Penelope Trunk

Penelope Trunk is no stranger to controversy. As a finance advice columnist for Yahoo and the Boston Globe, she advised women in their early 20s who want kids to “take that career drive and direct it toward mating — your ovaries will not last longer than your career." When the founder and CEO of Brazen Careerist who blogs about work-life issues for Gen Yers recently used Twitter to announce that she was in the middle of a board meeting and having a miscarriage, she set the blogosphere on fire. But for Trunk, 42, who began her career as a professional beach volleyball player and then spent a decade as a software exec before founding three companies — undergoing an IPO, merger and bankruptcy along the way — and writing a book, “Brazen Careerist: The New Rules for Success,” it’s all about honesty and transparency, including her own life. Not too long ago, she blogged that she has Asperger’s, as does one of her children. Divorced for about a year, the mother of two boys, 4 and 7, is about to marry again, this time to a farmer near her Madison, Wisc., house.



You were a stay-at-home mom for a while, but you say that was not the life for you. How long did you stay at home, how old were your kids and why wasn’t it right for you?


I stayed home until my youngest was 4. It wasn’t for me because it’s a very unstructured life — you don’t know when they’ll sleep, when they’ll wake up, when they’ll throw a fit. The level of unpredictability blew me away. Kids need constant attention and constant care. They’re in the moment and you can’t think about stuff. I felt like I was in limbo constantly. I don’t know how people do it. There’s no reward system, no structure for who’s better at it, there’s no performance measurement. Work is so easy compared to that. It’s frustrating not only how hard it is, but how little society respects it. I think day to day, people are just trying to get through the day; over time, it’s rewarding.


You told a funny story about trying to promo your book while mommying, which is something all parents on some level have to deal with. Do women have a harder time with this, and why?


They care more. Men don’t care as much. When women and men have the same job and the same hours, women will feel more guilt over the kids and women will compromise their work more. The difference in pay at work only occurs when they have kids.