Ready For Retirement The Surprising Regrets of Wealthy Retirees | Root Talks
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
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