Second Thoughts About FIRE - Things We Changed Our Minds About | MHFI 333

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1. 

   8 Sep 2026 · 1 hr 7 min

   Our Financial Mistakes on the Path to FIRE | MHFI 336

   Doug chats with Bill Yount (Catching Up to FI) about the reality of pursuing FIRE: nobody does it perfectly. They discuss mistakes each of them made before and after their “financial wake-up calls,” including lack of money education, lifestyle inflation, bad insurance policies, debt, real estate blunders, predatory advisors, and the struggle to shift from aggressive saving to spending in retirement. Do you like the podcast and want to support the show? Follow the links to find out how: https://buymeacoffee.com/milehighfi https://milehighfi.com/support/ Links Catching Up to FI Catching Up to…

2. 

   1 Sep 2026 · 54 min

   Mr. Money Mustache Goes to Camp (Live CampFI) | MHFI 335

   Doug, Pete Adeney (Mr. Money Mustache), and Rox Duckels (FinanceRox) answer audience questions live at CampFI Rocky Mountain. The trio tackles topics such as financial strategies for younger generations, attracting younger audiences to FIRE, the most valuable self-investments, the real value of factoring Social Security into a FIRE plan, smooth transition strategies out of the workplace, and how to embrace idleness & art after reaching Financial Independence. Do you like the podcast and want to support the show? Follow the links to find out how: https://buymeacoffee.com/milehighfi…

3. 

   28 Aug 2026 · 19 min

   Mr. Money Mustache: Preparing for WifeFI | MHFI 334.5

   Mr. Money Mustache & I answer a listener question about how a family can best transition to Wife FI! You can get your question on the show by recording a voice memo and emailing me. Get priority by supporting the show via Buy Me a Coffee. It’s listener supported with no ads. Follow the link to find out how: https://milehighfi.com/support/ I put together the MMM episode guide: Mr. Money Mustache Episode Guide & Index Links Pete Adeney/Mr. Money Mustache MHFI episode 305, “Mr. Money Mustache Explores Pop Culture Through the Lens of FIRE” JL Collins, “The Simple Path to Wealth” Email the show:…

4. 

   25 Aug 2026 · 1 hr 8 min

   Identifying & Overcoming Cognitive Biases in the FIRE Community (Live CampFI) | MHFI 334

   Doug reunites with Carl at CampFI to chat about cognitive biases in the FIRE community – psychological shortcuts and blind spots that influence financial decisions, spending habits, and mindsets. The pair are joined by Kristen Knapp (FI Friends Travel) & Amberly Grant (FinTalks) to explore how our brains can get in the way of building a fulfilling life. Do you like the podcast and want to support the show? Follow the link to find out how: https://milehighfi.com/support/ Curious to know exactly what products Doug uses? Check out his Amazon lists below. *Affiliate links below, so if you buy…

5. 

   22 Aug 2026 · 29 min

   Asset Driven Lifestyle Creep

   Do you like the podcast and want to support the show? Referenced Mad Fientist: Decade of Freedom **Disclaimer: The podcast is for informational purposes. Maybe entertainment but we won’t even make such a claim. You shouldn’t take the info as financial, legal, or tax advice. We aren’t certified financial planners or advisors. We’re not qualified for much. So get advice from professionals.** [email protected] 00:00 asset driven lifestyle creep 03:57 decumulation 07:35 overoptimizing and simplicity 12:16 reviews & support

6. 

   11 Aug 2026 · 1 hr 15 min

   We Failed at Early Retirement, But We're Trying it Again | MHFI 332

   Doug chats with Natalie & Bill about reaching Financial Independence, attempting early retirement, and how a lack of post-work identity & structured hobbies led them both back to the workforce. They discuss what they learned along the way and how returning to work confirmed that they’re now financially & mentally ready to stop for good. Do you like the podcast and want to support the show? Follow the link to find out how: https://milehighfi.com/support/ Curious to know exactly what products Doug uses? Check out his Amazon lists below. *Affiliate links below, so if you buy something or spend…

7. 

   4 Aug 2026 · 1 hr 23 min

   Buy Back Your Time & Pay for Convenience | MHFI 331

   Doug chats with Carl & Rusty about a classic debate in the FI community – DIY vs. outsourcing. They discuss situations when outsourcing makes sense, emphasizing intentionality, buying back time, overcoming psychological hurdles of hiring help, and avoiding letting outside forces rewrite core values. Do you like the podcast and want to support the show? Follow the link to find out how: https://milehighfi.com/support/ Curious to know exactly what products Doug uses? Check out his Amazon lists below. *Affiliate links below, so if you buy something or spend money, we might earn a commission.…

8. 

   28 Jul 2026 · 1 hr 20 min

   How to Stop Working and Start Living - Rusty | MHFI 330

   Doug chats with Rusty about the concept of “quiet quitting”, spurred by an email from listener “Brian”. They discuss the psychological shifts needed to step back from overachieving, provide strategies for reclaiming personal time & prioritizing health, and share tips on leadership, strategic delegation, prioritizing high-value problem solving, and setting firm boundaries. Do you like the podcast and want to support the show? Follow the link to find out how: https://milehighfi.com/support/ Curious to know exactly what products Doug uses? Check out his Amazon lists below. *Affiliate links…

9. 

   26 Jul 2026 · 26 min

   Mr. Money Mustache on Too Much Freedom in Early Retirement [Q&A Bonus] | MHFI 329.5

   Mr. Money Mustache & I answer your questions! You can get your question on the show by recording a voice memo and emailing me. Get priority by supporting the show via Buy Me a Coffee. It’s listener supported with no ads. Follow the link to find out how: https://milehighfi.com/support/ Mr. Money Mustache Episode Guide & Index Email the show: [email protected] 00:00 Welcome and Setup 01:03 Too Much Freedom 04:19 Childhood Independence 08:13 Routines and Productivity 10:17 Long Term Care Fears 11:47 Prevention and Self Insurance 15:48 Worry Math and Dementia 18:02 Charity and Volunteering…

10. 

    21 Jul 2026 · 1 hr 19 min

    Exercising Optionality With FIRE: Quitting Work... Then Going Back - JT | MHFI 329

    Doug chats with JT about quitting his tech job due to burnout, taking time off to spend with family & decompress, but ultimately deciding to return to work. JT discusses his sudden decision to give an eight-day notice, the psychological transition of being “unemployed” vs. “retired”, why the FI community can sometimes be too prescriptive about never working again, and how he evaluated a new opportunity at a startup while emphasizing optionality, boundaries, and success criteria to avoid repeating burnout. Do you like the podcast and want to support the show? Follow the link to find out how:…