The Hardest Year of Retirement: What No One Warned Me About | Retirement Reality

James Conole, CFP® December 18, 2025
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James Conole, CFP®

@rootfp

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

Retirement doesn’t always arrive on your schedule. Sometimes it shows up early, uninvited, and forces you to rethink everything you thought you knew. For Jim, that moment came at 5, four years before the retirement date he’d carefully planned for. One unexpected layoff, and suddenly the identity he’d built over decades in big tech was shaking underneath him. In this episode of Retirement Reality, James shares the stress, the fear, and the sense of disorientation that came with having the rug pulled out from under him… and the surprising clarity that followed once the dust settled. What started as panic slowly revealed itself as a turning point — a chance to reexamine what he really wanted from his next chapter, not just what he thought he should do. He opens up about reevaluating his timeline, rebuilding confidence, and discovering that being forced off the treadmill early didn’t break his plan, it accelerated it. The layoff he once dreaded became the sharpening moment he didn’t know he needed. As you listen, consider this: Sometimes the moments you fear most end up freeing you the most. 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: Four-Year Review 01:18 - Meet The Guest: Jim 01:31 - Career: Software Engineer 02:00 - One Word: Challenging 03:22 - Financial Readiness & Numbers 06:03 - Volunteering & Office Skills 09:02 - Retirement As A New Chapter 12:00 - Hardest Emotions: Purpose Loss 14:29 - Yearly Breakdown: Years 1–4 16:16 - Thrive: Not A Death Sentence 17:18 - Writing Journey Begins 20:10 - Publishing, Business & Learning 28:59 - Community, Social Life & Turning Point 35:11 - Advice For Future Retirees _ _ Jim 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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