Copyright © 2007 by Penelope Trunk

All rights reserved. Except as permitted under the U.S. Copyright Act of 1976, no part of this publication may be reproduced, distributed, or transmitted in any form or by any means, or stored in a database or retrieval system, without the prior written permission of the publisher.

Some names and identifying characteristics have been changed to protect the privacy of certain individuals in the book.

Warner Business Books

Hachette Book Group

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New York, NY 10017

Visit our website at www.HachetteBookGroup.com.

Warner Business Books is an imprint of Warner Books.

Warner Business Books is a trademark of Hachette Book Group, Inc. or an affiliated company.

Used under license by Hachette Book Group, which is not affiliated with Time Warner Inc.

First eBook Edition: May 2007

ISBN: 978-0-446-56165-5

ACCLAIM FOR BRAZEN CAREERIST

“ This book has the street smarts you need to make your career and life work for you from the start. Read it now, or you’ll wish you had when you’re forty!”

—KEITH FERRAZZI, BESTSELLING AUTHOR OF NEVER EAT ALONE: AND OTHER SECRETS TO SUCCESS, ONE RELATIONSHIP AT A TIME

“ A road map specifically for young people to help them navigate corporate life . . . Trunk’s style is direct, practical, and anecdotal, and most important, incredibly helpful.”

—JULIE JANSEN, AUTHOR OF I DON’T KNOW WHAT I WANT, BUT I KNOW IT’S NOT THIS

“ There are two kinds of people in the workplace: careerists and achievers. If you’ve been too busy achieving to focus on how to move your career forward, this book is a must read. It will teach you how to find just the right balance between the two.”

—DR. LOIS P. FRANKEL, NEW YORK TIMES BESTSELLING AUTHOR OF NICE GIRLS DON’T GET THE CORNER OFFICE

“ Trunk brings considerable savvy and a fresh new perspective to the business of career success. Bold and sometimes unconventional, BRAZEN CAREERIST gives readers much to think about as well as concrete, practical suggestions that will help them know what they want and know how to get it.”

—PAUL D. TIEGER, COAUTHOR OF DO WHAT YOU ARE AND CEO, SPEEDREADING PEOPLE, LLC

“ This book is the What Color Is Your Parachute? for the new young generation.”

—BRUCE TULGAN, AUTHOR OF MANAGING GENERATION X

Acknowledgments

My agent, Susan Rabiner, saw all my weaknesses within three minutes of first meeting me, which made life with her great because there was nothing I could hide. She has encouraged me in all aspects of life, and she has taught me how to follow the rules while at the same time inspiring me to succeed in unorthodox ways.

I would be lying if I told you that writing a book was easy. My editor, Diana Baroni, transformed me from a columnist to an author. No small feat. Sometimes I imagine that while she was going through edits with me on the phone, she was throwing darts at a wall to keep her voice so even. Leila Porteous saw me through rocky moments, and Jamie Raab and Rick Wolff believed in this book even when I wished it was a book but it wasn’t.

I am a writer who loves a good editor. So I am thankful to a slew of editors who have helped me along the way. The easiest lesson was from Jessica Pompei: to just be myself. The hardest lesson was from Daniel Ray: to follow the rules. Jim Krusoe made me believe I was a writer and taught me not to write about writing. Leslie Epstein accepted me into grad school and accepted that I was not grad school material. Susanna Kaysen fed me rice at night while I spent my days as a starving grad student. Tim Carvell encouraged me to nag people until I got a column. Ned Desmond and Josh Macht gave me my first column, and Josh taught me to never write about my sex life in a business magazine. Riza Cruz taught me that I am more interesting when I am useful. David Wallis taught me to stop worrying about the last column and focus on the one I am writing. Perri Capell was my editor and then my networking project, but she also turned out to be a friend. Caleb Solomon gave me a chance to write for the Boston Globe. Doreen Vigue taught me to pay attention to pictures. Andrew Caffrey taught me the value of editorial banter. Tanya Singer gave me the opportunity to write for Yahoo! Hundreds of other editors have run my syndicated column in print and online, and this broad editorial enthusiasm has allowed me to keep writing.

My husband has been flexible with his own life so that I could go after my dreams, no matter what they were. He stayed up late teaching me HTML so that I could run a Fortune 500 Web site (yes, that’s all it took in 1994). He managed a long-distance relationship so I could continue to run my company. He encouraged me when I took an 80 percent pay cut to be a full-time writer. He took care of our kids so I could finish my book.

Finally, I want to thank the people who have read my column and my blog. Some have been reading since 1999. Some have just started. Everyone who has written to me has taught me something. I write about careers because I love the dialogue about what we can do to find happiness in work and life. I hope this book continues that dialogue.

