Ready to Retire? Here's How to Tell Your Company │ Root Talks

Ready For Retirement

In this episode, Ari and James explore the emotional and practical sides of retiring—specifically, how to have the conversation that officially ends your career.
Whether you're months away or years out, this discussion tackles the fear, hesitation, and freedom that come with telling your boss you're done. You'll hear real stories from Root Collective members who’ve taken the leap, insights on counteroffers, and a powerful reframe: every “yes” to more work is a “no” to your time, your family, your dreams.

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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. A Story From The Root Collective (00:00:00)

2. Thinking About Your Why & Logistics (00:01:28)

3. What Are You Saying Yes To? (00:03:53)

4. Choosing Your Hard (00:06:59)

5. James' Jet Ski Story: Facing Hard Conversations (00:07:58)

6. Why You're Really Retiring (00:10:18)

7. What Would You Do If You Could Choose? (00:16:20)

8. Stories from Root Collective (00:18:38)

9. How Do You Quit Your Job? (00:20:19)

10. Work Relationships (00:21:30)

11. Final Thoughts (00:23:21)