Advice from Retirees that Won’t Surprise You – and Some that Will

Picture your retirement. It’s fantastic, right? After a life of hard work, you’re rewarded with complete freedom to do whatever you want.

But what is that, exactly? How are you paying for it? And are you still physically able to do whatever “it” is?

WHY RETIREMENT PLANNING ADVICE FROM RETIREES MATTERS

Retirement planning isn’t just about numbers (although there are plenty of those too). Missing important pieces of your planning can lead to regret. Knowing what many retirees say they would have done differently can help you make your retirement even better.

You won’t find these retirement readiness tips in a spreadsheet, or a calculator ... or even a financial plan. You get them from going to the people who have been through it. Here are the top tips from retirees and their lessons learned in retirement.

WOULDA, COULDA, SHOULDA: TOP LESSONS RETIREES WISH THEY KNEW SOONER

1. START SAVING AND INVESTING EARLY – AND SAVE MORE THAN YOU THINK

OK, this one’s not a surprise: In a Retiree Reflections survey by the Employee Benefits Research Institute, supported by Edelman Financial Engines, the most resounding regret among retirees is not saving earlier or more – a staggering 70% agreed. Many retirees underestimate how much they'll need, with a separate survey by Schroders finding that 47% of retirees reported higher-than-expected expenses and 33% were concerned about financial stress impacting their health.

Lesson: Begin saving and investing as early as possible. Even small contributions can compound significantly over time. $10k saved at age 30 could be worth about $110k at age 70 (with a 6% annual rate of return). But save that same $10k at age 50, and it could grow to just $33k.

2. MAKE SURE YOU UNDERSTAND MEDICARE AND SOCIAL SECURITY

In the Schroeder’s survey, nearly half of retirees said they believed Medicare would cover more than it does, and in a survey by EBRI and Greenwald,, only a quarter of retirees said they understood Social Security very well. That may be why a working paper from the National Bureau of Economic Research found that a fifth of respondents regretted claiming Social Security too early.

Lesson: Educate yourself on retirement benefits and know how your early decisions could impact your future options.

3. TAKE CARE OF YOUR HEALTH NOW

Hopefully you’re reading this at the gym or on a walk, because health-related regrets are common among retirees. In fact, a survey by MedicareFAQ, a Medicare resource center, found that prioritizing your health  was the second-most-mentioned piece of retiree advice, after prioritizing their finances and saving enough money.

It’s not just about staying active, getting rest and eating well, as important as they are. At some point, aging will start to take a toll, no matter what you do. And you need to make a plan for potential long-term care needs well before they become a reality. One potential avenue is long-term care insurance – in the NBER working paper, a third of retirees said they regret not buying it.

Lesson: Invest in your health now and explore long-term care options before retirement.

4. PLAN FOR THE MENTAL, SOCIAL AND EMOTIONAL ASPECTS OF RETIREMENT

Retirement isn’t just a financial transition; it’s an emotional one. And believe it or not, the emotions you’ll feel might not be pure joy and satisfaction.

In a survey by Second Wind Movement, a life coaching program for retirees, the biggest set of regrets surprisingly wasn’t about being financially prepared, but mentally. Almost 60% felt only moderately or poorly prepared. Many miss the structure, purpose and social connections that work provided.

Lesson: Think beyond money when it comes to retirement; plan for how you’ll spend your time. Develop hobbies, volunteer or consider part-time work to maintain a sense of purpose.

5. DON’T RELY ON PERFECT TIMING

In the NBER working paper, 34% of retirees said they regret not working longer. But the truth is that timing can be unpredictable. The EBRI/Greenwald survey found that 40% of respondents said they retired sooner than planned, very often due to issues out of their control.

Lesson: Prepare for flexibility and consider multiple retirement scenarios.

6. PAY ATTENTION TO RELATIONSHIPS AND LIFESTYLE TOO

Money isn’t the only “more” that retirees wish they had. For many, the opportunities of time feel like they’ve slipped away as well. In a variety of the surveys we mentioned, retirees said they regretted not spending more time with loved ones, deepening friendships and community ties and traveling more when younger. Career regrets also surface, with some wishing they had pursued passion projects or second-act careers.

