A few weeks ago I plugged an exceptional podcast:
The Risk of Ruin podcast is exceptional. It’s a gambling podcast hosted by John Reeder aka @halfkelly….This podcast series is special. @halfkelly adds many recorded notes to frame the questions — they are an amazing education in their own right. It’s an outstanding format.
There’s a ton of subtle wisdom that comes through that probably doesn’t land to a novice but rewards experienced listeners. Pixar-ish. He overtly side-steps complexity but somehow conveys novel frames on evergreen topics that have been picked to death. I think I’m jealous of his skill even — which is a strong signal of how much work goes into these. Reward him and listen to it.
Well…John just published:
An Interim Update on the Progress of this Podcast Series (5 min read)
It’s not just a punchy, vulnerable post…it’s packed with insight both in what’s said and in how John reasons through his choices, opportunities and constraints in what is both a creative and commercial project.
A few hooks in the post:
- When I started this podcast I had some general ideas for what the show would be, and the value it could offer to listeners. Those ideas were roughly…
- Over the fours years since the show has launched I’ve made some progress in proving up those ideas. Here are some of the positive signals that I see…
- That all sounds positive, but perhaps you can see the problem?
- A Now What? section filled with tactical questions. Many portable to other types of projects.
- A serious bout of soul-searching aloud
This show is top quality and yet John is undoubtedly at a crossroads. It’s a lot to think about for anyone considering what it takes to make passion projects sustainable. Very early in my writing, Khe encouraged me to simply focus on showing up. Something like if you publish a letter for 20 consecutive weeks you are already in the top 1% (this only sounds like a low bar to people who have the uncharitable reflex of saying things like “I could do that” to everything but actually don’t do anything. It’s a child’s posture and a great filter for spotting immature adults).
Khe’s advice is spot on because it focuses you perfectly on what matters most.
At the start.
But what about once you are past showing up? Once you have traction. Once you are validated by the marketplace. Proven a lot to yourself. When you find yourself 7 tosses of heads…into a chain that requires 15 heads in a row?
That’s an expression I picked up from my dear friend and longtime biz partner Fonz. After 20+ years trading I was probably about 10 heads deep. Put in the work. Had my share of luck and built the trust of good smart people (this is the largest dose of luck — the professionals in my sphere took risks on me. You can be great but nobody is an island. If your bosses and colleagues don’t care or have an interest in your growth, you are in a rotten place and that can easily happen for no fault of your own).
But I was probably another 8 flips from where I wanted to be but I no longer had the will for that path. (So of course the only thing to do was blow up my life and go back to flip #1…I’m kidding but only a little. Heck, when people come to me looking for a sympathetic ear to their desires to bail, I push back hard. Not because I regret it but because I think you need to be incredibly tactical in how you think about it. By pushing back I can stress-test the decision. The last thing you need are enablers. In fact, if you need them you definitely shouldn’t bail).
@halfkelly’s post is a glimpse into the gut check when you find success but have seen, felt, and internalized just how long that chain of heads needs to be.
John, there’s no shame in whatever you choose. I’d support you either way. Everything starts with doing great work and only you can understand the conditions you need to sustain it.