How to Prioritize Happiness On Your Quest for Meaning
Magazine / How to Prioritize Happiness On Your Quest for Meaning

How to Prioritize Happiness On Your Quest for Meaning

How to Prioritize Happiness On Your Quest for Meaning

Why do billionaires, CEOs, and other titans of industry work so hard? Why do they maintain such relentless professional ambition?

Look up and down the Forbes 400 list and you’ll find hedge fund managers who already have a lot going for them— meaning, more money than God, and fame — who are continuing to work on Saturdays, Sundays, and Christmas Day in pursuit of yet one more accomplishment. Rather than dial back work hours and dial up time for yoga, their kids’ football games, hobbies, travel, or non-profit work, they push even harder, sacrificing sleep, friendships, and family in an effort to expand their empires.

It’s not just billionaires. I, for one, work massively harder than I need to, and I’m not flying a Gulfstream. I work most weekends, circumnavigate the world on low sleep, and feel a compulsion to be productive even when I’m on vacation. I’ve frequently recited and extolled the text of the Apple Computer “Think Different” TV ad that celebrates those “crazy enough to think that they can change the world.” It seems I’ve been this way for some time. My 8th grade classmates voted me “Most Ambitious” in our yearbook survey, which I’m not sure is something to be proud of or embarrassed by!

Recently, I’ve been probing the nature of my ambition. What’s driving me? Am I optimizing enough for happiness in my quest to make an impact and achieve meaning? And, looking outward at others, what’s really driving so many successful people I know who sacrifice day to day happiness in pursuit of more professional success? We often admire our heroes without understanding what drives them. Figuring out how they derive satisfaction will better inform our admiration. It helps us figure out how to live our version of the good life.

When it comes to evaluating the decisions that make up a person’s life, the why question is hard. Humans are not pure, rational processing machines. Each of us is a bundle of both selfish and selfless motivations; riddled with unconscious biases; and deeply influenced by the the people in our social circles.

What’s more, people can be unreliable narrators of their own lives. Ask successful people whether they are glad they sacrificed a lot to achieve their professional ambitions and you’ll likely hear politically correct yet somewhat problematic answers.

A common catch-all answer to the “what motivates you?” question you hear in Silicon Valley is: “I want to change the world.” I once had dinner with a prominent entrepreneur in his late 30’s who confessed to me that he’d put on 30 pounds since starting his company, was addicted to email, had basically no friends outside of his wife…but no matter, because he was “changing the world.” Maybe he is, but as I looked across the table at his haggard eyes, it hardly seemed like he accepted the right tradeoffs.

The most complicated of politically correct descriptions for why successful people work constantly is: I love what I do. Passion: the ultimate 21st century virtue. Now, it’s true that jobs today are far safer and more enjoyable than jobs were 100 years ago. Thus a straightforward exploration for many people’s sustained professional ambitions in an economically abundant era is that they enjoy the work and enjoy making and spending money. The economist Tyler Cowen, in a recent lecture exploring why, contra Keynes’s prediction, we’re all still working long hours despite great prosperity, says: “One of the big lessons of economic data is that people really like work.”

That’s definitely true on average across the workforce. But let’s zoom in on the top 10% here. It’s the elite billionaire race, but it’s also the people around that race who are industrious, who are sacrificing, who are setting ambitious goals and going after those goals with quixotic fervor. These are the people I spend time with; I am one of these people. Some of them are quite happy. (And I should note here that I think the billionaire I know best, Reid, is happy!) But many of them are not happy or have prolonged bouts of unhappiness—even though they’re way ahead in the global rat race.

The thing with successful people is they are often too busy to recognize their own unhappiness. The malaise bubbles beneath the surface.

What’s happening with these successful and ambitious people? There are of course many reasons—I’m not going to explore all the elements of happiness. But I think there’s one underrated element worth understanding that especially chips away at goal-oriented professionals.

And I believe understanding this element of human nature—which I’ll discuss in the next section—is key to building a life that: a) involves ambitious striving toward goals and having impact in the world, which contributes to a sense of meaning, and b) gives you a shot at realizing true happiness by avoiding a soul-sucking competitive rat race. A life, in other words, that strikes a balance between meaning and happiness.

What’s a deeper reason some successful and wealthy people continue to sacrifice happiness for more money and achievement?

Status. I believe the quest for status drives the behavior of the “post-economic” population to an extreme degree—people for whom there is there no economic imperative to work—and, for that matter, most of the rest of us, too.

