When to Jump: If the Job You Have Isn't the Life You Want

When to Jump: If the Job You Have Isn't the Life You Want


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“A lively and inspiring guidebook for anyone who wants to make the jump from normal to extraordinary.”

—Tony Robbins, #1 New York Times bestselling author of Unshakeable and MONEY: Master the Game

An inspirational book that lays out the “Jump Curve”—four steps to wholeheartedly pursuing the career of your dreams—through experiences from a variety of people who have jumped and never looked back

When Mike Lewis was twenty-four and working in a prestigious corporate job, he eagerly wanted to leave and pursue his dream of becoming a professional squash player. But he had questions: When is the right time to move from work that is comfortable to a career you have only dared to dream of? How have other people made such a jump? What did they feel when making that jump—and afterward?

Mike sought guidance from others who had “jumped,” and the responses he got—from a banker who started a brewery, a publicist who became a Bishop, a garbage collector who became a furniture designer, and on and on—were so clear-eyed and inspiring that Mike wanted to share what he had learned with others who might be helped by those stories. First, though, he started playing squash professionally.

The right book at the right time, When to Jump offers more than forty heartening stories (from the founder of Bonobos, the author of The Big Short, the designer of the Lyft logo, the Humans of New York creator, and many more) and takeaways that will inspire, instruct, and reassure, including the ingenious four-phase Jump Curve.

Product Details

ISBN-13: 9781250124210
Publisher: Holt, Henry & Company, Inc.
Publication date: 01/09/2018
Pages: 334
Product dimensions: 6.40(w) x 9.30(h) x 1.30(d)

About the Author

Mike Lewis worked at Bain Capital before chasing his dream of playing professional squash. He is the founder and CEO of When to Jump, a global community of people who have left one path to pursue a very different one. When to Jump has reached millions through media impressions, in-person events, and brand collaborations. When to Jump, a collection of case studies with clear guidance on how and when to jump, is Mike's first book. He received his BA from Dartmouth College and lives in San Francisco.

Read an Excerpt




"That little voice ... it's your true voice."

— Jeff Arch

I HAD JUST polished off a supersized schnitzel outside a youth hostel in Vienna when two traveling Kiwis hanging out in the lobby extended an invite to join their trek heading east to see their friend in Romania. I was twenty-one years old, on a one-week intermission from the steady, firmly planned trajectory of college, internships, graduation, work. Naturally, I leapt at the chance to toss my travel plans. I couldn't say yes fast enough.

We cruised through Slovakia and past the Czech Republic, around Hungary and into Romania, two teachers from New Zealand and their American sidekick. As the overnight train pulled into Bucharest, I stumbled upon what I had been quietly craving. Squash courts.

In the dusty depths of a basement gym in Bucharest, carved out of a couple of worn slabs of concrete, sat three decaying squash courts. Inside the court to the far right, a pair of older men shrieked and lunged, laughed and shouted, barking out game scores in a blur of foreign sounds that I figured to be Romanian. I crept past the men and slid into the court on the far left, spending the next forty-five minutes hitting a series of practice shots against the wall, the ball flying back in a familiar cadence. The grunts from the far court echoed through the cavernous concrete lair, and as I finished my solo practice and headed for the locker room, I stopped to watch the two sweat-drenched Romanians finish their duel. Moments later, their contest done, their eyes suddenly turned my way, a flexed index finger of one player pointed in my direction. It was my turn.

The better of the two Romanians passed me off to his playing partner, watching casually as we went into battle. When I took out his partner in one game and then another, the better player stepped in. A couple hours of body banging and ball bashing later, I had triumphed over both players as the club manager sat watching, waiting patiently with an offer as I walked off the court: Stick around Bucharest. Crash with one of our players. You coach our team; we'll show you life in eastern Europe.

First: shock. I simply couldn't believe it. This was what I wanted: a bizarre, total unknown adventure, a surprise detour from the "path" toward a life of culturally sanctioned accomplishments. This was the sort of story Shawn the squash pro had told me when I was a kid, while he was staying in our house in Santa Barbara. I had reveled in those stories but never thought I would find myself in one of them. And here I was, far below street level, deep inside a dusty Bucharest basement. A friendly Romanian squash club manager was giving me a chance.

