The Biggest Money Mistake Is Not What You Think | Bill Perkins

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Dec 13, 2025

In this enlightening discussion, guest Bill Perkins, an entrepreneur and investor known for his unique perspective on risk, emphasizes a shocking truth: fearing financial loss often overshadows the danger of wasting life. He paints life as a series of ‘buckets’ filled with unique experiences that can only be savored once. Drawn from a poignant moment in St. Petersburg, Perkins warns of the physical limitations that come with age and urges listeners to prioritize meaningful adventures while they still can, likening it to sorting experiences in a Tetris game.

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INSIGHT

Fear Of Money Over Life

People fear running out of money more than they fear wasting their life.
Bill Perkins argues this reverses priorities and leads to missed life‑specific experiences.

ADVICE

Prioritize Experiences By Life Stage

Order your life experiences so you can do physically and emotionally demanding things when you can.
Prioritize buckets like your 20s or parenting years instead of postponing them for later savings.

ADVICE

Use Money When It Works Best

Recognize life as a sequence where timing matters and plan experiences accordingly.
Use money when it best enables the experience, not just when it accumulates.

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Check out the full episode: https://greatness.lnk.to/1529

"I think the biggest psychological crime is people fear running outta money instead of fear of wasting their life." - Bill Perkins

Bill Perkins watched busloads of senior citizens arrive in St. Petersburg, Russia. Not a single person climbed the 115 steps to see the breathtaking view from the church balcony. They had the money for the trip, the time to travel, but their bodies wouldn't cooperate anymore. That moment crystallized everything he'd been thinking about how we get life backwards. We treat money like it's the goal when it's actually just a tool, one that loses effectiveness as our bodies and minds decline. Your body peaks at 33. After that, it's plateau and decline. Those hiking trips, those physical adventures, those experiences that require energy and health—they have expiration dates we refuse to acknowledge. We tell ourselves we'll do them later, when we're more financially secure, but later means weaker knees, less stamina, different limitations.

Perkins talks about life in buckets, periods you'll never get back. Your twenties happen once. The years with small children happen once. Each phase has experiences designed for it, and if you miss them, they interfere with each other or disappear entirely. He uses a Tetris metaphor: imagine standing in heaven with God, throwing every experience you want into a bucket. Hiking, building businesses, raising kids, traveling to places that require climbing, all of it. God says you can have everything, you just have to get the order right. That's the game. That's what most people get catastrophically wrong. They're so afraid of judgment, so terrified of running out of money that they waste the periods of life when those experiences would mean the most, when their bodies could actually do them. This isn't about reckless spending. It's about understanding that your ability to convert money into fulfilling experiences decays over time, and no amount of savings can buy back the body you had at 33.

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