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April 3rd, 2025

Root Talks: How to Get Past the Fear of Retiring Even When You Have Enough

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James Conole, CFP®Root Talks: How to Get Past the Fear of Retiring Even When You Have Enough
  1. Root Talks: How to Get Past the Fear of Retiring Even When You Have Enough James Conole, CFP® 22:02

Many professionals find that retiring isn’t just about having enough Money—it’s about feeling ready to leave behind the structure, identity, and comfort of a career. 

In this Root Financial podcast episode, James and Ari explore the emotional hurdles of retiring from a high-paying, high-Stress job, even when financially prepared. They highlight the value of aligning Retirement with your future self’s goals and priorities, not just your current fears. 

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here  

Timestamps:
0:00 – A comment from the Collective
3:03 – A first-day-of-school analogy
4:25 – What would my future self do?
6:47 – Helpful feedback
8:32 – Make sure you're ready financially
10:20 – A life you don't retire from
13:18 – The opportunity cost
16:39 – More words of Wisdom
18:44 – Making the decision is the scary part

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Join the new Root Collective HERE!

James Conole CFP®, Podcaster

James Conole is the founder of Root Financial and the host of the Ready For Retirement podcast and YouTube channel.

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