Yesterday at the bank, I watched a couple in their seventies withdraw a substantial amount for what sounded like an extended Mediterranean cruise. The teller’s expression said it all: Shouldn’t these people be saving every penny for medical emergencies?
That moment crystallized something I’ve been observing since retiring. The financially comfortable retirees who seem happiest aren’t following the conventional playbook. They’re doing things that make financial advisors nervous and adult children uncomfortable.
Yet when you understand the logic behind their choices, these “irresponsible” decisions reveal themselves as surprisingly strategic.
After decades of saving, scrimping, and planning for retirement, many of us arrive at this phase still operating from scarcity. We’ve internalized so many rules about money and aging that we forget to ask whether those rules still serve us.
The truth is, financially comfortable retirees who thrive understand something others miss: The calculations change completely when your timeline shifts and your priorities clarify.
1) They spend “too much” on experiences while healthy
A former colleague recently spent $30,000 on a three-week African safari. His adult children were horrified. That money could have covered two years of potential nursing home supplements.
But here’s what his kids missed: At 68 with arthritic knees, this was his window. Wait five more years, and no amount of money would make that trip possible.
Financially comfortable retirees understand that mobility and health are depreciating assets.
They front-load experiences while their bodies can still climb Temple steps in Cambodia or snorkel in the Galapagos. They recognize that $30,000 spent at 68 on adventure might be worth more than $300,000 sitting in an account at 85 when they can barely leave the house.
The conventional wisdom says to preserve capital above all else. But what good is dying with a pristine portfolio if you never used that money to truly live?
2) They give money to adult children before they “need” it
Estate planning orthodoxy says to hold onto everything until the end.
But savvy retirees are increasingly rejecting this model. They’re helping children with down payments now, funding grandchildren’s education today, and watching their money make a difference while they’re alive to see it.
Yes, this reduces their estate. Yes, it might mean less cushion for extreme longevity.
But they understand something profound: Money given at 40 when their children are struggling with mortgages and tuition is exponentially more valuable than inheritance at 65 when those same children are themselves approaching retirement.
I recently helped my daughter with a business investment. Could that money compound more in my index funds? Probably. But the compound interest on family relationships and the joy of watching her succeed beats any market return.
3) They buy the expensive, high-quality version
Watch a financially comfortable retiree shop for anything from shoes to appliances, and you might think they’re being reckless.
They’ll spend $300 on walking shoes, $5,000 on a recliner, or $50,000 on a car when cheaper options exist.
But here’s their calculation: At 70, if a high-quality item lasts ten years, it might be the last one they ever buy.
They’re not amortizing over decades anymore. They’re buying for comfort, reliability, and the simple pleasure of finally having the best version of something after years of making do.
That expensive ergonomic recliner isn’t frivolous when you’re spending four hours a day in it with a bad back. Those $300 shoes aren’t wasteful when they’re the difference between walking daily and giving up exercise due to foot pain.
4) They maintain two homes (or long-term travel arrangements)
Financial advisors often push downsizing to a single, smaller home.
But many comfortable retirees are keeping their family homes while also maintaining winter condos or investing in extended stays elsewhere. The carrying costs make planners cringe.
Yet this “irresponsible” choice often reflects deep wisdom. They know that variety and stimulation prevent cognitive decline. They understand that winter in harsh climates becomes genuinely dangerous after 75.
They recognize that maintaining connections in multiple communities provides social insurance against isolation.
The mental and physical health benefits of escaping brutal winters or stifling summers can’t be quantified on a spreadsheet, but they’re very real in terms of quality of life and even longevity.
5) They hire help for things they could technically do themselves
Lawn service, house cleaning, meal delivery – financially comfortable retirees often outsource tasks that they’re physically capable of doing.
Their Depression-era parents would be appalled. Why pay someone $150 to clean when you’re home all day?
Because they’ve learned to value their energy as a finite resource. Every hour spent on maintenance is an hour not spent on relationships, hobbies, or health.
They understand that preserving physical capacity for things that bring joy makes more sense than proving they can still scrub floors.
6) They invest in learning and personal development
I recently enrolled in Your Retirement Your Way, Jeanette Brown’s new course on reimagining retirement. At first, spending money on a retirement course when already retired seemed indulgent.
But Jeanette’s guidance reminded me that retirement isn’t an ending but a beginning for reinvention.
The course inspired me to stop seeing this phase through inherited programming about what retirement “should” look like and instead design it around my actual values. I wish I’d had this resource when I first retired.
This kind of investment in continued growth seems frivolous to those who think learning stops at 65.
But comfortable retirees understand that intellectual engagement and personal development aren’t luxuries – they’re investments in cognitive health and life satisfaction.
7) They say no to “smart” financial opportunities
A friend recently turned down a consulting gig that would have netted him $50,000 for three months of part-time work. His financial advisor was baffled. Free money!
But my friend understood what that “free money” would actually cost: The stress of deadlines, the obligation to be available, the mental energy diverted from his grandchildren and volunteer work.
He’d already won the financial game. Why keep playing with house money when the real currency now is time and peace?
8) They spend on seemingly frivolous comforts
First-class flights for domestic travel. Daily coffee shop visits. Premium cable packages. Fresh flowers weekly. These small indulgences add up to thousands annually that could be saved or invested.
But comfortable retirees who’ve done the math know something important: If they’ve already secured their basic financial future, these daily pleasures provide more value than marginal portfolio growth.
The daily $5 latte that gets them out of the house and into social interaction might be the best investment they make in mental health.
Closing thoughts
The brilliance in these seemingly irresponsible choices lies in a fundamental shift in perspective. These retirees have moved from accumulation to utilization, from saving for someday to living for today, from theoretical future needs to actual present desires.
They understand that after a certain point of financial security, the highest return on investment isn’t more money – it’s more life. They’ve learned that responsible financial management in retirement doesn’t mean dying with the most money.
It means using money strategically to maximize health, relationships, experiences, and joy while you still can.
The next time you see a comfortable retiree “wasting” money on something that seems frivolous, look closer. They might be executing a brilliant strategy that values the only currency that truly matters in the end: Well-lived days.
