Mitch Joel
speaker
3,100 appearances
12 recordings
1 series
first heard May 2026
last heard 9 Aug
Mitch Joel’s voice in public audio — every appearance, attributed to the second.
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recordings per month · last 12 monthsRecordings per month over the last 12 months — 12 in all, peaking in Jul 2026 with 4.
Appearances
Let people know where they can find out more about the book and other content you might be creating or where they can best connect to you.
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That's great.
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Well, Marcus, thank you so much for your time.
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Thank you so much, Mitch.
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It was a pleasure.
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Thinking With Mitch Joel · The Value Of Uncertainty With Simone Stolzoff - TWMJ #1037 · 24 May 2026
podcast
Well, hey there and welcome to episode number 1037 of Thinking with Mitch Joel. It's Sunday, May the 24th, 2026. Also, weirdly enough, it happens to be my birthday. This is the show that used to be called Six Pixels of Separation. Let's get on with the conversation. Let's get on with the conversation.
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What if the real danger of uncertainty isn't that we don't know what happens next, but that we've lost the actual ability to sit with not knowing at all? That question sits underneath this entire conversation with Simone Stolzop. He's a journalist, author of The Good Enough Job, and now his new book, How to Not Know.
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Simo writes about uncertainty in a way that feels unusually human, not as a productivity problem to solve, but as a condition of modern life that many of us are increasingly unequipped to handle. We talk about why our identities have become so entangled with work, why endless choice can feel paralyzing instead of liberating, and how modern technology has conditioned us to expect instant answers for questions that don't actually have any clear answers.
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What makes this discussion especially interesting is that Simu isn't arguing for certainty at all. He's making the case that uncertainty may actually be the prerequisite for growth, for resilience, for innovation, and even intimacy. That the goal isn't predicting the future perfectly, but developing enough trust in ourselves to move forward before we fully understand where the road leads. In a culture obsessed with confidence, certainty, and hot takes, this conversation feels like an argument for intellectual humility. Enjoy the conversation.
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I got to tell you, I found out about the book. I know we were supposed to talk about your previous book a couple years back, The Good Enough Jobs, which we might traipse into. But I saw the topic for this book. I thought it was just so interesting. And I get books. I read books from time to time. I just was like neck deep in yours, highlighting stuff. It really struck me. So what I want to do for the context of this conversation is...
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And the ability to get better at dealing with what we don't know became book number two. So I want to talk about the first part, which is, I think it's something we all struggle with. You go out for dinner and someone says, what do you do? And it's the job title. I mean, that is what it is. And I always struggle with that, especially post exit when I sold my business, because now I'm doing four things now.
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And I kind of break into this long diatribe about how I do four things. And some of them are like high yield, low time efforts. Some of them are low time effort. Like, it's just like, I'm always, and then I'll ask, this is crazy. Am I an entrepreneur? Am I, I always struggle with that. And then I think at the core, which is what you're getting at, we struggle with, I mean, is that what I am? Am I just the vocation I chose? So what was that journey like for you? And why are we, including me, thinking about this all wrong?
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How do we deal with uncertainty? The book really talks a lot about why we have this uncertainty in our very mammalian brain and very biological humanity. It's an interesting thing to pull out as something we think about because as you explain in the book, and I'd love your thinking on this,
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we also really need it. Like it's a really important, it's not a bad thing. It's actually a really important thing. And this is what the paradox is of, I think, just consciousness, isn't it? It's these things that are really important, even though we don't really like them. Anxiety would be another one. Like if you didn't have anxiety, like we need anxiety, a certain level of it, obviously. How do you reconcile that? How should we be thinking about this?
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And so the more tolerance we can build, the more gracefully we can adapt to whatever might come our way. I want to tangent a little bit and get your feedback. And I'm hesitant to do it because it's become somewhat political in our day and age, which is I live in Canada, you're in the US. And culturally a year ago, it probably wouldn't be the type of conversation we're having now, just the nature of politics. But I think it's still interesting. I'm an entrepreneur. I've basically always been an entrepreneur.
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And I spent a lot of my time in the States. And when I came back to Canada, there's a bunch of sayings we use up here. Things like we have small poppy syndrome. We don't like to celebrate our wins or promote our wins. When a company has an exit here, you usually don't know the number. It's kind of private. We don't have a high level of entrepreneurship, but we have these conversations all the time. It's interesting now because it's way more on the radar for everybody up here, building a country of entrepreneurs, as my friend Harley from Shopify would say.
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And what you would net out at before the politics is this idea that Canadians are much more risk averse than our American friends and family. And so what was interesting when I was reading your book is I was thinking about this idea of, oh, we have a higher risk averse as a culture. That's also super fascinating that you have cultures where Seth Godin would always say the safest thing you can do is be risky and the riskiest thing you can do is be safe.
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It's a crazy thing to hear and it's super related to what you're saying.
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And by the way, the more traditional institutions would never take that risk. Like there's an institutionalization of this. Like a bank would never act as a, now they might because they see the wins, but historically they wouldn't. Totally. Yeah. I remember I was interviewing an investor for the book and he said, the best deals are always contentious for my team.
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You reminded me of a doc, mini documentary I saw about the making of U2's album, The Joshua Tree. Have you seen this or not? Because Brian Eno is intimately involved in this because he was the producer. Yeah. And what they were talking about, and I'm not sure if it was Brian or the co-producer, which was Paul Lanois.
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Showing 3041–3060 of 3,100 · page 153 of 155
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