Then: reality. My heart burrowed deep inside my gut. My mind began to consider the truth. I wasn't ready to jump. I was in the middle of laying the groundwork for a bigger jump, and that groundwork would only be laid after I completed my internships, wrapped up my degree, and found professional footing. From there, I'd need to start saving money and get a lot better at my sport. There was a lot to do.

I turned back to the friendly Romanian club manager and, with all the self-control I could muster, politely declined the offer.

The next day, I flew to Zurich and moved into corporate housing for a privately owned commodities trading firm headquartered an hour train ride past Lake Zurich at the bottom of a hill in a sleepy Swiss village, surrounded by sheep. The day after that, I put on a business suit and began a monthlong work exchange, quietly commuting to the village by day, returning alone to the silent streets of Waffenplatzstrasse by night. Later, someone told me this neighborhood catered to families and retirees, and that made sense to me as I never bumped into anyone else my age. At work, I shadowed a commodities trader — a world expert in understanding the supply and demand around chemicals like ammonium nitrates. I followed his daily routines while wondering what the guys in the Romanian basement were up to. A month later, I was back in the States, in New York City, unpacking from a box my dad's pin-striped, bell-bottom wool suit from the late 1970s, beginning my first real corporate internship: a summerlong rotational program at Goldman Sachs, a rare opportunity, something that seemed out of reach to me and to my parents. I was moving from one prestigious internship to another, from spring to summer, with graduation less than a year away.

If I had jumped while in Romania during the spring of my junior year, it would have been impulsive and shortsighted. Holding off had benefits. But an inner voice emerged from that encounter. Right adventure, wrong time; but right adventure. A year and a half after I played squash in Bucharest, I was waking up to "I Think Ur a Contra" on my phone alarm at 7:20 a.m., hitting snooze once before getting dressed and heading to the towering castle at Bain Capital Ventures. Out the office windows facing north, runners walked, dogs played, and students napped in the grassy field of the Boston Commons far below.

The scripted sequence rolled along, but the little voice wouldn't go away.

* * *

A few years after leaving the dungeon courts in Romania, I looked across my desk to the map of the world taped across my office wall, and two things became crystal clear. First, I still wanted to chase my dream of playing professional squash full-time while traveling all around the world. And second, no one — not parents, siblings, or colleagues — was going to come into my office and tell me when my dream could begin. Instead, a little voice was doing the talking.

I didn't know what to do with this voice. On the one hand, it had to be wrong. My parents provided me with the education and guidance so I could land a job exactly like the one I had — stable, prestigious, lucrative. I enjoyed the work and felt challenged by it. Wasn't this the goal? The thought of mixing things up for any reason — let alone for my grand vision of playing an obscure sport and making no money while couch surfing with strangers — seemed not only disrespectful to my parents but logistically unreasonable and financially impossible.

Yet the voice grew louder.

I pretended not to listen. Rather, I listened, but I tried to forget what I'd heard, to send the thoughts to the back of my mind.

My Boston squash club was located (very conveniently!) across the street from the Bain office, and I started to find myself slipping over to the club anytime I wasn't working. Walking in one day during my lunch break, I caught hold of a conversation near the front desk. Dan was in his late twenties, a lanky, affable, curly-haired Irishman sporting a devilish grin. A former Irish junior champion, now an assistant teaching professional, Dan was on the phone, telling the person on the other end about his experience playing the tour circuits in Australia and New Zealand a few years earlier. I stood awkwardly in the doorway, just out of the elevator, hanging on to every word of advice Dan was giving: when to go, where to play — Dan even knew a few former training partners who could help provide places to stay along the way. When Dan finished, I walked slowly past the desk and to the court, closing the door behind me, pretending for just a second that it was me on the other end of the line. I hit by myself that day, smacking the hard rubber ball again and again against the wall, wondering when it really would be me on the other end of that phone call. On my way out of the gym, I stopped by Dan's desk: "Dan, at some point — you know, not right now, or anytime soon, but at some point, I may go play the tour. Can I get those names and tips you gave the other guy?" Without missing a beat, Dan, replied: "Shaw, mate. Anytime. Jus' lemme know when ya want ta talk." I disappeared back toward the locker room, back toward work.

