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

Childfree Life by Design

Childfree Life by Design
The "Die With Zero" Dilemma: Can Don Learn to Spend?, Ep 167
Dec 03, 2025
Dr. Jay Zigmont, CFPĀ® & 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.

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

šŸ”¹ 3:15 Gifting to nieces: Monetary gifts without preconceived notions

šŸ”¹ 4:40 Exploring 529 plans vs. Roth for a grandniece's college fund

šŸ”¹ 8:44 Don's significant philanthropic goals: $100,000 to Tunnel to Towers

šŸ”¹ 12:07 Navigating healthcare: HSAs, high-deductible plans, and the VA

šŸ”¹ 17:40 The mental challenge of spending after years of saving

šŸ”¹ 20:35 Optimizing investments: HSA in stock, international exposure, and ditching high fees

šŸ”¹ 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

- Essential Retirement Planning for Solo Agers by Sara Zeff Geber, PhD

- Living the Golden Life: Solo Aging Strategies with Dr. Sara Zeff Geber, Ep 130 https://www.buzzsprout.com/2002436/episodes/16368024 

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