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.
Most people say time away from the workforce will undermine a woman’s career. You say that’s no longer true today. Why?
We don’t have any data to show that leaving the workforce undermines a woman’s career. We don’t even have a generation of women who had a career and came back, so we can’t even have a real debate about that. If you had a good career when you left the workforce, you should get a good career when you come back. The real problem is if you never knew what you wanted to do. Then it’s not a reentry problem.
You’ve surrounded yourself with helpers — not only a full-time nanny and housecleaners, but also a $50,000-a-year house manager. You advise women to “marry a stay-at-home spouse or buy the equivalent.” But, you had a stay-at-home spouse and it didn’t work out, and many women or men can’t afford that kind of help. What’s the answer?
Everyone can afford that kind of help. I don’t own a house, I have a $4,000 car, I haven’t taken a vacation in eight years. We never go out to eat. It’s just about sacrifices. People assume I’m living this crazy lifestyle, and I’m not. I live in a 1-½ bedroom house. We have no space so we have so little stuff.
You’re admitted that you’re “jealous of all the guys who kept a family together while they built up their career.” How realistic is it for women to think that they can really do that?
It’s not that realistic. There are very few women at senior management who have kids. The divorce rate of women who are startup entrepreneurs is almost 100 percent. I look at men who have the exact job I have and they don’t care if they make it home. The world falls in place for them. I’m still looking at what I would want that to look like for me.
You don’t hold much hope for shared care either, because you need a lot of money and “two people who can make miracles happen in their chosen profession.” Yet you and your former husband move in and out of your house so your boys can stay put, a novel idea that isn’t all that different from shared parenting; it puts the kids first. What’s wrong with that?
If you think of the personality types it takes to raise kids, they don’t marry. It’s not a good marriage. That’s why it looks like a miracle because someone’s lying about what they want. If two people want to stay home, they should probably marry someone else. It’s a situation for liars. Shared care is compromising your career in order to take care of your kids. It’s slicing and dicing your career; when you’re sharing your house, you’re just slicing and dicing your house.
How do you and your former husband split time caring for your boys?
My ex comes and goes when he wants and I move my schedule around. He stays here two nights a week. I have full custody.
Has the divorce made you a better mother or him a better father?
I hope I’ve become a better mother. Actually, everyone becomes a better parent. Anyone who’s honestly trying because they care so much does.
Let’s talk about fathers. In a post on CEO Fathers, you pointed out the double standard in our society: “If you are poor and you abandon your kids you are a bad parent. But if you are rich and you abandon them to run a company, you are profiled in Fortune magazine.” Is that any different for women, and is that changing?
There are no women doing that. Who’s a woman doing that? (Former Hewlett-Packard CEO) Carly Fiorina doesn’t have kids. (California gubernatorial candidate and former eBay CEO) Meg Whitman’s husband stopped being a surgeon to watch their kids.
As a child, you were a latchkey kid and hated it. How do you think your own kids will look back at their childhood?
I don’t know. They’ll know I worked a lot.
Your son has Asperger’s, and you have talked quite openly about the toll special needs kids place on a marriage. Now, you are about to get married again, adding a stepdad in the mix. How will you approach things differently this time?
I don’t know how; how could you ever know? We all hope for “normal.” I hope it’s fun.
I’m sure many women get asked the same thing as you do — how do you run a company when you have young kids, which you say is basically saying that "you suck as a parent." Why are people, especially women, so judgmental of other people’s parenting?
I don’t actually encounter that. I don’t run in circles where that happens. I’m with men, and men don’t care about parenting. Because I stayed home for a while, I’m not a person who would start ripping on the other world; I’ve been in both places.
Which leads me to your phrase, mommy porn. Why do we buy into that image of the Perfect Mother?
I think we all want that. I do. I want Angelina’s body. I look at Kate Hudson’s butt. She’s got such a hot butt — when does she get PMS? — and she’s got a 5-year-old trailing her.
You recently caught a lot of flak by tweeting about your miscarriage while you were in the middle of a board meeting. You are big on honesty and transparency, and many bloggers, particularly mommy bloggers, are sharing very personal details online. When does sharing become oversharing?
When you wish you didn’t do it. People who are new to the medium make more mistakes. I have an editor. I’m pretty clear on my boundaries with my kids and with the farmer. I never use their names, and I don’t really want to be telling their story. I don’t want my life to be telling about my kids.
In of your wonderfully outrageous posts, you point out that boys (and men) are having all the fun — whether through sports or breaking rules or playing video games — while girls take things way too seriously, especially investing so much in school, and not having enough orgasms. How can women have more fun, and will that lead to more orgasms?
Women need to know what’s fun for them and make it a priority, and if they think orgasms are fun, they’ll figure out how to have more of them.
Finance advice columnist and author Penelope Trunk was interviewed by Vicki Larson, Around the Watercooler  contributor. She is a journalist and single mom.
Looking for more interviews with opinionated moms? Don't miss our discussions with Bad Mother author Ayelet Waldman  and Perfect Madness author Judith Warner .