* * *

Through the windows of the Bain Capital London offices, Buckingham Palace looked just like it did in the movies: grand, proper, historic. Six months into my job at Bain, I was riding high, having successfully pitched the idea of spending a few days in the company's offices in London, though no one in our venture capital department was based there. I'd borrowed space from a different part of the firm, and I promised my bosses no dip in productivity. If anything, I'd suggested, perhaps the international business landscape could help me uncover new investment opportunities. My bosses seemed amused by my effort and likely had more important things to figure out, so I was given the go-ahead.

It was March and my first-ever visit to the United Kingdom. I had been determined to inch toward an adventure overseas, even if it meant doing the same job but six hours east and at a makeshift desk and chair inside a bare, white-walled office that could have been mistaken for a hospital closet. I had bent the rules and got to work in London. If I could make this happen, maybe I could bend things even more.

I was squatting in the European headquarters of Bain Capital Private Equity. Leading this office was Dwight Poler, a thoughtful, brilliant investor widely respected both within the firm and in the broader finance industry. As it happened, Dwight went to graduate school where I went to undergrad, and we had been introduced by older colleagues based on this shared connection. Before I left London, Dwight found a few minutes to invite me into his office.

I tiptoed down the elegant hallway, each step taking on significance, as if while I lapped the space used by such a highly regarded businessman, some of his talent might rub off on me. I was in awe of Bain's operations, its sterling reputation, and the leaders like Dwight who had helped sculpt what Bain had become. While the little voice in my head was starting to speak up, I wasn't going to let it out during this visit with Dwight.

But while retracing his memories of business school, Dwight shared something else: he had once jumped to pursue his own dream. "I had a couple buddies, and we always promised each other we'd take a year to travel. So I worked out a deferral to graduate school, and we did it. We budgeted only as much as the lowest-earning traveler, and we left."

I couldn't hold back; I confessed my own wanderlust. And when I gave Dwight a thumbnail of how my little voice was telling me to play squash professionally, he replied simply: "Do it. Everyone will have a reason for you not to go: they'll say you're crazy, you're losing your edge, you could be earning more money. But do it."

My little voice had gotten out, and to receive advice on my jump idea from a role model in business was completely unexpected and exhilarating.

"But," Dwight added, "jump a few years out. You'll value it more. You'll have more money to spend." I made sure to remember that part, and a few minutes later, we concluded our conversation. On my way out, I thanked Dwight for his honest thoughts and for his advice to invest in my passion and to take the chance to jump. He smiled and said, "Life is long."

I walked firmly out of Dwight's office and down the hallway, straight past the palace in the backdrop. Before I made it back to the hospital closet, I messaged my friend Dan: "If I don't go play pro squash, I'm going to regret it forever."

* * *

One day at work two years later, in the winter of my third year at Bain, I took a phone call with an executive who was running a business somewhere in Connecticut. We had never spoken before and would never speak again, but for whatever reason, after we'd wrapped up the business portion of our conversation, the stranger on the other end asked about my story. What did I want to do? Was this job it?

It was like he knew.

I laughed nervously and explained how lucky I was to snag the job I had, how I'd have to be crazy to change anything, how I was truly quite happy. He paused, then finished by saying, "Listen, kid, you seem like a nice guy. My advice to you is go where your heart is."

I hung up the phone but broke from my autopilot routine of filing away notes and returning to e-mails. And in that momentary break, I was done. I stopped ignoring the voice, stopped pretending not to hear it. From then on, I was going to turn up the volume.

* * *

If there was a subtitle to the subtitle of this section ("Listen to the Little Voice"), it would be "And then tell people what that voice is saying." For too long, I sat at my desk alone and brooding over the validity of my idea, embarrassed to vocalize it, worried that my parents would never understand that I needed to see this idea through so that someday when I was gray and old, at least I could say I tried.

