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Written by: Salvatore M. Capizzi | Dunham & Associates Investment Counsel, Inc
Most people spend decades preparing financially for retirement. They contribute to retirement accounts, work with advisors to build portfolios, pay down debt, and make sacrifices so work can eventually become optional. Yet very few prepare for what retirement actually feels like once it arrives. That lack of emotional preparation explains why many retirees experience unexpected regrets. For example, the Exit Planning Institute reports that 75% of business owners regret selling their business within one year of the sale. This statistic surprises many because these successful individuals just received the largest check of their lives. From the outside, it appears they won the game. Yet many still struggle after leaving work behind.
This phenomenon extends well beyond entrepreneurs. In fact, the Nationwide Retirement Institute found that 55% of people who retired in the last five years say they have regrets about how they saved for retirement. Even individuals who retire comfortably and on their own terms often find that the emotional and psychological transition is more difficult than expected. Like business owners who sell, they may have spent decades building a career that defined their sense of self, only to discover that financial readiness does not always equal personal fulfillment in retirement.
Longevity expert Mark Pace, founder of Vital Lifelong Alignment, believes these regrets stem from a fundamental flaw in traditional retirement planning: people are preparing for retirement financially, but neglect to fully prepare emotionally.
People are living longer and remaining active, healthy, and mentally sharp for far longer than expected. Yet emotionally, many still approach retirement as though life simply winds down. This creates a distinct challenge for advisors helping clients navigate this transition. Retirement is no longer a short final chapter; it can easily last twenty, thirty, or forty years. It is an entirely new phase of life for which many enter emotionally unprepared.
Retirement Does Not Automatically Create Happiness
One of the biggest surprises retirees face is discovering that retirement does not automatically create happiness. Throughout their professional lives, people often imagine retirement as total freedom from meetings, deadlines, and responsibility. They picture travel, hobbies, and endless flexibility.
Then retirement arrives, and something feels missing. Work gave people more than a paycheck; it provided structure, goals, social interaction, and a sense of importance. Many underestimate how much meaning comes from simply feeling needed each day.
That is why many retirees return to work through consulting, volunteering, mentoring, or starting new businesses. They are not necessarily chasing income; they are chasing purpose.
As Pace notes, many people are not preparing for retirement, they are preparing for escape. But freedom alone does not create happiness. For advisors, this raises an important consideration. Many retirement plans answer the question, “When can I retire?” Far fewer address the question, “What am I retiring to?”
Postponing Life for a Future That Changes
Another frequent regret is realizing they waited too long to enjoy life. Many individuals postpone family time and personal interests during their peak working years, assuming they will enjoy them later.
But when "later" arrives, reality often looks different. Health challenges emerge, energy levels shift, and physical limitations become real. Many retirees quietly realize they sacrificed their healthiest years waiting for a future that does not match the picture they imagined. Advisors have a unique opportunity to help clients avoid wishing they had enjoyed life sooner. Comprehensive planning should not just protect a client's financial future; it should give them permission to build a meaningful life along the way.
Identity Shock and Emotional Shifts
For decades, professionals introduce themselves by what they do: “I’m a teacher,” “I’m a business owner,” or “I’m a contractor.” Work becomes deeply connected to identity, routine, and self-worth. Then with a traditional full retirement date, overnight, that role disappears.
This emotional shift is often far more difficult than anticipated, thus explaining the high levels of regret among business owners post-sale or retirees post-employment. They do not just lose income; they lose structure, mission, and identity. The business (or employment) was how they measured progress and contributed to the world. Suddenly, they face soul-piercing questions: Who am I now? What is my purpose? What am I building toward?
These questions create deep anxiety even when finances are secure. The happiest retirees rarely stop building toward something meaningful; they simply redirect their energy toward new goals, relationships, and experiences.
Underestimating Healthcare and Inflation
Retirement can also bring financial and health surprises, even for those who are active and planned carefully. According to Fidelity, the average retired couple may need hundreds of thousands of dollars during retirement for healthcare expenses alone.
