Today’s episode is a special rerun from the Afford Anything “greatest hits” vault, one that’s especially timely as we move through peak shopping season.
Originally aired in January 2020, this conversation with behavioral economist Jeff Kreisler digs into the hidden psychology behind sales, discounts, so-called “free shipping,” and all the subtle emotional triggers that influence how we spend. If you’ve ever wondered why a $100 sweater marked down to $60 feels so much better than buying a regular $60 sweater (even though the price is identical), this episode explains exactly why.
Jeff and Paula explore five common money mistakes and the four behavioral shifts that can help you save more, spend intentionally, and avoid mental traps that separate your best intentions from your actual financial decisions.
Key Takeaways
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Wealth-building is a balance: growth matters, but so does protection; defensive moves like thoughtful insurance or tax planning are part of long-term success.
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Umbrella insurance can be a smart hedge when you reach higher net worth — especially if you have risk factors like teenage drivers, real estate, or rental properties.
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Small Roth contributions (or diversified tax-type allocations) build optionality — giving you flexibility to react to future tax and income changes.
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Converting a traditional IRA into a 401(k) (to enable backdoor Roth) isn’t just about tricking a system — it can provide real, long-term benefit if you value tax diversification over short-term flexibility.
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Your financial strategy should evolve as life changes — income, risk exposures, family, and plans all shift over time.
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Avoid “set-and-forget” thinking: review your liability exposures, account mix, and insurance coverage periodically to stay aligned with your growing net worth.
Resources Mentioned
Chapters
Note: Timestamps are approximate and may vary greatly across listening platforms due to dynamically inserted ads.
00:00 — Intro: Why we’re replaying this greatest-hits episode
02:00 — The emotional side of money decisions
07:30 — Why sales and discounts trick our brains
13:00 — JCPenney’s failed “fair and square” pricing experiment
18:30 — Relativity and the psychology of “winning the deal”
22:00 — How frictionless payments encourage overspending
28:40 — Delayed payment vs. immediate reward
34:10 — The endowment effect and overvaluing what we own
39:00 — Why opportunity cost is so hard to grasp
44:50 — Four ways to save yourself from yourself
45:10 — Make your future concrete
46:40 — Hide money from yourself
48:30 — Make savings visible
51:00 — Build an identity around smart financial choices
55:00 — Where to find Jeff
57:00 — Closing thoughts and next steps
60:00 — Outro
Thanks to our sponsors!
Wayfair
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Prolon
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