Yowei Cares Too Much
Oct 13, 2026 · 46 min · 18 segments
**The case of the tryhard who wants to care less.** Yowei has a problem. She overprepares, overthinks, and gets so caught up in worrying about doing a good job that sometimes it makes her worse at…
**The case of the tryhard who wants to care less.** Yowei has a problem. She overprepares, overthinks, and gets so caught up in worrying about doing a good job that sometimes it makes her worse at her job Jay Caspian Kang is a staff writer for *The New Yorker* and co-host of *Time to Say Goodbye*. He manages to do serious, thoughtful work, while giving the impression that he couldn't care less what. anyone thinks. What's his secret? Can you care deeply about your work without being consumed by whether it succeeds? Together in this episode, Yowei and Jay explore rejection, ambition, Buddhism, and the surprising costs and benefits of not giving a fuck. Plus, Jay shares his recipe for low investment. **From the episode:** - Listen to *Time to Say Goodbye*, Jay's weekly podcast about politics, culture, fishing, surfing and some other stuff. - See the photo hanging in Yowei's recording booth and get the low-investment reading list and the photo of Jay in Yowei's recording booth in our free newsletter **File Under Feelings.** Sign up at proxyhq.org **—** just click "Join for free." - Hear more of Jay's advice on speaking bro in a bonus episode of *Bad Hang*, available to paid members at proxyhq.org. New to Proxy? Try *Bisexual Wife Guy* for a classic case, or *Yowei Can't Speak Bro**,* about what happens when friends have different ways of talking and connecting. Follow us on Instagram — @proxypodcast @yoweishaw Get in touch — [**proxythepod@gmail.com**](mailto:proxythepod@gmail.com)
**The case of the tryhard who wants to care less.** Yowei has a problem. She overprepares, overthinks, and gets so caught up in worrying about doing a good job that sometimes it makes her worse at…
