Today’s episode is a special rerun from the Afford Anything “Greatest Hits” vault, which is especially timely as we go through peak shopping season.
Originally broadcast in January 2020, this conversation with behavioral economist Jeff Crisler explores the psychology behind sales, discounts, so-called “free shipping,” and all the subtle emotional triggers that influence the way we spend. If you have ever wondered what a $100 sweater marked down to $60 Feels so much better than buying a regular $60 sweater (even though the price is the same), this episode makes exactly why.
Jeff and Paula explore five common money mistakes and four behavioral changes that can help you save more, spend intentionally, and avoid the mental traps that separate your best intentions from your real financial decisions.
key takeaways
Wealth-creation is a balance: growth matters, but security also matters; Defensive steps like thoughtful insurance or tax planning are part of long-term success.
Umbrella insurance can be a smart defense when you reach a high net worth – especially if you have risk factors like teenage drivers, real estate or rental property.
Small Roth contributions (or diversified tax-type allocations) create optionality – giving you the flexibility to react to future tax and income changes.
Converting a traditional IRA to a 401(k) (to enable backdoor Roth) isn’t just about cheating the system — it can provide real, long-term benefits if you value tax diversification over short-term flexibility.
Your financial strategy should evolve with life changes – income, risk exposure, family and plans all change over time.
Avoid “set and forget” thinking: Periodically review your liability exposure, account mix, and insurance coverage to stay in line with your growing net worth.
mentioned resources
Chapter
Note: Timestamps are approximate and may vary significantly across listening platforms due to dynamically inserted commercials.
00:00 — Intro: Why we’re revisiting 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 seamless payments encourage overspending
28:40 – Delayed Payment vs. Immediate Reward
34:10 – The endowment effect and overvaluing what we have
39:00 — Why opportunity cost is so hard to understand
44:50 — Four ways to protect yourself from yourself
45:10 — Solidify your future
46:40 – Hide money from yourself
48:30 — Make savings visible
51:00 — Build your identity around smart financial choices
55:00 – Where to find Jeff
57:00 – Concluding thoughts and next steps
60:00 – Outro
Thank you to our sponsors!
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