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The Surprising Regrets of Wealthy Retirees | Root Talks

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Manage episode 482888614 series 3307298
Content provided by James Conole, CFP® and James Conole. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by James Conole, CFP® and James Conole or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://podcastplayer.com/legal.

Retired with millions—but full of regret?
In this episode of Root Talks, James and Ari share the real stories no one talks about: wealthy retirees who did everything “right” financially but still feel like they missed out. From sacrificing health and relationships for more savings, to realizing too late that they were planning for someone else’s version of success, these lessons are emotional, practical, and essential.
What you’ll learn:
Common regrets wealthy retirees confess after leaving work
Why financial freedom means nothing without health, time, or joy
How to avoid estate planning mistakes that burden your spouse or family
Why intentional living matters more than chasing a number
Simple, high-impact ways to prepare for retirement now
If you're building wealth, nearing retirement, or want to live more meaningfully today—this conversation is for you

Create Your Custom Strategy ⬇️

Get Started Here.
Join the new Root Collective HERE!

  continue reading

Chapters

1. Introduction (00:00:00)

2. The Saver's Mindset Challenge (00:02:12)

3. Balance Between Personal & Financial Goals (00:05:46)

4. Paying for Peace of Mind (00:07:13)

5. Set Your Family Up for Success (00:09:47)

6. Making Time for What Matters (00:10:41)

7. Living Your Best Life While You Can (00:12:11)

8. Strategies For Best Spending & Closing Thoughts (00:13:38)

287 episodes

Artwork
iconShare
 
Manage episode 482888614 series 3307298
Content provided by James Conole, CFP® and James Conole. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by James Conole, CFP® and James Conole or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://podcastplayer.com/legal.

Retired with millions—but full of regret?
In this episode of Root Talks, James and Ari share the real stories no one talks about: wealthy retirees who did everything “right” financially but still feel like they missed out. From sacrificing health and relationships for more savings, to realizing too late that they were planning for someone else’s version of success, these lessons are emotional, practical, and essential.
What you’ll learn:
Common regrets wealthy retirees confess after leaving work
Why financial freedom means nothing without health, time, or joy
How to avoid estate planning mistakes that burden your spouse or family
Why intentional living matters more than chasing a number
Simple, high-impact ways to prepare for retirement now
If you're building wealth, nearing retirement, or want to live more meaningfully today—this conversation is for you

Create Your Custom Strategy ⬇️

Get Started Here.
Join the new Root Collective HERE!

  continue reading

Chapters

1. Introduction (00:00:00)

2. The Saver's Mindset Challenge (00:02:12)

3. Balance Between Personal & Financial Goals (00:05:46)

4. Paying for Peace of Mind (00:07:13)

5. Set Your Family Up for Success (00:09:47)

6. Making Time for What Matters (00:10:41)

7. Living Your Best Life While You Can (00:12:11)

8. Strategies For Best Spending & Closing Thoughts (00:13:38)

287 episodes

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