Craig Constantine

Persistence with Tim Winders →

Published March 31, 2025 · All posts on Mar 31

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.

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What’s something podcasters tend to overcomplicate? →

Published March 30, 2025 · All posts on Mar 30 · Podcasting

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.

Paying attention →

Published March 29, 2025 · All posts on Mar 29

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.
~ Robert Richardson, from Robert Richardson – The Talks

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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.

Out of sight, out of mind →

Published March 28, 2025 · All posts on Mar 28 · Books, 7 for Sunday

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.
~ Ross Andersen, from Stagnant and dull, can digital books ever replace print?

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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.

If you know →

Published March 27, 2025 · All posts on Mar 27

If you know, you know. And if you don’t know… well, let’s talk about shrikes.
~ Doug Muir, from Occasional paper: The Suplex Bird

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I spotted this in RSS, and before I could mark it for later reading, I was halfway through.

Community canvas →

Published March 25, 2025 · All posts on Mar 25 · Society

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.
~ from 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.

Presence with Mary Chan →

Published March 24, 2025 · All posts on Mar 24

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.

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Demonstrate →

Published March 24, 2025 · All posts on Mar 24

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.
~ Michael Lopp, from Ok. So, You’re Failing

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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.

Altered states →

Published March 23, 2025 · All posts on Mar 23

While depressed people are not literally in a different world, they are in a different state of consciousness.
~ Cecily Whiteley, from Depression is more than low mood – it’s a change of consciousness

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Which then leads to the question: How does one change one’s consciousness. In the moment. Right when everything feels hopeless.

Architecture →

Published March 22, 2025 · All posts on Mar 22

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.
~ Tadao Ando, from Tadao Ando – The Talks

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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.