Inside Out Money

Latest Episodes:

184. Teaching Teens About Money - Co-Learning, Setting The Example, and the Power of Psychological Safety - Part 3 of 3 Oct 03, 2026

Show notes

Teaching teens about money requires us to look past the spreadsheets and tackle the exhausting real-world money traps happening right inside our homes. We are wrapping up our special three-part series with my 17-year-old stepdaughter, Maddie, by flipping the script to focus entirely on actionable parent tactics. Together, we explore practical strategies to combat sibling scorekeeping, navigate the "invisible ledger" of blended families, and successfully implement the decision-maker pays rule. By stepping back and letting teens manage their own seasonal clothing budgets and vacation envelopes, we can break the money taboo and co-learn together as a unified family.

Get the full show notes, show references, and more information here: https://www.insideoutmoney.org/184-teaching-teens-about-money/

183. Teen Money Basics - 4 Hacks for Shifting From Anxiety to Agency - Part 2 of 3 Oct 01, 2026

Show notes

Mastering teen money basics is the ultimate key to transforming Gen Z's financial anxiety into agency and empowerment. In part two of our special series with my 17-year-old stepdaughter, Maddie, we are moving past the psychological traps of spending guilt and laying down highly actionable advice for young adults. We explore how to outsmart the "invisible cash" effect by deleting saved credit cards, using the 24-hour rule to limit impulse buys, and reframing purchases into actual hours worked. From establishing strict student loan rules of thumb for college to embracing an internal locus of control, we outline exactly how to navigate social proof and build resilient financial habits before teenagers step into their next phase of life.

Get the full show notes, show references, and more information here: https://www.insideoutmoney.org/183-teen-money-basics/

182. The Psychology of Teen Money - Fake Money, Future Anxiety, & The Death of the Allowance - Part 1 of 3 Sep 27, 2026

Show notes

Raising financially confident teens requires us to look past simple budgeting and understand the psychology they face every single day. We are kicking off an actionable three-part series with my 17-year-old stepdaughter, Maddie, to unpack the reality of teen financial anxiety, the death of the traditional allowance, and modern spending habits. Together, we explore ways to combat the "invisible cash" effect of digital wallets and navigate the cognitive dissonance that leaves young adults feeling guilty after impulse purchases. By blending psychological insights with open conversations about how teens think about money, we can help you actively guide your kids and raise financially confident young adults.

Get the full show notes, show references, and more information here: https://www.insideoutmoney.org/psychology-of-teen-money-part1/

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

Show notes

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/

180. Social Comparison Theory and 7 Ways to Cure Aspirational Fatigue Sep 14, 2026

Show notes

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/

179. Mindset Shifts - Changing Our Minds About Money and Life Choices Sep 06, 2026

Show notes

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/

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

Show notes

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/

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

Show notes

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/

176. Outsmarting Your Brain - The Financial Psychology of Behavioral Biases and Mental Traps Aug 16, 2026

Show notes

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/

175. The High Cost of Staying Comfortable: The Comfort Crisis, Stoicism, and Misogis Aug 09, 2026

Show notes

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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