Why Retirees Are Flocking To This One Special Community | Retirement Reality

Ari Taublieb, CFP® November 28, 2025
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Ari Taublieb, CFP®

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About

I help people retire before 65 (without worry). I’m Ari Taublieb, CFP® — Chief Growth Officer at Root Financial Partners and host of the Early Retirement Podcast. 📧 Reach out at [email protected] 👇 And don’t forget to hit SUBSCRIBE so you never miss a video! Root Financial Partners, LLC (“Root”) is a Registered Investment Adviser. Content may include topics related to tax and estate planning but should not be considered tax or legal advice. This material is for informational purposes only and not personalized advice. Always consult your CPA, attorney, or financial planner before making financial decisions.

Video Description

After years of research searching for the perfect retirement community, Judy found Woodside. She visited the Villages, Del Webb, and so many others that she found didn’t fit what she was looking for - other active retirees of similar age. Now she’s IN LOVE with retirement and shared her entire story with me on my show, Retirement Reality. This NOT a paid advertisement. If you wish to reach out for a Discovery tour of Woodside, you can email David directly at [email protected] and if you let him know you found him through my channel, he’ll make sure to treat you well! I’m flying from Los Angeles to Aiken, South Carolina to visit the Woodside community next month myself to do a full review of the community (similar to a restaurant review, but for retirement communities)! Is there a retirement community you’re excited to go to? If so, let me know in the comments and I’ll add them to my list of communities to review! For Judy, early retirement comes down to one word: choices. At 57, two years into life after work, she wakes up with the freedom to choose slow mornings, long walks, golf leagues, pickleball lessons, and spontaneous trips. Her plan was always early retirement at 55, and she never lost sight of it... even when fear, routine, and the temptation of “one more year” crept in. She shares how she built her “superhero account,” prepared for healthcare, learned to balance enjoying today with planning for tomorrow, and embraced the courage to leave a career she liked for a life she loves. Want to be a guest on THIS show and help others by sharing your story? Complete this: https://vwo3759x8i7.typeform.com/to/gh00JmnZ Interested in a custom strategy to retire early? → https://www.rootfinancial.com/start-here/ Get access to the same software I use in my videos and join the Early Retirement Academy here → https://ari-taublieb.mykajabi.com/early-retirement-academy –––––––––––––––––––––––––––––– Time Stamp 00:00 - Introduction 00:47 - About the Show & Guest Invitation 01:12 - Meet Judy — The Poster Child For Early Retirement 02:07 - Why Judy Retired at 55 05:00 - The Two-Year Tour of Retirement Communities 06:29 - Choosing the Right Retirement Community 09:11 - How Financial Planning Influenced the Move 10:00 - Was It Hard to Retire Logistically? 13:02 - Why Judy Wanted to Retire Early 14:49 - Life Isn’t Guaranteed — The Motivation to Retire 19:20 - A Day in the Life of a Retiree 24:50 - How Retirement Changed Judy 27:59 - Monthly Expenses & Spending Philosophy 33:05 - Avoiding “One More Year” Syndrome 41:22 - Judy’s Advice for Future Retirees 45:16 - Closing Thoughts 45:23 - Working With Root –––––––––––––––––––––––––––––– PODCAST - https://earlyretirementpodcast.com/ INSTAGRAM - https://www.instagram.com/earlyretirementari/ LINKEDIN - https://www.linkedin.com/in/aritaublieb/ What video topic would you like to see discussed in a future video? Ari Taublieb, CFP®, MBA, is the Chief Growth Officer of Root Financial Partners and host of the Early Retirement Podcast. –––––––––––––––––––––––––––––– 📣 Are you taking advantage of tax planning before 2026? Most people hoping to retire early know they're leaving money on the table but don't know how to fix it. 👉 Subscribe to our channel and press the bell icon. ––––––––––––––––––––––––––––– Darren 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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