These Professionals Aren’t Retired, They Just Have Zero to Prove

They came, they saw, they conquered work. Then they shrugged.

Some strivers who piled up money and status say they’re over the endless hustle and are embracing what they call a “post-achievement” lifestyle with family, health and passion projects taking priority over career accomplishments.

Another promotion? Too busy surfing. Deferred compensation that’s oh-so-close to vesting? Slipping the golden handcuffs is less painful than you might think.

Post-achievement professionals aren’t necessarily retired, even if they’re financially set for life. Many have transitioned to roles with fewer hours and responsibilities to make time for pursuits they find more meaningful such as podcasting, meditating and playing guitar.

Rather than grab every available dollar and accolade, Kevin Dahlstrom quit a seven-figure, round-the-clock job in 2018. He prefers to be seen as a bold, slightly mysterious figure who could have risen higher but opted out on his own terms.

“I’d be lying if I said that doesn’t stroke my ego,” says Dahlstrom, who left a chief-marketing-officer role and moved to Boulder, Colo., to rock climb. Professional acquaintances sometimes refer to him as a legend because he jumped off the corporate ladder in a way that most people only dream about. “Who wouldn’t like being called a legend, right?”

At age 53, he estimates that he passed up more than $10 million of future earnings but says he doesn’t need to make another penny. He recalls an executive meeting where he looked around the room, saw high-powered colleagues who seemed unhappy, and thought: What’s the point of grinding if it doesn’t bring joy?

He’s still ambitious and recently accepted a more flexible marketing-executive position at a smaller company that allows him to be on task as needed, and on a mountain whenever climbing conditions are good.

“To me, that’s nirvana because I still want to do hard things and work on fun projects,” he says. “But I also want that to be only one part of my life—and not the biggest part of my life anymore.”

Less money, more passion

Here’s the thing about getting to post-achievement status: You have to earn it by doing something impressive first.

The former go-getters I’ve met aren’t the types who could have coasted through middling careers from day one, despite being full of potential. (That would make them quiet quitters or, perhaps, masters of work-life balance .) They needed to prove, to themselves and others, that they could excel at high levels. Only then—with killer résumés and F-you money—could they make dramatic life changes.

Khe Hy , who helped popularise the term post-achievement on his website and YouTube channel , RadReads, says it’s hard not to look back. He left his job as a hedge-fund managing director in 2015 and still feels the occasional pang of envy when he considers the riches that former colleagues have accumulated. Hy, 44, says he’s sitting on about $5 million, probably enough to retire to a frugal lifestyle, but likely not enough to sustain his family forever in pricey, coastal California. Had he remained on Wall Street for a few more years, he might never have to work again.

Still, he moves past those feelings by remembering how numb he’d become to big paydays in finance.

“The key moment is when you realise that no next achievement will significantly change your baseline happiness,” he says. “I consider myself post-achievement because I’m not really striving for anything.”

That’s not entirely true. Hy is trying to bulk up but struggles to add weight to his 155-pound frame. Between running 25 miles a week and surfing almost daily, it’s tough to sculpt more than a lean six-pack, you know?

His RadReads business, which includes coaching for hard-charging professionals who want to rebalance their lives, generates about $200,000 annually. He works about 35 hours a week but controls his schedule and no longer fixates on career advancement.

Rachel Barek , 44, isn’t ready to step down as chief executive of Said Differently, the marketing agency she co-founded, anytime soon. But the majority stake she and her partner sold to a private-equity firm comes with a lifetime of financial security, she says.

“I could very easily fall into the trap of being a serial entrepreneur. I was born that way,” she says. “A lot of serial entrepreneurs are scared of the white space in their lives, and I’m really excited by that white space.”

In her future post-achievement phase, Barek plans to do something radically different: beauty school. She developed the interest while cutting her son’s hair at home during the pandemic and wants to offer pro bono barber services for children with special sensory needs and others who can’t afford to pay. But she concedes her clipping skills could use some work.

Avoiding the success trap

Kristopher Abdelmessih says he was six months shy of collecting about $1 million of deferred compensation when he walked away from his job as an options trader in 2021.

“Maybe it was rash, but I’ve replayed this in my head many times, and I don’t think I would do it any differently,” he says. “I was done.”

Abdelmessih, 45, was motivated to succeed by his modest upbringing in an immigrant household. There would be no safety net if he sputtered professionally, so he picked a field that paid well, played to his strengths and didn’t require graduate school.

But trading was never a calling. Leaving wasn’t so much about losing ambition as it was about a desire to chase fulfilling interests, like tutoring low-income students, gaining the confidence to play guitar on stage for the first time and traveling with his family six to eight weeks a year.

He and a business partner are in the early stages of developing a trading software tool that Abdelmessih hopes will become profitable. If it takes off and demands more of his time someday, that’s OK with him because it’s a passion project.

