This solo episode with host Travis Chappell dives into his “25 questions to ask yourself to live a better life,” focusing on five powerful prompts that can reshape your habits, relationships, and financial trajectory. Travis shares personal examples from health, marriage, and money to illustrate how better questions lead to better decisions and, ultimately, a more intentional and prosperous life.

On this episode we talk about:

What your 90-year-old self would tell you to cut out of your life immediately
How the five people you spend the most time with shape your future success and income
The power of hard conversations in marriages, friendships, and business
Using a “repeat this day 365 times” audit to evaluate your habits and goals
Updating old stories you tell yourself about money, career, and what’s possible

Top 3 Takeaways

Your future self is a powerful filter: many habits you justify today (like skipping workouts or certain vices) have no place in the life you actually want, so cut them sooner rather than later.
You really are the average of the five people you’re around most; you don’t need to “dump” good friends, but you do need to intentionally add higher-level people into your life to grow.
Avoided hard conversations compound into years of low-level pain, while one uncomfortable but honest conversation can unlock healthier relationships, better culture, and more aligned results.

Notable Quotes

"The quality of your life is determined by the quality of the questions you ask."
"You can't hang out with high-level people and stay the same person—either you level up or you get pushed out of that group."
"Most of us are living a life limited by stories we never even thought to question."

Connect with Travis Shapell:

LinkedIn: https://www.linkedin.com/in/travischappell
Youtube: https://www.youtube.com/@travischappellclips
Instagram: https://www.instagram.com/travischappell
Other: https://travischappell.com

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SOLO | Make Money Asking Yourself Better Questions, part 4