Episode 185

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Published on:

17th Dec 2025

End-of-Life & Estate Planning With Your Parents (In A Compassionate Way) | 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


Connect With Justin

Email me at Justin@FIMinded.com or connect with me on LinkedIn.


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About the Podcast

FI Minded - Financial Independence, Early Retirement & Lifestyle Design
Achieve Financial Independence & Have Fun Doing It
Pursuing financial independence, financial freedom, or early retirement often leads to the same questions: How do I become financially independent? How much should I save? What happens after I reach FI?

FI Minded helps you use money to create more freedom, without turning your entire life into a financial optimization project.

Host Justin Peters explores the decisions behind building a flexible, work-optional life, from reaching financial independence and navigating Coast FI and Slow FI to spending your money, changing careers, stepping away from work, and figuring out what comes after FI.

Each episode combines practical personal finance with conversations about early retirement, lifestyle design, work, spending, healthcare, self-employment, and life after financial independence. The goal isn't simply to reach FI as quickly as possible. It's to make progress toward financial freedom while actually enjoying your life along the way.

On FI Minded, you'll learn how to:
- Reach financial independence without burning out
- Build a flexible, work-optional lifestyle
- Navigate Coast FI, Slow FI, and other paths to FI
- Make smarter decisions about spending and saving
- Prepare financially and emotionally for early retirement
- Figure out what life can look like after financial independence
- Think through the tradeoffs behind major money and lifestyle decisions
- Make progress toward financial independence while actually living your life.

Some of our past guests include Carl Jensen (1500 Days), Jeremy Schneider (Personal Finance Club), Nick Loper (Side Hustle Show), Andrew Giancola (The Personal Finance Podcast), Jordan Grumet (Earn & Invest), Rachael Camp (Work Optional), Jillian Johnsrud (Retire Often), Sean Mullaney (FI Tax Guy), Jill Sirianni (Frugal Friends), Jackie Cummings-Koski (Catching Up to FI), Joel Larsgaard (How to Money), Cody Garrett (Measure Twice), Jesse Cramer (Personal Finance for Long-Term Investors), Jess (The Fioneers), Chris Hutchins (All The Hacks), Diania Merriam (EconoMe), Andy Hill (Marriage Kids Money), Fritz Gilbert (Retirement Manifesto), Maggie Tucker (Inside Out Money), Cody Berman (The Financial Independence Show), Joe Saul-Sehy (Stacking Benjamins), Doug Cunnington (Mile High FI), and and others helping you rethink how to approach financial independence.
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