Introduction

Every generation is known for something. My generation is revolutionizing work. Today there are new rules, new expectations, and new standards for success. If, like me, you are a member of Generation X or Y, that is, between the ages of eighteen and forty, this book will help you make good decisions so that you can get an exciting, rewarding career that helps you grow and accommodates your personal life.

As an older member of Generation X, I found myself constantly out of step with coworkers at the beginning of my career. I did not value the same things they did, I did not want their lives, I did not want their jobs—I wanted something different. After ten years in the workforce, I realized that I wasn’t weird for expecting my job to be fun (and for being disappointed when it wasn’t). I wasn’t lazy for moving back home with my parents. I was actually part of a large trend, but when you’re helping start a trend, often you look less like a trendsetter and more like a freak.

I wrote this book to provide a road map that I wish I’d had when I started out in business. This isn’t a book by a career coach, advising you on how to navigate a world she never had to navigate. These are firsthand stories and practical advice on how our generation can successfully maneuver in the new workplace, from someone who’s been there.

Here are some characteristics of the new generation of workers that set us apart from those who came before us:

We move back with parents after college: In 2005 65 percent of college seniors planned to move back home.

Career instability is a given and we hold more than eight jobs before age thirty-two.

We invented the quarterlife crisis in which career and relationship problems come to a boiling point at around age thirty.

Women don’t aspire to be Superwomen; in fact, five years after business school, only 60 percent of women are working outside the home.

We demand control and flexibility when it comes to work, which explains why 40 percent of all new businesses are started by people under thirty-four.

These new workers are forcing revolutionary changes in corporate life, and these changes will occur on magnitudes we have not seen since women entered the all-male office.

Work will become more fun, more fulfilling, and more accommodating of a personal life in the next five years. This revolution is due to the seemingly outrageous expectations of young people—and their already apparent ability to get them met. One of the biggest topics in management consulting right now is how to change corporate life in order to retain young workers, because they won’t stay if they don’t like what’s happening.

But don’t mistake Generations X and Y for lazy. We are passionate, hardworking, and devoted to our friends and family. We are ambitious, we work hard to be inclusive and to make the world a better place, and we have an unparalleled ability to make things in our lives happen fast.

So we need new rules and new guidelines for success. The old discussion about workplace issues is quickly becoming irrelevant because we are seeing the end of work as we—and our bosses—know it:

The end of gender-based pay disparity. Today, pay is equal for men and women until they have kids. But this inequality will change when Generation Y starts having kids, because the men of that generation are committed to being equal partners in child rearing and are choosing low-stress jobs from the start of their careers. Young men today are prepared to trade power and money for time at home with their children.

The end of the glass ceiling. It will end not because women will finally make it into the top ranks of the Fortune 500 in significant numbers, but because most women will stop caring. And so will men.

Generations X and Y will give up a lot to achieve balance in work and life—something the older generations were not willing to do. So advice like “Don’t leave gaps in your resume” is simply unsupportive and unrealistic. Young people need to cope with inevitable gaps in clever, new ways.

The end of the grind. More and more people will choose a career because they love what they do. People will want to work to be part of something larger than themselves and as a path to personal growth. People will choose a career as a way to keep the job of raising children from becoming dull and alienating.

The end of consulting. All workers will feel like consultants, so the term will be useless. Employers will decrease costs by encouraging consulting rather than long-term, salaried employment in the office. Employees will push for this to get more flexible hours. This is not a large leap given that younger workers already feel no long-term loyalty and tend to be project-focused instead of job-focused.

The end of the stay-at-home parent. Both men and women will look for flexible jobs that accommodate child rearing. Many younger women have already rejected the idea of sacrificing time with their children to a relentless, high-powered, long-houred job, and men are following suit. The most fulfilled moms tend to be those with a flexible job that accommodates young kids in a way that doesn’t make the mom crazy with guilt or stress. Like women, men who plan to stay at home with kids actually plan to work part-time, too.

So the question “Should you be a stay-at-home mom?” is not all that useful to the men and women of this generation, first, because it is gender-specific, and second, because it is too black and white. A more relevant discussion is how to plan for shared parenting and flexible work to accommodate raising children.

The end of hierarchy. Pecking order really only matters if you are working at the office all day, reinforcing ranks. So the less time people spend at their desks, the less they will care about rank. Young people have no interest in climbing ladders when they know they probably won’t be working at one place long enough to hit every rung.

The classic career topic of “How to Get a Promotion” will become irrelevant. That’s not what today’s employees are after. The younger generation of workers cares more about personal development and honing job skills they can take with them to their next job or career.

