How to Escape the Success Trap


By Nathan Havey

Alan Watts, a philosopher who helped interpret Eastern religion for a Western audience in the 1950s and ’60s, offered Westerners a stinging challenge to our popular notion of success. He observed that we get caught up in misleading expectations about how to live. We are taught in childhood that we must do well in school to be successful when we are grown up. Fixation on success therefore begins in grade school, as you “succeed” by progressing from one grade to the next. This continues as you go on to high school, and then to college, and maybe even to grad school. And when you finally join the real world, eager for that success you have spent your whole life preparing for, you get a job and find that success still depends on hitting that next sales target, or getting that promotion. 

“And all the time this thing is coming. It’s coming, it’s coming, that great thing, the success you’re working for. Then when you wake up one day about 40 years old, you say ‘My God, I’ve arrived! I’m there!’ And you don’t feel very different from what you always felt. And there’s a slight letdown, because you feel there’s a hoax. And there was a hoax.” — Alan Watts

Last October, Sum and Substance held an event in Boston, and while there, we toured the office of one of our storytellers, John Hilliard. Hilliard works at Next Jump, a company so committed to its employees that it hires them for life. On the reception desk sat a number of books, free for visitors to take. One of the books was Jim Loehr’s “The Only Way to Win,” which criticizes our notion of success in ways Watts might appreciate.

John Hillard

Loehr has spent his career working with athletes and business executives at the top of their game, and he has observed, as Watts did, that even if you attain tremendous success by society’s standards — even if you are rich beyond reason, famous, and respected — you are left feeling hollow and unfulfilled. What is worse, you are likely to be trapped in a vicious cycle wherein you try to chase away unhappiness by ever striving to attain the next big goal, only to discover that you enjoy but a few moments of triumph before the unhappiness creeps in again, causing you to chase an even bigger goal, and so on. With each cycle, you actually begin to feel worse. You start to think something must really be wrong with you if you can have achieved so much and have all this wealth and fame and still be unhappy.

Success is not only a hoax; it is a trap.

Fortunately, Loehr thinks he has found a way out:

“The massive body of research we now have in this area all points...to the same thing: meaning. ‘Our souls are not hungry for fame, comfort, wealth or power,’ writes author and rabbi Harold Kushner. ‘Our souls are hungry for meaning, for the sense that we have figured out how to live so that our lives matter.’”

The real issue, Loehr suggests, is that all of society’s measures of success are extrinsic — your job title and net worth, the car you drive, the house you live in, etc. — but meaning is intrinsic. So what we must do is reject society’s scorecard for success and create our own. “The Only Way to Win” features a detailed guide for how to do this. The crux of the process Loehr suggests is this: if success is a hoax when measured by external achievement or results, we must instead focus on our own values and actions; we must focus on character.

According to Loehr, there are two types of character strengths: performance, and moral. Performance character strengths include skills like perseverance, focus, courage, and critical thinking; they are important in helping us achieve things. Moral character strengths include things like kindness, humility, compassion, and gratefulness; these are what give us meaning. A scorecard that will lead to happiness may include several performance character strengths, but the moral character strengths are the way out of society’s “success” trap.

“I maintain that moral character strengths represent the fundamental core of what it means to be a fully functional, healthy human being. And if that’s so, business leaders should do everything they can to teach them. Rather than being obsessed by financial outcomes, managers should focus on the path employees take to achieve those outcomes. Ethical leadership should be granted preeminent status by corporate boards and all C-suite executives.” — Jim Loehr

It has been widely reported that Millennials prioritize meaning more than other segments of the workforce do. So as Millennials rise through the ranks of every industry on earth, they would do well to make sure they have a personal scorecard they can be proud of — otherwise, they, too, may find that success is hoax.

This article appeared in Issue 7 | May/June 2016

Issue 7 features exciting interviews and profiles all focusing on youth and Millennials including: Sweetgreen; Radha and Miki Agrawal; Nisolo; a spotlight on the higher education system including a look at the student debt crisis and the top 15 sustainable MBA programs; and our inspiring cover story — Nikhil Arora and Alejandro Velez of one of the most exciting food companies in the nation, Back to the Roots.

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