How to Have End-of-Life Conversations with the People You Love | E185 Tess Waresmith

Talking about end-of-life planning is one of the hardest conversations we’ll ever have, but also one of the most important. Whether you’re pursuing financial independence or already work-optional, someone in your life will eventually rely on you to make decisions on their behalf. And without clarity, that responsibility becomes emotionally heavy, financially stressful, and often filled with guesswork.

In this episode, Financial Educator Tess Waresmith (Wealth With Tess) walks us through how to approach these conversations with compassion and confidence. Tess has navigated caregiving and loss firsthand, including the passing of her stepfather and aunt. She brings a personal and practical approach to preparing families for the future.

You’ll learn how to make these conversations feel less overwhelming, how to use Tess’s 3-Layer Talk Framework to guide your discussion, and which estate-planning essentials every FI-minded person should have squared away. More than anything, this episode will help you strengthen connections, reduce uncertainty, and create peace of mind for yourself and the people you love.

Key Takeaways:

• How to start end-of-life conversations in a way that feels natural, not heavy
• The 3-Layer Talk Framework for discussing logistics, values, and legacy
• Essential estate-planning documents every family needs (Will, POA, Healthcare Directive)
• Questions that help uncover a loved one’s hopes, fears, stories, and wishes
• Why acknowledging mortality can lead to more intentional spending, saving, and FI planning

Other Episodes You’ll Love:

3 Hidden Traps That Make FIRE Feel Empty | E182 Jordan Grumet

How to Negotiate Your Medical Bills | E161 Dr. Virgie Bright Ellington

Does My FIRE Number Account for Inflation? | E140 Jesse Cramer

Guest Summary:

Tess Waresmith is a financial educator, speaker, and the creator of Wealth With Tess, where she teaches women how to build confidence with money and investing. Through her workshops, courses, and content, she shares clear, compassionate financial guidance to help women reduce stress and prioritize what truly matters.

Instagram: https://www.instagram.com/wealthwithtess/

Talking About Death: https://www.moneyconfidentclub.com/talkdeath

Deathly Yours Workbook ($60 off with code FIMINDED):

https://www.moneyconfidentclub.com/offers/BkfzyzKV?coupon_code=FIMINDED

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