Sam doesn’t know how to be rich, from “Proxy with Yowei Shaw”

2026-07-02

Download

This week, we’re sharing an episode of “Proxy,” a podcast about the emotional questions that make people feel alone — and the conversation that unfolds when you find someone who gets it. Sam is a progressive person who suddenly has more money than friends and family — and he doesn’t know how to feel about it. He wants to be generous. He wants to be responsible. He wants to stop feeling guilty and secretive and afraid. But the more he thinks about what money can do, the less clear it becomes what having “enough” is...

This week, we’re sharing an episode of “Proxy,” a podcast about the emotional questions that make people feel alone — and the conversation that unfolds when you find someone who gets it.

Sam is a progressive person who suddenly has more money than friends and family — and he doesn’t know how to feel about it. He wants to be generous. He wants to be responsible. He wants to stop feeling guilty and secretive and afraid. But the more he thinks about what money can do, the less clear it becomes what having “enough” is supposed to mean.

In this episode, host Yowei Shaw connects Sam with David Steely, a man who has spent years wrestling with the same questions — and has given away most of his money.

We’ll be back with a new episode of “This Is Uncomfortable” next week! If you want to answer our “Uncomfortable Questions” see more info here.

Support This Is Uncomfortable with your donation today: https://bit.ly/mkp_tiu_pod

Comments (3)