Childfree Life by Design Tax Planning To and Through Early Retirement with Cody Garrett, CFP®, Ep 166
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.
About Childfree Life by Design:
Childfree Life By Design is dedicated to helping Childfree individuals thrive by providing resources, guidance, and community. We recognize that when you've made a decision roughly 75% of the population doesn't make, conventional wisdom simply doesn't apply to you. Our mission is to help you design a life that works for you, covering everything from finances and relationships to career decisions and building support networks that will actually be there when you need them.
Connect with Us:
Ready to design your ideal Childfree life? Connect with our financial planning team at childfreewealth.com or learn more about estate planning at childfreetrust.com
Join the conversation on social media:
Instagram: https://www.instagram.com/childfreeinsights
Facebook: https://www.facebook.com/ChildfreeInsights/
LinkedIn: https://www.linkedin.com/company/childfreeinsights
YouTube: https://www.youtube.com/@ChildfreeInsights
Disclaimer: This podcast is for educational & entertainment purposes. Please consult your advisor before implementing any ideas heard on this podcast...