Introduction: Mike’s Story


SCOTT WAS MY cousin’s friend before he was my friend. We had met during a party at my cousin’s house and had grown close through coffee dates every so often, like the one just now ending on a neatly groomed sidewalk in downtown Palo Alto. It was a late February afternoon.

Midforties, tall, with a boyish smile and sharp blue eyes, Scott was soft spoken and a good listener, and he had a gift for making time spent with him feel important. With me, he played the thoughtful mentor, loyal older brother, and trusted confidant—a sounding board for the dreamer, the kid. As we parted that afternoon, I wasn’t quite ready to let him vanish into the dusk. After taking a couple of steps in the direction of my car, I turned around.

“Is this crazy?” I asked. I was squeezing the stained coffee cup lid in my left palm. The culmination of several years of fantasizing and planning was a few hours away, and I was fishing for a final bit of reassurance.

Scott had started his hustle toward home, his lanky frame hunched over his phone, checking back in to his own work and life. Our time together had run a bit long, and for Scott, there were business calls to return and kids to pick up from school. But he slowed his step and gently returned his attention to me. The sun had disappeared behind us. New customers scurried into the coffee shop.

“What you have in mind is absolutely crazy,” he said, quietly pushing his phone back into his jean pocket. “But there’s a difference between crazy and stupid.”

* * *

Two years earlier, in an office toward the top of a pristine glass tower, above the bustling heart of Boston, I sat at my desk and stared at the wall. Taped to the top edge of my computer screen, printed in a size 50 font on leftover printer paper, was a quote from a commencement speech that Amazon’s founder and CEO Jeff Bezos had made to graduating Princeton students in 2010: “When you are eighty years old, and in a quiet moment of reflection narrating for only yourself the most personal version of your life story, the telling that will be most compact and meaningful will be the series of choices you have made. In the end, we are our choices. Build yourself a great story.”

What would I want my story to look like?

I knew my answer—I wanted to become a professional squash player—but I didn’t know how to make that life happen.

Twenty-three years old, the youngest of six kids, born in New York City, raised in Nashville, Tennessee, and then in the beach town of Santa Barbara, California, I was the only child to live in Boston. A year out of college, I was ready to put down roots in Massachusetts. Or that was the plan, anyway.

I had moved to the city for what I viewed as my dream job, working in the shiny, wood-paneled offices of a venture capital firm. My job was the type of employment you get and don’t give up, the type of work you ride into the sunset of your career if they’ll let you. I had chased this job since the start of my senior year. I had been walking out the back steps of my fraternity house when I read the job description in a career services bulletin on my phone, and I’d immediately copied and pasted the text into an e-mail, sending it straight to my parents. I told them I’d seen an opening for the perfect job, working at Bain Capital Ventures, the venture capital investment arm of the international private equity firm Bain Capital. My parents agreed that the role seemed written for me: go out and meet entrepreneurs, listen to the stories behind their start-up companies, review their business plans and ideas, analyze and help decide if that start-up might be a good investment for the firm. Fast-forward to the wood-paneled office. I was only months into this plum job but performing well. I read everything I could, listened to everyone who would talk to me, and the effort was starting to pay off: one of the first entrepreneurs I came across was launching a company that, a couple of years later, would disrupt the health care industry and become one of the largest investments by our firm ever brought in by an analyst.

My coworkers were engaging, my bosses thoughtful leaders, my hours manageable: in by 8 a.m., out by 7 or 8 p.m. every day. I earned a couple weeks of vacation each year, and I figured I’d satiate my craving for travel and adventure then—heading wherever I could go, for as long as I could, combining public holidays and weekends to maximize my time off. I’d spent the second Christmas of my time at Bain hiking the famed Angkor Wat temples in Cambodia with one of my best friends, Dan. My coworkers gave me kudos for finding a way to cobble together three whole weeks off whereas my fellow travelers and the local guides we met in Southeast Asia asked why we bothered traveling for such a short sliver of time. For my part, I believed that three weeks in Southeast Asia would fulfill whatever I was looking for outside of work. Yep, I thought, I could scratch the itch for adventure between Christmas and New Year’s, then get back to the desk without missing a beat.

