Common Retirement Regrets—And Proactive Moves to Consider
Many people don’t regret being retired. They regret how they got there.1
“I wish I had saved earlier.”
“I didn’t think long-term care would matter.”
“I should’ve waited to claim Social Security.”
Hindsight hits hard when it’s tied to your potential freedom and options.
The good news? There may still be opportunities to make meaningful changes that could
benefit your future.
Let's break down the most common retirement regrets—and what you can do right now to consider addressing them.
The Power of Starting Early
Save on Schedule
Retirement doesn't feel urgent… until it's right in front of you.
One of the biggest regrets? Not saving soon enough. And here's the math that illustrates
why: if you save $1,000 a month starting at age 40, with a 7% return, you could potentially
build a nest egg worth around $758,000 by 65.* But if you wait until 50? You'd need to save
approximately $2,520 a month to reach a similar goal.
That's the potential cost of waiting.
Start smaller. Start now. Automate it.
Every dollar today may help create more flexibility tomorrow.
Consider Your Benefits Timeline
Time Your Benefits Strategically
Many folks claim Social Security the second they're eligible—usually out of fear or habit. But
that early move locks in a lower monthly check for life.
Waiting until age 70 can raise your monthly benefits by about 32%.2 That's not a small
bump—it's the difference between making ends meet and having extra breathing room.
Delaying won't be right for everyone. But if your situation allows, waiting may
increase your benefits over time. Consider working with a financial professional to evaluate
your specific circumstances, weigh your options, and ensure your claiming strategy aligns
with your broader retirement goals and needs.
Managing Debt Before Retirement
Put Debt on a Deadline
Carrying debt into retirement may potentially limit your choices. It could keep money tied up
in interest instead of letting you use it where it counts.
If you've still got a mortgage, credit cards, or car loans, now may be a good time to consider
creating a payoff plan. Pick a target date. Set up automatic extra payments. Each balance
you pay off may help add flexibility down the road.
A retirement with fewer financial obligations often provides more peace of mind.
Planning for Long-Term Care Needs
Decide Long-Term Care on Purpose
Most people assume Medicare covers nursing homes. It doesn’t.3
And most haven’t named someone to make medical decisions for them. That means when something unexpected happens, families can be left scrambling instead of confidently following a plan.
Developing a long-term care strategy may help protect both your financial resources and
preserve more choices for you and your family.
Keep Options Open With Work
Extend Optionality
Not everyone wants to work longer—but some retirees wish they had.
Working just a few more years or shifting into part-time work can stretch savings, delay
withdrawals, and reduce financial pressure. Think of it like adding time to the game clock.
Of course, this approach isn't for everyone—review your personal situation, goals, and health
considerations to determine what makes sense for your circumstances.
It's not about never retiring. It's about having options when life throws a curveball.
Your Career Path Matters, Too
Play Offense with Your Career
Some people leave the workforce earlier than planned—not by choice.4
They stayed too long in stalled roles, didn’t grow their network, or let their skills get rusty. Staying proactive now—by upskilling, networking, or even exploring new roles—can protect you from being caught off guard later.
A great defense against an unexpected career shift? Stay engaged and keep moving forward.
Life’s Not Just About the Numbers
Enjoy the Good Stuff
Some regrets don’t show up on a balance sheet.
They show up in stories that never happened. Trips that never got booked. Experiences that were saved “for later”… and never taken.5
Health changes. Priorities shift. That’s why building a plan that lets you enjoy life now—without sacrificing the future—can be so powerful.
Money is a tool. Use it to create memories, not just security.
Consider Professional Guidance
Call the Right Plays Together
Even well-prepared retirees say they missed things.
They underestimated how much they’d need. They didn’t know how survivor benefits worked. They weren’t sure about withdrawal rules or tax impacts.
These details can potentially impact a hard-earned nest egg over time.
Working with a financial advisor may help identify and address these considerations before they become more challenging to manage.
Bringing It Together
What decision would future-you thank present-you for?
Retirement planning isn’t about perfection. It’s about progress.
Automate your savings. Talk about long-term care. Rethink your timeline for claiming benefits. Pick one move to start with—then build from there.
A few intentional plays today can mean more freedom, fewer regrets, and a retirement that truly fits your values.
Ready to talk through your retirement planning questions? I'm here to help you explore your
options and create a strategy that fits your unique situation.
*Assumes consistent monthly contributions and a 7% average annual return, compounded annually. This is a hypothetical example for illustrative purposes only. Actual performance will vary. Past performance does not guarantee future results.
Sources:
- Bankrate, 2025 [URL: https://www.bankrate.com/f/102997/x/e4980803dd/august-fsp-press-release-8-20.pdf]
- Social Security Administration, 2025 [URL: https://www.ssa.gov/benefits/retirement/planner/1943-delay.html?utm_source=chatgpt.com]
- The Institute for Healthcare Policy and Innovation, 2025 [URL: https://ihpi.umich.edu/national-poll-healthy-aging/reports-and-resources/long-term-care-are-older-adults-ready]
- Business Insider, 2024 [URL: https://www.businessinsider.com/older-americans-regret-retirement-savings-taking-social-security-early-investments-2024-10]
- Nasdaq, 2024 [URL: https://www.nasdaq.com/articles/6-reasons-retirees-regret-not-traveling-more-retirement]
Disclosure: This content is developed from sources believed to be providing accurate information. The information provided is not written or intended as tax or legal advice and may not be relied on for purposes of avoiding any Federal tax penalties. Individuals are encouraged to seek advice from their own tax or legal counsel. Individuals involved in the estate planning process should work with an estate planning team, including their own personal legal or tax counsel. Neither the information presented nor any opinion expressed constitutes a representation by us of a specific investment or the purchase or sale of any securities. Asset allocation and diversification do not ensure a profit or protect against loss in declining markets. This material was developed and produced by Advisor Websites to provide information on a topic that may be of interest. Copyright 2025 Advisor Websites.
