How many times do you really face a choice in life? How many times will you get the benefit of arriving at a crossroads, where you don't have to fight the tug of rolling inertia, and your choice isn't going to hurt someone you love? Not many. Make them count. They will define you.

"What Should I Do With My Life" . . . is mostly about the job, not the heart, not character, not love, not issues that matter . . . It's a little more pragmatic than its philosophical and religious antecedents, reflecting the bottom-line reality that we can search for our identity only so long without making ends meet. Asking the question aspires to end the conflict between who you are and what you do.

Failure's hard, but success is far more dangerous. If you're successful at the wrong thing, the mix of praise and money and opportunity can lock you in forever. It is so, so much harder to leave a good thing.

Why not get rich, then do your dream? When I started this book, I assumed I'd find numerous examples of that path. Surely, among all the young millionaires who left Wall Street or Silicon Valley, I'd find some who used their money to bankroll a successful run at the dream they always harbored. But I didn't find any . . . I've seen lots of people get rich. It takes twice as long as anyone plans for. It's more work than anyone expects . . . Dream. Lockbox. Fuck You Money. Lockbox. Dream. That cold, calculated formula. Rarer than I ever imagined. I'm not advocating giving up your day job to chase pipe dreams. But don't put your dreams in lockboxes, and don't invest years of your life in a day job for the wad you expect to have at the end. Believe in that myth at your own peril.

Here's another thought that stops people: there are a lot of possibilities that sound exciting – but you're not sure you'd want to do them forever. And because of their quirky nature, they're resume killers – they slam a lot of doors shut. Sure, it'd be a fun ride, but where do you go from there?

The Brilliant Masses are composed of nothing less than the many great people of our generation, the bright, the talented, the intelligent, the resourceful, and the creative – far too many of whom are operating at quarter-speed, unsure of their place in the world, contributing far too little to the productive engine of modern civilization, still feeling like observers, all feeling like they haven't come close to living up to their potential.

We are our own worst enemy . . . struggling against external obstacles only to find that, once those obstacles are cleared, we still have our old urges to fight . . . the real challenge is to overcome one's own weaknesses.

"I decided to go to Oxford for a year, because, well, it was Oxford. I told the other women at work and one said, 'I wish I could just up and go to Oxford.' So I asked, 'Why don't you?' She said, 'I would, but I bought a couch.' I always remembered that moment, and I never wanted to be that woman. I never wanted to be trapped by my belongings, my past, my commitments."

She'd given up the need to come across looking brilliant. That's not easy, and once it's done, it's very liberating.

What's wrong with being permanently restless? I'd met many people who were change artists. They'd given up the notion that any of their passions could stay lit for long. "Life is a great opportunity to try out all the things I'm interested in," one wrote. Their only constant was wanderlust. "It took me awhile to realize that I was born to wonder what to do with my life," wrote another. "And in the wondering, experience constant metamorphosis."

"What it feels like to find your thing? You stop getting bored."

I thought about how so many other people saved themselves only when pushed to the brink. George seemed cursed by his nine million dollars. He didn't have to change. He had nine million dollars of padding to insulate him from the pain.

Nobody made a dime until 1997, and nobody cared. People were giddy to have a job where they could wear a skintight latex bodysuit or skateboard down the hallway. The Internet reinvented work culture, and in so doing turned on a generation, tapping into their potential for the first time.

What I've found is that . . . if you succeed at something in which you're honest to yourself, and in line with your values, and not wearing a mask to the world, then that does seem to make people happy.

Can what-we-do really be in alignment that deeply with who-we-are? I think it can, if we let "I'm going to be truer to myself" be the principle that drives our decisions every time we come to a crossroad.

Most people jump through life, asking what's next, and choosing based on where they can make the most money, what offers the most upside or opportunity . . . I'd like to suggest an alternative "success" story – one where, with each next, the protagonist is closer to finding that spot where he's no longer held back by his heart, and he explodes with talent, and his character blossoms, and the gift he has to offer the world is apparent.

I tracked a dozen people who'd recently realized that the too-competitive rat-race pressure of their big cities was the source of their unhappiness. So they moved to small towns, which they chose either for their idyllic picturesque character, or because they'd grown up there and wanted to feel at home . . . all of them struggled, and it was never the cure-all they hoped for. They grew bored, some because they couldn't find interesting work, others because they couldn't find interesting people. They missed the chaotic melting pot of the city.

. . . they felt their ambition was running too high, like an engine, unsustainably, dangerously, burning too much oil. New Orleans succeeded in idling down their ambition, and helped them enjoy life. But frequently it succeeded too well, and their ambition shifted into neutral, and then just puttered out completely. Those who left did so because they needed a little pressure, like a turbo boost, to remind them of what they could become with some hard work and a little opportunity.

Because the hardest thing was not learning to write; the hardest thing was to never give up.