Jason Chow , a financial-services firm vice president, isn’t post-achievement yet, but he wants to be. Chow, 45, and many others say they’ve climbed high enough to realise each progressive rung brings new hassles and fleeting satisfaction.

“It resonates with me because my life is work, and I know there’s more,” he says. “I just haven’t found what that is yet.”

Wall Street’s hottest trade has gone ice cold.

For years, it paid off to buy stocks that were rising in price—and bet against struggling shares. The momentum trade was especially profitable this year, as investors piled into hot stocks including Micron Technology, Nvidia, Advanced Micro Devices and other artificial-intelligence darlings while wagering against those likely to be hurt by the embrace of AI.

The S&P 500 Momentum Index soared 44% in the second quarter, its best quarterly performance on record, and it surged 133% over the past five years, nearly double the broad market’s performance.

Mega funds and rookie investors alike piled into the trade, some using leverage and options contracts in an effort to amplify their returns, propelling the underlying shares higher.

“It is a self-fulfilling prophecy,” said Matthew Tym, managing director at Cantor Fitzgerald, of the trade.

Suddenly, the trade is a loser. The momentum index has tumbled more than 9% since July 1, lagging behind the S&P 500’s 2.8% gain. The index—which tracks stocks in the S&P 500 based on a “momentum score”—is on track for the biggest quarterly underperformance in 25 years. July was the second-worst month for the momentum trade in around 40 years, according to Bank of America estimates; the only month worse was April 2009, in the teeth of the global financial crisis.

Hedge funds that bought momentum shares while shorting low-momentum stocks suffered even more. At the same time, a basket of the most popular stocks held by hedge funds tracked by Goldman Sachs recorded its biggest one-month underperformance in July relative to the S&P 500 in more than 20 years, according to the bank’s analysts.

Momentum trading is based on a rather simple observation: Investments that go up tend to keep outperforming; those that underperform often remain laggards. This kind of trading might seem too simple a stock-picking strategy to work. Yet it often has.

“For decades, it didn’t take a lot of sophistication to run a momentum strategy and make a decent living at it,” says Agustin Lebron, senior researcher at EquiLibre, a trading firm.

Part of the reason: It takes a while for corporate and other information to spread to various investors, so they slowly build positions, producing buying momentum.

“A huge pension fund can’t flip around its positions in a day,” says Lebron. “Behavioral biases also account for some of the effect, as well—people tend to sell their winners too early and hold losers too long.”

Fans of the strategy point to the human tendency to extrapolate from past results—and chase investment returns—noting that momentum patterns have been evident in markets for decades, even centuries. They also say that some of the worst months for momentum strategies are during longer periods of outperformance.

Some have been doing the trade by buying the strongest investments in a sector while shorting the weakest; others lean in to rising markets or asset classes. Still others use a quantitative approach or turn to banks or others who sell ways to make distinct wagers on momentum as a “tradable factor” or a “thematic basket.”

The fans remain believers. “Any strategy has disappointing periods,” says Antti Ilmanen, global co-head of the portfolio solutions group at AQR Capital Management.

The surge in Moderna and other biotech stocks helped crush the momentum trade. These shares were among the most heavily shorted in recent years, but positive news on a cancer vaccine from Moderna and Merck sent those stocks flying, crushing some quant and other hedge funds. Moderna is up around 150% so far this month.

These traders had an especially rough day on Aug. 19, which Goldman Sachs told its clients was the worst day for “systematic long-short managers” in more than two years. About half of the losses were because of momentum trades, the bank said.

Some traders have begun to short, or bet against, the very stocks that propelled the momentum trade earlier this year. Net short positions in futures tied to the Nasdaq-100 index among speculators recently climbed to some of the highest levels of the past two decades, according to data from the Commodity Futures Trading Commission.

The about-face is a sign of how markets have become more treacherous for investors, even as indexes keep climbing. Part of the issue: the recent meltdown of Situational Awareness, a hedge fund that had piled into some of the most popular momentum shares, including chip stocks. After a period of market tumult, Nvidia shares rocketed almost 9% after its earnings, showing how quickly sentiment can shift.

Some investors say the run-up in share prices driving tech stocks higher reminds them at times of the dot-com frenzy decades ago.

Mike Ogborne, the founder of San Francisco-based Ogborne Capital Management, said he has grown more cautious on technology stocks and is keeping more of his portfolio in cash than he typically does.

And he is nervous about the surge in spending by technology giants and quarterly capital expenditures that keep rising.

“It is a little bit like Cinderella and the clock striking midnight. You don’t know when midnight is going to come around,” Ogborne said. “They don’t send a memo around telling you when the capex cycle is over.”

These Professionals Aren’t Retired, They Just Have Zero to Prove

Numb to raises and promotions, some people chase different kinds of success

Less money, more passion

Avoiding the success trap

Wall Street’s hottest momentum trade has reversed sharply, as former winners tumble and heavily shorted stocks surge.