They had this idea, just one shot in which three very, very unlikely people were seen as NASCAR drivers. And I think they approached Julian Schnabel, Lou Reed, and me. (Laughs) And we were all supposed to be wearing the uniforms and the helmet, walking in slow motion with the heat haze. That would have been fantastic, but all of us couldn’t do it.
I was a junior in high school when Rushdie’s, Satanic Verses was published in 1988. The book was widely mentioned; It wasn’t really discussed, but rather it was just that everyone knew about its existence, and everyone had an opinion about it. Thinking back, I’m sure my opinion was simply a *hunh* and “that’s interesting.” To this day, I’ve not read the book, not for any particular reason but simply because there are way to many books I have reasons to read. The whole thing (back in the 80s) now feels like some sort of mirage: Real, vivid, and important, but in the end it wasn’t a real thing. The mirage was about a real thing, but it wasn’t real.
While rock climbing (outdoors, on real rocks, at real heights) I was once told that there are three types of fun: Type-1 fun is when something is fun, right now. Type-2 fun is when it’s not fun now, but is nonetheless great because of the experience, stories and learning being gained. …and then there’s Type-3 fun when nope, this is bad, mistakes have been made, and I want out of here.
I wonder if a big part of what draws me to be professional about what I do is that it’s really just Type-2 fun?
What does redefining success look like after you’ve lost everything?
Podcasting becomes a vehicle for self-discovery, long-form connection, and client engagement.
I’ve talked to a lot of podcasters. I’m able to talk to people for roughly 60 minutes without any interruption. It nourishes my soul, and I love it. That’s the real foundation.
~ Tim Winders (19:18)
This conversation explores the origin and evolution of the long-running podcast, Seek. Go. Create., and its relationship to Tim Winder’s personal and professional journey. Tim describes how the podcast began as a response to a client’s needs, but quickly became a spiritually driven endeavor. He was encouraged to share personal stories, including difficult experiences like financial collapse and homelessness. Over time, the show developed into a platform that not only supports a coaching business but also nourishes a desire for deep, uninterrupted conversations.
This conversation also touches on the structure and process behind maintaining consistency over hundreds of episodes, the relationship between control and creativity, and the integration of podcasting with writing and coaching work. Tim explains how the podcast serves as both an outlet and a tool for building content across platforms like YouTube and LinkedIn. There’s a recurring theme of redefining success, with reflections on audience size, personal growth, and the impact of letting go of expectations.
Takeaways
Passion and discipline in creative work — Staying consistent with a long-form podcast over six years requires both intrinsic motivation and structured systems.
Spiritual foundation and calling — The podcast began with a directive to share personal stories, rooted in a spiritual sense of purpose.
Redefining success — Personal hardship and shifting values led to a reevaluation of what constitutes meaningful achievement.
Homelessness and recovery — A journey from living in a mansion to being homeless influenced the depth and direction of the content.
Audience clarity — Over time, there was a realization that the audience consists of mature, critical thinkers rather than the masses.
Content repurposing — Long-form conversations are mined for short clips and articles to extend reach on platforms like YouTube and Medium.
Use of systems and strategy — The production relies on detailed checklists and project management tools to maintain quality and consistency.
Role of the podcast in coaching — The podcast supports coaching by offering thought leadership and lightly integrated calls to action.
Illusion of control — There is acknowledgment that striving for control causes stress, and much of the journey involves releasing that illusion.
Fiction writing as expression — A novel emerged from the same journey, written to reach men reconsidering the meaning of success.
Contemplation of stopping — The work continues only as long as the speaker feels nourished by the conversations; there’s comfort with the idea of ending when the interest fades.
Branding reflections — While the podcast title “Seek, Go, Create” is occasionally reconsidered for discoverability, it remains due to its deep personal significance and consistent branding.
Resources
SeekGoCreate.com — Tim’s website for the podcast and related content.
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.
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.
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!
No one gets everything right in their first few episodes (or even after 100 episodes). Looking back, what’s something you used to do—or believe—that you’ve completely changed your mind about?
~ Asked by the LLM(1)
By far my biggest mistake was chasing perfection.
It’s subtle when simply improving as one does more work, tips over into chasing perfection. Improvement is fine, but it’s not the reason why I’m making podcasts. I first had to figure out my reasons for podcasting, then it became easier to see when an improvement was fine, and when an improvement was an unnecessary detour. (Perfection, after all, can be hiding from the actual work.)
