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Brazen Careerist
ByPenelope Trunk

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Brazen Careerist

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Brazen Careerist
By Penelope Trunk
Genre:Business & Money

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Chapter Excerpt from:Brazen Careerist, by Penelope Trunk


Detours Are the Route to Happiness

One of the best decisions you can make in your twenties is to explore. Exploring postcollege options looks a lot like being lost; in fact, being lost is normal and productive at this stage in life. “I tell students there is no rush here. Career interests typically don’t solidify until about the age of twenty-five. All the research shows that,” said Linda Arra, director of career services at Lafayette College.

At earlier points in life, people are penalized for getting lost. For example, dropping out of high school for a year to explore makes colleges think you were hospitalized for mental instability. But it’s a different story right after college: you don’t get dinged for taking time off. “Most graduate and professional schools today would prefer the students take time to go away, have different experiences, and then come back refocused,” said Bill Wright-Swadel, director of career services at Harvard College.

Part of the reason there is so much institutional respect for exploration is that there is no better way of figuring out what will make you happy. “We are not very good at using our imaginations when it comes to how we’ll feel in a given circumstance,” says Daniel Gilbert, a professor of psychology at Harvard University who specializes in figuring out what makes people happy. Therefore Gilbert recommends that we test out a lot of different careers. He admits that this tactic takes time, but he says it’s worth it because otherwise you’re likely to make a decision based on money, which, research shows, is not likely to have much impact on your happiness.

What about the people who pull their life together in a tight little package by age twenty-four? They’re the exception to the rule, according to Wayne Osgood, professor of sociology at Pennsylvania State University. He labels these people “fast starters” and explains that they are only about 12 percent of the population. This group typically does not finish college and appears to have conventional personalities and the same expectations as their parents’ generation. Some fast starters are just plain lucky: they love the first job they get after college. The other 88 percent of us have to trudge through our twenties formulating a new career plan.

The good news is that this is what most people are doing in their twenties: wandering. Taking trips to Thailand, changing jobs every year, volunteering for unpaid work while living at their parents’ house, and starting businesses that fail. All these options are, surprisingly, right on track for making a good decision about what to do with yourself in adult life.


There are lots of paths to happiness and most of them include an annoying job or maybe even ten. The most important thing about an annoying job is that you make sure you are learning and growing. Before you throw a fit and leave, consider that the most successful people are curious, with a broad range of interests, and can learn from anyone.

I spent the majority of my twenties doing jobs that raised eyebrows—as in “Are you a loser?” But I learned a lot from each job I had because any job—really, any job—can help your career if you let it. Each person, no matter how weird, has something to teach you. And each business has a gem of genius because, hey, they’re making enough money to pay you, aren’t they?

Some of the best negotiating training I got was from a job I had on a French chicken farm. I only took the job because I had a deal with the family who owned it: I would perform household chores in exchange for room and board (in France). To me, “chores” meant sweeping and dusting. To them, it meant killing and plucking chickens. In my lame French, I told the matron of the house that killing animals was not among my duties. She said I’d be kicked out for breaking the agreement. So I learned to pluck. Lesson #1: Get all your agreements in writing.

It was important to move the chickens into the buyer’s truck before they realized what was happening. So in the middle of the night, while they were sleeping, we grabbed the chickens by the legs and held them upside down. The farmer couldn’t believe I did it without throwing up. Immediately I asked for three days off and got them. Lesson #2: Timing is everything when you ask for a concession.

I picked cherries from the branches that were too high for the eight-year-old daughter who was also doing chores. Later she gathered the eggs out from under the hens so I wouldn’t get pecked. Lesson #3: Everything in life is open to negotiation because everyone has something they can give you.

Relatives of the host family came to visit from Lyon. I had more in common with the city French than the rural French did. They invited me to stay with them in the city so their kids could learn English: another job offer! And the farmer overheard. So I told the farmer I would stay to harvest the hay only if I didn’t have to feed the pigs anymore. Lesson #4: Get a job offer in your hand to get more leverage at the job you have.

The truth is that negotiating skills apply to every situation, and the worse shape you’re in, the more essential the skills are. Had I not been suffering with the animals I probably wouldn’t have paid so close attention to how to negotiate a break.

