Podcast Summary

ChooseFI Ep 567: "Are We Taking the Wrong Risks?" with Chris Hutchins

Released: October 6, 2025

Episode Overview

In this wide-ranging conversation, Brad Barrett welcomes Chris Hutchins (host of All the Hacks) to discuss risk-taking, financial independence (FI), and reconsidering the balance between saving and living meaningfully. Building off recent interviews (notably with Tim Ferriss, Tyler Gardner, and Bill Perkins), they tackle whether the FI community’s ultra-conservative saving approaches may be leading to missed opportunities in life, especially regarding time, memories, and experiences with loved ones.

Tone: Thoughtful, inquisitive, and candid. Both hosts share personal reflections and challenge prevailing FI “sacred cows,” making this episode highly relatable for anyone navigating the journey to FI.

Key Discussion Points & Insights

1. Are FI Practitioners Too Conservative With Their Risks?

• Conserving Money, Not Time:
  Both hosts reflect on the ingrained tendency of FI-minded people to “play it safe” — often at the cost of lost opportunities in other valuable, non-financial life areas.
• Opportunity Cost of Certainty:
  • "By looking for certainty, we are giving something up. There is an opportunity cost."
    — Brad Barrett (07:38)
    The drive for a 100% FI “success rate” actually means over-saving, over-working, and missing out on finite life experiences.

2. The 4% Rule: Risks vs. Realities

• Actual Outcomes vs. Expected Fears:
  Chris shares the insight from Tyler Gardner: the 4% rule (withdraw 4% of your portfolio annually in retirement) is extremely conservative — the median outcome is ending up with as much as 10x your starting pot, not running out of money.
  • "The median outcome is actually that that million [dollars] turns into like $10 million... we're optimizing for almost certainty that we don’t run out of money."
    — Chris Hutchins (03:42)
  • Aubrey Williams’ quote, relayed by Brad:
    "A 100% chance of success of your withdrawal is a 100% chance that you over-saved by definition." (06:06)

3. Volatility vs. Risk: Reframing the Issue

• Many people equate market volatility with risk, but not investing (i.e., only parking money in checking accounts) is often riskier in the long run: it guarantees loss of purchasing power and opportunity for growth.
  • "Which is truly riskier? ... It’s riskier to put it in a checking account in that scenario."
    — Brad Barrett (08:00)
• The Real Risk:
  Sacrificing precious years and memories just to nudge your portfolio’s safe withdrawal probability from 95% to 99%.
  • "...those years don’t come back. To give up two, three, five of them or more just to go from some crazy success rate chance to a marginally higher one — that seems crazy to me."
    — Brad Barrett (09:13)

4. Lifestyle Design & Family Time

• Seasonal Realities:
  Both reflect on kids growing up fast; time with children is front-loaded and fleeting.
  • Referencing Sahil Bloom and the “tail end” concept: by 18, you’ve spent 90% of your total time with your kids (16:05).
• A Practical Test:
  Chris and his wife routinely review their budget:
  • "If we cut 20% of the costs, and if we increase 20%, what would that look like?...The things we would increase are more valuable than the things we’d cut."
    — Chris Hutchins (18:25)
• Questioning Rituals:
  Encourage critical examination of family routines and “sacred cows” (e.g., always traveling for holidays), suggesting intentionality over tradition:
  • "What am I just doing as a matter of course? What if I did it differently?"
    — Brad Barrett (24:36)

5. Practical Guardrails & Adjustments

• Guardrails > Absolute Certainty:
  Aubrey Williams’ “guardrails” method: set withdrawal rates for a 90% success rate; if your portfolio drops, course-correct as needed (14:02).
  • "All of us can earn 5, 10, $20,000 pretty easily if we have to fill a gap." — Brad
• Regular Life Re-Evaluation:
  • Family meetings about what experiences truly matter; reallocate time/money away from what’s “just routine.”

