We Got Ann Friedman's Take on the 5 Questions to Ask a Mentor

When I first met Ann Friedman, I had just locked my keys in my car. I underestimated L.A. traffic, parked 15 minutes after our meeting was set to begin, and spotted my keys between my driver's seat and the door as soon as it slammed shut. I couldn't think of anything else to do but laugh.

At the time, I was mostly an unpaid freelance writer, regularly steeling myself for an inbox filled with silence and rejection—so the car keys were the least of my problems. Ann, on the other hand, was and is a recognizable name in media. She's a longtime contributor to New York Magazine and a monthly columnist in The Los Angeles Times. Aside from her many other bylines, including in the likes of the New York Times Book Review and Elle, she hosts the popular podcast Call Your Girlfriend with Aminatou Sow and sends out a weekly newsletter that likely reaches every single cool girl you know. Somehow, given our two extremes, Ann became my mentor.

"It's another way of knowing about how my industry is evolving," Ann told me when I asked about what she's gotten out of mentorship. "Also, it feels really good to pass along the knowledge I've gained to people who can use it!" In the last three years, Ann has helped me polish pitches, edit drafts, navigate the corporate world, and return to freelancing with success. She's also introduced me to a tight-knit group of female creatives who I've leaned on for work and friendship.

Looking back on the car fiasco, I got lucky: It was the rocky but real start of my professional career. So, using a few of my experiences, I reached out to Ann to explain why some questions to ask a mentor may be considered "good" or "bad" based on how constructive they are to fostering this type of relationship. I posed five hypothetically "good" questions, five hypothetically "bad" questions, and a bonus question to help if ever you're lucky enough to meet Ann in person, too.