At another point in my life my friend got me a job signing Esther Williams’s autograph for fans. In the 1940s and ’50s Esther was a star of MGM water musicals: think Ginger Rogers with nose plugs.

I hated the job because I felt like I was wasting my time. I thought of myself as a misplaced generator of big ideas. But in hindsight I’d have to say that Esther Williams was my first marketing mentor, and later I built my own marketing career around rules I learned from lame tasks I did while working for her.

During my first week, Esther gave me three copies of her signature (different pens, different sizes) and told me to practice. I submitted my best shot to Esther and she said, “Make the E’s loopier.” I looped and resubmitted and then she gave me the go-ahead. Lesson #5: Quality assurance is part of marketing—you can’t brand something that is inconsistent.

We had stacks of old MGM promotional photos in which she looks like a showgirl. But for the die-hard fans who requested it, I also had a headshot photo of Esther when she was about fifty years old. Lesson #6: Give the customers what they want.

We had 8×10s, but I only sent those if the person enclosed postage. Otherwise, Esther instructed me to send a 5×7. Sometimes people would request an 8×10, and even if they didn’t send postage, I’d send a big photo. I figured it would make a happy customer and it wouldn’t break Esther’s bank—after all, she was still receiving residual checks from Million Dollar Mermaid. Lesson #7: Know when to follow rules and when to use your own judgment.

At the time I didn’t understand that Esther Williams had spent a lifetime cultivating her own brand. I was lucky to see the intricacies of maintaining the brand, even if the operation was a little eccentric.

I realize now that the reason I picked up so much information about negotiating and marketing from these less-than-challenging jobs is because those are areas that interest me. I’m good at them and I like watching how other people do it. You will notice in your early, random jobs that you gravitate toward certain lessons. What you like learning about is probably what you like to do. Learn from yourself by watching how you learn from others.

So if you find yourself in a job in which you’re not learning anything, ask yourself whose fault that is. You can’t stay at a dead-end job forever, but don’t ever assume there’s nothing to learn. The first step is to figure out what interests you most about the job, and then watch very carefully and ask a lot of questions.


If you could see a movie of your life before you lived it, would you want to live it? Probably not. The thrill of living is that you don’t know what’s coming. In other words, uncertainty is what makes our lives fun.

Sure, it’s hard to see uncertainty in such a positive light when you’re out of work, or when you feel like you’re flailing. But uncertainty is really another word for opportunity, and you can’t harness an opportunity until you recognize it’s there.

When Allison graduated from Harvard, she had opportunities all over the place and no idea what she wanted to do. She took a job in consulting but she knew she wouldn’t stay there. She took the GRE and scored so high that she was able to supplement her income by tutoring students at Stanley Kaplan. Still, she didn’t think she wanted to go to graduate school. Allison knew she wasn’t doing what she wanted, but she didn’t know what she wanted.

She worried. All her friends were going to graduate school or starting their own businesses. She was lost and panicking that she would never figure anything out. She wasn’t even living in a city she planned to stay in, but she couldn’t figure out where to go.

After six years, reality set in. Many of her friends who went directly to professional school had crises when they graduated because they weren’t sure if they had picked the right profession. And Allison, by going with the flow and having a general plan in mind, got married, moved to the Midwest, and leveraged her consulting experience to get a great position at a foundation she is very happy with and where her job is to dole out money to nonprofits.

In hindsight, Allison realizes that her years spent being lost were actually just a period during which she was finding her way: time well spent, and time we must all take if we’re being honest with ourselves.

The only way to lead an interesting life is to encounter uncertainty and make a choice. Otherwise your life is not your own—it is a path someone else has chosen. Moments of uncertainty are when you create your life, when you become who you are.

Uncertainty usually begins with a job hunt, but it doesn’t end there. Every new role we take on means another round of instability. Instead of fearing it, here are some new approaches to dealing with uncertainty:

Accept uncertainty instead of fighting it. Some of you work for unstable companies, or hold tenuous positions at stable companies, or have no idea where you will go next. If you can focus in the face of instability, you are more likely to be able to leverage opportunity.

The best way to focus is to gain a better understanding of what you want and what you can control in order to achieve your goal. Maybe you don’t know exactly what you want, but no one ever has all the information they need. Paul Stevens trains career coaches and one of the topics he spends the most time on is how to teach people to deal with uncertainty in their career. “The more information you have, the more you realize you don’t know. The key is to accept this, but not be paralyzed by it. Not knowing for certain opens opportunities for new knowledge, new career options, being free to invent your own career future.”

