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StitcherEven when you make the right decision, there can still be regret at the end. Not because you’re bad with money, but because car buying is literally designed to mess with your head. Jen and Jill share both the regrets and the wins they experienced when buying a car plus the things they wish they had done differently.
Transportation should support your life — not define it.
What Jen Regrets and Is Proud Of
Cars aren’t just about transportation anymore. Jill shares that safety, identity, success, and even a sense of adulthood now factor into how we choose a car. And it’s not simple because car buying isn’t one decision, it’s hundreds of tiny ones. The whole system is designed to overwhelm you, so when everything feels important, nothing feels clear.
But what Jen regrets most is prioritizing price over longevity. She tells the story about the time when she was pregnant with her second child, Jen knew she needed a van after her car kept stalling. Even though she felt embarrassed replacing a fairly new car and worried about minivan stigma, she chose a $25k Pacifica because price mattered most.
What She Would Do Differently
Jen says one thing she’d do differently is keep her cards closer. Because she told the dealer upfront about her trade-in and how much she could put down, that hurt her negotiating power. A better strategy is to act like you have no down payment or trade-in at first, so the dealer thinks they’ll make more from financing and is more likely to offer a better deal before you reveal your advantages.
Car horror story
Jill’s brakes stopped working on 3 occasions and Jen’s car was caught on fire on I-4 during college.
Bill of The Week
Thank you Natalie for sharing your bill about starting a small business sewing nametags onto Jerseys (with $20 overhead!)
Thanks so Much for Listening!
Thanks so much for listening. We love love love reading your kind reviews of our book Buy What You Love Without Going Broke and we especially loved this one from:
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book no.5 for the year
Very practical way of controlling your spending. Tackled the root cause not just band aid solutions
Book forces you to look at your inner self and what are your triggers. More of psychological book rather than financial. Some of the tips can be redundant as other financial book but it’s written lightly with real world examples
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