Meet the boomers cashing in on the golden age of retirement

Younger boomer/older Gen X couple hugging and gazing at sunset, with the wife holding a chubby golden piggy bank

Some retirees are now cashing in on the golden age for retirement savings, when benefits were more generous and investments in real estate and stocks boomed.Getty Images; Alyssa Powell/BI

  • Amid a widespread retirement crisis in the US, some boomers are entering their golden years flush with savings.

  • They’re benefiting from now-rare pensions, real estate value increases, and stock market gains.

  • But lower-income households face challenges with retirement savings and dwindling pension plans.

If you’re looking for Michael, 75, try looking to the sky.

The retiree has a unique retirement side gig: He’s a corporate airplane pilot.

He dabbles just with contract gigs because he loves it; that’s a common theme for Michael at this stage in life. He’s living the retirement dream, and splitting his time between Florida and Denver. According to documentation that Business Insider reviewed, his net worth, after a career spent in the Navy and then working in geology, is just over $6 million.

“It’s totally comfortable. We absolutely have all the money that we need to live our life,” he said. And that nest egg has made a huge emotional difference: He has no financial stress.

It’s a similar story for Connie, a 79-year-old who said she didn’t really start retirement planning until she was in her 30s, newly divorced, and working a state government job in Oregon. After about 20 years in the public sector, she was able to retire with a nice pension — a type of benefit that’s increasingly rare these days. Her Social Security checks were also bolstered when her former spouse’s survivor benefits kicked in. In her retirement, she earns more than she did from her previous salary.

“It gives me great peace of mind,” Connie said. It also fills her with some pride: Her research and frugality paid off.

“I definitely fall into that category of people who had just a totally ordinary career and never made big money, and yet now my retirement income is probably one and a half times what I ever made working,” she said.

The three retirees Business Insider spoke with for this story are bright spots amid a retirement crisis in which over half of Americans 65 and older live on just $30,000 a year, and Social Security funds are expected to start depleting in 2035 without legislative intervention. All of their full names are known to BI, but their last names have been withheld over privacy concerns.

As the way we save for retirement has evolved, some people are now cashing in on the golden age for retirement savings — when benefits were more generous and investments in real estate and stocks boomed. While it’s still possible to achieve, a fat retirement account has become rarer. And the retirees who are living that dream are grateful.

“Being in retirement and not having any financial stress and being able to help our kids and travel to go see them and stuff like that, it is just a fantastic place to be,” Michael said.

The confluence of factors that led to flush retirement accounts

A stable retirement based on a lifetime of savings and smart decisions is possible — Michael and Connie are examples of that. But it’s also a reality that’s becoming increasingly rare, especially for lower-earning Americans.

The Government Accountability Office found in a 2023 report that lower-income households age 51 to 64 — those earning about a median of $19,100 — are increasingly less likely to have anything in a retirement account.

Back in 2007, per GAO’s calculations of the Survey of Consumer Finances, around 21% of low-income households had a retirement account balance. By 2019, that had fallen to 10%. While losses weren’t as profound for those in the middle-income quintile, their retirement account balances did fall slightly from 2007 to 2019. As GAO finds:For all but the highest income group, there was no detectable difference between the median balances in 2019 and 2007.”

The decline of one type of account, in particular, could be to blame. In recent decades, the US has shifted away from pensions, in which employers offer consistent payouts to former employees in their post-working years. Now, more American workers have defined contribution plans, like 401(k)s, which rely on workers to contribute funds to grow their coffers.

The share of low-income households with a defined benefit pension also fell by half from 2007 to 2019.

Michael acknowledges that some people have likely worked hard for their whole lives, but didn’t have higher-paying jobs — meaning they were able to put away less.

“Retirement could have gone the other way for us. I could have made a few bad decisions and we could have lost a lot of money and it would’ve been a different scenario in terms of comfort,” he said.

“We got fortunate with a few investments and it just took off and grew,” Michael added.

The assets that today’s retirees do have are also prospering; 401(k) investments have been bolstered by a soaring stock market, meaning that people cashing in on retirement investments right now are on the winning end of historic S&P 500 highs.

“If we look at someone who had a 401(k) fairly early on, so between roughly 1982 and 2002, we had stock market returns that went fairly high,” David John, senior strategic policy advisor at the AARP, told BI. He added: “They managed to build retirement savings at a time where there was both stock market returns but also fairly low inflation.”

Connie opted for a variable account to fund her pension — her employers’ contributions went into investments, rather than promising a fixed return each year. While her account lost money some years due to the market, overall, her earnings have still outpaced what she would’ve had with a simply fixed amount.

“There are a lot less pensions out there these days. That’s true,” Connie said.

And for the current group of retirees with those perks, another thing might be boosting their bottom lines: Boomers are holding onto immensely valuable real estate. Thirty years ago, when today’s retirees may have started buying real estate, homes were selling for a median of around $130,000. Today, they’re going for nearly $300,000 more.

Today’s retirees also still have full Social Security benefits, something that’s increasingly imperiled for the next generation of workers who are throwing in the towel. All of that comes as retirement savings become more of an individual onus.

“Essentially, the people who need it the most are the ones who are least likely to have a retirement savings plan or a pension,” John said.

Some have still been able to achieve this stability, but it’s more of an uphill battle

Valerie, 46, is one of the Gen Xers trying to follow in the footsteps of prospering boomers. Valerie, who’s based in Seattle, has already retired. According to documentation viewed by BI, she has over a million in her 401(k), but it’s been hard-fought. Valerie — a former retail worker — tried to invest in real estate, but ended up on the other end of a hard market: Her properties went into foreclosure during the mortgage crisis, she said, and she “barely had 20 bucks to survive.”

“I kept thinking of all these other ideas, well, how do I build wealth again? Do I just give up? Is this the end of my life?” she said. For Valerie, the answer ended up hinging on her 401(k) — she said she’d borrow against it to invest back into the market, and then repay those loans. Now that she has a retirement plan secured, she’s more willing to take risks to build more wealth.

“When I was 18 to 19 years old, I remember predicting I’d be where I’m at financially in my retirement account if I didn’t touch it and didn’t bother it. And sure enough, the calculations are right,” she said.

Valerie is one data point showing that it’s also not all bad news for future retirees, but instead, perhaps more of an uphill battle.

“We have an economy that is changing rapidly and there are going to be opportunities for investment growth and savings and new products. I mean, there’s an amazing amount of innovation going on there,” John said. There is a chance it won’t be as easy as it was for someone “who started investing say in the 1980s or the 1990s and are now reaching the end of their careers,” he said.

“But yes, going forward, it’s still possible.”

Are you doing well in retirement, or worried you won’t be able to retire? Contact this reporter at

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