Episode 59: No Regrets, The Case Against Empathy, and Is AI Coming for Us All?

About the Episode

This week, we dive headfirst into the messy, uncomfortable topic of regret. From the aches and grays that come with hitting a new decade to the deeper realizations about relationships, selfish mistakes, and missed opportunities, we unpack how regret shapes who we are. And there’s a twist: what if regret isn’t something to fear or avoid? What if it’s a tool for growth? I share my own stories of taking people for granted, self-destructive habits, and the lessons I’ve learned about self-forgiveness and choosing your regrets wisely.

We also tackle some fascinating questions about whether empathy is actually good for society. Is it always a good thing, or can it sometimes lead us astray? To round things off, we share our thoughts on AI and its impact on creativity and human connection.

Enjoy.

Quotes From the Episode

Part of who you are as a person is all of your past experiences. If you regret something, you’re essentially wishing for part of yourself to not exist.

Empathy is not inherently good or bad—it can blind you, bias you, and even justify awful things.

The real issue behind regret isn’t what you did or didn’t do—it’s self-loathing manifesting as constant preoccupation with mistakes.