Interviews with Big Bloggers

Interview with Brazen Careerist Founder Penelope Trunk

0 Comments 26 March 2012

Penelope Trunk Interview

On the list of top nerve-wracking experiences of my life, calling Penelope Trunk for our phone interview was undoubtedly at the top.

We all have career idols. She’s one of mine.

We all have personal idols. She’s one of mine.

Penelope is a writer, blogger, and entrepreneur who focuses on the intersection between work and life, often chronicling her own personal and professional experiences while drawing on the expertise that dubbed her “the world’s most influential guidance counselor” by Inc. Magazine.

I write on MsMorphosis about my opinions on sex, marriage, and my body. I’m often terrified, because sometimes people pay attention. Penelope is far more adventurous than I am, and the whole world is paying attention.

When she famously tweeted “I’m in a board meeting. Having a miscarriage. Thank goodness, because there’s a fucked-up 3-week hoop-jump to have an abortion in Wisconsin” she dealt with the shitstorm that ensued with unwavering strength and grace. She later stook up for her controversial tweet with remarkable persuasiveness in the post You Can’t Manage Your Work Life if You Can’t Talk About It.

Penelope’s third startup is, a website that helps young ambitious professionals network and find jobs.

Today, she lives on a farm in southwest Wisconsin with her husband, who she refers to on her blog as “The Farmer.”

penelope trunk and the farmer

A picture of Penelope and her husband, The Farmer. Taken from her blog,

Pick a type of bra and stay with it

Jen: The internet is notorious for destroying professional opportunities because of the things we do privately (Facebook, blogs, social sharing, etc), yet your blog merges your professional life with a very candid view of your private life.

You’re very brave for doing this, and it’s something I worry about how to approach in my own life and blog.

So the question is, how does this make you feel? Does it make you nervous or do you feel comfortable having such a blurred line between your career and your private blog?

Penelope: First of all, the internet isn’t notorious for ruining people’s careers, people are notorious for ruining their careers.

People have been hooking up with co-workers at office parties way before the internet, and that ruins their career, too. Women go into the office and cry to their co-worker about their abusive boyfriend and then don’t leave him, making everyone hate her and lose respect for her, and that ruins her career. Penelope Trunk quote blogging

Anytime you share something about yourself in a way that people around you don’t want to be around, you’re in trouble. It’s like if the CEO of a Fortune 500 company cried about their dog dying; it would get them in trouble because no one wants that from that person.

So, it’s more about letting people know what to expect from you, and then being consistent with that.

Someone once told me at the beginning of my career that I should pick a type of bra and stay with it. It doesn’t matter what kind, but you can’t have huge perfectly rounded breasts one day and then saggy sloppy breasts the other day. You have to find your bra that fits and stick with it, because people like consistency.

So today, nobody expects me to be perfect, so it’s not any news to people that I’m not perfect. And because I’m known as someone that gives career advice, and I’m also known as someone who has the type of career that a lot of other people want, it would be ridiculous for me to even present myself as perfect – because then everything that I’m telling people looks unattainable. People who present themselves as perfect and then give advice about how perfect people run their life, well then, who cares? Because no one has that kind of life.

So, to me, the most valuable career advice comes from somebody who’s really honest about all the stuff that’s not working for them. Otherwise, you’re just taking career advice from someone who’s full of shit. So for me it works really well to just be totally honest about where I am in my life.

Most people are working two jobs

Jen: That makes a lot of sense, and your honesty really does pay off.

However, when it comes to your life and career advice for young adults, I’ve felt a bit of a disconnect between when you talk about how we should “stop being so picky” – we should take any job we can find in this economy, that any job is better than no job – and the brand of the company you’ve built, where Brazen Careerist feels so shameless and bold, built to inspire young adults to go against the grain and reach their dreams.

To me, the idea of “settling” and yet “going for it” all at the same time feels like a bit of a juxtaposition.

Penelope Trunk Career Advice

Penelope: Well why can’t you do both? You can go get a retail job at Forever 21 and have a really exciting blog about big ideas and then eventually get hired for your big ideas.

Most people are doing more than one job. Everyone whose a parent is doing more than one job. Everyone whose trying to get to the Olympics is doing more than one job. They’re trying to get to the Olympics, which is a full time job, but they still have to support themselves. Everyone who is writing a novel is doing more than one job.

So, the idea that you can’t work at Forever 21 and be managing your personal brand as a thought leader is totally wrong – of course you can do both.

Jen: Ok, so all you’re arguing against is the laziness of people believing they can’t accomplish things because they’re “too busy”..?

Penelope: It’s not laziness, it’s priorities.

I mean, maybe you are too busy. But if you are too busy to do your blog, than that just means your blog isn’t that important to you because the other things you’re doing in your life are more important to you.

No one is too busy to do the stuff that’s important to them because they’re doing the stuff that’s important to them.