More practically, I worried, what if no one ever hired me again, EVER? I was a few years into a career, and I had thousands of peers capable of taking my job without missing a beat, not to mention the new grads, waiting and hungry. I remembered what my older coworker, early thirties with a wife and young child, had told me when he decided not to make a jump he wanted because it meant leaving the company. "In this job, I'm in line to become a managing director. I don't want to get out of line and miss my turn. I'd have to start over."

If I played pro squash for a while, I would certainly be getting out of line at Bain, but what scared me more was the idea that I wouldn't even be allowed to start over later on.

What if squash didn't work out? What if I didn't win any matches? Or what if it did work out, and I was miserable? There was no promise that my business career could resume — and in my head, I had settled on the possibility that it wouldn't. I'd be the guy my coworkers and classmates would talk about at happy hours or college reunions — what was his name, Mike? Mark? — who got too caught up in a dream and now, poor guy, couldn't get back to reality. If I pulled the right strings, maybe I would be able to start over as an intern, and my friends, now senior associates and vice presidents, would let me work for them, if they could swing such an arrangement with their colleagues.

I knew exactly what I would be giving up by leaving Bain — the money, the benefits, the security, the social status. And if I jumped to play pro squash, I didn't know anything exact about what I'd be getting in return. I feared it would be much, much less than I had at Bain. And in this kind of dark abyss of fear, most jumps die before they are born.

To keep a jump alive, it helps to tell someone.

Nine months into my job at Bain, three years after meeting my Bucharest buddies in the squash basement, and a decade after Shawn sparked my dreams about the pro tour, I first revealed to someone the entire, honest intention that came from my little voice. I ran my own internal vetting process before speaking up about what was on my mind, settling on a friend's dad, a man I considered to be a neutral and objective observer of my life, someone unencumbered by family ties or deep friendship bonds, who could deliver a candid assessment of my idea.

We met for morning coffee at the Blue Glass Café, a grab-and-go food shop tucked into the lobby of my office building. Blue Glass was crowded, bustling in the worst way, with everyone needing to be somewhere else, and no one seeming particularly happy about where it was they had to go. Sandwiched into a table between a blur of moving laptops and briefcases, I pulled my chair in tight. I surveyed the surroundings — the coffee cups and newspapers. Any faces I recognized? Any chances of being overheard? The idea of someone I knew taking notice was frightening. I scooted my chair even closer, chest pressed against the hard white edge of the tabletop. My friend's dad patiently waited for me to begin. After a few false starts, I spilled out my secret.

When it was all out, he said, "Go for it. As I tell my kids: you don't get redos in life."

After that, I allowed myself to share my dream more. Many days later, in the far back table of an empty office cafeteria during a midafternoon snack break, I confided in my coworker Noah. As I peeled an orange and awaited feedback, Noah framed things in a different way: "Dude. Which will be more interesting: another year spent in a job you know how to do or a year spent trying something you love?"

With each new conversation, my voice gained confidence. Another older coworker put it bluntly: "Do you believe in yourself?" I said I did. "Who is responsible for how this jump turns out?" I said I was. "Then you have no risk in trying. You're betting on yourself here. And you believe in that bet. You have no risk."

I was slowly starting to acknowledge that I might actually give my dream a try. In the copy room near my cubicle, I caught up with Paige, a mainstay in our office, a woman in the twilight of her career as an executive assistant. Separated by a generation, Paige and I had often kicked around ideas of jumps we'd like to make someday. As I finished telling her my secret plan, Paige stepped closer, her tone turning serious and her smile disappearing. Wedged next to the printers, in that thick, no-nonsense Boston accent of hers, Paige laid it straight:

"Honey, don't end up like me. Don't wait fah any-thin or any-wun. Just spread yah wings and act. Fear will fail yah. Courage will not."

Four months after sharing the full dream aloud with my friend's father, I'd told another half dozen people what I had in mind. The voice from inside my head was out in the open, and I was going to act on what it said. I just had to figure out when.


Excerpted from "When to Jump"
by .
Copyright © 2018 Mike Lewis.
Excerpted by permission of Henry Holt and Company.
All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.
Excerpts are provided by Dial-A-Book Inc. solely for the personal use of visitors to this web site.

