Childfree Life by Design
Childfree Life by Design is a podcast for people who are Childfree or permanently childless and thinking seriously about money, legacy, and what comes next. It tackles financial planning, estate planning, and life decisions for adults building a future without children and without a default script to follow.
Hosted by experts in financial and life planning, the show cuts through outdated assumptions about family, retirement, and aging. Conversations focus on utilizing wealth, solo aging, long-term care, relationships, and how to plan with clarity when you don’t have kids.
This isn’t about justifying your choices or debating labels. It’s about practical guidance for planning life without children making smart financial decisions, defining legacy on your own terms, and building support systems that actually work.
If you’re Childfree, childless, or planning without kids and want thoughtful, trusted education, this is where those conversations happen.
Disclosure: This podcast is for educational and entertainment purposes only. Please consult your professional advisors before implementing any ideas discussed. For full disclosures, visit Childfreewealth.com.
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.com/in/codylgarrett/
