There’s something I believe in greatly: intuition. At one point when I had finished my second year at the American Film Institute,I desperately felt my character as a human being needed a political waking up. I felt that I was too naïve. I ended up doing a Frontline piece on El Salvador that led me to working with Oliver. I wanted something, I was given a sign, and I followed it. That’s what I mean by intuition — and I believe that each step of the way I have gone I have been given these fortunate signs and I’ve been able to see them and to move with them.
People who self-identify as creatives make this point quite often: They are fortunate in opportunities. But the key to their success was in being able to see it, and in having the courage to try.
The pile of unread books we have on our bedside tables is often referred to as a graveyard of good intentions. The list of unread books on our Kindles is more of a black hole of fleeting intentions.
Digital is great for consumption, but consumption is not the only reason for having a book.
Having the books physically take up space in my environment is a key feature of books! My anti-library—the collection of books I’ve not yet read—serves the important purpose of reminding what I don’t yet know. Also, when I have a spare moment the books’ proximity draws me to them; This enables me to affect my future self (albeit only slightly) by setting in sight things that would improve me through their reading.
Language is the amber in which a thousand precious and subtle thoughts have been safely embedded and preserved. It has arrested ten thousand lightning flashes of genius, which, unless thus fixed and arrested, might have been as bright, but would have also been as quickly passing and perishing, as the lightning.
We have spent the last 15 years building and participating in communities and found tremendous joy in them. Based on our own experience and with the generous help of leading community builders, we have developed a framework that helps build stronger communities and make our society a bit more connected: the Community Canvas.
There was a time when I said “I am a community builder.” I am currently the steward of the Podcaster Community—because the people there and podcasting itself are near and dear to me. But, I’m no longer interested in communities generally. I no longer go around seeing everything as a nail that should be fixed with the community hammer. That said, I wish I had seen that work above, about 20 years ago.
What does it take to use your voice with intention and create meaningful connection through audio?
This conversation reveals how intentional voice, genuine connection, and thoughtful preparation shape meaningful podcast experiences.
It’s not about good or bad. Loud is good. Projecting is good. Soft is bad. It’s having that variety in your voice and knowing when to use it. That knowing piece just comes from daily practice and listening back. That comes from my radio school days. I mean, most people are like, ‘Oh, I published the episode. I don’t want to listen to it anymore.’ But if you want to learn and grow, you need to listen. Subscribe to your own show. Listen to it.
~ Mary Chan (36:30)
Craig and Mary explore the tension between creative ambition and strategic clarity in podcasting, focusing on the decision to adopt video. Mary cautions against following trends without first understanding one’s audience, arguing that the additional effort required for quality video production is often unjustified. Craig reflects on his own temptation to “just hit record” and appreciates the freedom that comes with embracing audio-only formats. Together, they highlight the importance of intentionality—knowing where listeners actually engage and tailoring production efforts accordingly.
Beyond format choices, the conversation centers on voice as a tool for authentic connection. Mary explains how vocal tone, pacing, and emotional presence create intimacy with listeners, especially in solo episodes. Craig notes how podcasting builds lasting relationships, both with guests and unseen listeners, and how even small gestures of feedback can be deeply rewarding. They agree that successful podcasting requires self-awareness, clear purpose, and a commitment to serving the listener’s experience above all.
Takeaways
The pressure to add video — Many podcasters feel compelled to incorporate video due to platform trends, but this may not serve their actual audience.
The complexity of video production — Creating video content requires more than just hitting record; elements like lighting, editing, and set design significantly impact quality.
Knowing the audience — Understanding where listeners consume content is crucial before adopting new formats like video or written newsletters.
The power of voice — Voice carries meaning beyond words, and thoughtful delivery can make content more engaging and memorable.
Podcasting as an intimate medium — Listeners form deep connections with hosts, often feeling like they personally know them.
Self-doubt in content creation — Many podcasters second-guess themselves, wondering if they should be doing more or following new trends.
Authenticity in podcasting — A podcast host should sound like themselves, not an artificial version, to build a genuine connection with the audience.
The importance of show preparation — Planning a conversation’s direction helps create a natural flow while allowing for spontaneous moments.
Building relationships in podcasting — Long-term connections with other podcasters can lead to opportunities, collaborations, and shared growth.
Podcast listener engagement — Many hosts wish for more feedback from their audience, but this requires encouraging interaction and setting the expectation.
The difference between podcasting and cinematographic content — High-production video podcasts differ significantly from casual video recordings of audio-based shows.
The hidden work in podcasting — Even for audio-only podcasts, preparation, editing, and audience engagement require significant effort.
Off Camera with Sam Jones — A documentary-style interview series mentioned, which features long-form conversations with creatives and includes high production-value video.
The final challenge isn’t just to do the work but to exceed expectations. My approach at Borland and whenever a helpful someone gives me constructive feedback is to hear it, address it, and act on it in a fashion that demonstrates that I am the expert.
Exceeding expectations is a slippery slope. By definition, that’s moving beyond the point of success. (Assuming those expectations are reasonably set.) A little bit of better, is better. But how much of myself do I want to sacrifice as I push farther? A key part of the dance of being professional is learning how to set my own goals and expectations which are beyond those of others and still reasonable.
Nature and artificial, entirety and piece, universality and uniqueness, the past and the present. Architects are tormented by the constant conflict of these dualistic propositions! The deeper and more intense the tension is, the more dynamic the creation becomes. That is why architects must continue thinking.
Of course, not just architects must continue thinking. I find so much more value within things (for example, a conversation) when I hold up pairs of opposites as Ando suggests. Each pair suggests a dimension for consideration, and it’s easier than just staring into the original thing looking for the interesting parts.
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How do you personally evaluate whether your podcast is working for you? →
There’s no correct answer to this question. The only important thing is that each of us takes the time to find our own answer. This is not a “set it and forget it” situation: You have to reconsider this question periodically too.
Yesterday I was talking with a podcaster who is in the middle of a significant pivot of their show. Why the pivot? It wasn’t working for them any more.
I’ve pivoted shows, started new shows, intentionally stopped publishing episodes of a show, and completely deleted shows from existence. Each time because there was a clear sign (often a sign I’d been in denial about) that the show was no longer working for me.
That’s what you have to figure out for yourself.
I did 1,400 episodes of Little Box of Quotes as a daily show. I had specific things I was practicing. When creating new episodes became a thing I started avoiding, I stopped. A year later, I’m thinking of resuming publishing the show, but my reasons for publishing it are now completely different.
I’ve tried two different show-formats for the Open + Curious podcast. Now in 2025, I’m scheduling guests for its 3rd season which will be in my signature style of conversation.
The Movers Mindset podcast hasn’t been the same format since day one. There’s been a bunch of experiments within that show. As I have new ideas, and new questions about what can a recorded conversation be, that’s where I’ve done most of my experimentation.
Even Podtalk has changed over time. What began as “the companion podcast to the Podcaster Community” (conversations with the community’s members) expanded to conversations with any independent podcast creator.
As I said: There’s no one, correct answer for everyone. There isn’t even one, correct answer for each of us!