What do I mean by “status”? Status is your position in society. Status represents your place on the community pecking order. Public recognition, fame, respect, money, power, and other such factors—these are the things that collectively comprise a person’s status.

It is, crucially, a social construct and inherently relative. You cannot self-declare high status; it’s instead determined collectively by the people in the society in which you’re enmeshed. Status markers are not determined by God. They are arbitrary markers that we make up to help us sort through who’s hot and who’s not. Evolutionarily speaking, figuring out who we should follow, who we should be scared of, who we should have sex with: these were useful things for our ancestors to know, and so natural selection “designed” our brains to care about status a great deal.

As recently as a couple centuries ago, tens of thousands of men died “dueling” each other with sword and rifle. Dueling was a practice in which men so obsessed with remaining “honorable” in the eyes of the people around them, people who perceived physical manliness as a proxy for respect—that men would sooner risk being stabbed or shot to death than be thought a coward. Alexander Hamilton lost his life in a duel, at the age of 38.

Today, money is the most obvious proxy for status. Because we don’t walk around with a money sign over our heads that displays our net worth, we often engage in consumption that signals to others how much money we have. You might buy and wear a Rolex watch, say, which works just as well as a cheap Casio watch but also does the nifty job of signaling to others that you have money, which thus helps you win respect and power among your competitors.

Wall Street titans, Hollywood moguls, and tech billionaires do not physically duel. And they’ve often made so much money that they all have nice watches and cars and houses. But they do continue to race each other for prestige and power and other non-monetary status markers.

And that horse race is a zero-sum attention game. It’s zero sum because if you and I are peers or competitors — say, we both live in California and we both work in the tech sector — and if you get more status in whatever social sphere we operate in, then I have less status. It’s an attention game because for the rich and successful, status manifests in things like lifetime appreciation awards, media profiles, and charitable recognition. There are only so many New York Times profiles to go around in any given day.

So, status considerations might drive some people who’ve already decorated a second home in Aspen to work really hard…in order to be profiled in the New York Times or in order to win a “philanthropist of the year” award. What’s so wrong with that you might ask?

Indeed, regardless of whether you’re super rich or middle class, the core hunger for status motivates us to improve our life and the world. In his book Status Anxiety, the writer Alain De Botton writes that status “spurs us to do justice to our talents, encourages excellence, restrains us from harmful eccentricities and cements members of a society around a common value system.”

But like all appetites, the excesses of status-driven ambition can also drive you down the road of misery. The zero sum, social nature of the status game goads people into a life of continual dissatisfaction. Status-fueled ambition might be a decent tool to spur you to take action now and then but it’s a terrible master of your career and your life. Status is like fire: it can heat your home and cook your food, but if not managed thoughtfully, it can burn down your house and kill you.

Why is status questing ultimately unfulfilling and addictive?

Seeing your name atop a leader board offers a jolt of excitement–a quick high of insta-satisfaction. It’s an age-old phenomenon that social media amplifies. You can tweet something or share a photo on Facebook and within minutes see if people are “liking” it; you can then count how many likes you have compared to a friend. frequently publishes rankings (“Top Leaders Under 30)”) of leaders under a certain age in a certain industry that always seem to go viral. People love leaderboards.

Leaderboards, both formal and informal, are all around us. When we surge up them, we get a dopamine hit.

But the hit doesn’t last. Like a drug, status is insatiable. Just like you crave a greater and greater high with cocaine—needing to up the dose over time to achieve previously-felt pleasures—so too with status. You’ll inevitably be unsatisfied by whatever it is you thought would finally make you happy, be that material possessions like a big house and nice car, or non-monetary status wins like an honorary degree from Yale, your name on the outside of a hospital, or the long media profile heralding your accomplishments.

As Sam Harris writes in his excellent book Waking Up, “…our pleasures are, by their very nature, fleeting. If we enjoy some great professional success, our feelings of accomplishment remain vivid and intoxicating for an hour, or perhaps a day, but then they subside. And the search goes on. The effort required to keep boredom and other unpleasantness at bay must continue, moment to moment. …”

Or as De Botton puts it, “We are tempted to believe that certain achievements and possessions will give us enduring satisfaction. We are invited to imagine ourselves scaling the steep cliff face of happiness in order to reach a wide, high plateau on which we will live out the rest of our lives; we are not reminded that soon after gaining the summit, we will be called down again into fresh lowlands of anxiety and desire.”

