Episodes

  • 181. Avoiding Deathbed Regrets - How to Reverse-Engineer Your Money and Life
    Sep 20 2026

    Examining our deathbed regrets is the ultimate framework for reverse-engineering how we spend our time and money today. We unpack the difference between resume virtues and eulogy virtues, challenging the common instinct to hoard resources for a distant retirement when our peak energy and time with family are happening right now. We explore the power of life-stage time buckets, why buying back time during the messy parenting years beats waiting for traditional retirement, and how to find the middle ground between daily stability and big adventures. Building true wealth means aligning our finances with what we want to be remembered for, ensuring we look back on our choices with deep fulfillment rather than regret.

    Get the full show notes, show references, and more information here: https://www.insideoutmoney.org/181-avoiding-deathbed-regrets/


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    1 hr and 2 mins
  • 180. Social Comparison Theory and 7 Ways to Cure Aspirational Fatigue
    Sep 14 2026

    Social comparison theory explains why our brains constantly compare our lives to everything we see on social media, leaving us with a heavy dose of aspirational fatigue. We unpack how measuring ourselves against algorithmic facades quietly drains both our mental well-being and our wallets. We share seven ways you can cure aspirational fatigue, including practical steps to reset your digital inputs, implement the humility hack, and use intentional generosity to dismantle a scarcity mindset. By focusing on financial fundamentals and extending ourselves grace, we can stop chasing someone else's baseline and build lasting wealth on our own terms.

    Get the full show notes, show references, and more information here: https://www.insideoutmoney.org/180-social-comparison-theory/

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    51 mins
  • 179. Mindset Shifts - Changing Our Minds About Money and Life Choices
    Sep 6 2026

    We’ve certainly had some mindset shifts about our financial and life choices over the years, and according to Sahil Bloom, adapting your beliefs is the ultimate sign of intelligence. We get incredibly honest about the things we’ve changed our stance on over the years, and why. We unpack how our shifting mindsets have evolved alongside our lives, like downsizing to a smaller home, paying off our mortgages, and even our closely held beliefs about eyelash curlers. From rethinking our strict views on monthly subscriptions to abandoning the exhausting hustle of travel hacking, we explore how changing your mind is a critical part of personal growth.

    Get the full show notes, show references, and more information here: https://www.insideoutmoney.org/179-money-mindset-shifts/

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    48 mins
  • 178. Leaving It All Behind - When Burnout Screams for a Boundary
    Aug 30 2026

    We are experiencing burnout, so we fantasize about leaving it all behind. What does this mean, and how can we find the middle way to achieve balance, boundaries, and ultimately a happy and content life? It turns out it’s normal to fantasize about packing it all in, ditching the corporate grind, and running away to live in a tree with the squirrels. Rather than just daydreaming about abandoning all our adult responsibilities, we explore how to bring that elusive "cabin in the woods" peace directly into our messy, everyday lives. We break down practical ways to reclaim your time and sanity so you don't actually have to leave society to find your peace.

    Get the full show notes, show references, and more information here: https://www.insideoutmoney.org/178-burnout-boundaries-balance-middle-way/


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    57 mins
  • 177. The Ultimate FIRE Bridge - The Truth About Deferred Compensation Plans vs. Brokerage Accounts
    Aug 24 2026

    Are Deferred Compensation Plans (DCPs) the strategic and supercharged path to FIRE, or can a taxable brokerage account get you to the exact same place? We break down exactly how DCPs work, their risks, their realities, and how they've worked for each of us personally. The forced-savings approach of a DCP could be the ultimate in forced savings, or the flexibility of a taxable brokerage account could be just the solution we all have access to. Are you missing out if you don’t have access to a DCP? Let's figure out if this is the most amazing perk ever or a trap we should avoid.

    Get the full show notes, show references, and more information here: https://www.insideoutmoney.org/177-the-ultimate-fire-bridge-the-truth-about-deferred-compensation-plans-vs-brokerage-accounts/


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    1 hr and 10 mins
  • 176. Outsmarting Your Brain - The Financial Psychology of Behavioral Biases and Mental Traps
    Aug 16 2026

    We dive into the psychology of money and discuss behavioral biases that explain why we make the financial decisions we do, even when we know better. In breaking down some of these common behavioral finance traps and mental biases, we share actionable tips to help us outsmart our own brains and improve our money habits.

    Get the full show notes, show references, and more information here: https://www.insideoutmoney.org/176-outsmarting-your-brain-the-financial-psychology-of-behavioral-biases-and-mental-traps/

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    52 mins
  • 175. The High Cost of Staying Comfortable: The Comfort Crisis, Stoicism, and Misogis
    Aug 9 2026

    Is our obsession with comfort quietly draining our wealth and resilience? Our modern lives have engineered almost all of the friction and discomfort away. We explore the mental and financial traps of modern convenience, and why leaning into voluntary discomfort builds a more resilient mind and wallet. We share actionable practices for improving your ability to tolerate discomfort, from Misogis to pre-porterms to meditation.

    Get the full show notes, show references, and more information here: https://www.insideoutmoney.org/175-the-high-cost-of-staying-comfortable-the-comfort-crisis-stoicism-and-misogis/

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    55 mins
  • 174. The Friendship Dividend - Why Community Is Your Best Financial Asset - Live from CampFI
    Aug 2 2026

    They say FI is better with friends, and we definitely think that’s true. Recorded live from CampFI Rocky Mountain week 2.0 with Liz from the Liz Gets Loaded podcast and Kathleen from The Reframe podcast, we tackle the critical role of friendship within our financial independence journey and life in general. Navigating money matters can feel incredibly isolating, especially when doing something that feels a bit against the grain. We break down four levels of FI friendships that we totally just made up, and give you our best advice for making friends in the FI community. By stepping out of your comfort zone and connecting with like-minded people, you can dramatically accelerate your financial goals and make the journey so much more fun.

    Get the full show notes, show references, and more information here: https://www.insideoutmoney.org/174-the-friendship-dividend-why-community-is-your-best-financial-asset-live-from-campfi/


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    52 mins