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 being less attached to outcomes. 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

The case of the other woman.

Ellie never thought she’d be the other woman. Then she fell in love with a married man.

In this episode, we find Ellie a proxy: another woman who knows what it’s like to end up in the same impossible position. Together, they talk about shame, responsibility, and what it means to live with a choice you regret when you don’t regret where it led.

Proxy’s fall membership drive is happening now. If you want to help keep the show independent — and get bonus episodes, ad-free listening, live Proxy hangs, and more — become a paid member at proxyhq.org 🍏

New to Proxy? Try Bisexual Wife Guy for a classic case, or Alex's Husband Is Too Straight, about a nonbinary person married to a man who still identifies as straight.

Follow us on Instagram — @proxypodcast @yoweishaw

Visit — proxypodcast.com

Get in touch — proxythepod@gmail.com

The case of the guy who keeps falling for his female friends.

Ryan Jay has a problem. He makes friends with women. They get close. Then he falls for them.

It’s happened enough times that Ryan Jay is starting to question whether he actually knows how to be friends with women without wanting to date them.

So we bring in a proxy to help Ryan Jay figure out why friendship keeps turning into romance for him — and whether there’s another way to do this.

Proxy’s fall membership drive is happening now. If you want to help keep the show independent — and get bonus episodes, ad-free listening, live Proxy hangs, and more — become a paid member at proxyhq.org 🍏

From the episode:

— Andrew Smiler, a licensed therapist and the author of Clinical Work with Men: Understanding Masculinity in Psychotherapy. Find out more about his work at www.andrewsmiler.com.

New to Proxy? Try Bisexual Wife Guy for a classic case, or Taelor Doesn't Want to Have Sex, about an asexual woman trying to figure out how to find the kind of intimacy she wants, without the part she doesn’t.

Follow us on Instagram — @proxypodcast @yoweishaw

Visit — proxypodcast.com

Get in touch — proxythepod@gmail.com