What does it really take to plan your taxes to - and through - early retirement?

In this week's episode, Dr. Jay sits down with Certified Financial Planner® and author Cody Garrett to unpack the key ideas from Cody’s new book, Measure Twice, Money Once. Together, they explore how intentional tax planning can turn early retirement from a financial dream into a sustainable reality.

From understanding how tax brackets shift when your income changes, to strategically timing Roth conversions and managing healthcare costs before Medicare — they cover it all. You’ll also hear practical, values-based advice on aligning your tax and income strategies with the kind of life you actually want to live.

Whether you’re five years from early retirement or already there, this conversation will help you create a tax strategy designed for freedom, flexibility, and purpose.

We'll Cover:
00:00 — Welcome and why early retirement tax planning matters
04:32 — The three stages of tax planning: before, during, and after retirement
10:48 — Roth conversions: when they make sense (and when they don’t)
18:25 — Managing healthcare costs before Medicare eligibility
27:10 — Building a tax-efficient income plan for the long run

Mentioned in this Episode:
- Get Cody's book here: https://www.measuretwicemoney.com/book
- Get Dr. Jay's book "The Childfree Guide to Life and Money" here: https://childfreewealth.com/childfree-guide/
- Learn more about Childfree financial www.childfreewealth.com
- Learn more about Childfree Trust: https://www.childfreetrust.com

About our Guest: Cody Garrett is an advice-only financial planner, educator, and founder of Measure Twice® Money, where he helps DIY investors make informed financial decisions aligned with their values. He also leads Measure Twice(R) Planners, an educational community for financial planners. Cody's insights have been featured by The Wall Street Journal, Barron's, Forbes, and CNBC. He's a frequent guest on personal finance podcasts, including ChooseFI, The Long View (Morningstar), and Bogleheads on Investing.

Connect with Cody here: https://www.linkedin.com/in/codylgarrett/

The Childfree Wealth Podcast, hosted by Bri Conn, CFP®, and Dr. Jay Zigmont, CFP®, is a financial and lifestyle podcast that explores the unique perspectives and concerns of Childfree individuals and couples.

Like the show? Leave us a rating & review!

If you want to join the conversation, email us at media@childfreewealth.com, follow Childfree Wealth® on social media, or visit our website www.childfreewealth.com!

Join our newsletter HERE.
Schedule a meeting with a Childfree Wealth Specialist® HERE.

Instagram: @childfreewealth

Facebook: @childfreewealth

LinkedIn: @childfree-wealth

YouTube: @ChildfreeWealthPodcast

Disclaimer: This podcast is for educational & entertainment purposes. Please consult your advisor before implementing any ideas heard on this podcast.

Ever wonder if you truly have enough to retire, or if your long-term plans are actually achievable? This week, we dive deep with Claudia, a bright, resourceful, and wonderfully human individual who, despite a significant net worth, finds herself grappling with the emotional side of financial independence. We tackle her core question: should 60% of her portfolio be in fixed index annuities? But as always, we dig beyond the numbers to uncover the real questions: What life does she truly want to live, and what's holding her back from embracing it?

🔹1:05: Navigating market fluctuations and the unexpected shifts in retirement timelines (including a cancer diagnosis that changed everything).

🔹3:16: Unpacking Claudia's dream retirement in Arkansas, from free university courses to attending sports games.

🔹8:50: The surprisingly emotional struggle with leaving a high-paying job, even when you're financially ready.

🔹10:47: A jaw-dropping revelation about Claudia's net worth and the incredible possibilities it unlocks.

🔹18:51: The complexities of estate planning for childfree individuals, including supporting loved ones without enabling poor financial habits.

🔹36:14: The profound mental shift from "can I retire?" to "what do I want to do in retirement?"

🔹49:00: Exploring "encore careers" and how meaningful part-time work can enhance your retirement joy (and budget!).

🔹53:45: The unique challenges and solutions for "solo agers" and ensuring your wishes are honored, chips and all.

This episode is a must-listen for anyone navigating retirement decisions, seeking financial clarity, or simply trying to align their money with their ideal life. You'll hear how the "math is the easy part" and why understanding your "head trash" is crucial to unlocking true financial freedom.

Mentioned in this Episode:

- Childfree Trust®

- The Childfree Guide to Life & Money by Dr. Jay Zigmont, CFP®

The Childfree Wealth Podcast, hosted by Bri Conn, CFP®, and Dr. Jay Zigmont, CFP®, is a financial and lifestyle podcast that explores the unique perspectives and concerns of Childfree individuals and couples.

Like the show? Leave us a rating & review!

If you want to join the conversation, email us at media@childfreewealth.com, follow Childfree Wealth® on social media, or visit our website www.childfreewealth.com!

Join our newsletter HERE.
Schedule a meeting with a Childfree Wealth Specialist® HERE.

Instagram: @childfreewealth

Facebook: @childfreewealth

LinkedIn: @childfree-wealth

YouTube: @ChildfreeWealthPodcast

Disclaimer: This podcast is for educational & entertainment purposes. Please consult your advisor before implementing any ideas heard on this podcast.

Today, Bri Conn, CFP® and Dr. Jay, CFP® dig into what it really means to retire as a Childfree person—and why it might not look like what you’ve been told. Whether you're dreaming of beaches or terrified of boredom, this episode helps you get real about what comes after work.

🔹 00:40 – When retirement chooses you
🔹 02:00 – Why retiring to something matters more than retiring from something
🔹 04:00 – Test-driving retirement before you commit
🔹 06:15 – The “Retirement Smile” and how spending changes over time
🔹 10:00 – Why the 4% rule might not apply to you
🔹 14:30 – Taxes, RMDs, and IRMA—oh my!
🔹 18:45 – How to plan for retirement abroad without tax surprises
🔹 23:30 – Why most people could’ve retired earlier (but didn’t)

Whether you’re a “never work again” dreamer or just want to know your options, this is your sign to make a plan before life forces your hand.

Mentioned in this episode:

🔹Navigating Your "Second Half of Life": FIRE vs. FILE and Accessing Your Money Early, Ep 162 https://www.buzzsprout.com/2002436/episodes/17816731

The Childfree Wealth Podcast, hosted by Bri Conn, CFP®, and Dr. Jay Zigmont, CFP®, is a financial and lifestyle podcast that explores the unique perspectives and concerns of Childfree individuals and couples.

Like the show? Leave us a rating & review!

If you want to join the conversation, email us at media@childfreewealth.com, follow Childfree Wealth® on social media, or visit our website www.childfreewealth.com!

Join our newsletter HERE.
Schedule a meeting with a Childfree Wealth Specialist® HERE.

Instagram: @childfreewealth

Facebook: @childfreewealth

LinkedIn: @childfree-wealth

YouTube: @ChildfreeWealthPodcast

Disclaimer: This podcast is for educational & entertainment purposes. Please consult your advisor before implementing any ideas heard on this podcast.