Or as Don Draper put it in Mad Men, “What is happiness? It’s the moment before you need more happiness.”

I know many executives in business who, some years ago, declared on a “number” they wanted to hit in terms of net worth at which point they promised themselves (and their families) that they would stop worrying about money. Except, every time they have hit the number, they doubled the previously announced number. And then vowed, “Okay, at that point I’ll stop caring.” In other words, the definition of their dream home enlarges shortly after they’ve purchased all their furniture and settled into their original dream home. (For more on my thoughts on the ideal amount of money to have, see my earlier essay The Goldilocks Theory of Wealth.)

In short, whenever we achieve our goals, we immediately lust after new goals.

It’s a rather remarkable, even startling, truth about human nature: the things we think will make us happy if and when we obtain them—success, money, status—rarely do. The thing gives us a hit, but then we need more. The Buddha taught, in one translation, that “life is unsatisfactoriness”: by which he meant a process of perpetual craving and disappointment. Much of Buddhism is devoted to the idea that our craving for success is leading us to misery, and if we can liberate ourselves from that constant craving, we can achieve true, sustaining happiness.

You don’t want to turn off ambition altogether. Balancing ambitious striving and happiness.

To be sure, if you reduce ambition to zero, I don’t think you’ll be happy. I do not believe meditating all day for the rest of your life is what will lead to the happiest existence. As homo sapiens, we ventured out of Africa and explored the earth. We’re designed to explore, expand our territory, grow, learn. Striving is natural. It’s human. It’s why I’ve never advised friends who’ve made a phenomenal amount of money to stop working and sit on the beach. In such a life, they’re bound to feel estranged from the real world. Various studies of the modern workplace reinforce our evolutionary heritage: the most engaged employees today are the ones who have opportunities to grow and develop.

Gilbert Brim, in his thoughtful book Ambition: How to Manage Success and Failure Throughout Our Lives, argues that calibrating your growth path so that it offers “manageable difficulty” is a balancing act at the core of achieving human happiness. He says happiness depends upon “working on tasks at a suitable level of difficulty, neither too hard nor too easy.”

As part of this process of seeking out manageably difficult projects, it’s foolish to completely stop caring about your status—your rank in a pack—because status considerations help you jumpstart action, measure progress, and refine difficulty over time.

After all, there are plenty of people who lead ultra ambitious careers who have consciously and honestly reflected about their tradeoffs and decide to keep up the fast pace. They even seem to manage to stay happy, too.

Consider the journalist Ryan Avent, who recently wrote a piece titled Why do we work so hard? He confesses to an internal struggle about the pros and cons of his self-described workaholic life. But he ends up optimistic about his tradeoffs. For his grandparents, he says, work was a means to an end. “Work” was the thing you did during the week to make money in order to enjoy “life” on the weekends. For our grandparents, in a different economy, work was duller and more physically taxing. Today, for the educated among us, work can be intellectually invigorating as never before. It’s easier to love your work, as he says he loves journalism. When his parents worry about his job and its long hours, Avent observes the disconnect: They are asking him about his “work,” he says, but “I am thinking about identity, community, purpose – the things that provide meaning and motivation. I am talking about my life.”

I admire Avent’s life if it’s as he describes it. Some people, despite my earlier point that it can be hard to always trust people’s self-analyses, really do love their work and all the 80 hour weeks it demands.

In any case, the point is you don’t want to dial down ambition to zero. And sometimes ambition can be at 100 and you can still be living a good happy life. Everyone’s different.

My goal: I want a life of meaning, which often comes from pursuing difficult ambitions. I also want a life of lasting happiness—of feeling good most days and maintaining a level of equanimity on the bad days.

Hence, the conundrum: How to strive and grow and be ambitious without getting caught up in a rat race against your peers—in other words, without becoming obsessed with your relative status, as that is an obsession that I believe can seriously dent your happiness.

The Components of Happy Ambition: Tweaks to Prioritize Happiness As You Quest for Meaning

Are there sources of satisfaction and motivation that are more sustainable than Status Cocaine? Is it possible to strive without being addicted to checking the leaderboard?

Below are some ideas that might contribute to a life strategy of what I’m calling “Happy Ambition.” They are less revolutionary changes or ideas and more a series of (hopefully) thoughtful tweaks, nudges, and hacks.

Become mindful of status triggers with mindfulness meditation

Mindfulness meditation is perhaps the best way to gain better control over your status obsessed, reactive impulses. Think of meditation like lifting weights but for your brain—building new mental muscles that give you greater clarity into the truth of your thoughts. Mindfulness meditation involves, in part, training the mind to be less reactive and more proactive about what it—that is, you—thinks.

