Most people spend decades dreaming about retirement, yet a striking number arrive there carrying regrets about the final stretch of preparation. The year immediately before leaving the workforce turns out to be one of the most consequential windows in the entire retirement journey. It’s the moment when decisions that felt abstract for years suddenly become urgent and real.
What’s revealing is how consistent the patterns are across survey after survey. Many retirees are rethinking the decisions they made before leaving the workforce, wishing they had saved earlier and better prepared for healthcare and other costs in retirement. These aren’t obscure financial moves. They’re straightforward steps that most people simply never got around to taking.
1. Max Out Every Savings Opportunity Still Available
More than three-quarters of current retirees – roughly 76% – say they regret not starting to save earlier in life, while 71% wish they had saved more, according to TIAA’s Bridging the Gaps in Retirement Expectations report. For those still working, the year before retirement is a final chance to close some of that gap.
An overwhelming 82% of surveyed Americans over 45 said they wish they had taken retirement planning more seriously in their younger years, including seeking financial advice, understanding the power of compounding interest, and focusing on income protection strategies earlier. Just over three-quarters also said they regretted not starting to save sooner.
Workers aged 50 and over are eligible for catch-up contributions to 401(k) and IRA accounts, making that final pre-retirement year a real opportunity to build a larger cushion. The Federal Reserve’s October 2025 Survey of Household Economics and Decisionmaking found that only 35% of U.S. adults who were not yet retired said their retirement savings plan was on track, unchanged from 2024 and still below the 40% recorded in 2021.
2. Get a Realistic Handle on Healthcare Costs
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. That number catches many people completely off guard, particularly those who spent decades with employer-sponsored coverage and never looked closely at out-of-pocket realities.
About half of retirees told Schroders they thought Medicare would cover more of their health care expenses than it actually does. Medicare Part B alone carries a monthly premium, and the gaps in coverage for prescriptions, dental, and vision add up fast. Nearly half of retirees say they fell short in preparing for key retirement challenges, including estimating healthcare and long-term care costs, cited by 49% of respondents.
3. Think Carefully About When to Claim Social Security
The median age at which retirees started receiving benefits is 63, according to the Transamerica report. Nearly 3 in 10 retirees started receiving benefits at age 62, the earliest age possible, resulting in a much-reduced benefit. Only a slim 4% of retirees waited until age 70.
About 19% of retirees say they regret claiming Social Security too early, according to Motley Fool survey data. The math on waiting is compelling. Waiting until age 70 can raise monthly Social Security benefits by about 32%. That’s an increase that compounds over years and can meaningfully change the financial picture of a long retirement.
The age you choose to start taking benefits directly impacts the amount you receive. Starting before your full retirement age, which falls between 66 and 67 depending on your birth year, means your monthly payments are permanently reduced. The year before retiring is the right time to model these scenarios rather than default to the earliest option out of habit.
4. Pay Down High-Interest Debt Before the Last Paycheck
Debt, especially credit card and other high-interest debt, increases your cost of living and reduces your flexibility in retirement. Lincoln Financial’s research found that about one-third of retirees wish they had paid off debts sooner. Carrying a monthly debt payment into retirement on a fixed income is a burden that compounds quietly and quickly erodes financial freedom.
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 final working year often brings peak earnings, making it one of the best opportunities to aggressively eliminate balances before the income stops flowing.
5. Consult a Financial Advisor – Seriously
Transamerica’s 2025 Retirement Realities report shows that about two-thirds of retirees wish they had been more knowledgeable about financial planning. Common examples include underestimating taxes in high-RMD years, mis-timing Social Security, or not aligning investment risk with withdrawal needs. These are precisely the kinds of errors a good advisor helps prevent.
Data from a 2024 Northwestern Mutual report shows U.S. adults who partner with an advisor expect to retire at age 64, two years sooner than Americans who don’t work with one. The same study shows retirement saver-and-advisor teams save twice as much money over the long haul as savers with no professional investing help.
6. Build a Concrete Retirement Budget – Not Just a Rough Estimate
Two-thirds of pre-retirees have never created a retirement budget, according to Fidelity, and that gap shows up quickly once paychecks stop. Many retirees spend more in the first few years of retirement than they expected, not less. Travel, home repairs, and lifestyle expenses tend to spike early on, not taper off.
Savings regrets are having real repercussions in retirement. Only 40% of recent retirees are on track with their original budgets and decumulation plans, and 21% have had to be more conservative with spending than they had anticipated. Running the actual numbers in the final pre-retirement year, including inflation, taxes, and discretionary spending, helps avoid a rude awakening on day one of retirement.
7. Plan for Long-Term Care – Not Just Healthcare
Some retirees regret not buying long-term care insurance prior to retirement, when it may be more affordable. More than a quarter of those surveyed for a 2023 National Bureau of Economic Research working paper said that was one of their financial regrets. Long-term care is a separate and often far more expensive category than routine medical costs, and it tends to catch families off guard.
Nearly half of TIAA survey respondents say they regret not having clear retirement goals, while 49% expressed remorse over miscalculating healthcare and long-term care costs. Another 49% regret not accounting for late working-year financial factors, including health issues, career shifts, job loss, and caregiving responsibilities. The year before retirement is the time to have a frank conversation with family and an insurance professional about what long-term care might realistically cost.
8. Account for the Possibility of an Earlier-Than-Planned Exit
Those planning gaps may reflect the unexpected disruptions many retirees faced before leaving the workforce. More than half say they left the workforce for longer than one year because of an unplanned event. Health problems, layoffs, family caregiving demands – any of these can cut a career short without warning.
Current retirees retired at an average age of 57, while future retirees expect to leave the workforce at 62, representing a striking five-year gap between expected and actual retirement ages, according to TIAA’s Bridging the Gaps report. Planning as if retirement might arrive several years early is not pessimistic. It’s realistic. Workers who retire early have less time to save, and their savings must cover a longer retirement.
9. Think About What You’re Retiring To – Not Just From
When planning for retirement, it’s important to remember that certain aspects of life will change. For many people, work provides not only a steady income but also social connections, purpose and goals, and mental stimulation. Losing all of that at once, without a plan to replace it, is one of the more common sources of quiet regret that rarely shows up in financial surveys.
Achieving a happy retirement is as much about your purpose – what you want to do and where you want to do it – as your portfolio. People who spend the final pre-retirement year cultivating hobbies, strengthening friendships outside work, and identifying how they want to spend their time tend to transition far more smoothly. Retirees who thrive tend to be active and engaged: spending more time with family and friends, pursuing hobbies, traveling, doing volunteer work, or caregiving – keeping life full and structured by their own design.
The Takeaway
More than 60% of retirees said they would go back and do things differently when planning for retirement, according to the 2023 Consumer Sentiment Tracker from Lincoln Financial Group. That’s a majority of people looking back with a specific wish: that they’d used the final year before retirement more intentionally.
The good news is that most of the gaps retirees identify are not about decades-long failures. Many of them come down to decisions that could have been made in that last twelve-month window: a conversation with a financial advisor, a Social Security projection, a budget built on real numbers rather than assumptions. The year before retiring is genuinely consequential. It rewards attention.
AI Disclaimer: This article was created with the assistance of AI tools and reviewed by a human editor.