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May 6, 2026 • 14 minutes
Recent research shows that many retirees look back and wish they had planned differently. Bankrate’s Financial Regrets Survey finds that roughly three in four Americans have a financial regret, with not saving enough for retirement and taking on too much debt among the most common. The good news: most of the mistakes retirees report are still fixable with better planning, even if you’re already retired.
In this guide, you’ll see the 15 retirement regrets retirees talk about most, plus specific actions you can still take to improve your own plan.
Retirement regrets trace back to a few consistent patterns. Here are the 15 retirees report most, and what you can still do about each one.
A large majority of retirees wish they had saved more. Transamerica’s 2025 Retirement Realities report found that 78% of retirees would change their saving behavior, and recent surveys from Bankrate and Nationwide confirm that not saving enough for retirement is still one of Americans’ biggest financial regrets.
The pain shows up in missed 401(k) matches, years of low contributions, and starting late. Advisors see many people only begin serious retirement saving in their 50s or early 60s, which compresses the time for compounding and leaves fewer options.
Takeaway: Saving more is still one of the highest-impact moves you can make, even if you feel behind. Use the Boldin Planner to see how higher contributions, later retirement, or spending changes affect your odds of success. Learn more about:
Debt, especially credit card and other high-interest debt, increases your cost of living and reduces your flexibility. Lincoln Financial’s research found that about one-third of retirees wish they had paid off debts sooner.
For retirees, carrying debt can be more stressful because options to earn more or extend working years are limited compared to mid-career. Debt payments can crowd out spending on healthcare, travel, and family support.
Takeaway: If you’re still working, prioritize paying down high-interest debt before retirement. If you’re already retired, map out payoff strategies to see how faster payoff changes your long-term income projections and where to focus first.
Two-thirds of pre-retirees have never created a retirement budget, according to Fidelity, and that shows up quickly once paychecks stop. Many retirees spend more in the first few years of retirement than they expected, not less.
“Retirees often go out more — dinners with friends, vacations, hobbies,” says Mike Niemczyk of MLN Retirement Planning. “Without a plan, many find they’re spending faster than expected.” Advisor John Soudan adds: “When you retire, every day is Saturday. If your weekends usually mean golf and dinner out, imagine that seven days a week. You need to budget for it.”
Takeaway: Decide what your version of fun looks like in retirement, estimate how much it will cost each year, and build that spending into your written plan. Explore ideas and tools:
Many retirees say that, in hindsight, they stayed in the workforce longer than they needed to. After decades of saving and being financially cautious, the hard part wasn’t building the nest egg. It was trusting themselves enough to start spending it.
Staying in a job for extra years when your plan already works often means trading irreplaceable time and health for extra security you don’t require. Later, that lost time can feel like one of retirement’s deepest regrets.
Takeaway: If your numbers support retirement or partial retirement, consider whether fear is the only thing keeping you at work. Use scenario modeling to test dates, part-time work, and different spending levels so you can retire with confidence instead of second-guessing.
Fidelity estimates that a 65-year-old couple retiring in 2025 will need about $315,000 over their lifetimes just to cover medical expenses, excluding long-term care. More than one in five adults 65 and older report having some form of medical or dental debt, according to KFF.
For people who retire before Medicare eligibility, marketplace or private health insurance can cost thousands per year, with premiums and out-of-pocket costs rising with age. Many would-be retirees keep working mainly to hold on to employer coverage.
Takeaway: Medical costs will rise. What you can control is how much planning you put into them. Use a comprehensive retirement planner to:
Transamerica’s 2025 Retirement Realities report shows that about two-thirds of retirees wish they had been more knowledgeable about financial planning. The knowledge shortfalls that cause the most damage are repeatable: how 401(k) and IRA withdrawals are taxed, how Social Security timing affects lifetime benefits, when Medicare enrollment periods open, and how sequence-of-returns risk can hurt early-retirement portfolios.
Many people only encounter these rules once they’re already making decisions or looking back on them, which is exactly when mistakes are hardest to undo.
Takeaway: Treat financial literacy as an ongoing project. Start with the topics that affect you most: taxes, Social Security, investing, Medicare. Layer deeper knowledge over time. Boldin’s retirement blog and classes can help.
Many retirees regret that they didn’t strike a better balance between growth and safety. Keeping too much in very conservative investments meant their money didn’t keep up with inflation over decades, which steadily eroded purchasing power. Federal Reserve data shows that household balances in money market funds, a common proxy for cash on the sidelines, have climbed to nearly $5 trillion in recent years, up from under $2 trillion in 2018, underscoring how many investors have stayed in low-return vehicles.
Taking too much risk close to retirement creates a different problem. Large portfolio drops right at the start of withdrawals can reduce what you can safely spend, even if markets recover later.
Takeaway: Your investment mix should evolve as you age, but it should still be grounded in your actual goals and risk capacity. Use planning software to see how different stock-bond-cash mixes affect your probability of success and to test how your plan holds up under market stress.
Feeling like a passenger of your own financial plan is a common regret. Some retirees paid years of advisory fees and ended up feeling like they were in the back seat, unsure how decisions were made or whether those choices aligned with their goals.
Working with advisors and staying in control aren’t mutually exclusive. The more you understand your own numbers — how withdrawals are taxed, when Social Security makes sense, how your asset mix affects income — the better questions you’ll ask, and the less you’ll have to take anyone’s word for it.
Takeaway: You can work with advisors and still own the decisions. Staying hands-on means you understand your own numbers, can run your own scenarios, and bring professionals in on your terms rather than theirs.
One of the biggest financial surprises for many retirees is how much ongoing “assets under management” (AUM) fees cost over time. One percent charged annually on a $1 million portfolio over 30 years equals $300,000 in fees, before considering the compounding on money that left the portfolio, according to research on retiree regrets.