Table of Contents

Foreword by Sheryl Sandberg xiii

Introduction: Mike's Story 1

The Jump Curve 13

Phase 1: Listen to the Little Voice 17

Jeff Arch—Karate School Owner to Hollywood Screenwriter 27

Teresa Marie Williams, MD—Nurse to Doctor 35

Nate Chambers—Mechanical Engineer to Fitness Entrepreneur 40

Laura McKowen—Marketing Executive to Writer 49

Tommy Clark—Medical School Research Fellow to Nonprofit Founder and Executive Director 54

Elle Luna—Technology Designer to Painter 58

Rashard Mendenhall—Professional Football Player to Writer 64

Jhovany Castaneda—Warehouse Worker to High School Student Supervisor 67

Merle R. Saferstein—Education Administrator to Author and Teacher 72

Kelly O'Hara—Advertising Professional to Advocate for Sexual Assault Survivors 76

Listen to the Little Voice: Section Takeaways 82

Phase 2: Make a Plan 87

Debbie Sterling—Marketing Director of Jewelry Company to Founder and CEO of Multimedia Company for Children 97

Brian Spaly—Private Equity Investor to Founder of Men's Clothing Company 101

Barbara Harris—PR Executive to Bishop in the Episcopal Church 105

Adrian Cárdenas—Professional Baseball Player to College Student 108

Adam Braun—Consultant to Nonprofit Founder and Executive Director 112

Akansha Agrawal—Internal Jump: Advertising Operations Associate to Market Research Analyst to Sales Analytics Professional 116

Maia Josebachvili—Wall Street Derivatives Trader to Founder of Social Adventure Company 123

Eric Wu—Investment Banker to Tech Professional to Designer of an Activewear Brand 128

Paige Johnson (pseudonym)—Internal Jump: Customer Support Representative to Sales Engineer 133

Alexandra Stein—Investment Professional to Coxswain of US Paralympic Rowing Team 139

Rahul Razdan—Financial Services Professional to Social Impact Entrepreneur 144

Make a Plan: Section Takeaways 148

Phase 3: Let Yourself Be Lucky 155

Michael Lewis—Finance Professional to Bestselling Author 162

Juan Romero—Curator of National Marine Aquarium and BBC Field Producer to Sailing Explorer 166

Ethan Eyler—Video Game Marketer to Inventor of the Lyft Carstache 171

Abigail Ogilvy Ryan—Technology Operations Manager to Art Gallery Owner 177

Olakunle Oladehin—Health Care Researcher to Nonprofit Executive Director 182

Brian Kelly—Human Resources Professional to Founder of Travel Rewards Media Platform 187

Bruce Huber—Lawyer to Pastor to Professor 193

Eleanor Watson—Teacher to Ski Instructor 199

United States Senator Angus King—Lawyer to Journalist to Energy Entrepreneur to Politician 204

Greg Klassen—Garbage Collector to Luxury Furniture Designer/Maker 209

Let Yourself Be Lucky: Section Takeaways 214

Phase 4: Don't Look Back 219

Dan Kenary—Commercial Banker to Brewery Owner 225

Kyle Battle—IT Consultant to Digital Director at Special Olympics 231

James Bourque—Corporate Hospitality Services Professional to Restaurant Owner 235

Elizabeth Hague—Secretary to Photographer 240

Jack Manning (pseudonym)—Private Wealth Manager to Sober-Home Operator 245

Matt Pottinger—Journalist to United States Marine 251

Sarah Dvorak—Retail Operations Analyst to Cheese Shop Owner 257

Danni Pomplun—Bartender to Yoga Instructor 264

Manisha Snoyer—Actress to Education Entrepreneur 270

Jacob Licht—Corporate Lawyer to Government Lawyer 274

Anoopreet Rehncy—Investment Banker to Fashion Entrepreneur 278

Brenda Berkman—Lawyer to Firefighter 284

Brandon Stanton—Bond Trader to Photographer 288

Don't Look Back: Section Takeaways 296

Conclusion: Jumping Again 303

Acknowledgments (or, The Story Behind the Story) 307

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