Trunk, Penelope

Penelope TrunkPenelope Trunk has been a software executive, an entrepreneur who founded two companies, and before that, a professional beach volleyball player. She has been through an IPO, an acquisition, and a bankruptcy. As an expert career adviser, she writes two popular business columns: the syndicated column "Brazen Careerist," which is featured on Yahoo! Finance, and her column, "The Climb," which runs in the Boston Globe. She writes career advice for a new generation of workers. She explains why old advice—like pay your dues, climb the ladder, and don't have gaps in your resume—is outdated and irrelevant in today's workplace. She has a reputation for giving advice that is counterintuitive but effective, like take long lunches, ignore people who steal your ideas, and stop vying for a promotion.

Penelope Trunk has used her own companies as proving grounds for her theories, and, in her book, Brazen Careerist: The New Rules for Success, she shares the lessons she's learned. Erik Hansen talked to her about the book for our Cool Friends interview.

[Bio adapted from her website and book jacket.—CM]

Brazen Careerist book cover asks …

Let’s start with your name, Penelope, which isn’t really Penelope.

PT: It is now. I started out as Adrienne Greenheart. I began writing my column under the pseudonym that my editor gave me, Penelope Trunk.

It’s a great story. Who’s the ideal audience for your book, Brazen Careerist:The New Rules for Success?

[For more on the evolution of Penelope’s name, read her website here.—CM]

PT: A wise person once told me that when you write a book, you can never be sure who’s going to like it. Authors are always surprised. I thought my audience was young people in the workplace. But, in fact, management loves buying my book. They buy it in huge quantities to understand how to recruit and retain Generation Y. So my audience is Generations Y, X, and the people who have to deal with them. The beginning of the book is for those who are new to the workforce and the second half is for people who are trying to figure out how to have meaningful work and have a meaningful life simultaneously.

I learned from your blog that I’m part of Generation Jones.

PT: On my blog I complain about the Baby Boomers—how self absorbed they are, how they’ve sold out. People your age will write to me and say, “I do not identify with this stuff.” As it turns out, all the people who are complaining about being identified with the Baby Boomers have been separated into Generation Jones. The demographers have answered their wishes.

I was born in 1954, so I’m apparently at the leading edge of Generation Jones. I recently spent time with my brothers, who are five and six years older. These guys are clearly Boomers. My work life is totally different from theirs; it’s an amazing gap.

PT: It is a rip-off for the Baby Boomers who climbed the ladder and sold so much of their lives in exchange for being at the top of the ladder. It’s no fun being at the top.

For a lot of these folks, they’ve reached the top and then the ladder has been ripped out from underneath them. The value of loyalty disappeared somewhere along the way, as did whatever massive payback they expected for all their hard work.

PT: I think it’s painful for them to see young people not have to do any of that.

So Baby Boomer managers think these Xs and Ys have it a lot easier, that the younger group don’t have to pay their dues the way they once did?

PT: Yes. Here’s a great example: Baby Boomer women spent their whole lives trying to smash the glass ceiling, doing everything they could to get pay equity. Then Generation X sweeps in and takes advantage of what the Boomer women worked so hard for. They get flex time and go home and stay with their kids. It infuriates Baby Boomers; it makes them nuts. And Generation X doesn’t care.

I recently interviewed Sylvia Ann Hewlett, author of Off-Ramps and On-Ramps

PT: The problem with her book is that she says that the extreme work week, the sixty-hour work week, excludes women from the workplace. But no one in Generation X or Y wants to work those extreme hours, so it’s a non-issue for our generation. The men don’t want it. The women don’t want it. Nobody cares. The only people who will do it are Baby Boomers. She has this whole treatise about what we should do to help Generation X get on the on-ramp and off the off-ramp, but it’s irrelevant, because we don’t work that way.

If I had only known this before! I’d love to get the two of you in a room together. But you’re probably right; it’s only affecting the Boomers.

PT: There are several Baby Boomers doing research on how to solve the problems that they had, and then telling Generation X what to do. Leslie Bennetts does it, as well. The Baby Boomers just need to shut up about what Generation X should do. We don’t want to hear from them.