I had taken the job at Bain because of a genuine enthusiastic interest in the work, but I have to admit also that I had somehow got it into my head that I was supposed to stick to a certain kind of postcollege path—and the job at Bain fit into that kind of path: from college to internship to well-paying corporate job. At Bain, I was on the “right” path, surrounded by smart people, doing interesting work, and enjoying well-paid vacations. What else could I want?

Yet deep down, as time went by, I began to realize that I wanted this life mostly because I thought I should. And all the while, tucked somewhere off to the side in my mind, a very distinct if faint voice whispered an idea of something very different.

* * *

I was in love with the sport of squash.

Squash is a British game and a close cousin to tennis but played indoors against a wall. I had fallen in love with squash as a teenager, just after my family moved to California. It’s a niche sport in the United States, particularly in places outside the Northeast. While it’s a growing sport, there are relatively few courts and few competitive players west of New York City. This was especially true when I was a kid in California, but when my family joined a gym, the Santa Barbara Athletic Club, I was in luck: there were squash courts.

Converted out of racquetball courts a few decades earlier, the SBAC squash court dimensions were not exactly regulation, but they were close enough to attract a handful of enthusiastic recreational adult players. And SBAC had the only five-court setup for another seventy-five miles, until Los Angeles. So, for the bulk of my teenage years, I lived at this club. Breakfast and lunch from the sandwich bar, homework at the tables in the café, squash on the converted courts with anyone who wanted to play. Day in and day out: dropped off on weekend mornings and after school, picked up at closing. Ferdinand the clockmaker, Dirk the tech guru, Robert the British ex-pat, Debbie the office manager—for the better part of junior high and high school, my other family was the group of adult squash players who met at the courts each night.

Beyond the courts and this other family, the biggest gift the club offered me was its tradition of hosting a tiny professional squash competition each year. That’s how I learned of it: the pro squash tour. I was fourteen when the pro competition rolled in, bringing with it players from around the world. Professional squash events usually don’t offer much in the way of prize money, and to lighten the expense for the players, most tournaments offer lodging through local players in the member community. I signed up our family to host Shawn Delierre, a young and rising talent out of Canada. Over take-out burgers and fries at the dinner table, Shawn captured my imagination with stories of competing around the world, staying with friends and with host families along the way. From mountaintops in Brazil to cities in Japan to the suburbs of Switzerland, Shawn had me hooked. He told me I too could someday play the tour, though even for an optimistic fourteen-year-old like me that possibility seemed far-fetched: I was new to the sport and hundreds of miles from most of the competitive players my age. After I met Shawn though, I began tracking the website of the pro squash tour, enamored by the tiny lights that sprawled across a spinning sphere, representing the competitions that dotted the globe.

Eight years later, at my desk at Bain Capital, having long assumed that Shawn’s visit and the image of the dotted globe would fade from my memory, I was unable to focus wholeheartedly on my “grown-up” professional track. The idea of playing pro squash wouldn’t budge.

It feels awkward when a little inner voice talks to you, a voice you’re scared to listen to. It feels even more awkward when that voice won’t go away.

How do you start doing what you really want to be doing? How do you know when to take a chance? I had no idea. And no one was coming along to hand me the answer. I had the job and lifestyle I had thought I wanted, yet I secretly held out hope—for a knock on the door, for someone to enter my tiny office, walk up to my desk, and give me permission to leave: “Mike, it’s July 1, time to go chase your dream, remember?”

There was what my friend Nick called a “circularity” to my life. Weekdays I’d wake up at 7:20 a.m. to “I Think Ur a Contra” by Vampire Weekend, hit snooze once, shower and dress, head left out of the apartment and take a right toward Symphony Hall, left alongside the Christian Science museum, up the escalators and past the manicured shops and blinding white lights of the Prudential Center, and straight through the revolving doors of the glistening Hancock Tower. Ride the elevator to thirty-nine, order eggs and juice from my friends working in the cafeteria, talk football and weekend plans with coworkers across the hall, then quietly close the door to my office. Just me, a wall, and the taped inspirational quote on printer paper above the computer screen. Ten to twelve hours later, I’d walk home the way I came. Monday, Tuesday, Wednesday, Thursday, Friday.

