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

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. Create Your Custom Early Retirement Strategy Here Get access to the same software I use for my clients and join the Early Retirement Academy here Ari Taublieb, CFP ®, MBA is the Chief Growth Officer of Root Financial Partners and a Fiduciary Financial Planner specializing in helping clients retire early with confidence.