Early Retirement - Financial Freedom (Investing, Tax Planning, Retirement Strategy, Personal Finance)

David’s story feels familiar to a lot of people in their late fifties and early sixties. After a long career in asset management, a role change and pandemic burnout became the nudge he didn’t know he needed. At sixty, he finally decided to stop working not because he had to, but because he could.

He describes retirement in one word: possibility. Time with friends, hikes during the week, early dinners without rushing, and yes, plenty of pickleball. The new rhythm isn’t about adding more activities. It’s about having choice. He’s still curious, still learning, still pushing himself with new skills and fresh goals, just without the pressure to perform.

David also talks about what made the decision easy and what made it hard. Leaving a good job wasn’t simple. Letting go of structure took practice. But he found freedom in quiet mornings, long walks, and realizing he didn’t need a title to feel fulfilled.

The conversation turns to money, too. The reality of how decades of steady saving built flexibility, how modest spending supports a rich life, and how “enough” means something different now. He’s planning thoughtfully for Social Security, Roth conversions, and even legacy for his daughters, while still reminding himself to enjoy the present.

If you’re in your fifties or sixties wondering what’s next, this episode is for you. You’ll hear how stepping away from work can open new space to live, learn, and move at your own pace. Sometimes the next chapter isn’t about doing more. It’s about finally breathing.

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

Want to be a guest on THIS show and help others by sharing your story? Complete this: https://vwo3759x8i7.typeform.com/to/gh00JmnZ
--

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.

Slava shares how he retired early and his whole journey to get there. Enjoy.

Want to be a guest? → https://vwo3759x8i7.typeform.com/to/gh00JmnZ
–––––––––––––––––––––––––––––
The statements provided are from individuals who are not clients of Root Financial Partners, LLC. These individuals were not compensated for their comments, and their views do not necessarily reflect those of Root Financial Partners, LLC. The information shared is for informational purposes only and should not be considered a recommendation or testimonial regarding advisory services.

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.

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 
–––––––––––––––––––––––––––––
Judy is not a client of Root Financial Partners, LLC and received no compensation for participating in this video. Her statements reflect her 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 offere
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.

Ex-silicon valley guest turned Scuba Diver shares the truth behind retiring early!

Hope you enjoy the insights shared!

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
–––––––––––––––––––––––––––––
Suzi 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.
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.

Hiring a financial advisor isn’t about credentials alone, it’s about timing. And for many people, getting that timing wrong can cost years of freedom.
Ari explores when it doesn’t make sense to hire a financial advisor, when it absolutely does, and why the decision often has less to do with intelligence or interest in finances and more to do with stress, life stage, and opportunity cost. Drawing from personal experience, real client conversations, and a story from his own life, Ari explains why pushing back, asking questions, and trusting your instincts matter just as much as spreadsheets and projections. 

The discussion reframes financial advice away from credentials and rules of thumb and toward partnership, value, and peace of mind. Some people genuinely enjoy managing their own finances and are well-equipped to do so — until complexity, time constraints, or major transitions enter the picture. Others reach a point where the cost of doing everything themselves quietly becomes higher than the cost of professional help. 

Rather than offering a one-size-fits-all answer, Ari breaks down the signals that matter most: losing sleep, worrying about missed opportunities, navigating retirement timing, tax strategy, healthcare decisions, or coordinating finances with a spouse. The goal isn’t to convince anyone to hire an advisor — it’s to help people make the decision intentionally, with clarity and confidence. 

This conversation is for anyone who has ever wondered whether they’re doing just fine on their own, or whether having the right partner could help them work less, worry less, and live more.
-
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.