Penelope TrunkOne of the aspects I most love about blogging is the new friends I’ve had the opportunity to meet along the way. One of those people is Penelope Trunk. Penelope is a columnist for the Boston Globe. Her syndicated column has run in more than 200 publications. Her book, Brazen Careerist: The New Rules for Success, provides non-conventional career advice for younger generations hitting today’s marketplace.

Beyond her writings on career issues, though, what I most appreciate about Penelope is her brutal honesty about the life issues she’s facing. It’s refreshing. It’s insightful. And, fortunately, I think you’ll get a sense of that in this brief interview.

TONY: What’s a woman like you doing in a place like this?

PENELOPE: I think I got here because I would write anyway, so why not write where people are actually talking intelligently in conversation. I love the blogosphere because no one is writing in a vacuum. I have a background in hard-core creative writing programs where everyone wants a book deal, but no one wants to hear criticism. I love the blogosphere because we are all honing our ideas and our communication skills by letting other people trounce them. And we think it’s fun.

TONY: Your blog is one of only a handful of blogs I follow that’s written by a woman. Is that a sign that I’m a male chauvinist or are there other contributing factors?

PENELOPE: I think good blogging comes from a history of good op-ed writing: Very short, contrarian opinions and strong reasoning skills. And, of course, op-eds are very male-oriented. I think this is because in general (brace yourself for post-feminist generalizations with no evidence to back myself up) women are not as interested as men are in telling everyone their opinions and making sure everyone thinks they are right. So men are giving opinions in this world and women are taking care of people. I know. Very general. But there is, in fact, hard evidence to show that men write op-eds and women take care of kids. I take the liberty of extrapolating the rest. Which is maybe why you like my blog. :)

TONY: You typically write about career issues. What do you believe are the key challenges that career-minded people are dealing with today?

PENELOPE: Actually, I think the same issues that face people in their faith face people in their career: Why are we here? How can we make a difference? How can we take care of ourselves and still make room for taking care of other people? When people ask themselves what should they be doing and how much money do they need, they are really asking these very very fundamental questions about being human. Unfortunately, it’s easier to answer the question “how many pages should my resume be?” so people are more likely to put that sort of question into words.

TONY: From my perspective, the Church should be a refuge for folks dealing with the daily grind. From your perspective, why do you think fewer and fewer career-types are turning to the Church?

PENELOPE: Really, fewer career types are turning to the Church? I’m surprised. I am also surprised, by the way, that the Church is capitalized. I’m doing it because you did it, but as a Jewish person, I always thought there were a lot of churches, like, a lot of types of church, so I don’t actually know which church I’m writing about when I write the Church. I will have to ask you this offline maybe.

The more I write about careers the more I feel compelled to write about faith. I know my readers don’t expect religion on my blog, so I have to tread lightly. Also, I feel that I am not so sure of myself in the what-are-we-here-for department as I am in the what-is-a-good-interview-answer department. But I am certain that if you are really serious about your career you have to be really serious about asking the question “why are you here?” and this is a question about faith… Isn’t it?

TONY: Now that you’re dating again, any recommendations for the single guys in the audience?

PENELOPE: I think that women who are professional, and doing big things in their career do not expect to be in charge in the relationship. We are already in charge everywhere else. Here is something a friend’s brother said: He lives in New York City and he dates investment bankers. He says the line that works on them every time is “Stop being so professional and just be a girl.”

I deleted this answer. But then I decided to put it back. I am not sure what I think of this answer, but maybe it will spark good conversation on your blog and then I will know what I think of the answer. Here’s an interesting statistic: Women in Gen Y make more than the men do, on balance, but the women still choose to marry men who make more than they do. Which tells me that women do not want the power in a relationship. There. There is some evidence to back stuff up.

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