Lesson: Balance work and savings with personal fulfillment. Make time for relationships and experiences.

7. DON’T OVERLOOK TAXES

Taxes are one of the most underestimated aspects of retirement planning. In the EBRI Retiree Reflections survey, nearly half of retirees (48%) admitted they didn’t understand how taxes would impact their retirement finances. And among those who faced a tax surprise in retirement, 60% ended up paying more than they had planned.

Lesson: Understanding how your retirement income will be taxed – whether it’s from Social Security, pensions, IRAs or investments – can help you avoid costly surprises. Consider working with your tax professional and a financial advisor to build a tax-efficient retirement strategy.

8. STAY IN CONTROL OF HOW RETIREMENT WILL PROGRESS

Some retirees choose to downsize or otherwise move to a different location as they age. That said, many would prefer to stay in their current home for as long as possible.

If that’s your preference, think about how it will likely unfold. Will someone move in to care for you if needed? Can you move your bedroom downstairs? Can you modify your home with aids like a wheelchair ramp and handlebars? Make sure you have a workable plan.

Research by the University of Alabama showed that older adults were more satisfied with a downsizing move if they were the ones driving the decision. If the move was strongly influenced by factors outside of their control, they felt lower levels of psychological wellbeing.

Lesson: Think about how you prefer to simplify your life as you age, and take control of those decisions and their timing.

9. GET PROFESSIONAL HELP

Inthe Retiree Reflections survey, about half of retirees who didn’t work with an advisor on a financial plan said they would have benefitted from speaking with a financial advice professional during their career. And among those who did start working with an advisor only as they approached or after retirement, an even greater portion said they should have done it earlier : the number of retirees who said they would have changed their financial habits to improve their current financial situation was lower among those who reported they had worked with an advisor on a financial plan versus those that did not work with an advisor on a financial plan.

Lesson: Don’t go it alone. A financial advisor can give you advice for retirement, including helping you navigate retirement savings and guidance on Social Security, Medicare, tax planning and drawdown strategies.

A PRERETIREMENT CHECKLIST TO CONSIDER, STRAIGHT FROM REAL RETIREES

1. Save as much as you can, as early as you can
2. Research Social Security and Medicare
3. Take care of your health now and make plans for later
4. Spend time considering what you’ll do with your retirement
5. Build a flexible retirement timeline and know your “plan B”
6. Make the most of your time and relationships
7. Explore how taxes could affect you in retirement
8. Think about how life will progress as you age
9. Hire an advisor to help develop a comprehensive retirement plan

HOW A FINANCIAL ADVISOR CAN HELP YOU AVOID REGRETS

Retirement regrets are powerful reminders that planning for the future is about more than just numbers. It’s about aligning your financial, emotional and lifestyle goals to create a fulfilling post-work life.

The types of regrets a retiree might have can vary, but one thing a lot of them have in common is this – they may have been avoided with the right help. That said, retirement planning mistakes don’t have to be permanent! You just need to address them early enough.

Retirement will be new for you, but our financial advisors have seen it all. From helping set your retirement goals and motivating you to stay on track, to helping you understand Medicare and Social Security financial decisions, to responding to the unexpected surprises that threaten to derail your plans, to suggesting tax planning strategies that can save you money – an advisor can be by your side throughout your journey. Talk to us today to get started.

Haass, David, and Ashlee Zareczny. “Retirement Regrets Statistics: Advice for the Next Generation.” MedicareFAQ, 26 June 2025, www.medicarefaq.com/blog/retirement-regrets-of-seniors/

Costlow K, Choi S, Roskos B, Parmelee P. When Less Is More: Downsizing, Sense of Place, and Well-Being in Late Life. Innov Aging. 2020 Dec 16;4(Suppl 1):440–1. doi: 10.1093/geroni/igaa057.1423