The Entrepreneur Podcast · Eric Janssen and Eric Morse

80. Scott Stirrett and The Uncertainty Advantage

·1 hr 5 min·15 clips

Eric Jansen opens by asking Scott Stirrett to rewind to age 22. Stirrett says that period was full of uncertainty and soul-searching, and that he was still figuring out what he wanted to do. The conversation then follows the choices that came next. Stirrett talks about turning down a job at Goldman Sachs. He goes on to describe launching Venture for Canada. The organization recruits, trains, and supports young Canadians who work for innovative small businesses and startups. Over a decade of building it, he collected a lot of lessons about uncertainty and how careers actually unfold. Those lessons became The Uncertainty Advantage, his book about launching a career in an era of rapid change. The episode keeps coming back to the idea that uncertainty is not just something to survive. It can be strengthened like a muscle. Stirrett points to six pillars in the book that are meant to help with that. The host keeps the focus on concrete choices throughout. One section turns to social media and the comparison trap. Stirrett says the posts that resonate most are the ones that are honest and vulnerable. He contrasts that with the old habit of posting only polished vacation moments and other highlight-reel details. He says that kind of posting can feed comparison without people noticing it. The conversation also lingers on how easy it is to look at someone else’s possessions or status and feel the pull. Stirrett suggests naming that feeling instead of letting it run the show. He asks whether the thing being envied is actually wanted, or whether it is just triggering an instinctive response. The closing stretch keeps that same reflective tone, circling back to uncertainty, perspective, and the comparison trap.

As heard by us

A clear case for treating uncertainty like a muscle.

Scott Stirrett's conversation stays grounded in work, risk, and the cost of guessing wrong. It follows his path from turning down Goldman Sachs to building Venture for Canada, then into the book that pulls a decade of lessons together in The Uncertainty Advantage.

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Why you'd press play

You want a grounded way to think about a career that keeps changing.

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