Penelope TrunkOver the weekend, I had the opportunity to interview Penelope Trunk, author of Brazen Careerist: The New Rules For Success, and columnist for Yahoo Finance and the Boston Globe. Her blog, Brazen Careerist, is also a well-established blog and a worthwhile read for aspiring professionals everywhere.

I had the opportunity to interview her at length, so enjoy!

Daniel Dessinger: First off, thanks for agreeing to take the time to talk with me. I know you’re busy with your columns, a new book, and speaking engagements. I recently read on Wendy Piersall’s blog,, that you just spoke at the BlogHer Conference in Chicago just a few days ago. You spoke with Stephanie Cockerl and Nina Burokas about personal branding, correct? What were the top three takeaways from that session?

Penelope Trunk: I am not sure what people actually took away from the session, since there was subsequent online hoop-la. But here are three things to think about when you want to create a brand out of yourself:
1. What do you stand for?
2. What do you not stand for?
3. What do you give people that is unique to you?

Daniel: Is this your first time at BlogHer? Can you describe the atmosphere of the conference and tell us how it differs from other conferences you attend?

Penelope: Well, I can compare this recent BlogHer to BlogHer Business — I went to that. And, not surprisingly, it was much more business oriented. I went to SXSW earlier this year, which is also full of bloggers. SXSW had a lot more men.

Daniel: Based on Wendy’s comments, I’m picturing a collection of professional work-from-home women who have the conversational floodgates burst open for this three day event. Is that a fair description?

Penelope: Um. I don’t know very many of the work-from-home bloggers and I didn’t talk with many when I was at BlogHer, so I’m not really sure about the answer to your question. I do know Wendy. I have come across her blog before because she has such a successful business.

Write regularly, write on a focused topic, and write great posts. – Penelope Trunk

Daniel: Gotcha. Okay, changing subjects a bit, I’d like to talk about your blog. I’ve kept with Brazen Careerist for a little while now. My coworker is infatuated with you and, sadly, he is passively wishing you were single. I guess you’ve found a professional way to turn on the charm!

Penelope: Not a question, right? But tell your co-worker thanks 🙂

Daniel: Ha! I will. I really like the balance you bring to your own brand with your tagline:  Advice at the intersection of work and life. How would you say you’ve done at balancing “work and life?”

Penelope: I don’t believe in balance because it implies that the two things are competing. I try to create a life where things are working together, and I feel whole and integrated. That said, I’d have to say I’m not doing the greatest job. It’s very hard to do. One of the reasons I blog is to be with a community of people who are trying to improve things at the intersection of work and life and we’re all doing it together.

Daniel: The reason I ask is because, for all your interesting perspectives on work culture and Generation Y, you manage to throw everyone off with a few posts on your marriage and the difficulties that arise in your personal life. Do you ever regret exposing your issues to the world? Does the transparency adversely or positively affect your life at home?

Penelope: I never regret talking about myself in an authentic way. I don’t really know another way to connect with people. I’m sure that one of the things that my husband likes about me is that I’m authentic, no matter what. He is that way, too. So doing it on the blog seems inevitable.

Daniel: One more personal question I have to ask: How does your husband feel about having your marriage issues made public knowledge? This is a tender subject for me, since I guard my relationship with my wife very closely. I don’t pretend that we don’t have our problems, because we have plenty. But until something is dealt with, I feel that to expose her faults to anyone other than a trusted adviser is disrespectful.

Since I’m willing to accept that everyone can and does feel differently about how to approach these types of issues, I’d just like to hear your thoughts on the subject.

Penelope: Newsflash: Your wife talks about your sex life with her friends. Every woman does. Men have a skewed idea of how private their marriage is because men don’t talk about marriage with men. How do you think women learn to give blow jobs? Not from men.

That said, my husband doesn’t care about what I write. I know it’s hard to imagine. But try to imagine being married to me at all. A handful, right? In that sense, blogging about the marriage is nothing.

Daniel: My instinct is to apologize for mentioning your personal life, but I remind myself that you intentionally made it public, so there you go. I read a bio about you somewhere, and it mentioned how you went from professional volleyball player to writer. Could you tell us what it was that opened the door for you to transition into being a writer? If you could, highlight a circumstance that you might call an open door or an unexpected turn of events in your favor.