Inflation creates another challenge that erodes purchasing power. Groceries, insurance, utilities, and medical care all cost more over time. A retirement plan that once felt comfortable can slowly feel much tighter, especially given increased longevity. Research done for a paper I authored last year on if the industry is prepared for retiree’s longer lifespans shows that a retired couple with $1 million in assets could spend approximately $2.7 million on food alone over a 40-to-50-year retirement, based on historical food inflation data. They could, quite literally, eat through their retirement assets. Financial stress does not disappear in retirement; in some cases, it increases because the safety net of active earning power is gone.
Altered Relationships and Social Connections
Many people underestimate how much retirement changes social dynamics. Work friendships often fade once the shared environment is removed. Spouses who spent decades apart during the workday suddenly find themselves together nearly every hour, sometimes creating unexpected tension. Meanwhile, children and grandchildren have busy schedules of their own.
Some retirees experience genuine isolation for the first time in decades. Research published by Kiplinger has linked social isolation among older adults to increased risks of depression, anxiety, and cognitive decline. Yet these emotional and social realities rarely receive the same attention as asset allocation.
Shifting from Financial Plans to Life Plans
This disconnect represents the real issue beneath most retirement regrets: people spend years building financial plans but very little time building life plans. A successful retirement is not simply about escaping work; it is about moving toward something meaningful.
For financial advisors, this reality presents an opportunity to broaden the conversation. Clients absolutely need guidance around investments, income strategies, taxes, healthcare costs, and inflation. But they also need a trusted partner to help them think through purpose, identity, and relationships. Retirement is not just about having enough money to stop working. It is about helping clients secure enough purpose to continue living well long after the work ends.
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Salvatore M. Capizzi, CEPA, CBDA, Executive Vice President of Dunham & Associates Investment Counsel, Inc., Member FINRA/SIPC, is the author of the whitepaper “Is Our Industry Prepared for Retirees’ Longer Lifespans?” The paper explains how longevity, inflation, and sequence risk challenge traditional retirement planning and why advisors may need a new portfolio model. Click to access: The Retirement and Longevity Paper.
Sources:
(1) Exit Planning Institute, 75% of Entrepreneurs Regret Their Exit. Here’s What They’re Missing, by Scott Snider, May 14, 2026, https://www.entrepreneur.com/leadership/75-of-entrepreneurs-regret-their-exit-here-are-the-3/504265
(2) Nationwide Retirement Institute survey, February 3, 2026 https://news.nationwide.com/download/2f29339a-1e79-4dc4-98c9-bcdb101792c0/nfm-25301aonationwideadvisorauthorityrecentinvestorsdatadeck.pdf
(3) The Vital Lifeline Alignment, presentation at Dunham Advisory Board Meeting, by Mark Pace, May 21, 2026 https://vitallifelong.com/
(4) Fidelity Investments® Releases 2025 Retiree Health Care Cost Estimate, a Timely Reminder for All Generations to Begin Planning, by Fidelity, July 30, 2025, https://newsroom.fidelity.com/pressreleases/fidelity-investments--releases-2025-retiree-health-care-cost-estimate--a-timely-reminder-for-all-gen/s/3c62e988-12e2-4dc8-afb4-f44b06c6d52e
(5) Is Our Industry Prepared for Retirees’ Longer Lifespans?, By Salvatore M. Capizzi, EVP, Dunham, February 2025. Dunham https://23808446.fs1.hubspotusercontent-na1.net/hubfs/23808446/Dunham%20Website%20White%20Papers/Dunham%20Retirement%20Whitepaper%20-%20Pages%20v6.pdf
(6) Combating Loneliness in Retirement: Why Strengthening Your Connections Could Lengthen Your Life, by Kiplinger, April 25, 2026, https://www.kiplinger.com/retirement/happy-retirement/combating-loneliness-in-retirement-strengthening-connections