Remember we employed a visual to help us understand this. We said that the Dream is like a tree in the middle of a sunny meadow. The tree casts a shadow.
I find Pressfield’s metaphor to be striking. The tree in the meadow casts a real shadow. I was struck by the layers in this metaphor: light and darkness, the singular clarity of lone tree in an open space as a symbol of a life’s purpose, the proportional relationship of the larger the tree the larger and darker the shadow, and that one’s ability to avoid or at least escape the shadow is a choice we make.
By extension then, if one attempts to nurture multiple callings, visions or projects, one has multiple big trees. That’s at least a copse of trees whose shadows merge together creating something much more significant to avoid or escape from.
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.
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?
We don’t want reactions. We don’t want first impressions. We don’t want knee-jerks. We want considered feedback. Read it over. Read it twice, three times even. Ponder. Sleep on it. Take your time to gather and present your thoughts — just like the person who pitched the original idea took their time to gather and present theirs.
Sure, a little bit of snark. The point stands. It’s so easy to raise the first objection that comes to mind. (As if that hadn’t already been thought of.) What’s harder is to read, reflect, and then put in some actual effort to reply. This level of engagement certainly isn’t necessary in every interaction, but there are many interactions that would be vastly improved by it.
I’m in a continuous over-analysis loop. Some aspects of podcasting are harder than I feel they need to be. I try to imagine ways to make whatever-it-is easier. But it will never be that all of it is easy. Why would I do it, if it was all easy?
I think that’s my over-complication: I spend too much time trying to make things easier.
Do the work. Do more of the work. Do still more of the work.
It’s great to assess one’s work. But I need to not get lost in over-thinking. It’s vanishingly rare (for me, these days) that anything is actually “wrong” with the work. Don’t over think it.
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.
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.
In summary – I believe you should be publishing something to the web, maybe an esoteric spreadsheet, perhaps an open source javascript library, a deep dive into semantic analysis of your favorite author? Who knows? Publish, but keep it weird and humble.
It’s probably confirmation bias, but I definitely agree with this sentiment. The internet enables an endless array of things. For me it’s mostly about me being enabled to share what I’m creating. Weird? Definitely. Humble? …uh, okay okay still working on that.
This point about presence is one I’ve not seen made before about ‘mise en place.’ I’ve always focused on the preparation part, and how that then makes it possible to do great work (under press, amidst chaos, etc.) The idea that you can set yourself up for being present is quite enticing.
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.