Vanguard research has found that lower investment costs are strongly associated with better long-term investor outcomes because more of each return stays in the portfolio. Many retirees only run this math after they’ve already paid years of percentage-based fees.
Takeaway: Know exactly what you’re paying for advice and investment management, and model those fees in your plan. If long-term costs are too high, consider shifting to lower-cost investments and flat-fee or hourly advice while using Boldin to stay in control of your strategy.
Many retirees say they wish they had asked a second professional to review their plan before making key decisions. Common examples include underestimating taxes in high-RMD years, mis-timing Social Security, or not aligning investment risk with withdrawal needs, according to Transamerica’s 2025 Retirement Realities report.
A fixed-fee review from a CERTIFIED FINANCIAL PLANNER™ professional can validate your plan, catch oversights, and give you confidence to move forward. You keep control of your plan, but you’re not relying only on your own perspective.
Takeaway: Do-it-yourself planning doesn’t mean doing it entirely alone. Use the Boldin Planner to build your plan, then consider:
Many retirees don’t realize how much taxes can reduce their retirement income until they start taking withdrawals. Distributions from traditional 401(k)s and similar pre-tax retirement accounts are taxed as ordinary income, and they’re also subject to state income tax in most states, which can push retirees into higher combined tax brackets than they expected.
Without a plan, retirees can face concentrated high-tax years when required minimum distributions (RMDs) begin, or when they sell appreciated assets and trigger capital gains.
Takeaway: Treat tax planning as a core part of your retirement strategy, not an afterthought. The Boldin Planner lets you see projected taxes year by year and experiment with Roth conversions, withdrawal sequencing, and other strategies that can reduce lifetime taxes.
Many retirees say they wish they had built more resilience into their plan before real disruptions hit. Inflation spikes, market downturns, health events, natural disasters, fraud, and adult children needing financial help are just some of the surprises that can knock a plan off course, as Transamerica’s research on retirement spending surprises documents.
Recent years have shown that many retirees hadn’t fully accounted for extended periods of higher inflation or large market swings. The regret isn’t that surprises happened; it’s that the plan didn’t have enough resilience built in.
Takeaway: Build buffers into your plan now. That includes maintaining an emergency reserve, holding an appropriate mix of safe assets, and running “what if” scenarios in your planner for market drops, health shocks, and support for family members so you know how you’d respond.
Many retirees say they focused so much on saving that they never built a plan for turning those savings into income. According to Lincoln Financial Group research, more than a third of retirees wish they had chosen investments that provide a steady stream of income. While you’re working, the focus is on saving. Once retired, the challenge is turning those savings into sustainable income.
Without a clear income strategy, retirees can feel unsure about how much they can safely spend, which accounts to draw from first, and how to coordinate withdrawals with Social Security, pensions, and any annuities.
Takeaway: Build an income plan that combines guaranteed sources (like Social Security, pensions, and certain annuities) with flexible withdrawals from investment accounts. Use Boldin to compare withdrawal strategies, test different start dates for Social Security, and explore retirement income strategies.
Not taking full advantage of an employer match is one of the simplest and costliest mistakes. Bankrate and other surveys find that not capturing matches early is among Americans’ top financial regrets.
Even small missed matches can grow into large shortfalls after decades of compounding. Once a year passes, that free contribution is gone for good.
Takeaway: Always try to contribute at least enough to receive the full employer match when it’s available. If you missed matches in the past, increase contributions now if you can, and adjust other parts of your plan, like retirement age or spending, to help make up ground.
Only about 22% of retirees have a written financial plan, according to Transamerica’s 2025 Retirement Realities report. Broader surveys of U.S. adults show that roughly one-third have a written plan, but among those who do, three in four say it makes them feel more in control of their finances, and 96% say they feel confident they’ll reach their financial goals, according to the 2024 Schwab Modern Wealth Survey.
Boldin users report similar effects: 95% of subscribers with a written plan say they feel very confident or somewhat confident about their financial future. A written plan doesn’t eliminate uncertainty, but it turns vague worries into specific numbers and choices you can act on.
Takeaway: If you’ve been worrying about retirement without a written plan, start one now. The Boldin Planner, featuring Boldin AI, is designed to help you build a comprehensive, dynamic plan that integrates savings, spending, investing, taxes, healthcare, and estate goals in one place.
Not saving enough tops most retirement regret surveys, with missed years of contributions and starting late among the most cited specifics. Planning shortfalls around healthcare costs, taxes on withdrawals, and Social Security timing follow closely. For most people, the underlying issue is a plan that started late, covered too little ground, or was never written down.
Bankrate’s 2024 Financial Regrets Survey found that 77% of U.S. adults have at least one financial regret. Separate research from Lincoln Financial Group focusing on retirees found that 62% would go back and plan differently for retirement. Together, these studies suggest that the majority of people reach later life wishing they had made different financial decisions.
For most people, no. Tax strategy, withdrawal sequencing, Social Security timing, and investment risk can all be adjusted after retirement. Some missed opportunities, like old employer matches, can’t be recovered, but their impact can often be offset with changes elsewhere in the plan.
The mistake that does the most lasting damage to retirement is treating planning as a series of separate decisions rather than one integrated picture. Choices about taxes on withdrawals, income sources, and timing interact in ways that matter. A plan that addresses them together tends to hold up better than one built in pieces.
The best way to avoid retirement regrets is to start planning early, put your plan in writing, and revisit it regularly. Focus on saving adequately, capturing employer matches, understanding taxes and benefits, planning for healthcare, and choosing an investment mix that matches your goals and risk capacity. Using a comprehensive planning tool and seeking a second opinion when needed can help you catch blind spots before they become regrets.
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