You should be focused and flexible about what you want for yourself. “Treat your career goals as a hypothesis and balance time spent achieving your goals with time spent discovering them,” advises Stevens.

Prepare for uncertainty. The most extreme example of this preparation is in Pema Chödrön’s writings on accepting uncertainty (see, for example, Comfortable with Uncertainty: 108 Teachings on Cultivating Fearlessness and Compassion). Chödrön, a Tibetan monk who lives in Canada, recommends that people spend their lives coping with uncertainty—through meditation, yoga, and self-knowledge, preferably at a monastery. Probably you will not do this, but you can follow her advice in principle: face the fact that uncertainty is difficult and that you are at least a little anxious. As Chödrön would say, just be with that, since you can’t change it.

Most of us will not have honed meditation as a coping tool, but there are other tools that can help you when instability hits your career. Building a network, saving money, being very good at something, and continuing to learn—these are all ways you can make yourself more prepared for uncertain times because you’ll have more flexibility in your approach to dealing with instability.

Use uncertainty to make yourself shine. For those of you who have no idea what to do next in your life, remember that uncertainty is what allows you to surprise yourself. If you could see each future step along the way, you’d never get the chance to be amazed at what you can do.

When I graduated from college, I went on to play professional beach volleyball. At the time I worried that the decision was crazy and that I wouldn’t make the cut, but in the face of massive instability, beach volleyball seemed like a reasonable choice. Now it is one of the parts of my life I am most proud of.

Create uncertainty. Some of you are stuck in your career. The only way to get unstuck is to create instability. Say to yourself, “Maybe I can change my approach, maybe I can find a new specialty.” In the face of a mortgage or a waning 401(k), creating instability seems absurd. But think of it another way: uncertainty is really another word for opportunity, and each of us should take responsibility for creating our own opportunities.

If you can see your life in front of you, you’ve got a problem. If you know what’s coming, then you probably won’t need to grow to deal with it. If you can see everything coming, then what is the challenge? You’re on autopilot. And who wants that for a life? So embrace instability. This is where you make your life your own.


Whether you’re thinking of a top-tier MBA or a PhD in anthropology, there is a right way and a wrong way to approach graduate school. You need to understand your dreams and what is required to achieve them. Also, you need to understand the marketplace and what it values.

If you dream of climbing ladders in the Fortune 500, John Challenger, CEO of the placement firm Challenger, Gray, and Christmas, advises you to get an MBA. “In today’s environment a graduate degree is as important as a college degree a generation ago.” And get it in your twenties when the degree can get you a better starting job. “Where you start is very important for where you end up.”

But think twice before cashing in your chips for a less-respected school. Challenger says, “Top business schools have a premium value. If you attend the third tier, do it at night because the financial loss and career stagnation while you’re in school do not outweigh the benefit of the degree.”

For some people, though, graduate school is not so much a way to fulfill a dream as a way to put off finding one. We spend eighteen years in school being told what to do and being rewarded for meeting other people’s goals for us. The adult world requires us to set our own goals and this is something school does not teach.

Much of the flight to graduate school is a result of grade inflation and fragile egos, says Thomas Benton, a pseudonym for an assistant professor who writes a column for the Chronicle of Higher Learning: “Humanities majors are used to being praised by professors. Many recent grads return to school when they discover that not everyone thinks they are as great as their humanities teachers did. Humanities don’t have the objective standards of business. Going back to grad school allows people to reestablish their ego. But it is short lived because they have to face the same market when they get out.”

Keep in mind that instead of making you more creative, MFA programs make you more qualified to teach. And the academic job market is extremely competitive. Take, for example, English literature: only one out of five people who enter PhD programs will get a job in that field. The rest will find themselves back at square one, waiting tables, albeit with improved literary banter, and looking for a career.

Lost humanities students with an eye for cash and stability often enter law school because other professional schools require too much math or science. Yet the land of lost lawyers is full, too, which confirms that if you don’t have a passion for what you are going to learn in graduate school, you shouldn’t go.

Jane Sommer, interim director of the career development office at Smith College, has heard all the bad reasons for going to graduate school and has some advice:

1. Try other jobs first. The people who do best in graduate school are those who find decent alternatives first and still want to go back to school.

