This American Life

Originally aired 6.24.2016

590: Choosing Wrong

Stories of people making the wrong choice, even though the right one is staring them squarely in the eye. Basketball players making a conscious decision to not do the thing that makes them better, pollsters refusing to see the truth of Donald Trump, and more.


I both relish and at times detest them. I’m not talking about small decisions. I’m talking about big ones. Should I invest in a company, and, if I’m wrong live with embarrassment and shame?  Should I keep propping up a company that just cannot ever hit its numbers?

Thankfully, many personal decisions are behind me. Whom should I marry? Where should I work?  How do I balance a spouse, young children, work, and my own needs for exercise and downtime (I’m not at 100% on this but have improved)?

In my job as a VC, I often am trying to help entrepreneurs make decisions. Should that person be hired and that person be fired? When is a good time to start fundraising? Is the market there? Does the product fit the market? Should we keep going? Should we give up? How do co-founders deal with each other’s quirks?

So, I over time have learned to deal with decisions. Yet, I often see that people know what they should do, yet do the opposite.

That’s why I found very interesting this podcast from This American Life, called “Choosing Wrong.” Link here, or up top. The podcast covers choosing a spouse, Wilt Chamberlain and basketball, Donald Trump, and ends with a very funny segment from a comic.

I think you’ll like it.


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