200 Podcast Episodes: Some of My Favorite Convos | #307

September 6th, 2025: Greetings from Chiang Mai! Last week I launched a magazine as part of a new experimental collective. You can read about that here.

My podcast has never been the “main” thing I do but its something I always get energy from. This week, I published “episode 200” of The Pathless Path Podcast and did so by experimenting with a new format, something I’m calling “Desktop AMA.” You can listen on Apple, Spotify, or watch on Youtube (it will make more sense if you’re watching).

While there’s lots of pressure to ship a podcast each week, I’ve only kept up that pace for a few different periods. 2024 was the first time I took an extended break from the format, but I’m back posting episodes as they come and trying to have more fun and experiment with the format. I’m not well suited to compete with well-coiffed podcaster dudes and highly produced 7-camera shows, but I’ve somehow seen the following of the show increase and there’s a couple thousand people still following the show. I’m going to just focus on following my curiosity and having deep conversations with people I genuinely want to learn from. We’ll see what happens.

While most people don’t listen to old episodes, most of my episodes are timeless. They talk about the deeper aspects of being on a weird journeys rather than focusing on tactics or how-to content.

So I pulled together some of my favorite episodes that deserve some more listens or views below.

I’ve linked to Apple below but you can find these on a YouTube playlist and Spotify here:

More Recent Episodes - 2021 to 2024

Angie Wang 安吉 - Our First Episode in 2020

My episodes with Angie are my most listened to and most watched episodes. My first episode with Angie was in 2020 as we were living in Mexico and right before I started writing my first book.

We also had multiple conversations after this:

We’re due for another episode and will likely record one when we are back in Taiwan next month as Angie finishes her book.

Anna Gát - Curiosity & intellectual Life

Anna’s story of blowing up her life and moving several times is inspiring. We talk about remaining curious and the challenges and upsides of a being a public intellectual in the modern world.

Lawrence Yeo - Arc of The Practical Creator

People still send me feedback about this episode a few years later. Lawrence and I talk about this weird path we are on and how to approach it with a long-term mindset.

Lawrence remains one of my favorite people to talk to about this path.

Tim Malnick - The Life Path or The Money Path

This was one of the first episodes I did on money. His idea of the “life path” versus the “money path” still sticks with me and is something I wrote about in Good Work:

A conversation with the organizational psychologist and coach Tim Malnick helped give me the language for these contrasting perspectives. In his words, I was embracing the “life path” rather than “money path.” To him, those on the "money path" see money as the answer to life’s problems and that, “one day, when I sort this out, I’ll get to do what I want.” Suffer now for a future payoff. In contrast, on the “life path” you can “do what you love, and the more you follow it, the more you will have your needs met with and without money.”1 And the key here is that on the life path, your needs are met with and without money, which is what I’ve experienced

Kevin Espiritu - Gardening & Learning In Life

Kevin’s story is great as he is a lifelong tinkerer. He’s had a lot of success recently with his gardening empire, but seems to be dabbling with learning how to sketch and draw now too. My favorite people on these paths always are like this - needing to learn something new.

Joe Hudson - Transformation for High Achievers

This has become my top viewed and listened to episode as Joe’s teaching has become more popular. Joe’s ideas have been very helpful in helping me navigate all the inevitable triggers of doing creative work in public.

Russ Roberts - The Beauty of Conversations

Russ if the host of my favorite podcast, EconTalk. It’s the show I’ve listened to the longest. I appreciate his unshakeable curiosity and willingness to change his mind and evolve with age. I made a list in 2022 of the top people I’d want to interview and Russ was #1 on the list. We talked about his book Wild Problems among other things I wanted to ask him.

The Art of Sabbaticals - Cécile Marion and Michelle Elisabeth Varghese

Cecile and Michelle have thought more about sabbaticals than I have and this episode was a great conversation about all of our experiences taking breaks from work:

Ali Abdaal - Doctor or YouTuber?