I felt alone as I considered the possibility of listening to that little voice, but when it became clear that the voice wasn’t going away, I started to do some research. What began as an innocent Google for “when to go chase dreams” turned into a full-fledged investigation for inspiration and, shortly afterward, a scavenger hunt for stories. I devoured books like Tim Ferriss’s The 4-Hour Workweek on why, and how, people jump to live a life on their own terms. I made a list of my favorite companies and read about how they started. If the founder had a nontraditional background—if he or she took an unusual risk to start the company—I wanted to know how he or she approached that start-up decision. Every “jump” story made me want to find another one. I began identifying and cold-calling people who did cool things: alumni from my college, siblings of my friends, strangers I read about in the newspaper. In the darkness of my office long after office hours ended, I tracked down other people—ex-electricians, consultants, teachers—each of whom had left a place of comfort to chase a passion. They had all jumped.

I wanted to know when to jump.

The first woman who called me back was an ex-banker turned cyclist. I had reached out after reading an interview with her in a recent issue of our college alumni magazine. When I asked about her jump, she didn’t tell me anything about how to ride a bike or how to become an elite athlete. Instead, she explained the behind-the-scenes preparations: how she’d saved up money, how she’d mentally prepared for the possibility of things not working out, how she’d told her boss she was quitting. I hung up the phone and rushed into my coworker’s office: he was also planning for something different, and I knew that these tidbits could help my jump and his.

Over the next year and a half, I picked up more when-to-jump insights—from a journalist turned politician, a bond trader turned adventure planner, a brand marketer turned toy maker. I had expected clichéd advice and feel-good fairy tales. Instead I got candid details about how to chase an unknown, honesty about the emotional and financial vulnerabilities of doing so, and frankness about the range of thoughts and feelings that come from taking such a risk. Following a dream is lofty and sounds admirable, but real consequences follow. Those costs were the truths I was searching to know.

After I’d heard about a dozen stories from people who had changed career paths, a pattern began to emerge. A few of the same ideas—even the same words and phrases—overlapped across experiences that, on the surface, had little to nothing in common. A onetime karate teacher in rural Virginia shared the same insights as a single mother in the Northeast. A brewery owner in Boston described a jump philosophy similar to that of an aspiring aviation entrepreneur who was half the brewer’s age and lived halfway around the world.

Discovering patterns in a random collection of career-switch stories was bizarre and thrilling. I collected more narratives, and more commonalities appeared. These mapped broadly across the jumping experience to form a curve. There was no surefire way to guarantee a jump’s success or predict what would happen post-jump, but the process of jumping began to seem less haphazard and random to me. It became clear that there is a smart way to try for a dream, a certain discipline around responsible planning. I saw that I would prepare myself for the best possible jump experience if I was alert to each of the broad phases of the jump process. The Jump Curve provided by the stories didn’t give me exact instructions on how to achieve my dream. But I didn’t need exact instructions; I needed a sign that I could make a jump, that I wasn’t stupid for trying.

The people willing to share their jump experiences also made me feel less alone in my desire to chase something that mattered to me. No longer was my career move going to be “me against the world.” The experiences these “jumpers” shared with me formed companionable case studies of how much determination and preparation changing my path would take.

For twenty-three years, I had chased plainly laid out goals. Goals that were easy to want to chase because they were popular with the older people around me and were even popular among my own peers. Also, more people chasing any single objective creates competition, and I’m competitive, so I felt compelled to run faster toward particular goals—at the risk of forgetting what I was hurtling toward, and why. There existed a baseline to each goal—graduate from high school, get to college, earn an internship—and there were higher-level, bonus goals attached to each baseline: graduate with high scores and excellent extracurricular activities, attend an Ivy League university, intern at Goldman Sachs. In this way, pursuing each goal was a game for me. Reach each new baseline and see how many bonus goals you can score. Who doesn’t want to win when playing a game?

So when the predetermined game I had been playing ran out of obvious new levels sometime during my first year at Bain Capital Ventures, my feet stopped sprinting. For the first time in a long time, no one was telling me what I was supposed to do next.

Until this moment, two words had summarized the biggest prize in the game I was playing: venture capital. Venture capital is the perceived Promised Land for anyone who wants to work in investing. Venture capital, it was explained to me during the corporate recruiting process, is what you go to business school to get to do someday, if you’re lucky. Unlike consulting or banking, venture capital is the “buy side,” the side where you have the money, and you choose how and where to invest it. Better hours, better pay, better success stories: if there was one uniform piece of advice that I received from my college career services director and from older alumni, from friends, and from my parents, it was that a job at a VC firm was above all else. Once, when I let it slip to an older colleague, who was my direct manager, that I had a dream of traveling around playing the pro squash tour, his reply was blunt: “Don’t quit your day job.” If you were lucky enough to fall into the rarefied air of a venture capital firm at any point in your career, let alone the beginning, you were to stay put. Period.

