This podcast episode was not planned.
While staying in San Diego during my sabbatical, my friend Caleb Wojcik invited me to his house to record a podcast. Caleb lives in Encinitas (about a one-hour train ride from where we were staying in downtown San Diego).
Caleb and I recorded two podcasts: one for his show, and another for mine. You’ll see that interview with Caleb on the podcast feed in the next day or two.
I was getting ready to take the 3:00pm train back to the city after recording with Caleb, when I received a new message on Instagram from Calvin Rosser:
“Hey dude, think I saw you’re in San Diego. I’m in Encinitas (north of San Diego) if you want to get together. Fairly free during the evenings this week. Just working and surfing.”
I’d met Calvin once last year at Craft + Commerce conference. We got coffee together the last morning before I went to the airport.
Calvin has been a nomadic traveler for many years now. Over coffee last year in Boise, Idaho, he shared stories of his travels, and emphasized the importance of going with the flow and not having an overly rigid plan.
“You may find that you love a place and want to stay longer.”
At the time, he spoke of settling down. Several years of traveling nomadically was an incredible experience, but he was ready to slow down and stay in one place for awhile.
We both just happened to be in Encinitas at the same exact time. How perfect was it that he messaged me without knowing?
This must have been where he settled down last year.
Calvin laughed. “I actually just got here a day ago.”
“What happened to settling down?”
“I still want to. I miss having friends I see regularly and with whom I can go deep.”
We met at a coffee shop in Encinitas, but Calvin hardly sat down. Right away, he asked if we’d be willing to go somewhere else.
“I actually have a car, but I prefer to walk. There’s a place nearby that’s really nice—it’s about a 14-minute walk from here. Is that okay?”
Calvin has a thoughtful tone, as you’ll hear in the recording. He doesn’t mince words, and he doesn’t waste any time getting straight to deep and meaningful matters.
Before I know it, we walk through an iron gate into another world. I’d never been in a meditation garden, but visiting at golden hour is everything you’d imagine: fish, flowers, and colorful foliage abound as you walk through winding pathways and up stairs.
As we go up, the trees give way to a bright sky with a sun that will set within the hour. We find a bench at the top in a little clearing that reveals a stunning panorama of the Pacific Ocean. We are high up on the cliff.
“I’m trying to remove guilt when not working,” Calvin says.
“Do you mind if I record our conversation?” I ask. “We don’t have to do anything with the recording, but if we end up discussing something worth sharing, then at least we have the option of making it available as a podcast.”
Calvin doesn’t mind. He almost seems indifferent.
I hand him the lavalier microphone to clip to his shirt. He doesn’t seem phased. We don’t begin with any formal introductions. The tone of our conversation remains the same. We just continue talking.
“With my work, I feel that there’s an endless list of things to do. When I’m not working, I should be focused on that list of things to do.”
The guilt. As a recovering workaholic, I know it all too well.
There were only ever two modes:
2. Feeling guilty about not working
I didn’t like feeling guilty.
Calvin’s the same. He’s internally driven, and unsatisfied with anything less than reaching his full potential.
That was me, and why I worked 18-hour days for a decade. Then I burned out.
“The times I feel the guilt the least, and the times I feel most alive, is when I’m connecting one-on-one with someone else,” Calvin says. “I’m able to engage with that in a way where the other stuff sort of melts away.”
The seanwes podcast has not, historically, been an interview show. Part of the reason is I, like Calvin, am not one for small talk. I like to go straight to the deep and meaningful stuff. That’s what I like about a co-hosted show: you know me, you know my co-host. Great. Now that the introductions are out of the way, let’s get straight to the topic.
Interviews always feel like they have so much preamble. I wasn’t a fan.
But during my sabbatical year, I decided I would record and share conversations I have with people along the way. Sometimes, that’s going to be a podcast interview that’s a planned event, but I also want to experiment with recording and sharing serendipitous conversations like this one. We didn’t plan to record anything, so it feels very raw. But I like that.
I thought about recording a formal introduction to explain who Calvin is, what he does, how we met, why we were talking, and what you’ll get out of the conversation. But that’s the furthest thing from what this actually was: a completely unplanned, unscripted, spontaneous moment. I want you to experience this conversation the way it happened in real life.
So I’m trying an experiment: rather than recording an introduction, I’m letting this written description provide the context for the episode. I’m curious to hear how you receive it. Feel free to send me a message on Instagram @seanwes with your thoughts on this raw format.
You can check out Calvin’s writing and sign up for his newsletter at https://CalvinRosser.com. Do reach out and encourage him to start his own podcast if you enjoyed this conversation.