On my first 10 day silent meditation retreat, I was taught to sit completely still and not scratch an itch on my body even if I felt the itch. “Just observe the itch,” the teacher said, “The sensation will eventually pass away.” Eventually, the itch on my nose went away. I don’t know how many times I’ve unconsciously moved my hand to scratch some itch on my body the moment the itch comes. On retreat was the first time I ever simply observed the itch and made a decision about whether to scratch. It occurred to me afterwards that this a metaphor for all our thoughts.

We have a range of natural drives that are not helpful for our pursuit of happiness, and blind pursuit of status is one of them. Learning to be more mindful of our thoughts and more deliberate in our actions in order to overcome our natural biases ought to be at the center of any effort to construct a new motivational north star for our life.

Specifically, you can short circuit a status trigger by being mindful of when status is introducing upon a decision. As you contemplate a given decision, ask, “Why do I care about the outcome I have in mind? Should I care about what so-and-so thinks of my decision? Will such-and-such really make me happy? Has such-and-such made otherpeople happy who already have it?” Easier said than done, but that’s why they call meditation a practice!

Set fewer goals. Love the craft itself: be process-driven, not goal-driven

If you’re driven primarily by a desire to achieve specific goals, be they goals radiating with sweetness and light (“Leave a good legacy! Eradicate malaria!”) or darkness (“Make billions of dollars!”) that goal-driven ambition is probably driving you to unhappiness. In other words, Wall Street analysts who dream of massive wealth or NGO types who dream of eradicating polio: If you don’t achieve the goal, you’re unhappy. If you do achieve the goal, you’re happy but only for a moment because there’s inevitably someone else you can compare yourself to who achieved a more audacious goal. The pleasure is fleeting. Impact-related career goals will cause you to obsess about the leaderboard.

Ideally, you love the process of the work itself and are non-attached to a specific outcome. Ideally, your work is more about doing the thing itself and reaping intrinsic rewards in the process. “The journey is the reward,” as Steve Jobs put it. “Intrinsic motivation” is what psychologists call it. “Master the discipline of non-grasping,” is how a Buddhist monk put it to me recently.

Here’s one test to see whether you’re doing something for the status boost of achieving a goal: If you could climb Mt. Everest, but no one would ever find out and you could never tell anyone, thus removing any gain in status that would accrue to you, would you still want to do it? I’d argue that many people would not climb that mountain—or undergo various other sacrifices on the road to general achievement. They don’t actually want to climb the mountain. They want to tell people about having climbed the mountain. They don’t want to write a book. They want to talk about having written a book. The achievement is the reward. The journey is just the path to the achievement.

I was once talking to a successful, New York-based journalist about Silicon Valley. He didn’t understand Silicon Valley entrepreneurs’ obsession with “impact.” He said that for him it’s all about the craft of writing. He loves writing profiles. All things being equal, he’d prefer for his articles to change the world. But he doesn’t track metrics around how many people read or share his articles, or how many emails it generates. His satisfaction and pride comes from practicing the craft itself, he says. Impact is decidedly secondary.

The idea of loving the process and not being driven to pursue selfish goals might be more plainly headlined “Be passionate about your work.” Which I think is good advice. Be passionate about the process. If you love playing the game, you don’t care as much the score at the end of the game—only that you got a chance to play. (As my friend Cal Newport argues, how you go about getting a point where you love your work is more complicated than many career gurus would suggest, but that’s outside the purview of this essay.)

Choose work and set goals where relative status is harder to compare or measure

It might be easier for my journalist friend in New York to be non-attached to impact and more attached to the pleasures of craftsmanship. After all, in his industry, there’s no clear leaderboard. Sure, there are more or less famous writers and people who have sold more or fewer books than their peers. But in artistic professions, quality is open to subjective interpretation. It’s harder to measure success as a writer to your peers. Thus, it’s thus harder to be taken captive by status as the primary motivational concern.

If one had to rank industries or types of work that are most likely to lead to happiness, jobs where status and success are easier or harder to measure might be a non-obvious factor. In corporate business, there’s a bottom line profit number that reveals success or failure in no uncertain terms. CEOs of public companies publish their profits every quarter and comparing their success to a peer CEO is as easy as entering a stock ticker into Google. Sports can be similarly measured without ambiguity: as a professional athlete you know exactly how you stack up against your peers. Teachers, however, are more like writers: there isn’t a clear “bottom line” or global hierarchy of teacher quality.

