The couple is also in an enviable spot: He calculates they have enough money to live comfortably for 30 more years. He attributes that to an experience at the first company he started, Kent Engineering, where some weeks he worried if he would be able to make payroll.

“That was very scary, and I decided that wasn’t a very comfortable position to be in,” Mr. Kent said.

Mr. Conley said many of the people who are older but spend their money in a youthful way — on things that are meaningful to them but not frivolous — have at some point gone through what he calls a “great midlife edit.”

Usually around 55, the edit helps them pare back all that they accumulated in the first phase of their life, and it makes them more realistic about how they’re going to live longer and be situated to do so. He said that paring-back exercise is as common among lower-middle-class wage-earners who realize they will have less to live on as it is upper-middle-class empty-nesters who downsize from a house to a condo.

“We try to help people understand the way we live today you’re going to have a lot of adult life ahead of you, so don’t get caught up on how Social Security is going to support you,” Mr. Conley, 58, said. “You’re not going to retire at 65. You’re going to have part-time work by desire or need.”

That reframing helps older people remain youthful but pragmatic on financial decisions. A big part of their shift in perception is continuing to earn money in some form much later in life.

“To encourage people to think of working way into their 70s, we talk about how retiring can be bad for your health,” Mr. Conley said, mentioning research on longevity rates and retirement. “People need to build skills that allow them to build money. They could be an Airbnb host with a cottage in their backyard, plus $20,000 from Social Security and then part-time consulting at $20,000. That’s enough to live for a very long time.”