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.
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.
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.
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.