B-Side Guys

Mike Leon sits with degrees he doesn’t use, thinking about traveling he didn’t do. “Take A Chance” arrives not as abstract encouragement but as specific testimony from someone who listened to voices saying doctor or psychologist would surely suit him best, who let those voices get in his head, and now recognizes the cost of playing it safe. The Hamilton singer-songwriter, stepping out from behind the drum kit after years touring with his brother Mattie Leon, has crafted a folk-pop reckoning with the difference between living where your heart is and chasing other people’s dreams.

The production keeps things appropriately feel-good for a summer afternoon track, but the lyrics carry more weight than typical motivational fare. Leon’s not just cheerleading about following dreams—he’s documenting the actual mechanics of how other people’s expectations colonize your thinking, how you end up with credentials that serve someone else’s vision of your life. The comparison to Jack Johnson, Noah Kahan, and Vance Joy holds sonically, but Leon brings a sharper edge of regret to the material than those references might suggest.

What makes the track resonate is its refusal to pretend failure is easy just because working is fun. Leon acknowledges mistakes, bad breaks, setbacks—the things we all have—while maintaining that the alternative is worse. His observation that he’s never heard someone criticized for taking too many chances or trying too hard cuts through typical risk-aversion logic. The real danger isn’t failure but watching opportunities pass by while waiting for permission to want what you actually want.

The follow-up to “Living Large” and his successful 2023 debut EP Ticket Home (which landed “Hey Boy” on SiriusXM North Americana and earned a Folk Music Ontario Song of the Year nomination), “Take A Chance” represents Leon establishing his own perspective after years of collaboration. Having opened for Rose Cousins, Elliot Brood, and Wild Rivers across Canada, he’s seen enough of the industry to understand that chasing dreams professionally still requires the same initial leap as any other life change.

For someone who could have traveled round and lived in other people’s shoes to change his point of view, Leon’s chosen to change his point of view by finally stepping into his own shoes. “Take A Chance” documents that transition with the clarity of someone who waited longer than he wanted to and doesn’t plan on making that mistake again.