6. The Value of Experiences & Social Connection

• Memorable Moments, Social Bonds:
  • Inspired by Tim Ferriss, Chris advocates pre-committing to trips and memorable events (“Monthly Memorables”) with friends and family, even if it’s just an escape room:
    "Every month, do something that makes that month memorable...We need more [of that]."
    — Chris Hutchins (31:06)
  • Chris’ story of his grandparents — organizing group travel in early retirement, enriching themselves and their community for decades (27:21).

7. Evolving Tactics: FI, Frugality, and Rewards

• From Extreme Frugality to Skillful Spending:
  • The importance of frugality at the start of the FI journey is acknowledged, but as you near FI, it’s more about spending on what lights you up.
  • "That skill of spending becomes a different skill altogether; now it’s spending money wisely, on things that you value, that light you up." — Brad Barrett (55:42)
• Travel Rewards and Points Game:
  • Chris and Brad discuss the evolution of credit card/points hacking, arguing the “game” is only worth it if you enjoy it and are willing to be flexible (especially with sign-up bonuses).
  • "If you don’t want to open 5, 6, 7 cards a year, the opportunity cost is not as high as people think." — Chris Hutchins (48:12)

8. The “Slippery Slope” Fallacy

• Frugal people will almost never turn into reckless spenders; the real risk is never practicing spending at all.

9. Personal Blockers & Real-Life Examples

• Chris confesses to having trouble spending on small upgrades (like a noisy garage door opener), prioritizing spending when things break instead of for comfort/joy (59:11).
• Brad shares how having the “money will solve this” mindset can lower stress and encourage intentional life decisions — whether that’s hiring movers, donating unused items, or booking a trip (64:29).

Notable Quotes & Timestamps

• “We’re so focused on saving...we’re just not living the life we really want to live.” — Chris Hutchins (09:53)
• “The risk that we’re not doing that [spending time, making memories] seems higher than the risk that I need to go make a little extra money or spend a little less in retirement.” — Chris Hutchins (31:05)
• “Money always solves this. That doesn’t mean you just throw cash around, but it lowers the ambient stress.” — Brad Barrett (64:29)
• “For some people, it might not change anything. For some people, it might be a giant light bulb moment.” — Chris Hutchins (75:45)
• “I’m not willing to take on more risk. I’m willing to take risk in different areas. I’m trading risk, not accumulating it.” — Chris Hutchins (73:40)
• “It’s way more risky to not live our lives than risking that we never run out of money.” — Chris Hutchins (75:01)

Highlighted Segments

• 03:41–06:57: Re-examining the 4% rule and its real-world outcomes — are we working too long for unnecessary safety?
• 14:02–18:25: Aubrey Williams’ 90% success “guardrail” approach; skillful course corrections beat over-saving.
• 24:36–31:06: Challenging holiday/family traditions, prioritizing memorable experiences over habit, and Monthly Memorables idea.
• 41:55–45:26: Points and miles, travel hacking, flexibility, and the hidden costs/opportunity costs.
• 59:11–63:39: Chris’s reticence to spend on “little luxuries”; Brad’s philosophy of using money to lower life stress.
• 73:40–75:45: Final reflections: “trading” risk, not avoiding it, and re-centering on living meaningfully now.

Conclusion: Core Takeaway

Both Chris and Brad urge listeners to challenge FI orthodoxy, shifting the focus from pursuing near-certainty of outliving your money — at the cost of time, connections, and memories — to a more holistic understanding of risk. For most FI-minded people, the true risk may be missing the best years of our lives in pursuit of unnecessary financial “safety.”

Action Step:
Regularly re-evaluate what matters most, experiment with intentional spending, and build more memorable, joyful moments into your life — long before you “have enough.”

For more from Chris Hutchins:

• Podcast: All the Hacks
• Newsletter: chrishutchins.com (with exclusive deals, hacks & personal updates)

This summary captures the episode’s central themes, thoughtful discussions, and key takeaways, with timestamps and quotes for deeper reference.