5 Things Retirees Regret - And What You Still Have Time to Get Right

Ready For Retirement

After working with hundreds of people navigating retirement, we’ve seen a clear pattern: the biggest regrets aren’t about money. They’re about meaning.

Too often, people retire from something—but never toward something. They solve the financial side without planning for the life side. And that leads to some common regrets:

• No clear purpose after work: Retirement without direction quickly turns from freedom to restlessness.
• Neglecting health too long: Wellness is what fuels the retirement you’ve dreamed about—don’t wait to prioritize it.
• Losing social connection: The workplace offers more structure and belonging than many realize until it’s gone.
• Expecting retirement to feel like a vacation forever: It won’t. But with intention, it can become a reinvention.
• Being too afraid to spend: Your money is a tool to live—not something to hoard while life passes by.

Don’t wait to think about what really matters. The best retirements are built not just on financial security—but on vision, relationships, health, and joy.

Start designing a life you won’t regret.

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Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation.
The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal.
Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements
Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial.

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Chapters

1. Introduction to Retirement Regrets (00:00:00)

2. Regret 1: Planning For Life (00:00:37)

3. Regret 2: Neglecting Your Health (00:02:53)

4. Regret 3: Letting Relationships Drift (00:04:24)

5. Regret 4: Expecting a Permanent Vacation (00:06:42)

6. Regret 5: Fear of Spending Money (00:10:17)

7. Final Thoughts & Call to Action (00:12:20)