This is why I like your blog; I enjoy your attitude. Yet it seems there are still massive numbers of folks going to Harvard and such and getting their MBAs. They must be jumping into the corporate ring.

PT: Most of them want to pursue entrepreneurship. If you look at the materials from business schools, they fall all over themselves saying how good they are at teaching entrepreneurship. Why do people want entrepreneurship? They want flexibility, control over their time, control over their workload. They want all the things that we know make work good. Whereas Baby Boomers just want some money and a title. We know those things don’t make work good.

But the reality of being an entrepreneur is that you’re going to work more hours than at any other kind of job. Entrepreneurship is beyond the extreme jobs as Sylvia Ann Hewlett describes them, right?

PT: Only if you want to be the next Microsoft. For example, most women are solo entrepreneurs. It’s a lifestyle thing. We used to say that the majority of new businesses fail. We throw that statistic around all the time. But, in fact, success as an entrepreneur today for Generations X and Y is achieving the lifestyle. Entrepreneurship is a success if you had a good time. I think very few people would want to run Microsoft. I think most people would want to sell it before it got that big. Who wants Bill Gates’ life? All he does is work.

I agree. But I think a lot of people, for some reason, are really attracted to eighteen gazillion dollars.

PT: I don’t think that’s true. I’ve read great real estate articles about the current glut of McMansions. Baby Boomers are selling them to retire to New York City and drive up housing prices there. Generation X is moving out to the suburbs to raise their kids, but they don’t want to live in those houses. Those houses look ridiculous to us. And if we don’t want those houses, we certainly don’t need eighteen million dollars to build a bigger house.

You say you need only 40 thousand dollars.

PT: I do say that. I’m a big fan of the Positive Psychology movement. I think positive psychology is the feminism of the new millennium. We used to look at everything through a feminist lens, a lens of equality. I think the new lens is positive psychology—how meaningful things in our life are, how optimistic we are, how resilient we are, how tight our relationships are. That has a huge impact on how we look at work.

You’re starting to sound very new age-y.

PT: That’s interesting, because positive psychology is a science, and it’s the most popular course at Harvard for undergrads. It’s taught at 150 universities in their psychology departments. It’s all based in hardcore research—

Á la Martin Seligman and—

PT: Or Daniel Gilbert. I love his book. [Stumbling on Happiness]

There’s a nice line in your book, “Learn from yourself by watching how you learn from others.”

PT: I think that we learn what our strengths are by observing others. I’m a great time manager, so I’m constantly looking around at other people and noticing their time management techniques. I can pick up a tip from anyone. But I’m a very bad listener. When I’m with a good listener, I’m not picking up any tips. I wish I were, but I’m not. I’m waiting for them to shut up. This is not, of course, about you, I’m listening to you very carefully—


PT: I’m trying to be a good listener. But I think you can assess your strengths by seeing how you learn from other people. That’s an important part of the positive psychology treatise of how to be happy in your life. We used to be about overcoming weaknesses. But you don’t have to do that if you just figure out what you’re good at and focus on that. What are your strengths?

I’m good with people.

PT: That is a huge strength.

It is. It took me a long time to understand that that meant something work-wise.

PT: I think it means everything work-wise.

You’re probably right. It’s scary to admit that because then you wonder if you’re actually any good at anything, or if you’re just good with people. Over time you understand that it’s about learning how to listen and be supportive of others.

PT: There’s been a big shift in the workplace. We now have data to show that people would rather work with somebody who is nice and incompetent than with somebody who is competent and a jerk.

Now I know what to put on my next business card, “Nice and incompetent.”

PT: A lot of people will get all huffy and say, “That’s so unfair. It’s just the brownnosers who get ahead.” But I’m happy about this change. Now everybody who’s nice, kind, considerate, and empathetic will get ahead, and the workplace will be a place where we’re all treating each other with respect. That’s so great. We don’t need to focus on skills.

