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Written by David Conti, CPRC
“Now as we indulge in things refined / we hide our hearts from harder times... / and I don't know why I even care / we’ve loved these days.” — Billy Joel
It’s a funny thing about retirement. After decades of hard work, diligent saving, and putting others first, many people finally cross the finish line—only to realize they’re not sure how to live the very life they worked so hard to afford.
Advisors and wealth managers often talk about preparing clients for retirement with numbers: asset allocations, Monte Carlo simulations, tax efficiency. But what many clients need in this new chapter isn’t a better withdrawal strategy—it’s emotional permission. Permission to spend. To enjoy. To indulge, without guilt, in the life they’ve built.
This tension reminds me of the Billy Joel song “I’ve Loved These Days.” It’s a bittersweet meditation on savoring the finer things in life, even while acknowledging their impermanence. The lyrics capture that emotional fork in the road many retirees face. They want to enjoy the fruits of their labor—but often feel conflicted, weighed down by guilt, uncertainty, or deeply ingrained scarcity mindsets. And they’re looking to their advisors, not just for numbers, but for clarity and reassurance.
From Accumulation to Distribution: A Tough Transition
Most clients didn’t become wealthy by accident. They worked hard, saved diligently, delayed gratification, and stayed disciplined during turbulent markets. Many followed a familiar playbook: get educated, get a good job, raise a family, live within your means. They saved 15% a year, maxed out their retirement accounts, and resisted the urge to splurge.
And it worked.
According to Fidelity’s latest data, the average retirement account balance for a 65-year-old stands at $249,300. Many high-net-worth households have accumulated far more across multiple accounts, properties, and business interests.
But turning off the accumulator mindset? That’s the real challenge.
“I’ve seen this time and again,” says Bill Love, CFP®, a retirement advisor and coach at RTD Financial in Philadelphia. “Clients come in with more than enough, but they’re still paralyzed when it comes to spending. They’ll say, ‘We built this for our kids,’ or ‘We’re just not comfortable tapping into the principal.’ And my job, increasingly, is to help them visualize the life they want and realize they can afford it.”
Love shares the story of an 80-year-old couple who came in for a planning review. “They had the resources, no doubt. But they were hesitant about booking a luxury cruise they’d dreamed about for years. They were worried about volatility, worried about outliving their money—even though the math clearly said otherwise.” After running through the plan again, Love and his team didn’t just give them permission—they helped them book the trip right there in the office.
“They came back and told me, ‘That was the last big trip we took together. Thank you for pushing us to take it. We might have missed it if we’d waited.’ One of them was later diagnosed with Alzheimer’s.”
Spending Guilt: A Byproduct of Success?
Retirees’ hesitation to spend isn’t always about financial insecurity. Often, it’s rooted in behavioral finance and family scripts absorbed over a lifetime.
“We were trained to scrimp and save for someday,” I tell clients. “And then someday comes—and we don’t know how to shift gears.” That’s especially true for those who lived through tough economic times or absorbed Depression-era thinking from their parents.
Behavioral biases like loss aversion—the fear of losing money—even when the odds are stacked in your favor, can be paralyzing. Add to that mental accounting, where retirees label money as either “for safety” or “for heirs,” and suddenly spending feels more like betrayal than freedom.
Joy Lere, PhD, a psychologist at Shaping Wealth who works closely with financial professionals, says guilt around spending often reveals something deeper. “Guilt is a signal,” she explains. “It’s not always a sign that you’ve done something wrong. Sometimes it means your actions are bumping up against long-held beliefs.” She often sees these mental models at play:
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Spend only on ‘important’ things
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Money equals love or safety
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You must earn your lifestyle
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Leaving a legacy is more virtuous than enjoying wealth
Lere encourages clients to pause when guilt shows up—not to suppress it, but to ask: What belief is driving this feeling? Is it still serving me?
That pause is powerful. It can turn a moment of conflict into one of clarity.
Your Role: Permission Giver and Legacy Architect
As advisors, you hold the technical tools to run retirement projections, optimize tax-efficient drawdowns, and ensure clients won’t outlive their wealth. But our role also includes helping clients feel financially secure—and emotionally free.
You become, in many ways, the behavioral translator. The one who says: “Yes, you can afford the trip. Yes, you can remodel the kitchen. Yes, you’ve earned this.”
Helping a client draw a “retirement paycheck” from a combination of Social Security, systematic withdrawals, and pensions can be a game-changer. Frame it as income, not depletion. Remind them that this is exactly what the money was for—not just survival, but satisfaction.
The Why Behind the Spend
Many wealthy retirees eventually overcome guilt and begin spending with intention. What drives that change? Here are the most common reasons I hear:
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Celebrating Achievements: After decades of hard work, retirement is the victory lap. It’s okay to enjoy it.
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Experiential Living: More time means more opportunities for travel, hobbies, and new adventures.
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Family Impact: Gifting experiences or funding education can be more meaningful than simply leaving an inheritance.
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Lifestyle Enhancements: From renovations to relocations, retirement can offer the space to upgrade.
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Giving Back: For many, philanthropy becomes a key part of their legacy—and it brings profound joy.
Loving These Days
Billy Joel sang about savoring life’s small luxuries, even as we acknowledge they won’t last forever. That tension—that knowing the good times are fleeting—is exactly why embracing them matters. Retirement isn’t a dress rehearsal. It’s the payoff.
As advisors, your highest calling may not be maximizing returns but maximizing meaning. To help clients spend with purpose. To help them rewrite the script they’ve lived by for decades. And to remind them that they’ve loved these days—and still can.
Related: The Inheritance Club