The "Die With Zero" Dilemma: Can Don Learn to Spend?, Ep 167 Artwork

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.

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Childfree Life by Design

The "Die With Zero" Dilemma: Can Don Learn to Spend?, Ep 167

December 03, 2025 • Dr. Jay Zigmont, CFP® & Bri Conn

Join us for a fascinating conversation with Don, a disciplined saver who's embracing the "Die With Zero" philosophy but finding it hard to shift gears! We dive into his journey of planning generous gifts to family and charities now, rather than later, and the mental gymnastics required to actually spend the money he's so diligently saved. We also tackle the nitty-gritty of optimizing investments, navigating healthcare, and the unique estate planning considerations for those who are Childfree. Get ready for some honest talk, a few laughs, and actionable insights on truly living your best life with your wealth.

🔹 1:35 Identifying key recipients: Veteran's causes, St. Jude's, and nieces

🔹 3:15 Gifting to nieces: Monetary gifts without preconceived notions

🔹 4:40 Exploring 529 plans vs. Roth for a grandniece's college fund

🔹 8:44 Don's significant philanthropic goals: $100,000 to Tunnel to Towers

🔹 12:07 Navigating healthcare: HSAs, high-deductible plans, and the VA

🔹 17:40 The mental challenge of spending after years of saving

🔹 20:35 Optimizing investments: HSA in stock, international exposure, and ditching high fees

🔹 37:43 Estate planning for solo agers: Trustees, power of attorney, and avoiding single points of failure

Mentioned in this Episode:

- Die with Zero by Bill Perkins https://bookshop.org/p/books/die-with-zero-getting-all-you-can-from-your-money-and-your-life-bill-perkins/15130122

- NokBox

- The Purpose Code by Jordan Grummet, MD