I interviewed Ali in 2021 as his YouTube was starting to explode but he was still working as a Doctor. This is a good peek into some of the challenges he was still wrestling with before deciding to leave medicine behind.

Jonny Miller - Waves of Knowingness

I’ve lived with Jonny in several places around the world since 2018 and he was one of my first pathless friends. We always intend to record episodes together but then forget, hanging out instead. But this convo was great. It was the first recorded convo we had about both of our journey’s after my book came out. Interesting enough this is right as both of our stuff was starting to take off, Jonny’s Nervous System Mastery and The Pathless Path. It’s always fun to catch up with Jonny and reflect back to the “early days” when we had no idea what we were doing.

Venkatesh Rao - Indie Life

If you’re going to be self-employed and at least considering freelancing, you should read Art of Gig. It has the best frameworks for thinking about doing consulting work and gig work generally. He doesn’t really promote it anymore but I can. We went through a lot of the ideas in this episode:

Dom Francks - Wandering In The Wilderness

This episode was great with a friend Dom who is building a life around trying to spend more time living outdoors. Best to listen to this outside.

Rick Lewis - Beyond The Rules

Rick still has so much energy for creating and pushing the boundaries of reality. I am inspired by his playful spirit

Derek Sivers - Life On Your Own Terms

We talked a lot about designing your life with kids and listening back again recently, this makes a lot more sense with an actual child :-)

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Earlier Episodes - 2018 to 2020

Steph Smith - 21st Century Careers

Steph has one of the best mindsets with approaching a modern career. She’s embraced a creative and tinkering spirit while shifting in and out of formal employment.

Amy McMillen - Wandering in Uncertainty

This was the episode where I first seriously thought about writing a book. I loved Amy’s book and told her that I wished there were more like it. I took my own advice later in the year and got started on it.

Lydia Lee - Screw The Cubicle

I remember recording this in a small back room of an iPhone repair shope where I was staying in Taipei, This interview from 2018 captures some of the early excitement I was starting to feel on my path as well as some residual confusion / frustration with the path I left behind.

Andrew Taggart - How Total Work Took Over The World

This interview from 2018 was very powerful in giving me a set of questions that helped me think about my path in new terms:

1. Are you a worker?

2. If you are not a worker, then who are you?

3. Given who you are, what life is sufficient?

Solo Episode - “I’m Moving to Asia”

This was a short episode but might be fun to listen to as I was still single, not having made money from anything except freelancing, and about to start a new chapter in Asia. More than seven years ago:

Janet Matta - Alternative Paths

Janet was one of my first six “test” episodes where I was going to see if I wanted to keep doing it. I found her story very inspiring as she started looking for alternatives as soon as college, realizing that going abroad to Canada for University was going to be better and cheaper than doing so in the US.

Noel Boyland - Doing The Things You Want To Do

Noel was the first person I asked to come on my podcast. We had met a couple of years prior when I got an offer at a company that lowballed me and promised me purpose instead of money (story in my first book). Sadly, Noel passed away two years ago but I still think of him often as he was the person I talked to whenever I was struggling with confidence and needed some support.

He left the default path in his 40s and dabbled with a bunch of various gigs for years while prioritizing his health and family. He was an inspiration to me and I miss him.

I’m still having fun, thanks for being here.

I’ve been doing some form of public writing since 2015. I’ve somehow figured out how to hack a living doing things like forming collective for 8+ years now. I’m amazed myself, don’t worry.

If you like what you read here, you’ll probably enjoy my books The Pathless Path and Good Work:

grab them here

If you’d like to meet others on “pathless paths,” or potentially get involved in the next release you can join The Pathless Path Community.

Some things I endorse: Readwise for book notes and reviewing highlights; Readwise Reader for my attempts at re-creating RSS readers (2 months free for each. Crowdhealth, an alternative to US health insurance that I’m still using while abroad; Kindred, a home-sharing app; Collective for handling your S-Corp accounting needs; and Nat Eliason’s Build Your Own AI Apps course

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