If you think your biggest regret in retirement will be spending too much, I’ve got news for you. After hearing retirement advice from 909 retirees, it turns out that money isn’t always the biggest source of regret. Sure, finances matter—but what truly shapes a happy retirement often has more to do with purpose, relationships, and how you spend your time.
In this post, I’m going to share the real feedback we heard from nearly a thousand retirees—their biggest regrets and the advice they’d give their younger selves. My hope is that you can learn from their experiences and apply these lessons as you plan your own retirement.
Regret #1: Waiting Too Long
Many retirees said they worked longer than they needed to. On paper, it made sense—one more year of income, one more year of 401(k) contributions, one more year toward Social Security. But as one retiree put it, “That money doesn’t matter if life passes you by while you’re still working.”
Working longer can help your financial projections, but it can also rob you of your healthiest years. The truth is, there’s no perfect moment when retirement suddenly feels “safe.” Waiting for that feeling means you may never take the leap.
If you’re financially prepared, don’t let fear keep you on the sidelines. Retirement isn’t just about having enough money—it’s about having enough time and energy to enjoy it.
Regret #2: Not Defining a Purpose
A big surprise for many retirees was how lost they felt once work stopped. They planned their finances but not their purpose. The idea of endless free time sounds great, but without direction, it can quickly turn into boredom or even loneliness.
You don’t accidentally stumble into purpose—it’s something you build. Think about what gives you energy. Is it volunteering, mentoring, traveling, or spending time with family? What activities make you feel useful and fulfilled?
Start exploring those things now, before you retire. Purpose doesn’t have to mean productivity—it just means having something that matters to you. The happiest retirees were the ones who planned their “what’s next” with the same care they gave their portfolios.
Regret #3: Not Thinking Enough About Location
Retirement isn’t just a financial decision—it’s a lifestyle one. Where you live shapes your experience more than almost anything else.
Some retirees told us they chose where to live based on weather or affordability but didn’t think about proximity to family, friends, or healthcare. Others realized they missed the community they’d built during their working years.
Ask yourself: What kind of environment supports the life you want? Maybe you dream of the ocean, the mountains, or the desert. Or maybe it’s more about who’s nearby—grandkids, close friends, or good hospitals.
The right location isn’t about luxury; it’s about access—to people, activities, and care that make your life richer and easier as you age.
Regret #4: Ignoring Hidden Tax Traps
Many retirees were surprised by how taxes still followed them into retirement. Some assumed they’d automatically drop into a lower tax bracket once they stopped working—but that wasn’t always true.
Required minimum distributions (RMDs) from traditional IRAs and 401(k)s often pushed people into higher brackets later in life. Add in Social Security income, investment gains, and Medicare’s IRMAA surcharges, and the tax bite can be steep.
A few comments we heard again and again: “I wish I’d used a Roth IRA earlier.” “I didn’t expect my RMDs to be so high.” “I didn’t know Medicare premiums could go up.”
The fix? Plan ahead. Incorporate tax strategy into your overall retirement planning. Consider partial Roth conversions, strategic withdrawals, and timing Social Security benefits. A thoughtful tax plan can save you thousands and prevent those mid-retirement surprises.
Regret #5: Prioritizing Money Over Relationships
This one hit home for a lot of people. Many retirees spent decades focusing on financial security—working, saving, investing, tracking their numbers. They thought once the money side was handled, happiness would follow.
But what they learned is that wealth alone doesn’t create joy. The quality of your retirement depends on the quality of your relationships.
Money gives you freedom, but people give you purpose. I’ve seen clients with perfect financial plans still feel empty because they lost connection with their spouse, friends, or children. Relationships drift when they aren’t maintained, and it’s easy to miss the warning signs.
Make time now for the people who matter. Plan experiences, not just investments. Nurture connection as deliberately as you grow your savings—it’s one of the best investments you can make.
Regret #6: Being Too Afraid to Spend
Here’s a common pattern I’ve seen for years: retirees spend decades saving and investing, then feel guilty about spending that money once they retire. The fear of “running out” keeps them from enjoying what they’ve earned.
Research shows that most retirees who follow a reasonable withdrawal plan—around 4% per year—actually end up with more money later than they started with. But many still live as if they’re one purchase away from disaster.
The goal of retirement isn’t to die with the biggest account balance. It’s to use your savings to create a life you love. That might mean travel, time with family, new hobbies, or giving generously.
Yes, you should spend wisely and have guardrails in place. But don’t let fear keep you from living. You built your financial foundation for a reason—so you could use it.
The Real Retirement Advice: Start Living Now
When we asked retirees what they’d do differently, almost no one said, “I wish I had more money.” Instead, they said:
“I wish I’d retired sooner.”
“I wish I’d spent more time with my family.”
“I wish I’d traveled while I was still healthy.”
Those regrets have nothing to do with spreadsheets—and everything to do with life.
Whether you’re 40, 50, or 60, the best time to start planning for a meaningful retirement is today. Think about what matters most to you. Define your purpose. Build your plan. And don’t wait for “someday” to live the life you’ve been saving for.
At Root Financial, that’s what we help people do every day—create financial plans that support the life they actually want to live. If you’re ready to align your money with your meaning, reach out to our team.
The information presented is for educational and informational purposes only and should not be construed as personalized investment or financial advice. The content discusses general retirement and life planning strategies and is not intended to recommend any specific course of action for any individual.
Examples provided are hypothetical and for illustrative purposes only. They do not reflect any specific client situation and should not be relied upon for investment decision-making. Past performance of investments is not indicative of future results. All investing involves risk, including the potential loss of principal.
Root Financial Partners, LLC provides tax planning as part of its financial planning services. However, we do not provide tax preparation services, represent clients before the IRS, or offer legal advice.
Clients should consult their CPA or attorney before implementing any investment, tax, or legal strategies discussed. Nothing in this content should be interpreted as a recommendation to take a specific tax position or legal action.