The new workplace emerges at a time when psychologists are just starting to quantify what, exactly, makes people happy. The new worker will respond to this data quickly: Happiness Studies 101 is the most popular course among Harvard undergrads, and the research is infiltrating every discipline imaginable. Here’s a sample of the research: you only need $40,000 to be happy; after that, what impacts your happiness the most is your personal relationships. So ladder-climbing advice like “pay your dues” does not ring true to workers who believe money doesn’t matter that much. What young people are looking for is advice about how to get interesting work without giving up a personal life.

If you recognize yourself in this new workplace, then this book is for you. If you don’t feel that the old, typical rules of business should apply, then the advice in this book is for you. This book will advise you on how to be successful at work, knowing full well that the definition of success has changed radically so the rules have to change, too. The advice in this book would not have applied to the workplace fifteen years ago. Tips like Use harassment to boost your career, Differentiate yourself by staring at the wall, and Make a strategic move to your mom’s house all provide tactics to get what you want from a career in the twenty-first century.

This book is for a generation that asks for more from their work than anyone has asked for in history—a generation that is making new roadmaps for new careers. This is a guide to getting the things that the current generation cares about from a generation that doesn’t understand that. This book is about achieving success on new terms.

My own work life has unfolded in a way similar to many workers in the new generation: I was lost. But then I learned how to get what I wanted from my boss and I used these new rules to make adjustments to fit both my personal and professional lives.

My resume depicts a successful marketing executive, serial entrepreneur, and widely read business columnist. But my story began in the sand, as a professional beach volleyball player. I spent three years training twelve hours a day to get to the beach tour. I worked insane jobs that accommodated beach hours, and I often went hungry when rent was due.

When I reached the upper echelons of the sport, I realized that the skill that made me stand out most on the professional beach volleyball tour was not my jump serve but my ability to market myself to sponsors.

After failed attempts at hijacking my boyfriend’s marketing business and at graduate school, I found my place in the software industry in Southern California. I rose through the ranks fast. I had a knack for writing and for office politics—a lethal combination that allowed me to land plum assignments, enlist the aid of top workers, and then write scintillating reports to highlight my successes. I sailed through Fortune 500 companies, startups, an IPO, and a merger.

Then I had the good fortune to work for a CEO who gave me seed funding for a new company. After the startup phase, I sold my shares of the company and I started another, which exploded at the same time as the Internet bubble.

Proving that failure is necessary for success, soon after that, Time Warner asked me to write a weekly column about my life as an executive in corporate America. The column, Brazen Careerist, which still runs today, had ironic timing: I was unemployed, single, strapped for cash, and, for the most part, lost. I worried about revealing too much about my plight in the column, but it turned out that I was documenting a journey through a quarterlife crisis before there was a name for it, and the column gained a huge readership.

As a serial career changer who has had many business roles in many different fields, I relied heavily on books to guide me through my personal reinvention. But I never saw a broad-sweeping career handbook with proven advice that specifically reflected the experience of my generation back to me. So I wrote this one.

The chapters in this book are based on my own experience and the career advice columns I’ve written for the new generation of workers for publications such as the Boston Globe, Business 2.0 magazine, and USATODAY.com, as well as advice I’ve gathered from successful young business people and a wide variety of experts. Many people who pop up in the chapters are those whom I’ve met through work during the past fifteen years, as well as friends and family who now know better than to tell me anything they don’t want to see in print.

Part One covers the first stages of a twenty-first-century career: being lost, figuring out the type of career that’s right for you, and marketing yourself to get the job you want. This section lays out options—grad school, the job search, entrepreneurship, travel—and helps you evaluate which are best for you. I’ll show you how to feel good about making decisions for yourself in a world where there is not necessarily a right decision. Lastly, Part One introduces you to the idea that there are scientifically proven rules for how to find a career that’s right for you and how to be happy, and you can follow them, easily, for great results.

Part Two helps you get what you want from your boss. This part of the book is for people who know what they want but are having a hard time getting it. You’ll find advice to help guide you if you feel impatient with your current job situation; if you have great ideas and your boss keeps shooting them down; or if you work with people who drive you nuts. These tips will help you stick to what you value while maneuvering around corporate roadblocks and annoying personalities that get in your way.

Along the way you’ll also find advice on how to protect your personal life from the demands of work. You must start planning early in order to position yourself to have synergy between your work and your home. This book is for visionaries who are changing the world one worker and one family at a time. It’s also for people who are already at the stage of their life when balance is imperative, but they don’t yet have it; these tips will help you see a new workplace with new possibilities that were not there even five years ago.

For Generations X and Y work is not just a means of support, but a lifestyle choice that must challenge, entertain, and encourage personal growth. But the current workplace is not set up to offer this sort of work to young people, so you will have to maneuver strategically within a baby-boomer-dominated workplace to attain goals that are unique to a new generation. This book outlines the new rules for success and provides tactical moves to ensure that you get the kind of work you want without getting derailed by outdated ideas of what work should be.