For me, an example of chasing perfection went like this…
In my initial recorded conversations, I first paid-per-minute for a human-done transcription. (It was 2017.) Then I printed the entire transcript. Then I reviewed the audio with the transcript as a guide, enabling me to keep track of the larger themes and story-arc in each conversation. Then I was annotating the transcript for various editing possibilities. Finally, I passed the editing off to another person (a paid, team member) that I was working with to create the show. Today, of course, this can all be done much quicker and with little (if any) actual cost.
Eventually, I realized that for what I’m trying to accomplish there’s no need to edit. So all that getting better editing, or doing it for less cost, turns out to be the wrong thing for me to be doing. Chasing improvement was hiding. Chasing perfection was an error.
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(1) I’m working with an LLM instance which has access to everything I’ve written about podcasting, and all the episodes I’ve published. It prompts me by asking me these questions.
Writing is essentially donkey work, manual labor of the mind. What makes it bearable are those moments (which sometimes can last for weeks, months) when the book takes over, takes on a life of its own, goes off in unexpected directions.
What makes parkour jam spaces unique, and how do they shape the experience of movement, community, and accessibility?
A church, a jam space, and a parkour gym—what do they have in common, and why does it matter?
The empowerment, and the kind of liberation to not care what other people think, does have a limit for some folk, I guess. I love it. I think for me, it’s been great and really powerful. I really like not caring anymore about being bad at stuff in particular— that’s so freeing.
~ Nina Ballantyne (14:00)
The conversation explores the concept of parkour jam spaces, emphasizing how they lack defined boundaries, making them more accessible in theory but sometimes intimidating in practice. The discussion touches on the contrast between structured athletic environments and the open, fluid nature of parkour, where new participants must navigate unspoken social norms rather than physical barriers. The conversation also highlights the paradox of accessibility—while jam spaces remove formal entry requirements, social and cultural factors can still create obstacles, especially for marginalized individuals.
The discussion transitions into broader themes of public space, inclusivity, and the intersection of parkour with community projects. A significant portion focuses on an initiative to purchase a historic church in Edinburgh and transform it into a community space. The conversation reflects on how physical spaces carry different meanings based on personal and cultural perspectives. The comparison between parkour jam spaces and community-driven spaces like the church highlights the broader theme of reclaiming and redefining public areas for collective benefit.
Takeaways
Jam spaces and accessibility — The absence of a physical boundary in a jam space doesn’t mean it’s truly open to everyone, as social and psychological barriers still exist.
The role of unstructured environments — Unlike traditional sports with defined spaces and rules, parkour operates in public spaces, leading to unique challenges in inclusivity and belonging.
Marginalized groups in public spaces — Individuals who are already scrutinized in society, whether due to gender, race, or body type, may experience additional barriers when engaging in parkour.
The impact of early experiences — Many practitioners come into parkour without formal athletic backgrounds, which shapes their approach to movement and learning.
Cultural norms within parkour — Different communities have their own customs, such as specific greetings or approaches to training, which can be both welcoming and exclusionary.
Reclaiming public space — Parkour’s ability to redefine urban spaces extends beyond movement, influencing broader discussions about who has access to and control over public areas.
Indoor vs. outdoor training — While some practitioners prefer the spontaneity of outdoor training, indoor spaces provide a structured environment that can be more accessible to beginners or marginalized groups.
The intersection of parkour and community work — The discussion about repurposing a church into a community space parallels parkour’s ethos of adapting and reclaiming environments.
The perception of churches as public spaces — Depending on cultural background, a church can be seen as either a welcoming community hub or an exclusive, imposing institution.
The role of storytelling in community building — Sharing experiences and narratives within parkour fosters a sense of shared culture and belonging.
The importance of understanding different motivations — Some practitioners seek challenge, while others prioritize playfulness, relaxation, or self-expression.
The limits of parkour’s inclusivity — While parkour prides itself on being an open and adaptable discipline, social realities can still make participation difficult for some individuals.
Resources
Access Parkour — A parkour organization in Scotland that provides training opportunities and works on community-focused projects.
Leith St Andrews Trust — The charitable organization working to purchase and repurpose a church in Edinburgh as a community space.
Coach Europe — A parkour coaching conference that brings together practitioners to discuss teaching methodologies and movement philosophy.
Richard Marshall — A parkour practitioner and speaker who discusses the importance of play in movement training.
Many podcasters start out assuming success looks like big audience numbers, sponsorships, or industry recognition. But in your experience, what’s something that actually matters way more than people think—or something people chase that turns out to be irrelevant?
~ Asked by the LLM(1)
All advice is useless until you first figure out why you are creating your podcast. There, that’s counterintuitive and contentious.
I’m not saying you must have a deeply considered, philosophical reason. But you must start with some reason for your podcasting. It can be any reason at all that you can imagine.
