How to Know If You’re Ready to Retire (Hint: It’s Not Just About Money)

Jul 24, 2025

Retirement isn't just about having the right finances; it involves a complex emotional journey. The discussion highlights how severance offers can serve as valuable trial runs for life beyond work. Golden handcuffs often trap high-achievers in jobs they wish to leave, overshadowing what truly matters: time and connections. Fear-setting emerges as a clever tool for tackling anxieties surrounding retirement. Ultimately, community support and shared experiences are emphasized as vital for navigating this significant life transition.

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ANECDOTE

Real Severance Retirement Dilemma

James shares his experience of being let go, which he found beneficial for retirement transition.
A client faces choosing severance to test retirement or keep working at reduced pay, illustrating real dilemmas.

INSIGHT

Psychological Barriers in Retirement

Retirement involves psychological barriers beyond financial readiness.
Losing work's identity and routine causes major adjustment fears for retirees.

ADVICE

Test Retirement With Severance

Use severance pay as a six-month test run for retirement.
Try spending progressively more time in retirement to explore what you truly want.

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The hardest part of retirement isn’t always financial, it’s psychological. For many, stepping away from work isn’t a light switch, but a dimmer that adjusts over time. This episode of Root Talks unpacks what makes the retirement decision so complex, especially for high-achieving professionals whose identity is tied to their careers.

Through a real-life case study, the conversation explores how severance offers can become powerful “test drives” for retirement, offering space to reimagine life beyond work. Ari and James examine the impact of golden handcuffs— when financial incentives cloud what really matters: time, health, and meaningful connection.

If retirement feels more like a mental block than a math problem, this episode offers a new lens. Learn how tools like Tim Ferriss’s fear-setting exercise can help unpack the real risk of not of leaving work, but of staying too long.

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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