I had no background in finance, no inside scoop into the firm or the industry when I entered the doors to the castle. My college didn’t offer finance to undergraduates, and I had never taken an economics course. While I wanted to go into business, I had decided to use the time in school to take courses that I’d never get to take again. My degree was in political science and environmental studies. And while I may have been qualified for Bain Capital Ventures based on my academics and genuine interests, so were thousands of other students. Being offered one of the two coveted spots at Bain was, without exaggeration, beyond the wildest dreams of my parents, my siblings, and myself.

Getting chosen for the job felt exactly like that: getting chosen. Like winning the lottery. I felt lucky to be there, lucky to be earning a good living, lucky to be doing something my parents could easily share with their friends at holiday parties. Mike’s a venture capitalist is a hell of a lot easier to explain, and for someone to digest, than Mike’s making no money while sleeping on couches playing an obscure sport somewhere near Fiji. As I thought of what I was doing, and what I really wanted to do, the emotion that repeatedly crept back up was guilt. I was the last of six children that my parents had sent to college. My job, and this career, felt implicitly like a way I could return the favor to my parents by taking good care of myself.

But when I tried to settle in where I’d landed, I’d end up staring at my office wall. My friend Emily had given me a paper map of the world, a map from the charity Doctors Without Borders, a map that was wrinkled and well-worn, as if sent from a field office for the organization in a rural village. Emily and I had both taken geography classes at school, and she was one of the few who knew my secret squash aspirations. I think that’s why she gave me the creased and fraying map, which I stretched out and pinned along the length of my office wall. Sitting at my desk, directly opposite eye level, were the jagged island contours of Australia and New Zealand. There, every June, a series of pro squash competitions took place for guys at my level. As months tumbled along, a nightmare scenario began to haunt me: this flimsy, creased map would remain pinned to the wall while the seasons cycled by, years rolling into years. I would grow older. And every June, I’d look over at the contours of Australia and New Zealand, and they’d look back at me, and I’d go to lunch and stop off at happy hours telling my colleagues how, at this very moment, I could be across the world chasing a dream. And then I’d go home, and the next day, the fraying old map would still be pinned to my office wall.

* * *

That nightmare did not come true. After I spoke with the banker turned cyclist in January of my second year at Bain, my jump was set in motion, a process that would take the next year and a half, an eighteen-month window during which I gathered more jump stories and began to lay out my own. I wrote plans and saved up money. I paid attention to where I seemed to be on the Jump Curve. To be clear, I don’t think there is any secret recipe or prescription that releases a person to make a jump. But the stories I heard and the common themes and insights from the Jump Curve helped me make a big change—and I believe these stories and an awareness of the curve can help others do the same.

Timing matters. If you’re supporting a family or have pressing debts to pay off, now is almost certainly not the time to quit a moneymaking job for a dream that does not pay. But that doesn’t mean you can never chase your dream; it means not just yet—as the Jump Curve will show.

During the time I was itching to jump, my situation was lucky. Throughout most of my three years at Bain Capital Ventures, I was able to divert part of each paycheck to a new “squash” bank account, which I didn’t allow myself to touch. For the last two years at Bain, I imitated the training, eating, and living routines of my full-time, professional athlete counterparts. Because I had no family, no kids, no mortgage, I could use all of my extra time to train my body and all of my extra money for healthy foods and wellness programs.

In my final year at Bain, I started to reach out to potential sponsors. I told them my story: my dream and my plan to go chase it. I let them know that, lucky for them, I was now accepting sponsors to provide cash in return for visible logo space on my playing jersey. It was terrifying to write down and share my most personal hopes and dreams, but I did it. A few months after making my first pitch, I sat across from a recreational squash player and member of my gym, Amrit, sharing with him the pitch materials that had, so far, collected a few nos and a couple maybe laters. As I flipped through the paper slides before us, my voice picked up in pace and grew into an excited whisper. Even though I had struck out in finding anyone to buy into the vision I was selling, the simple act of reading over my most personal, hopeful dreams made me feel a step closer to achieving them. And after taking a final sip from his beer and setting the bottle next to my scattered slide presentation sheets, Amrit told me he was in. I had my first jersey sponsor.

