An improv comic, an NHL player and a Fortune 500 CEO walk into a theater … but it’s no joke, it’s big business.

The Second City , the venerable Chicago-based improvisational comedy institution, has quietly built out a surprising side-hustle: Using the fundamentals and tactics of improv to teach corporate executives and professional athletes how to be better communicators.

That division, Second City Works, is not new. In fact it has been around for decades, but the rise of social media, where brands, executives and athletes are all expected to have a presence, has put a renewed emphasis on the skills necessary to succeed in 2025.

An improv comic, an NHL player and a Fortune 500 CEO walk into a theater … but it’s no joke, it’s big business.

The Second City , the venerable Chicago-based

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