On Asperger’s & Confidence

Jen:  Another thing that I want to talk to you about is your brave openness with the fact that you have Asperger’s syndrome.

When you describe your experiences with it, it seems to pose some anxiety, but also some fearlessness – because you aren’t able gauge certain social cues – and the discomfort or disproval that they can imply.

I was just wondering if you think it has influenced the part of your personality that makes you so comfortable saying things that other people can’t, or don’t want, to say out loud.

Penelope: Yeah, well, I don’t have a sense of awkwardness, because awkwardness presupposes that you’re following social conventions.

So, because i don’t have to ever worry about being awkward, it gives me freedom to do a lot more. I try to not be awkward because i know if there’s awkwardness other people feel bad. But it’s very hard because I can’t gauge that awkwardness.

Jen: Do you think maybe that’s one of the reasons you’ve been so successful as a woman in the business world? Because of the confidence that that allows you to have?

Penelope: No, I think that’s because I’m good looking. I was a beach volleyball player so all through my twenties. If you’re an attractive woman, you can get away with a lot.

I mean, really, if you’re a woman in your twenties, you’re generally hot, it’s pretty hard to not be hot in your twenties. And it’s all men in their 40s and 50s at work, and there are no women in their thirties at work because they’ve all dropped out to have kids, so I think I did well because I’m smart and good looking and it’s despite the fact that I’m socially awkward.

So stop talking, and start taking some goddamn risks

Jen: So then how did you take the leap into first having your own entrepreneurial ventures?

Penelope: I started as a bike messenger. I’ve been a dishwasher, an ice cream scooper, I worked in bookstores, I was a nude model, I worked on the trading floor, I’ve been fired from – I don’t know – 100 jobs. I moved to Los Angeles and Chicago with no friends and no money. I’ve taken tons and tons of risks and taken tons and tons of terrible jobs.

It just seems, to me, like everybody I know who has a great career did that – because you can’t really get a great career without taking a lot of risks.

If you’re not willing to take risks than you’re just competing with all the other people who don’t take risks, and it’s impossible to win. The number of people who don’t take risks is almost everybody. You can’t ever get anything special.

Penelope Trunk Advice Quote

The only way to get something that’s out of the ordinary is to accept risks that are out of the ordinary.

You can always paint a picture like “oh life’s been so great for me,” like I graduated from college and I played professional beach volleyball, and I got into a master’s program for English, and I got a free ride. and then I was early to the internet and had a successful startup. I could say that, or I could say I got arrested in Los Angeles for shoplifting because I was starving, and I ran out of money in graduate school and had to leave, and I’ve gotten fired from every Fortune 500 job I ever had. and I had to work in bookstores to keep from starving (even though I hated it) and one of my companies went under.

So people with jobs that look really awesome can tell you the story in two ways.

They can tell you the great story of their life, and how perfectly they’ve managed everything, but they also have the understory. The one with all of all the risks they took, and all the times they were living on the edge, doing things no one would ever admire, so that they could get by.

Penelope Trunk Career Advice


Want more Penelope?

It’s ok. You have options.

Sign up for my newsletter.

I’ll send you all the Blogging Fearlessly interviews, including this one.

But in the interview I’m sending to my subscribers, it will include some behind the scenes action where Penelope talks me through my own career and business plan and gives me some incredible advice. It was prompted by my final question, “then what would be your advice if you had one thing to say to women in their mid-twenties with big ideas and let’s say they’re not too bogged down by a job at a store and they’re able to go for it?”

and then once you’ve done that…

Buy the book.

“A cookbook for hacking the corporate world” - Wired Magazine

The book. $25.99.  Buy it here (and support me and Penelope)*

Description: Giving anything but standard tips, celebrated career advice columnist Trunk delivers a clear, goal-oriented, and in-your-face guide to getting what one wants in business and in life–aimed specifically at generations X and Y.

Or the e-book. $9.99. Buy it here.*

and then keep in touch with her…

Find her online.

Penelope Trunk Blog



Penelope Trunk Twitter


*These books are linked with affiliate links, which means if you buy them after clicking on these links I’ll receive a small commission for the sale. In my attempt to make money while having big ideas, affiliate links are one of the things that keep this ship afloat and help me pay my rent each month.


More than anything, thanks for reading. She’s pretty incredible, isn’t she?

If you enjoyed this post, please consider leaving a comment or subscribing to the RSS feed to have future articles delivered to your feed reader.

Share your view

Post a comment

CommentLuv badge


For unique, interesting, entertaining, and thought-provoking articles and interviews, MsMorphosis covers it like no one else can. MsMorphosis creator, Jennifer Gargotto, has the courage, curiosity, intelligence and spirit to challenge our thought processes by expressing different points of views on a variety of relationship topics. The articles are very well-written and interspersed with humor and humility. I enjoy it immensely. — Betsy Montgomery