stress and slower times, too. I think people are obsessed with the question of balance, which is really a question of how you can fit the pieces of your life together, when there’s often very little policy or social support for making them fit. I don’t just mean raising children and having a meaningful job. I mean living a healthy life where you take care of yourself, take breaks from your work, are able to be creative while paying your bills—all of these things pop up in the ‘having-it-all’ debate. I think it’s really fair to ask ‘What are my priorities? What does my week look like, and does that reflect what I care about?’

The worst thing about the having-it-all conversation is the perception that anyone does.

At this point in my career, when I get frustrated, I think: if I told my 25-year-old self that this is where I would end up, my younger self would be like, ‘What the fuck, you’re living the dream!’ I do what I love on a macro level. But on a micro level, at any given time, I may not necessarily be doing something that I love. I have to send invoices and answer emails and sometimes take assignments that don’t really excite me. In the same way, I think there are a lot of people who might enjoy the work they’re doing day-to-day, but on a big-picture level might not like the company they work for. I don’t think it’s helpful to tell people in the early stages of their career to just ‘do what you love.’ I think it’s something that you work towards as opposed to doing it on day one. Perhaps what’s more helpful is the ‘Fake it ’til you make it’ mantra, which I think is about managing your own insecurities, not projecting a false image of yourself. Sometimes, you just need to fake it.

When I was first hired as the executive editor of GOOD magazine, my boss came up to me and said, ‘We need to have a meeting about KPIs.’ Now I realize that this is bullshit management-speak for key performance indicators. But I just said something like, ‘Sure, what time?’

And I remember thinking, ‘What the fuck is a KPI?’ and furiously Googling it.

It was something that made me feel less qualified to be a boss, even though it was no big deal. ‘Fake it ’til you make it’ really came through for me.

Searching for guidance is not a new phenomenon, but people seem especially hungry for advice these days. I think there are a couple of things causing that. For example—take the coastal, 20- and 30-something professional/creative class who are a target demographic of the publications I write for, who are likely to be living far from family and not likely to be church-affiliated. I think there’s something appealing in searching for life guidance from someone you perceive to be a wise stranger—whether it’s from someone you follow on Twitter or a TED Talk you watched or whatever. I think that if you couple those things with how competitive the economy is, there’s pressure to consult with people who you perceive to be more successful, healthier and wiser. But every generation has had their gurus and best-selling self-help books. One of my favorite things to do is to go to the paperback section of a thrift store, or the self-help section of a used book store and witness all of the 80s shoulder-pad-era feminist self-help books, and see how we’ve changed since then. And how we haven’t.

IMG_0083-web.jpg

In terms of what I choose to write about, if I think a conversation is important, I want to help further it. I don’t think fear of saying the wrong thing is a valid excuse for choosing not to write about topics such as white privilege or gender identity.

I’m less afraid of saying the wrong thing than saying nothing at all.

With the topic of Caitlyn Jenner, for example, there were several writers whom I very much respect that wouldn’t touch it. Their reasoning was that there were going to be enough articles about her written by cisgender people, and that by choosing not to write anything at all, they would make space for more trans voices. While I thought that was admirable, I also feel an obligation to use the platform I have wisely. In the piece I ended up writing, I quoted trans people only—using your platform also means sharing it. I think smart people can disagree about how best to use their privileges and platforms. But for me, I would rather that more people talked about these issues than stay silent. So I talk.

In general, I don’t sit down and wonder, ‘What are people going to think about this one article?’ I see my writing as a body of work. I don’t think that one thing I write is going to tip the scales too far in any one direction, which is how I put my head down and get the work done. My number one fear (professionally speaking) is that there will be a bunch of people who have read my work, and they’re sitting around at happy hour, and one of them will say, ‘Remember when she used to be relevant and interesting?’ That’s my nightmare—being irrelevant. I think there’s always that fear that your work won’t live up to what you expect from it. Before I write an article, it often exists in my head as the best possible representation of that idea or topic. Then after I’ve written it and gone through the whole editing process, it’s just another article. It doesn’t do all of the things that I wanted to do. Maybe sometimes it does, but it’s rare. That disconnect between expectations and reality happens across the spectrum, from big and important to little and unimportant. Even just getting dressed in the morning. Like, I bought these culottes last week and thought they were going to be so chic, but when I put them on I felt like a midwestern mom.

There is constant work to be done in balancing your own expectations with reality.

My parting advice would be based on shine theory: I don’t shine if you don’t shine. The fundamental idea is that your network and the people in your life are really, really important—professionally and personally. I have a lot of people in my life who aren’t journalists who I turn to for professional advice. When I look back on my career and think, ‘How did I get that opportunity?’ I can almost always point to a person or group of people who were not official coworkers. Also, I really stand by the idea backing yourself. Which doesn’t mean that you can’t admit when you’re struggling with something, but there’s a lot of power in standing behind what you want and what you’re capable of.”

Ann’s #OKREALTALK Tips

  • What would your younger self think of you now?
  • Don’t be silenced by fear of saying the wrong thing.
  • Call your girlfriend.
ok

b. 1982

annfriedman.com

t. @annfriedman
i. @annfriedman

Photography courtesy Ann Friedman

As told to Amy Woodside, September 2015