Penelope Trunk is a career advisor and co-founder of Quistic—a program providing specialized, online courses for career management. Quistic is Penelope’s 4th VC funded startup. She is the author of a best-selling book, Brazen Careerist: The New Rules for Success, but perhaps most recognized for her blog. Her one million per month readership is hardly surprising—she draws from experience most keep hidden: divorce, abuse, miscarriage. Shock factor aside, in her prolific honesty are acute insights. If they strike a nerve, perhaps it’s because you recognize yourself in them—but do so quietly. 

“I started by writing a column for Time Warner about being a woman running a start up—there were so few women doing that at the time. I didn’t actually realize I had a special gift where I would say things that other people wouldn’t. I didn’t realize how closed people are with what they’re thinking and feeling, because it comes really naturally to me. It’s actually much harder for me to know what’s normal because of my Aspergers.

I’m not trying to be transparent, I’m trying to be normal. 

Aside from that, what I’m actually good at is raising money for investors. I have a good eye for trends and how to turn that trend into product. So my blog is just an automatic launching pad for those businesses. It’s not something I planned out carefully, although I carefully plan not starving to death. So it’s been part of the not starving plan. Otherwise, it takes a lot for me to just get out of bed and not do self-destructive things like eat brownies for breakfast. If I can do that and not scream at my husband, the next thing I try and do is be a good mom. In terms of impacting society, I can’t really think about that when I can barely do the other stuff.

I think the people who say they are impacting society are full of shit.

It’s hard for everyone to get out of bed and not eat brownies, don’t you think? I do try and be a good mom and wife—those are most important to me, as well as earning money because I’m the bread winner. I play a little game with myself where I think—If I marry a bazillionare, would I still be working? I would still be writing. I would still do my blog because I love it so much. But I don’t think I would do start ups, they’re very very hard. Honestly though, my family doesn’t require that much money, I earn way more than they need. I spend far more time worrying about being a good wife than if I’m doing well in my business, because I don’t believe in divorce. I hate that I got divorced, it killed me and my kids. I don’t want that to happen again. If your business fails, you can get through another one.

But having a marriage fail and getting another one? It doesn’t really work that way.

I’m always trying to be better. I try and treat myself better—I’m not very good at treating myself well. I want to be nicer, I have a hard time having empathy for people. I want to raise my kids in a way where they think they’ve had a nice childhood. That’s really my challenge. All that stuff is really, really, really hard for me. I have to keep my eye on the ball every second or I’ll just start being bulimic again. It could be like one little slip and it just goes downhill from there. Every day is more challenging than the last because I’m trying to get better at being the person I want to be. I do think that people really appreciate someone who’s honestly trying to be a better person. I appreciate that.”

Penelope’s #OKREALTALK Tips

  • A failed marriage and a failed business are not equal. Invest in your relationships.
  • Aim to be better than yesterday. You can't go wrong.
  • If you can get out of bed and not eat brownies, you are doing OK.

b. 1966 

t. @penelopetrunk

As told to Amy Woodside, May 2014