Uncomfortable Is Good

For those who simply feel trapped under their responsibilities and can't summon the initiative to quit, [traveling and] exposing yourself to how other people live loosens the mind. "Look at how happy they are with so little money!" for instance. You comprehend how many ways there are to get by. Choosing a new way seems possible. At home, at work, at school, there are always a ton of external inputs coaxing you in the direction you're already going.

"I know I had never demonstrated that I had it in me. But I did. And I just had to get in the right environment, where I could really put all this energy to good use. Hong Kong turned me on. It turned me from a guy headed nowhere to a guy really doing something."

He'd always admired how I had left sales and trading, despite having a talent for it, and gone on to find my true self. He also admired another coworker of ours who had moved to New Zealand. He respected the leaps we'd taken more than he respected any Big Swinging Dick on Wall Street. Wall Street pretends to take risks, but it's only with money – the big risk is with one's life. "I wanted to be a citizen of the world. I'm a small town kid from Oregon. Most people I grew up with never left. They're still here. I didn't want to lead a safe mundane life out of fear." Mark contemplated giving it all up and moving to Frankfurt. He'd climbed the ladder here, and he could do it again there. Once he considered this, the idea had a sway over him. He'd always felt like he got his start at First Boston out of serendipity and luck. He felt like an imposter. What his whole life a fluke? This was his chance to prove it wasn't a fluke. If he could rebuild his life in Frankfurt, he'd finally feel like he belonged, right? " . . . It's so easy to derail a career," he remarked. "It's scary."

So Mark took the job, sight unseen . . . "I go tomorrow," he said. "What the fuck? I wanted an adventure, right? You're either able to say yes to the unknown, or not . . . Wells Fargo can kiss my ass."

Tom was dreading the trip's end, because he was no closer to figuring out what he wanted to do with the rest of his life than he had been on the day he left the States. They were refugees from Washington DC, where they'd spent the last eight years working in politics. They did not intend to return to DC. They'd cleaned out their apartment, sold their car, and put their possessions in storage. They were not quite thirty.

Do not wait for the kind of clarity that comes with epiphanies. In the nine hundred plus stories I heard in my research, almost nobody was struck with an epiphany. It was one of my biggest surprises. Most people had a slim notion or a slight urge that they slowly nurtured until it grew into a faint hope which barely stayed alive for years until it could mature into a vision . . . The things we really want to do are usually the ones that scare us the most.

Beware of happiness chasing. The higher standard (and it's not for everybody) is to ask, Is doing _____ why I am here? Will _____ be meaningful to me? Is _____ what I want to contribute to the world?

My choices were ruled by that fear but I never would have called it a fear. I would have advertised it as one of the few things that I knew mattered to me. I would have called it self-knowledge. You want to know where your fears are hiding? Tell me what you know about yourself. Tell me what you can't live without.

"Everybody needs fuel for their engine. Making seven figures on Wall Street is cheap wood, it burns up too fast. I need something that burns well. That's substantive. That's real."

. . . don't pretend what you do doesn't shape you.

Our parents jumped into their adulthood quickly, saddling themselves with responsibilities like mortgages and children, and often compromising their dreams to support the family without quite realizing that's what they were doing. Later, they wanted to recapture the youth they'd abandoned too soon. Now it's our turn, and is it any wonder we're wary of taking on responsibilities before we're ready? We're extending our youth, getting married later and waiting to have children. If we have a midlife crisis, it's the other side of our parents' coin – we realize that endless youth isn't endlessly fulfilling. It gets old.

It suggested how deep the need for prestige is rooted . . . Does he struggle with being a "prestige dropout"? . . . "No disrespect to your friends, but do you ever miss the intellectual stimulation? Being surrounded by smart people?" "Hah! People think that's an issue, but really ask yourself, how many stimulating conversations have you ever really had in an office? You talk about work. My legal work was a glorified version of filling out forms. There was not a big intellectual challenge in it. I'm not trying to put down the law. My best friend is a lawyer, a good one, who hangs his own shingle and loves it. One man's hell is another man's salvation. So what I get in trucking is the benefit of perspective from very diverse people. They're not brilliant, but they've seen things I'll never see. I learn from how they see the world. I'll take that any day over a bunch of other white, college-educated smart alecks like myself."

"I had some good years. It was a good ride in life's amusement park."

"Changing my career saved my life. You tell people that. You put that in your book. Changing my career saved my life."

Everyone I asked had embraced a sink-or-swim philosophy, ie, you'll get over your fears if you're in a situation where you simply have to.

He's often called by people who want to know the secret of his success. He has none. He sat it out and endured until his chance came.

These last few stories are reminders to keep an eye on your Big Picture. By that I mean not everyone's got it figured out just yet, but in the meantime you can build skills that you might be able to draw on when the time comes to make your contribution, X.

Here's my point: usually, all we get is a glimmer. A story we read or someone we briefly met. A curiosity. A meek voice inside, whispering. It's up to us to hammer out the rest.