A financial planner's advice for spending without guilt

Jul 13, 2026 · 23 min

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asr · 5,035 words · docs
0:00This is Ira Glass.
0:01On This American Life, we tell stories about when things change.
0:04Like for this guy, David, whose entire life took a sharp, unexpected, and very unpleasant turn.
0:10And it did take me a while to realize that it's basically because the monkey pressed the button.
0:15That's right.
0:16Because the monkey pressed the button.
0:19Surprising stories every week, wherever you get your podcasts.
0:25What's something that you have felt financial guilt about?
0:29Oh, things that I have felt financial guilt about.
0:32There are so many.
0:33I bought a home in 2004.
0:37Then I went and bought another home in 2006.
0:40And basically in 2007, it was worthless.
0:43I held on to that home until, I think, 2017 and finally sold it short even all that time later.
0:52I did not make my money back on the home.
0:54I ended up having adverse credit history because I sold the home short.
0:58So that was a pretty embarrassing thing that happened.
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