THE ROTH GUY

Money Questions That Aren’t Really About Money
September 24, 2026

Talking about money can be hard for some people, and sometimes it just takes the right question to get things rolling. Jude goes over a few today that he thinks are worth asking. None of these questions are really about money. That’s kind of the point. Sometimes the best way into a financial conversation is to start somewhere else entirely.

📌 Here’s some of what we discuss in this episode:

🏔️ Financial Freedom: Moving from accumulating wealth to using money to buy back your time

🎯 Your Why: Putting purpose at the center of your wealth once you reach retirement

💭 Dream Sessions: Using thought-provoking questions to uncover what really matters

❤️ Retire to Something: Finding passions, experiences, and meaningful work beyond your career

🪣 Bucket List: Prioritizing experiences based on timing, health, and mobility

🧠 Financial Psychology: Why shifting from saving to spending can be one of retirement’s hardest transitions

0:00 – Intro

0:43 – Financial Life Phases

1:43 – Putting the “Why” in Wealth

4:08 – If Jude Was a Genie…

6:10 – Retiring to Something

7:53 – Looking Back at Financial Decisions

9:47 – Prioritizing the Bucket List

12:19 – Psychology of Spending After Saving

13:24 – Reach out to Jude

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5 Worlds of Holistic Financial Planning Document

Episode Transcript

Note: This transcript was produced using AI, so please excuse any typos and inaccuracies…

Marc Killian  00:00

All right, Jude. This week on the Roth Guy, we’re going to come at this from a different angle. We’re going to talk about money questions that aren’t really about money. So I’ve got some different ways here to phrase some questions that you guys probably already phrased to to clients or potential clients. We’ll have a little fun with this. It’s a different take on how to, you know, just kind of think about the I guess the esoteric and the philosophical questions of retirement.

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