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.

Ever feel like the traditional "work for 40 years, then retire" plan just isn't cutting it anymore? You're not alone! This week we're flipping the script with Jillian Johnsrud, author of Retire Often. We dive deep into the concept of "mini-retirements" – intentional breaks from your primary profession that are a month or longer and focused on something meaningful to you.

Jillian shares how these strategic breaks aren't just about vacations; they can actually boost your financial independence and career trajectory in surprising ways! We tackle everything from negotiating time off with your current employer (even if you think you're "too important"!) to navigating those well-meaning but often unhelpful opinions from friends and family. Get ready to challenge your assumptions about work, rest, and living your best life, now!

Timestamps:

• 0:48 Why Jillian wrote Retire Often and the life-changing potential of mini-retirements
• 1:42 Challenging the old life script: Why the 25-year grind to retirement might be outdated
• 2:07 The evolving economy and why frequent career breaks are becoming the new norm
• 3:00 What exactly is a mini-retirement? Defining the key elements
• 5:49 Unpacking the financial benefits: How taking time off can actually make you richer
• 8:57 The power of pausing: Gaining clarity and new opportunities by stepping off the treadmill
• 11:25 Keeping your job and taking a break: Negotiating a mini-retirement with your current employer
• 17:00 Tackling societal pressures and internal narratives around work and rest
• 25:07 Budgeting for your break: You don't need millions to take a mini-retirement

Connect with Jillian

• Website
• Retire Often Book
• Book Purchasing Link
• Free Opt-In Worksheets:
  • Planning
  • Negotiating
• Workbook
• Group Coaching
• Social Media:
  • Instagram
  • Twitter
  • LinkedIn
  • Youtube

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.

Are you tired of the traditional work-and-retire-at-65 plan? This episode is for you. We're diving into the concepts of FIRE (Financial Independence, Retire Early) and FILE (Financial Independence, Live Early), and exploring how you can break free from the traditional script. Dr. Jay and Bri challenge the idea that retirement is an "on/off switch" and introduce the "dimmer switch" approach of FILE, which allows you to design a life you love now, rather than waiting for a distant retirement.

Timestamps

🔹 0:48 - When can I retire vs. do you want to retire?

🔹 2:28 - Are you a FIRE or FILE person?

🔹 3:33 - Dr. Jay's "mental chew toy"

🔹 5:39 - The importance of planning for what you’ll do with your time

🔹 6:40 - The "Purpose Code" and living with lowercase "p" purpose

🔹 11:53 - The difficulty of giving up a specific career path

🔹 14:49 - Overcoming self-limiting beliefs

🔹 15:49 - Why age is the least important factor in retirement

🔹 18:24 - The debate: Are you ready to make a change?

🔹 19:13 - What brings you joy?

🔹 25:23 - Accessing your retirement money before 59½

🔹 28:37 - The rule of 55

🔹 32:17 - The rule of 72t, or SEPP

🔹 34:05 - Accessing Roth IRA contributions penalty-free

🔹 35:48 - Inherited IRAs

🔹 37:53 - 401k loans: The good, the bad, and the ugly

🔹 45:36 - Health insurance options for early retirees

Mentioned in this episode:

🔹 Andy & Libbi Financial Planning Sessions

1️⃣ https://www.buzzsprout.com/2002436/episodes/16367564

2️⃣ https://www.buzzsprout.com/2002436/episodes/16367713

3️⃣ https://www.buzzsprout.com/2002436/episodes/16368047

4️⃣ https://www.buzzsprout.com/2002436/episodes/16962286

5️⃣ https://www.buzzsprout.com/2002436/episodes/17411168

🔹 Finding Purpose Beyond Financial Independence with Doc G, Ep 120 https://www.buzzsprout.com/2002436/episodes/16367437

🔹 The Purpose Code by Jordan Grummet, MD https://jordangrumet.com/books/

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.

As the year comes to a close, it’s time to pause, review, and make sure your finances are in shape for what’s next. In this episode, Dr. Jay and Childfree Wealth Specialist® Scott Barnes walk through their 2025 Year-End Financial Checklist - covering everything from tax strategies and RMDs to Medicare IRMA surcharges, spending analysis, and estate planning for Childfree individuals.

