What thousands of retirees wish they had known before they left the workforce
When people imagine retirement, they usually picture freedom. More time with family. Less stress. The chance to finally enjoy the life they’ve worked so hard to build. But after years of helping older adults and speaking with retirees, I’ve learned something important. Very few people regret retiring. Many regret what they didn’t do before retirement. The encouraging news is that most of those regrets can still be avoided if you know what to prepare for. Several recent national surveys, including research from the TIAA Institute, the Employee Benefit Research Institute (EBRI), and Schroders, have asked retirees directly what they regret most. Their answers point to patterns that anyone still working can learn from today. Here are the 10 regrets that come up most often, along with what the research says about each one.
1. Not Saving Enough, Early Enough
The single most common regret is not starting to save sooner. According to the TIAA Institute’s Bridging the Gaps in Retirement Expectations survey, 76 percent of current retirees regret not beginning to save earlier in life, and 71 percent wish they had saved more overall before leaving the workforce. A separate study from the Transamerica Center for Retirement Studies indicates that 78 percent of retirees would change their saving behavior if they had the chance to do it again. The lesson is not about needing an extraordinary income, it is about giving compound growth as many years as possible to work.
2. Never Creating a Real Retirement Budget
Plenty of people track their spending closely while they are working, then walk into retirement without a clear budget for the next chapter. Per a Fidelity study, 68 percent of pre-retirees have never created a retirement budget, which often means the first year or two of retirement becomes a slow, uncomfortable process of trial and error rather than a plan.
3. Not Setting Clear Retirement Goals
Saving money is only part of the picture. According to the TIAA Institute survey, 47 percent of retirees wish they had established clearer retirement goals before they stopped working, things like where they wanted to live, how they wanted to spend their time, and what a meaningful weekly routine would look like without a job structuring the day.
4. Underestimating Health Care and Long-Term Care Costs
Medical expenses in retirement routinely surprise even careful planners. The TIAA Institute survey found that 49 percent of retirees regret underestimating health care and long-term care costs. This regret compounds with age, since the U.S. Department of Health and Human Services estimates that a large share of people turning 65 will eventually need some form of long-term care, an expense that Medicare does not fully cover.
5. Not Purchasing Long-Term Care Insurance
Related to the regret above, research from Abigail Hurwitz of the Hebrew University of Jerusalem and Olivia Mitchell of the Wharton School, based on interviews with more than 1,600 older Americans, indicates that roughly one in three retirees wish they had purchased long-term care insurance while they were still young enough to get an affordable rate. The earlier this type of coverage is purchased, the less expensive it tends to be.
6. Not Preparing for Life’s Unplanned Events
Retirement plans often assume a smooth, predictable exit from the workforce, but real life rarely cooperates. The TIAA Institute survey indicates that 49 percent of retirees regret not preparing for events such as health problems, job loss, career changes, and caregiving responsibilities, and 51 percent said they had to leave the workforce for more than a year earlier than planned because of one of these unplanned events.
Illustrative Example (fictional): Consider a hypothetical retiree we will call Diane, a 61 year old former office manager in Broward County who planned to work until 67. When she was diagnosed with a health condition that limited her mobility, she had to leave her job four years earlier than expected. Because she had not built a financial cushion for an early exit, she needed to file for Social Security at a reduced benefit rate and lean on part-time consulting work to cover the gap. Her experience mirrors the pattern described in the TIAA Institute research above, where unplanned health events forced many retirees out of the workforce sooner than they intended.
7. Claiming Social Security Without a Strategy
When and how to claim Social Security is one of the most consequential retirement decisions, and many retirees say they got it wrong. Research from Hurwitz and Mitchell found that not working longer, and by extension not delaying a Social Security claim to increase the monthly benefit, was cited as a regret by about a third of the retirees they surveyed. Claiming early locks in a permanently reduced benefit, while delaying can meaningfully increase guaranteed lifetime income.
8. Not Working a Few Years Longer
Beyond the Social Security angle, many retirees simply wish they had stayed employed a little longer. Per the Hurwitz and Mitchell research, 34 percent of retirees said that if they could do it again, they would have worked longer rather than retiring when they did. Some of this regret is financial, but a 2015 Bankers Life study indicates that a majority of retirees who return to work do so for non-financial reasons as well, including staying mentally sharp and maintaining a sense of purpose.
9. Ignoring the Impact of Inflation
Retirees who built their plans during years of low inflation have had to adjust quickly. According to the 2022 Retiree Reflections Survey from EBRI, 54 percent of retirees cited inflation as a financial concern, and the 2024 U.S. Retirement Survey from Schroders indicates that figure has climbed even higher, with nearly 90 percent of respondents now worried that inflation is eroding the value of their savings.
10. Not Working With a Financial Professional
The research suggests that guidance matters. According to reporting on the TIAA Institute study by NAPA Net, retirees who worked with a certified financial professional carried significantly fewer regrets across nearly every category, with only 26 percent regretting that they had underestimated life events, compared to 43 percent among those who did not work with an advisor. Despite this gap, the same research indicates that only about one in four retirees currently works with a financial professional.
What This Means for Anyone Planning Ahead
The encouraging part of every one of these studies is that they all point to the same conclusion: most retirement regrets are preventable.
You don’t have to make every perfect decision today. But every conversation you have, every dollar you save, every document you organize, and every plan you make gives your future self a little more freedom. Retirement shouldn’t be remembered for the things you wish you had done. With thoughtful planning, it can become the chapter you’ve been working toward all along. Building a clearer budget, discussing a Social Security claiming strategy, and reviewing long-term care coverage options before you need them are concrete steps that can address several of these regrets at once.
What about you?
If retirement is on your horizon, which of these regrets concerns you the most?
Share your thoughts in the comments. Your experience may help someone else prepare for a more confident retirement.
Disclaimer: I, Sanchia zlewis-Moore, is not an attorney, physician, or financial advisor. This article is for educational purposes only and is not a substitute for professional legal, medical, or financial advice. Please consult a qualified attorney, financial advisor, or healthcare provider regarding your individual circumstances.
Sources
- TIAA Institute, Bridging the Gaps in Retirement Expectations report, as reported by Employee Benefit News, Yahoo Finance, and Moneywise
- Transamerica Center for Retirement Studies, 2025 Retirement Realities report, as cited by Boldin
- Fidelity study on pre-retiree budgeting habits, as cited by MoneyTalksNews
- Employee Benefit Research Institute (EBRI), 2022 Retiree Reflections Survey, as cited by U.S. News
- Schroders, 2024 U.S. Retirement Survey, as cited by U.S. News
- Abigail Hurwitz (Hebrew University of Jerusalem) and Olivia S. Mitchell (Wharton School, University of Pennsylvania), retirement regrets research, as reported by The Motley Fool
- U.S. Department of Health and Human Services, long-term care needs estimates, as cited by The Motley Fool
- Bankers Life, 2015 study on retirees returning to work, as cited by The Motley Fool
- NAPA Net, reporting on TIAA Institute retiree regret data, July 2026
