Part One.

Meet Erin Diehl, a woman who turned “winging it” into a career strategy. She’s the founder and CEO of Improve It, a company that uses improv to help teams thrive.

As a kid, Erin dreamed of being a talk show host. Instead, she became a top podcast host and business leader, blending humor and learning to help others grow. She calls herself a failfluencer—because, in her world, failure isn’t an end, it’s a punchline and a lesson.

In this two-part series, we explore Erin’s journey, her philosophy on joy, and why failing might just be your best career move yet.

Improv Meets the Corporate World

“I didn’t plan to merge improv and business. But during my nine-to-five at a recruiting firm, my nights were dedicated to stages at Second City and ImprovOlympic. Suddenly, I saw how listening, empathy, and quick thinking from improv transformed my work life. The dots connected.”

United We Innovate

“Pitching an improv workshop to United Airlines was a gamble, but it paid off—literally. What started as a passion experiment became a calling when United became my first paying client. Improv wasn’t just for the stage anymore.”

“That feeling of guiding someone toward growth is intoxicating. It’s a high I kept chasing, and the more I taught, the more I wanted to do it. Seeing others find joy became my own source of joy.”

From ROI to ROO: The Objective Shift

“We don’t measure ROI; we measure ROO—Return on Objective. Every engagement starts with a consult call to pinpoint your specific challenges and objectives, ensuring everything aligns with the participants’ needs.”

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