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.

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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!

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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.

There’s a lot of conventional wisdom in podcasting—things like “You have to publish weekly” or “Shorter episodes are better.” But not all common advice applies to everyone. What’s something you’ve found doesn’t actually work or that people should rethink?

~ Asked by the LLM⁽¹⁾

Don’t go alone.

I don’t think people do well trying to do their podcast entirely by themselves. I think this is really a point about creating art in general.

Yes, one definitely should do the work for the work’s sake. (What is referred to as autotelic.) Yes, don’t depend on external motivation and reward. But it is not easy to do that entirely alone.

The easy way is to find others who share your passion. You don’t need to directly collaborate on your work. But you absolutely will be happier if you have others who speak your jargon, do the thing, and face the same struggles.

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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.

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.

With everything you’ve learned from running multiple shows, what are the biggest mistakes or inefficiencies you’d avoid if you were launching a new podcast from scratch? Would you approach production, audience growth, or personal mindset differently?

~ Asked by the LLM⁽¹⁾

Picture me smiling and chuckling nervously because, for more than a year, I have been trying to restart one of my shows. Certainly a big part of my 2024 was reallocated for health reasons, but my attempted restart of the Open + Curious podcast has had many months available to me before, and since. Still, there’s no new show. It’s all about the mindset, for me. I have a too-grand vision of what it should be. I can’t stop seeing all the things it could possibly become, and fixating on getting everything right (my vision of what it should be) from launch day.

However, the best wisdom that I have here for others, is just a repackaging of Heraclitus’s “no one steps in the same river twice” (the flowing water implies the river is different, and the person is also different.)

If someone is actually starting their first show: Once you understand how to do a podcast (it takes perhaps 10 minutes to learn that?) then do not spend more time asking people about starting. That’s hiding from the work. Rather, start. The experience of the doing is what you are actually seeking.

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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.

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.

In your post Having a Clear Why, you highlight the importance of having a reason for podcasting that goes beyond just releasing episodes. Looking back, has your core motivation for podcasting changed over time? Were there moments when your ‘why’ felt unclear, and how did you navigate that?

~ Asked by the LLM⁽¹⁾

It turns out that my core motivation has never wavered. What has changed drastically over the years is why I thought I was doing it.

My “Why” is that I’m curious. I have always been entirely motivated by simple, selfish reasons: I love conversations— in fact I love listening to people. The people and conversations energize me. Podcasting scratches my curiosity itch. (The cure for boredom is curiosity. There’s no cure for curiosity.)

It turns out that when I’m intentional about how I podcast—who I choose to give a platform to, what I steer us towards discussing, how I craft episode notes, titles, and all the countless details—I end up creating pieces of work that other people really enjoy and learn from. Godin’s phrasing, “make the world better by making better things,” nails it.

What’s changed over the years is that I was confused about my “Why”—not that my “Why” actually changed. At various times in the past I used to think, “people like what I’m creating, maybe I can generate some revenue.” But I’m not in podcasting to generate revenue, and if I wanted to do that I’d need to shift from “what do I want” to being clear about what problem I’m trying to solve for others.

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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.

You didn’t plan for a hiatus—it just kind of happened. Stepping away from the routine of podcasting, has it changed the way you see the relentless pace of content creation? Do you feel more or less pressure to keep up with a schedule now? Has this break made you rethink what “consistency” really means for a podcaster?

~ Asked by the LLM⁽¹⁾

Yes, it definitely changed how I look at everything about podcasting. I’ll unpack the reason for the hiatus, so that my take-aways make more sense.

First, in April 2024 we had an unexpected death in the family. Given the scale of things, it was a no-brainer to cancel the several guests who were scheduled for recording sessions. Unfortunately, I over-worked myself for a stretch of days, and that led to my being exhausted and getting sick. In those first days, as I sent “I’m really sorry, but…” messages to the guests, I was thinking about this in a very particular way: This is the right thing to do for these people who kindly set aside time for me.

The first take away from this experience is to be honest and realistic with myself. An unexpected death changed my daily priorities. I’m sick and my voice is crap. I need many weeks to recover, assess, and figure out what I can do in the coming months. In the past, I might have tried to work harder to try to keep juggling everything.

Then in May, a routine blood test returned results which one would prefer to never see. Through June and July, and then into August and September, I worked through a cancer diagnosis. This further “adjusted” my priorities and schedule for the rest of 2024.

The second take away is just having a conversation with anyone is a crazy-awesome gift. And (as I’m getting back to podcasting now, in Feb 2025) to be able to record and share them is just icing on the cake.

As for the grind, consistency, a schedule? No, not any of that. I hope I can hold on to this mindset:

I’m insanely lucky to get to do just one more episode, and it looks like I can do them for years to come. Grinding, being consistent, and sticking to a schedule are all forms of striving for something. (I am a professional even without any of those.) So, nope. No, thank you. I’m not signing up for that mindset again.

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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.

Working with the garage door up, means I’m really just thinking out loud. I’m talking mostly to myself. It’s been a long time since I’ve done an episode for one of my own shows. Obviously the break was begun because of health issues in 2024. In the last couple of months though, I again do have the time. And I miss it. So I shall resume.

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