And suddenly I felt I had no choice. I was really going to do this.

Nine months before leaving for the tour, I began competing as a pro part-time, to make sure I knew the lifestyle I’d be signing up for: traveling alone, trusting strangers, sleeping on couches. To attend my second pro event, I slipped out of the office and flew out to Chicago in the late afternoon, only to find out my opponent for that evening had defaulted. The default gave me my first victory, but it meant I’d be competing the next day, a workday. I told an understandably confused tournament director that I would now have to default; then I quickly took a shower (though I hadn’t done anything to break a sweat) and flew back to Boston in time for work the next morning, having spent a few hundred bucks and three hours in Illinois, earning my first official tour win without actually playing anyone.

* * *

The other thing I had in my favor was working in an industry that valued both risk-taking and compelling personal narratives. The only thing investors love more than an entrepreneur taking a big financial or social risk to start a company is if he or she has a great story behind that risk. And that fit my story line: while I wasn’t jumping to start my own company, I was risking significant income in the near term and potential career prospects in the long term, all because I wanted to go for something that I believed I had to try. I worked in a business where we spent every day investing money in people and their passions; my jump meant acting in a similar vein but on my own behalf. When I broke the news of my jump at lunchtimes or over a beer after work, I’d carefully explain to colleagues that my dream was a short-term experience—rather than a lifetime pursuit—in an effort to keep doors open, hoping to work with some of these people again in some way down the road. Many of my bosses were risk-takers and had been high school and college athletes themselves. A few years removed from their athletic primes and settled down with families, they could vicariously think of my journey as their journey. I’d stay in touch by sharing photos and stories from the road. Fortunately, when the time came to officially discuss my jump with everyone, the response from all of my colleagues and bosses was: go.

My jump was daunting, but it was feasible, and as I went about preparing for it, I understood how lucky I was.

But as the journey around my jump unfolded, what also became clear is that the desire to do what is meaningful to oneself and the will to find a way to make it happen was not specific to me. Bartenders, fellow bus passengers, brand marketers—many people I spoke to had something worth jumping for. The ability to jump is not limited to those who have a college degree or a certain-sized bank account. Applying for an internal promotion at work, going back to school at night, teaching cooking classes on the weekends—big jump or small jump, very many of us have something that we’ve longed to try doing. A jump is a jump. If you can’t do it now, write it down for later. And if you can do it now? Go.

And regardless of whether your jump will happen soon or much later, the stories in this book will offer inspiration and ideas that can help along the way.

* * *

By the time I met Scott for coffee on that afternoon in Palo Alto, I had made it through nearly two years and ten thousand little, unsexy steps of planning. An hour later, I officially quit my job at Bain, and very shortly afterward, I began to pack my life into a hulking, baby blue fifty-pound monster of a roller suitcase that I’d bought on sale at Marshalls and an extra wide Dunlop squash bag that I planned to carry slung heavily over my shoulder. In preparing for every climate and attire requirement, I chose three anchor pieces of clothing: a pair of khaki-colored Levi’s that were nice enough to pass for dress pants but sturdy enough to do everything else in (camp, travel, sleep—my roommate Catherine helped me pick out these pants); a black fleece with the collar of a nice sweater but the zipper of an athletic piece—I’d use it for both (my other roommate, Mike, had tossed me the fleece, which had accidentally shrunk in the wash and was too small for him but a perfect fit for me); and a knit hoodie from H&M (twenty bucks!) that looked hip but was also warm and heat absorbing, thus making itself useful across a variety of party vibes as well as in chilly climates.

I printed jerseys with logos of my sponsors on all sides and with “LEWIS” printed on the back beneath an American flag. Carefully unwrapping three new Dunlop racquets from the manufacturing plastic, I slid each racquet into a compartment in the squash bag, padding the surrounding space with rolls of socks, underwear, and my jerseys. I unpinned the worn paper map from my office wall, folded it back along the creases, and zipped it neatly inside the front outside pocket of my suitcase. And then I booked a one-way flight across the world.

As it turned out, Scott was right: there is a difference between crazy and stupid.

The difference lies in knowing when to jump.


Copyright © 2018 by Mike Lewis