They discuss what’s changed this year, what you need to know before the calendar resets, and how to make smart financial decisions that align with your goals and values.

From avoiding penalties to ensuring your estate plan reflects your wishes (including care for your pets), this conversation is packed with practical insights to help you end the year confident and prepared.

Tune in for clear guidance, actionable steps, and a reminder that financial planning isn’t just about saving money—it’s about designing a life that truly fits you.

We’ll cover:

00:00 — End-of-Year Financial Planning Overview
04:12 — Tax Strategies That Still Work (and What’s New)
09:45 — RMDs, IRMA Surcharges & Medicare Must-Knows
15:30 — Spending Analysis: Does Your Money Reflect Your Values?
22:18 — Estate Planning for the Childfree: Protecting Your Legacy

Mentioned in this episode:

- Get the Childfree Wealth®'s 2025 Childfree Tax Guide: https://childfreewealth.com/2025-childfree-tax-guide/

- Childfree Trust® Website: https://childfreetrust.com/

- Childfree Wealth® Checkup: https://childfreewealth.com/schedule-a-checkup/

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 fantasized about moving abroad or traveling the world while working? This episode is your permission slip to start! Join us as we talk with two incredible women living their best expat and digital nomad lives.

First, we chat with Maggie Dickens, founder of Unapologetically Childfree, who shares her inspiring journey as a therapist and business owner in Lisbon, Portugal. She gives us the real scoop on what it's like to transition to a new country and why living authentically is the key to a fulfilling life.

Then, we dive into the fascinating world of full-time digital nomad Sibu Szymanowska, who has perfected the art of house-sitting to see the world. As the founder of The Hybrid Tours, she shares her best tips on traveling the globe on a budget and how to find a community no matter where you are. Get ready to have your wanderlust sparked and learn that a life of travel doesn't have to break the bank.

Key Points:

🔹Introduction to the episode and Maggie

🔹Maggie's decision to move to Portugal

🔹The logistics of being a business owner while abroad

🔹Maggie's advice for those considering a move

🔹Sibu's introduction and her life as a full-time digital nomad

🔹The magic of house-sitting

🔹The story behind The Hybrid Tours

🔹Why traveling won't ruin your career

Connect with Maggie Dickens:

- Cathartic Counseling | Unapologetically Childfree™️

- Hello@MaggieDickens.com

- Instagram

- Facebook

- TikTok

- Find Group Coaching here or here.

- Book a FREE Consult here.

Connect with Sibu Szymanowska:

- The Hybrid Tours

- Go Global with Sibu

- Hey@GoGlobalWithSibu.com

- Instagram

- LinkedIn

- Find Free Accommodation through Trusted Housesitters here.

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.

Join us for a transparent and insightful Childfree Wealth® Checkup with Casey and Garrett, a couple who are preparing to trade in the corporate grind for time abroad. We dive deep into the unique financial fears and planning complexities of a childfree couple in their late 20s and early 30s with a solid net worth.

🔹0:15 What Casey and Garrett want to make sure they talk about in their financial checkup

🔹2:30 Why chasing a child-free financial plan means ditching your parents' and the "standard life script" advice

🔹8:45 Garrett's tax questions, specifically around Roth IRAs and future income clarity

🔹12:10 Casey's goal to live abroad in the next 10–15 years, seeking universal healthcare and residency status, and the emotional struggle between taking the leap and feeling secure

🔹18:55 The reality of remote work and digital nomad visas: why their current jobs won't allow it, and the potential to keep their US residency while wandering the world

🔹24:00 The "social pressures" roadblock: trying to time their big move around family milestones and friends' weddings (the "wedding-baby shower era")

🔹31:30 Breaking down their current spending ($150k in 2024, inflated by a wedding) and the realization that their money isn't always aligning with their values—especially the $30k of "stuff"

🔹38:15 Challenging the FIRE community's "scrimping" mindset and the fear of "mindlessly saving" when they already have a $450,000 net worth

🔹45:00 The goal: having a remote job by 2027, spending $50,000 for the entire move, and being living their best life in another country by 2028

🔹51:45 Actionable steps now: maxing out their Roth 401(k)s before worrying about the complexity of Roth IRAs

Mentioned in this episode:

🔹Andy & Libbi planning series - watch the full series here!

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.