Freedom at 60 Why He Left a Job He Loved (and Doesn’t Regret It) | Retirement Reality

James Conole, CFP® December 10, 2025
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James Conole, CFP®

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About

Hi, I'm James 👋 — a CERTIFIED FINANCIAL PLANNER™ and founder of Root Financial. Each week, I share videos to help you make smart decisions about saving, investing, spending, and tax strategies — all to help you get the most out of life with your money. But true fulfillment goes beyond finances, so I also explore how your values and money align to support the life you want to live. At Root, we help clients with retirement, investing, and financial planning. Learn more or schedule a call at rootfinancial.com. Root Financial Partners, LLC (“Root”) is a Registered Investment Adviser. Content may include topics related to tax planning and estate planning but should not be considered tax or legal advice. This material is for informational purposes only and not personalized advice. Investing involves risk. Past performance is not indicative of future results. Always consult your CPA, attorney, or financial planner before making financial decisions.

Video Description

Steve spent more than two decades building video games, working with a team that felt more like family than coworkers. By all measures, he loved his work. But a heart attack in 2021 changed everything, and it became the moment that pushed him to rethink the one thing he’d always said he wanted someday: an early retirement. In this episode, Steve sits down with James Conole, CFP®, to share how a health scare, a divorce, and years of slowly learning how to budget and invest turned into the freedom he now wakes up to every day. He didn’t leave work because he hated his job. He left because he finally understood how valuable his time had become and how much life he still wanted to live. Steve talks about losing 70 pounds, rebuilding his health through trial-and-error fitness routines, and the joy of discovering things he never had energy for during his career: jazz bands, improv lessons, spontaneous travel, and even acting classes. He also opens up about moving back to Arizona just in time to support his mom through a cancer diagnosis, a moment that revealed exactly how meaningful this new freedom is. His story is a reminder that retirement isn’t just a math problem. It’s a life problem that you can solve by knowing what you value and experimenting until your days feel like your own again. And for Steve, these last two and half years have been better than he imagined. Watch this episode of Retirement Reality — where real retirees share the wake-up calls, reinventions, and surprising joys that define life on the other side of work. Want to be a guest on James’ show to help others by sharing your story? Complete this form: https://vwo3759x8i7.typeform.com/to/IwyScIeR ======================= Work with us → https://www.rootfinancial.com/start-here/ Check out our Root Financial Youtube Channel → https://www.youtube.com/channel/UCopKwWs9ea1dAOxqZOqBjpg Get access to the retirement software I use and more → https://retirement-planning-academy.mykajabi.com/rpa _ _ ⏱Timestamps:⏱ 00:00 - Opening Question: One Word Summary 00:29 - Meet The Guest: Steve 01:06 - Two And A Half Years In 01:12 - Career: Video Game Programmer 03:11 - Heart Attack: The Wakeup Call 04:03 - From Health Wakeup To Planning Retirement 05:26 - Budgeting, Divorce & Financial Turnaround 12:00 - Telling The Company (Nine Months Notice) 13:21 - Moving To Arizona & Missing People 15:05 - First 2½ Years: Music, Acting & New Hobbies 20:11 - Travel Freedom & Open-Ended Trips 22:10 - Spending, Social Security Plans & HSA 23:52 - Health Routine: 70lb Loss & VR Cardio 30:01 - Key Moment: Being There For His Mom 35:31 - Advice For Future Retirees / Final Thoughts _ _ Steve is not a client of Root Financial Partners, LLC and received no compensation for participating in this video. His statements reflect his own opinions and experience and are not indicative of any specific client’s experience and are not a guarantee of results. No cash or non-cash compensation was provided, and no material conflicts are known. 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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