Here’s something I do every weekday as I drive my ten minutes to work in the morning and back home, often at eight or nine at night: I listen to Paul Millerd’s Pathless Path Podcast. And no matter how sleep-deprived or grumpy I am, I always feel deeply nourished by whatever episode snippets I listened to. In each episode, Paul — who quit full-time strategy consulting work in 2017 to craft “a much better path, an infinite game I want to keep playing” — has a conversation with someone about their thoughts on work, life, and more.
What I love about each of these episodes is how real and honest both Paul and his guest get. How do you deal with the uncertainty of not having an income? How do you navigate relationships with parents when they disapprove of your path? What really matters to you?
I’ve been wanting to talk about Paul’s podcast for over a month, but I felt hesitant about seeming like a shill. In the past few years, I’ve gotten constructive criticism from friends regarding my constant promotion of whatever I’m into. But I’ve personally gotten so much from listening to these podcasts, reading his book, and all of his generosity that I’d rather just publish this post.
Here are two of my favorite episodes:
The Shadow Side of Entrepreneurship with Darren Joe: My favorite portion of this episode was when Darren Joe — a Princeton graduate, former MBA admissions director, and now entrepreneur in Asia —described an argument with his parents: “Darren, you have a good education, a good work background. Your ancestors escaped China and Asia to come to the US and work, and now you’re going back there?” I haven’t found much content out there that captures the nuances and particularities of tensions with Asian parents, and I got a lot out of the honesty here.
The Nonlinear Life & Quitting Medicine with Aida Alston: Aida talks in this episode about pursuing dance seriously, graduating early from college, and doing medical school for free in Cuba before realizing she didn’t want to be a doctor. I was deeply moved by how she just went there and talked about her mental health struggles and her journey of letting go of the expectation of being exceptional. Throughout the episode, I kept thinking to myself in awe, holy shit, how do you put yourself out there like that? I’m so grateful you’re sharing your story.