There are a number of folks I’ve met over the years through work and we’ll talk about how we liked working together and we’re always just looking for an excuse to work together again. Life’s too short not to work with people you like.

PT: That seems so smart to me. I have a list of four or five people that I think I’m going to die if I don’t get to work with because they’re so much fun on the phone. Who cares what people’s skill sets are?

You have some very straightforward advice about email, which is on my mind because I interviewed Mark Hurst about his book, Bit Literacy.

PT: I don’t know that book.

You have to get this book because it will provide you with more ammunition for when you write about email. He says you should get your email inbox down to zero every day.

PT: I’ve realized just how essential it is to be in control of the inbox. There’s no way to feel in control of your work day if you don’t have control of your inbox. We’re all brokering information. When I say, “Get your inbox down to zero,” a lot of people think I’m a crackpot. Get with the program!

It’s going to be the new wave.

PT: I’ve been totally consumed with I go there but I can’t keep up with them because I haven’t read Getting Things Done three times. This is the time-management generation. Young people starting their careers do not feel overwhelmed by the Internet, they don’t feel overwhelmed by their email. They never say no to new information, and they process it very quickly.

In order to succeed in the workplace, you really have to be an amazingly productive person. I think that’s going to define who’s moving toward their goals in the workplace and who isn’t.

Or who can absorb the most information. Because in his book, Mark says figure out what the least amount of information is that you can get by with and still function. But, as you say, this generation coming up, they have built-in filters because this is where they’ve lived since they were kids.

I also interviewed David Freedman who coauthored A Perfect Mess with Eric Abrahamson. You say one should keep a neat desk because people perceive that neat desks belong to people who have intelligence and creativity. There’s nothing further from the truth!

PT: There are two different pieces. One is, how is your desk functioning for you? And the other is, how’s your image functioning for you? People can complain their whole lives about how it’s not fair that fat people are judged, and fat people are really smart. But we can’t help it—we are programmed to judge fat people poorly. There’s no point in deciding if it’s fair or not fair, or good or not good; we cannot do brain surgery on each person’s brain to change how they judge fat people. I think the same is true of messy people. You can spend your whole life having a messy desk and having everyone judge you poorly, or you can just clean it up and have your messy desk at home where no one can see it. If you can only be creative with a mess, then throw all your papers on your kitchen floor.

Or we could have everybody in the world read The Perfect Mess and they’d calm down.

PT: I don’t think that would help, though, because we tell people all the time that fat people are smart.

I worked in an office for a brief period of time. I thought the neat desk people were the ones who were most likely to go postal next. They lived in such a constrained environment.

PT: I think what matters is how you function away from your desk. You could have a clean desk and still be a flexible person, which I flatter myself to think that I am. Although no one who knows me well would think that I’m flexible.

You have a clean desk at home?

PT: I have a five-year-old and a two-year-old and a spotless house. This is not to say that my husband and I aren’t nut cases at night cleaning everything up after they go to bed. But I think that everybody thinks better when things are where they belong. That’s not supported by research but I think that if you come to our house, you’d think that we’re smarter because we’re neater.

Maybe. You make a convincing argument.

PT: You have a messy desk?

Yeah. You say follow the new rules, but you also say make your own rules. For someone in their twenties, they don’t have any rules to break yet. They’re looking for rules, particularly if they’re guys.

PT: I wrote the book because there was nobody telling me how to break rules. There were only people telling me I’d destroy my career and ruin my résumé by playing volleyball. People need advice that meets them where they are, instead of trying to drag them through some other set of rules that don’t apply.

Here in Tom Peters’ world, we’ve been advocates of gaps in résumés for a long time. It means you’re doing something more interesting. In corporate America, gaps are perceived as awful things. I think your stint as a volleyball player is what makes you interesting.

PT: I don’t consider that a gap; only my parents do. I worked really, really hard. People think, “Oh, the beach, eight hours a day, that’s not a job.” But it’s a very hard job.

Penelope, thanks so much for your time.

PT: It was a pleasure meeting you.

Email: penelope (at) –