Penelope: I think the most important thing was that when I was playing volleyball, I was great at getting sponsors to pay to put their name across my chest. So I inadvertently discovered that I was really good at marketing. I have used that knowledge each time I changed careers. I’ve said to myself, how can I leverage the marketing talent to make a smooth transition?

Daniel: You have a book out there for sale entitled: The Brazen Careerist: The New Rules for Success. I’ve read that another book is in the works. Can you give us a hint as to the title or subject matter of this one?

Penelope: No.

Daniel: Sigh. Fair enough. When can we expect release?

Penelope: 2008

Daniel: While the feedback on your blog is mostly positive, I’ve read some overwhelmingly negative feedback from readers of your article at Yahoo Finance. Did you make some enemies early on, or what? I get the automatic feeling that you’re rocking the boat too much for comfort in some reader’s minds.

Penelope: Yeah, I think you’re right.

Daniel: Do you think the feedback on Yahoo Finance is just the natural result of a wider audience, or is it the specific readership demographic that seems to be a bit more old fashioned and stuck inside-the-box?

Penelope: Both. I think when you get a wider audience you inevitably get more people who are not thinking along the same lines you are. It happens with everyone, I’m sure.

Daniel: Agreed. You mentioned to me recently that you’re already living my fantasy of blogging and writing for a living, and that this isn’t the end of the line for you. Given the ability to choose, what is the next step in your career? And maybe also five years down the road?

Penelope: I am actually in the middle of figuring that out right now. I’m thinking it’s getting time for a next step. Stay tuned….

To get a special career you need to specialize. People get nervous specializing because it narrows the types of jobs you can take. But being an expert instead of a generalist actually makes you more employable as long as you shift your expertise as the markets shift. – Penelop Trunk

Daniel: Does being a woman help to propel you in your career? I ask this because my wife is very attractive and intelligent and doors just open for her that wouldn’t budge for me. I think you’re the total package if you can pull off the intelligent, witty, fashionable, attractive, and confident woman image. I’m not calling women eye candy, but it seems that these days, the world (beyond redneck borders) opens its doors to attractive and intelligent women. Thoughts?

Penelope: I think men like to do business with women they would like to have sex with. It seems totally normal. The same is true in reverse. This is why good-looking men and women earn more money than ugly men and women.

Daniel: I often wonder if our (yours and mine) motivations aren’t opposite.While we both blog for personal branding purposes, my motive in blogging and writing is self-expression. The writing is the joy… The proverbial cake, if you will. Positive feedback is the icing. Would you say that writing is a means to an end, or the end itself in your career?

Penelope: Are you asking if I get joy from writing? The answer is yes. I could never write five posts a week if I didn’t truly love to write. In fact, I’ve written in lots of different formats, and there is nothing I have loved more than blogging.

Daniel: With millions of blogs out there in the space, what are the Top 3 recommendations you can make to someone who wants to build a readership for one reason or another but has no additional claim to fame such as writing for the Boston Globe or Yahoo Finance or publishing a book? Without those tools in their belts, what can bloggers do to establish a name for themselves?

Penelope: Write regularly, write on a focused topic, and write great posts.

Daniel: And there you have it. Simple. Yet Profound. While we’re at it, would you take a stab at predicting 3 of the most radical shifts we have yet to see but can expect in the workplace as Generation Y takes center stage?

Penelope: Decentralized leadership, unapologetic focus on family, and financial downshifting

Daniel: What common beliefs does the average Joe or Jane need to revise in order to break through the “average career” barrier?

Penelope: To get a special career you need to specialize. People get nervous specializing because it narrows the types of jobs you can take. But being an expert instead of a generalist actually makes you more employable as long as you shift your expertise as the markets shift.

Daniel: Any parting words of wisdom to the less Web savvy readers out there?

Penelope: Blogs do not require you to be web savvy. If you start reading them without worrying about whether you undertand them, you will start to understand them. Click a lot.

Thanks for taking the time to respond, Penelope.

One response to “An Interview With Penelope Trunk”

Leave a Reply

Your email address will not be published.

This site uses Akismet to reduce spam. Learn how your comment data is processed.