Because any useful advice must take your reason for podcasting into consideration. What’s the best mic? Should I publish on a schedule? Does the quality of the audio matter? What about show-length? …format? …social media? Even, what’s something that actually matters way more than people think? It depends.
All advice is going to be wrong if it doesn’t take your reasons into consideration. This applies to everything in life. Get up early? Stay up late? Avoid gluten? Read more? It depends.
Certainly you can change and refine your reasons. When you do that you can get real power from all that advice. If you get advice towards one course of action, but you don’t want to do that, then you need to dig into your reason, or you need to dig into that advice. One of them needs to be updated.
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(1) I’m working with an LLM instance which has access to everything I’ve written about podcasting, and all the episodes I’ve published. It prompts me by asking me these questions.
When it comes, this will be the fourth message received from Alsafi in my lifetime. Few have timed their career so fortuitously. The first came when I was a child. The second came just weeks after I joined the Intercivilizational Observatory’s San Francisco office, and I wormed my way onto the analysis team. The third came the year I met Cassio, and I was doubly lovestruck. Still, I was reading responses to questions another generation had asked. But now, a full 39-year round-trip after I began, I’ll finally get answers to my questions. Ones from my youth, maybe, but they’ll be mine. After all this time, I’ll finally be In Conversation.
This piece of fiction is one of those things I start skimming, thinking “should I mark this for later reading?” and then read it all the way through. So of course I recommend you do too.
I find tremendous value in considered conversation. Usually, a conversation about the weather isn’t such a valuable opportunity. But this conversation about “weather” is really about what are the limits of what can be considered a conversation… is understanding required for it to be a conversation? Or is simply trying to understand, enough?
Writing issues of 7 for Sunday has become familiar (not to be confused with “easy”). I have a checklist which I use when I’m writing each issue. It’s as much for scratch-paper thinking, as it is for ticking off completed steps. Originally, the checklist had a lot of notes about formatting, what goes where, how to typeset the specific parts, image sizing, etc. all nuts-and-bolts stuff. As I’ve modified it, it’s now mostly signposts and I use it to celebrate each phase of the issue’s development.
Today, I was down to just a couple of these checklists and I hit print. How many copies? Without hesitation I printed 20—because that would be checklists through issue 150. It simply struck me as interesting that I’ve moved beyond “should I continue” and even beyond “can I continue” for this neat little weekly missive that I enjoy putting together.
Podcasting is full of friction—technical issues, editing headaches, guests rescheduling, creative blocks. Some podcasters try to eliminate every obstacle, but sometimes, friction is where the best ideas come from. Where do you think friction helps creativity versus just getting in the way?
~ Asked by the LLM(1)
This question leads me to the idea of “simple.” I often ask myself: What is the simplest thing that could possibly work? Because that’s the idea I should start with. It requires no effort for me to imagine adding complications. Keep it simple stupid (KISS) is an adage because it is a valuable compass.
For me then, friction is a sign that there might be a simpler way to do something. It might be quite complicated and involve a lot of work to switch over to a simpler way of doing things, but it’s only when I’m directly considering the friction that I can understand the payoff of such effort.
On the other hand, there may not be a simpler way to do something. ¯\_(ツ)_/¯
In either case, it’s the friction which prompts me to apply mental effort to search for that simpler way. Creating meaningful work (podcasting in this case, but anything really) requires some amount of effort. Friction is a clear sign that—at the least—I’m actually doing the work.
I suppose that does mean that friction helps creativity. Is friction necessary for creativity? No. But it’s definitely not the enemy of creativity.
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(1) I’m working with an LLM instance which has access to everything I’ve written about podcasting, and all the episodes I’ve published. It prompts me by asking me these questions.
For greater happiness, a better way to live employs what behavioral scientists call metacognition. This simply refers to an impartial awareness of your emotions, a capacity to see them as important information but not as a mandate for any particular behavior. Good ways to practice metacognition include Vipassana meditation, journaling, and prayers, which shift the experience of involuntary emotion into the realm of conscious attention.
There are endless methods: Write that angry screed, but don’t send it (put the paper-letter in a drawer, or save the email as a draft.) Count to 10 before saying or doing anything when you are angry. Name your feelings, internally or out loud (“I’m a feeling angry.”) Viktor Frankl’s comments on the space between stimulus and response. I don’t have a specific takeaway, other than that I’m simply reminding myself of all these options which I’d like to continue to practice using more often.
These are serious fears. But they’re not the real fear. Not the Master Fear, the Mother of all Fears that’s so close to us that even when we verbalize it we don’t believe it. Fear That We Will Succeed. That we can access the powers we secretly know we possess. That we can become the person we sense in our hearts we truly are.