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What Retirees Regret Isn’t Usually About Money — It’s What They Didn’t Plan For

Over the years, we’ve helped hundreds of individuals and couples prepare for and step into retirement. While financial questions often dominate those early conversations—"Do I have enough saved?" "When should I claim Social Security?" "Can I afford to travel?"—we’ve noticed something consistent after the transition.

The regrets that tend to surface later aren't about investment returns or budgeting decisions. They’re about the parts of life that weren’t thoughtfully planned for: purpose, health, connection, and joy.

In short, retirement isn’t just a financial decision—it’s a life shift. And without planning for the life side of retirement, even the most financially secure retirees can find themselves feeling uncertain or unfulfilled.

Here are five common pitfalls—and how you can sidestep them.

1. Leaving work without a plan for what comes next

Many people know exactly when they want to leave work. Fewer have a clear idea of what they’re retiring to. After the initial honeymoon phase of rest and relaxation, some retirees feel adrift. A calendar that was once packed with meetings and responsibilities can quickly become unstructured and isolating.

Having something to look forward to—whether it's part-time work, volunteering, hobbies, travel, or a new pursuit altogether—adds structure and meaning. Retirement can be a reinvention, not just a withdrawal.

2. Putting health on the back burner too long

There’s often a temptation to delay self-care until “later”—when life slows down, when work ends, when the timing is better. But retirement isn’t a guarantee of good health; it’s a window of opportunity to protect and improve it.

Your well-being is the engine that powers all the things you hope to enjoy—walks with grandkids, bucket-list travel, outdoor adventures, or simply feeling good day to day. Don’t wait until retirement to prioritize sleep, movement, nutrition, and regular checkups. The best retirement lifestyle starts with taking care of your body now.

3. Underestimating the loss of daily connection

Many retirees are surprised to discover how much of their social life was built into their job—casual conversations, teamwork, shared goals, and regular interaction. When work stops, that daily human contact often disappears too.

Staying connected takes effort, but it’s vital to emotional health. Consider building routines that involve other people: classes, clubs, volunteer work, or regular meetups with friends. Community is just as important in retirement as it was during your working years.

4. Thinking retirement will feel like a permanent vacation

The idea of endless free time sounds great—at first. But over time, a life without direction can lose its shine. Retirement isn’t a pause—it’s a new chapter. And like any chapter, it needs structure, meaning, and purpose.

This is your chance to write a new story for yourself—one that fits who you are today and who you’re becoming. With some reflection and planning, retirement can be more than a break from work. It can be your most intentional and rewarding stage yet.

5. Being afraid to enjoy the money you’ve saved

It’s not uncommon for retirees to feel anxious about spending their savings—even when the math says they’re fine. The fear of running out of money can keep people from fully enjoying the life they worked so hard to afford.

A well-crafted financial plan can bring clarity and peace of mind. When you know what you can spend—and how long it can last—it becomes easier to say yes to things that matter: travel, family time, new experiences, or meaningful giving. Your money is a tool to support your life—not just a safety net to protect it.

The Best Retirements Are Designed, Not Just Funded

Financial readiness is just one part of retirement. Equally important is personal readiness—having a sense of purpose, strong relationships, good health, and a vision for how you want to spend your days.

If you're approaching retirement, don't just ask whether you can afford to stop working. Ask what kind of life you're hoping to build. The earlier you think about these questions, the more fulfilling your retirement can be.

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