2. Determine if an advanced degree is necessary. Talk to people who are where you want to be in ten years. Ask them if they needed a diploma to get where they are. If they say, “I didn’t get a diploma, these are the steps I took. . .,” you can do those steps, too.

3. Don’t bother using graduate school to wait out a bad economy. Chances are the one you’re in right now is not particularly bad for job hunters.


If you’re out of work, or if your job is so annoying that you wish you were out of work, then it’s time to take an adventure. It’s important to take adventures during the time when you have very little responsibility. With no one to take care of but yourself, an adventure is a way to bolster your skills and your resume without suffering through another dead-end job.

In your next job interview, you’ll need a good answer when someone asks, “So, what have you been doing?” You don’t want to sound like you are withering, uninteresting, or watching television at your mom and dad’s house, even if you are. Travel is a fine answer to this interview question. It’s true, and you seem worldly. Traveling does teach you a lot.

The older, very gainfully employed sector of society looks at these adventures as an expensive, childish way to avoid reality. This is partly true, but who cares? The reality of adulthood is hard. There are no teachers stroking your ego with As, and there are no parents making sure you’re doing fun and challenging activities every afternoon. So it is no surprise that putting off adulthood is appealing. In fact, taking an adventure to see how other people live is a good first step into adulthood.

There are some great things you can accomplish while you’re adventuring:

You can use an adventure as a way to hedge your bets. Robert Buckley was a health-care consultant and hated it. He decided to quit and try to get work as an actor. But he had no experience acting, and he was too scared to try it without having a plan B. So he decided that after six months, if he got no nibbles from agents, he’d go to Japan to teach English while he figured out what to do next. (Happy ending: he got acting jobs.)

You can sort out personal problems. A lot of career issues are actually personal issues. Do I really want to be a doctor or am I just doing it to please my parents? Do I want to move closer to my boyfriend or am I happy where I am? These are issues that dictate your career choices but that cannot be solved by changing jobs or rewriting your resume. Putting yourself in a new situation, away from the outside influences you are used to, will help you get a more clear perspective.

You can learn what you don’t want. When I worked on the chicken farm, one day we spent three hours looking for mushrooms in the forest. I said, “Why do we have to keep looking? It’s taking so long and it’s only mushrooms. Let’s go home.” The father said, “But how will we have wild mushrooms for salad?” I couldn’t believe it. I wanted to have my mom buy some at the grocery store and send them via airmail. This is when I knew that although I thought living and working close to the land would be appealing to me, it wasn’t. To me, it actually felt monotonous and intellectually dissatisfying.

There are a few ways to get the money to travel. The most obvious is that you should alter your lifestyle. Prolific travel blogger Ali Watters has a few suggestions:

• Don’t get a car or a mortgage unless you absolutely need one.

• Give up smoking or expensive trips to coffee shops—it wastes money each day.

• Stay away from material possessions. Before each purchase, ask yourself what you’ll do with it while you’re traveling.

Ali also recommends that you travel somewhere cheap; a month in Europe will cost you three times as much as a month in Southeast Asia.

If Ali’s advice is too hard to swallow, you might try lining up a job that’s an adventure. If you are under thirty years old, you can benefit from reciprocal work agreements that the United States has with the United Kingdom, Australia, and New Zealand.

If you want to travel to other places, or if you’re older than thirty, there’s still hope for finding work. The creative, entrepreneurial spirit that is often squashed in a beginner can thrive in an adventure. For example, Sarah Baer founded a nonprofit with about $1,000 so she could get papers to spend a year helping natural disaster victims in Asia. Ann Armony quit her job as a nanny but she didn’t have enough money for an adventure, so she got a job for the summer working at the South Pole. It’s a barren town of about 300 people, and “summer,” really, is no word for the place, but she loved the change of pace.

The bottom line about adventure is that there’s little difference between a good entry-level job and an adventure. Both are about learning, trying new things, and making sure you don’t starve. So when you are looking at your job choices, put travel right up there, on top with everything else. It’s good for your resume and good for your life.

Excerpted from Brazen Careerist, by Penelope Trunk. Copyright (c)2007 by Penelope Trunk. Reprinted by permission of Little, Brown and Company, New York, NY. All rights reserved.

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