Mom Interviews

Penelope Trunk

Freelance Writer & Blogger, Author of Brazen Careerist

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Penelope Trunk is a freelance writer and blogger. Her book, Brazen Careerist, has just come out and it's filled with refreshing and unexpected career advice from which we can all learn something valuable. She also writes one of our favorite career blogs; its tagline is "Advice at the intersection of work and life." Penelope lives in Madison, Wisconsin (where she moved to from New York City without ever having visited before), with her husband and two kids, ages two and five.

In her revealing interview, she talks about how being in the World Trade Center tower as it was collapsing changed her life and her career, from a software executive to a freelance writer. Penelope is also extremely honest about the challenges she consistently deals with while juggling work and family and why using a coffee shop as an office means that sometimes you have to cover more than just your own tab.


You are a freelance writer and many, many professional moms we speak with tell us that they would love to make a living as freelancers. Can you talk about your work, how you came to be a freelance writer, what it entails on a daily and longer-term basis?

I founded two startups and Time Warner asked me to write a column about life an as executive. Compared to the pay for a software industry executive, the pay for being a columnist was terrible, so I wrote it as an afterthought – from train stations, from department stores.

I had no idea how big it was until I wrote about my company’s beach party – about how stupid it was – and it turned out a large portion of the company subscribed to the column. And I got in trouble.

But I kept writing. Then the World Trade Center fell, and I was standing right there, at the bottom. I was so close that I didn’t even know the building fell. I thought it was a bomb.

I went through all those stages you read about when you die. My life flashed in front of me, I was sad, and then I got very calm and accepted death. But I didn’t die. Before I ran out of breath, someone broke a window in a building and I could see light shining and I pulled myself in the broken window.

After that, I couldn’t go back to work. I could barely even leave the apartment except to go to my trauma group meetings. But I kept writing my column. And I told everyone I was unemployed.

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