This line of thinking can apply to general goal setting, too. I have a friend in Colorado who devises goals that are intentionally obscure. For example, many serious hikers in Colorado love climbing “fourtneeners”—mountains with a peak that exceeds 14,000 feet. My friend prefers the high thirteeners: “They are actually more challenging,” he told me, “And it gives me a sort of smug pride that people don’t understand this. The dopamine hit from this is very different: it is much more internal because no else cares.”

The people around you shape the nature of your ambition, so pick your peer group carefully

“You are the average of the five people you spend the most time around” is the pithy phrase that captures an idea well supported by social science research. The best way to understand who a person is today and who they will likely be is to examine the types of people they spend time around.

Accordingly, I think it’s wise to be humble in your ability to truly decide your own motivations and goals. If everyone around you is on the more status, more status, more status track, and straining their necks to check the leaderboard, it’ll be hard to resist doing the same.

I find the peer pressure dynamic especially pronounced among entrepreneurs in Silicon Valley. I’ve had a few entrepreneur friends say they’re going to self-fund their next business and focus on profitable cash flow. It’ll make them happier to not give up so much control, they say. But after launching, they realize they’re not getting as much press as the venture-backed startup that just raised $7mm. And that the venture-backed entrepreneur gets a lot more respect at Silicon Valley cocktail parties. And so the entrepreneurs who were going to go on the “indie” route decide they, too, need to raise money from VCs.

Diversify your identity by operating a portfolio

If all of your self-esteem eggs are in one basket, you’ll become very obsessive about the state of that basket. As your identity is tied up in one job and one career, you compare yourself more easily to all the other professionals are also specializing in that single line of work.

An alternative career strategy is to operate a portfolio of professional activities. Perhaps you help start some companies, write books, give speeches, do some investing, and offer consulting services. In this portfolio, if you come upon someone who’s besting you in the realm of books, you can look elsewhere in your portfolio to tell yourself a story that while he may have grown better than you in X, you still have unrelated Y job in your life that he has no claims on.

This strategy can stretch beyond career activities and into the realm of hobbies, personal interests, friends, political affiliations, faith, and so on. The more idiosyncratic the bundle of things that makes up who you are, the harder to compare yourself to others. You get less caught up in a peer-driven rat race.

Operate a dashboard, not a leaderboard. Play against yourself, not an opponent

Think of how you monitor your car dashboard when you drive. It shows how fast you’re driving and displays other barometers of health of your vehicle. It does not display how fast the cars next to you are driving. Some cars are driving faster than you, some are driving slower than you—it doesn’t really matter. You’re not on a racetrack. You’re on a road just trying to make your way to your destination in whatever way and at whatever speed makes sense for you in that moment.

Dashboards are good. With a dashboard, you can and should measure yourself. You should push yourself. You should track your progress. If you want to get better at tennis, you should write down how you want to get better and hire a coach and measure improvement. So it is with everything.

But you should measure yourself in the spirit of improving upon your last best record, not what an opponent has accomplished. Leaderboards turn your attention to others; dashboards turn your attention within.

Physically move and be a big fish in a small pond

I have a friend who’s successful and wealthy. But he lives in the Bay Area, and he never feels rich enough or successful enough. He should have moved to Seattle (or some other lower-cost-of-living place where there’s still good industry activity for his line of work) a long time ago, but he’s still here, and he’s still complaining about his situation—in the most expensive real estate market in the country.

In smaller ponds, you’ll have an easier time defining your own flavor of success. You’ll feel less anguish when people you think of as peers grow richer than you. Here’s De Botton: “Rather than struggling to become bigger fish, we might concentrate our energies on finding smaller ponds or smaller species to swim with, so our own size will trouble us less.”

One strategy I sometimes recommend to people is that early in their career they live in the place where their industry is headquartered. Bay Area for tech, New York for finance and publishing, LA for movies, Michigan for furniture and cars, Nashville for country music, etc. Soak up everyone’s expertise. Study. Learn. Even if you don’t want to start the next Google, you’ll learn a lot by way of “network intelligence” from physically living in Silicon Valley. But feel free to leave and join a lower-cost-of-living secondary market if and when you begin to feel perpetually not-quite-good-enough. This doesn’t mean moving to the boonies, but to a place where there’s plenty of industry activity but less happiness-hurting status jostling.

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