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.”

Happy is the family whose members—parents, grandparents and grown children—trust each other enough to cooperate on shared goals, especially financial ones. When that is truly the case, Uncle Sam’s tax rules can help as well.

This matters especially now that mortgage rates are above 7%, and many families are looking for ways to help younger members. If the elders have resources and are confident younger ones can cooperate, a family loan could make homeownership possible while providing the elders with a useful income stream.

Other strategies can actually lower taxes, such as when funding 529 plans or Roth IRAs, or when someone inherits a traditional IRA with required withdrawals larger than they will need.

Here are three strategies useful for functional families.

Intrafamily loans

It is perfectly legal for families to lend money to a relative for a down payment or even a private mortgage.

But it is important not to cut corners, says Ryan McKeown, a CPA with Modern Wealth Enhancement in Minnesota. If the loan is for a down payment, be honest with the mortgage provider and have a formal agreement. The lender owes tax on the interest payments received.

If the loan is for a private mortgage, both sides should have legal representation with a formal written agreement, including payment terms. The lender owes tax on the interest, and the borrower often can deduct it if he or she itemizes.

To avoid IRS trouble, the interest rate shouldn’t be lower than the agency’s Applicable Federal Rate at the time of the loan. Currently that is about 5% for loans longer than nine years; about 4.5% for loans three to nine years; and about 4% for loans three years or less. Currently, traditional mortgage rates are generally above 7%.

In addition, the lender could use the $19,000 annual gift-tax exemption (described below) to forgive some or all of the interest or principal annually. If both lenders and borrowers are married, that is up to $76,000 a year. There is no tax for the borrower on such forgiveness, because it is from a gift.

If you’re going this route, McKeown advises against having a fixed plan to forgive the debt. Instead, do it in one-off letters specifying the amount—and keep careful records. Otherwise the IRS might try to treat the loan as a taxable gift.

Asset gifts

Powerful tax-saving moves for families often use gift-tax provisions. Under current law, anyone can give anyone else up to $19,000 of assets annually, free of gift tax. That means a married couple with three grandchildren could give them a total of $114,000 in 2026.

The gifts can be cash or other assets, like stock. For noncash gifts, the cost basis—which is the starting point for measuring taxable gain after a sale—“carries over” to the recipient. So if someone buys $1,000 of stock and gives it away when it is worth $5,000, the recipient’s cost basis is $1,000. If the recipient later sells the shares for $8,000, the taxable gain is $7,000.

Here’s an example showing how gifts could save a family taxes. Grandma is a widow of modest means, while her child and spouse have prospered. The couple has two children, and they want to contribute $5,000 to a 529 college-savings plan for each—but they need to sell stock to do it. Their tax rate on the sale would be 18.8%, and they would need to sell about $11,000 of stock.

However, Grandma’s federal tax rate on the stock sale is 0%. If the couple gives $10,000 of shares to Grandma, she could sell them, pay no tax, and fund the grandchildren’s 529 plans. This saves about $1,000 of tax.

These moves are legal, and they could be used in other ways, such as to help a young person fund a Roth IRA.

But trust among family members is essential: Under the law, givers can’t put conditions on a gift. Grandma could use her stock proceeds to take a cruise, but she makes 529 contributions instead.

Mark Sellner, a retired tax attorney and CPA living in Sarasota, Fla., uses this strategy. His children sell stock he gives them and fund 529 plans for his grandchildren.

The family’s tax savings aren’t huge, but he likes other benefits. The sales by his children don’t boost his adjusted gross income, which in turn could raise his Medicare Irmaa premiums or his 3.8% surtax on net investment income.

Sellner doesn’t worry about his children using the funds for another purpose.

“There can’t be any strings attached to gifts. Of course, it is up to us to decide whether to make them in the future,” he says.

Two caveats: The “kiddie tax” applies to most children under age 24, and it is levied at the parents’ rate on investment income above $2,700 in 2026. Consider this before making gifts to a young person.

Investors who give away stock also forgo the step-up, an important provision that exempts assets held at death from capital-gains tax.

Sellner knows he’s losing a step-up, but says, “The children could use a little more now. Why should they wait 20 years to get it?”

Disclaimers

A disclaimer is a highly useful strategy in which one heir renounces an inheritance in favor of another heir. Assuming family members cooperate, this can save taxes.

Here’s one example. Dad died and had a large traditional IRA that he left to Mom. She has enough assets and income to cover her expenses, and she lives in a state with a stiff estate tax. The inherited IRA would put her estate over the threshold.

Also surviving are three young-adult children. If Mom disclaims all or part of Dad’s IRA within nine months of his death, that amount could go directly to the children. They will have 10 years to empty the account, and the family as a whole will likely save estate and income taxes.

Disclaimers have many key details, especially regarding beneficiary documents. Although heirs have great freedom in choosing what assets to disclaim, the rules about who gets disclaimed property are rigid. It is best if the original owner names tiers of heirs so that if one disclaims, the next recipient is clear.