#335 Waverly Deutsch: Computer, Broadway, and the Beautiful Mess of Career Design

We meet Waverly Deutsch not as a Chicago Booth professor or coach for entrepreneurs, but as a real human navigating career decisions in a world that often asks us to pick between passion and practicality. 

From falling in love with theater to entering computer science as one of only three women in a class of 30, Waverly’s story is one of blending head and heart across every career twist. She shares the real story behind leaving academia for Forrester Research, breaking down in a meeting and still making her case, and learning how to navigate gut instinct and logic without losing either. 

For Gen Xers raised on rules, she shows what it means to rewrite your own—with emotional truth and strategic clarity.

>>Two Majors, One Mindset

“I ended up with two majors—one in theater and one in computer science.”

Waverly explains how her early passions—performance and programming—formed a lifelong blend of emotion and logic.

>>Early Outsider, Early Awareness

“There were three or four women in a class of 30.”

She shares what it was like being one of the only women in computer science, and how that shaped her views on identity and acceptance.

>>Teaching as a Lifelong Thread

“I knew that what I wanted to do was teach. That was truly my calling.”

From undergrad to her PhD in theater history, teaching remained her throughline—even as industries changed.

>>Forrester and the First Real Pivot

“I was employee number 27.”

She tells the story of joining Forrester Research during its startup phase, helping it scale through the internet boom, and falling in love with entrepreneurship.

>>The Crying Meeting

“George, I can cry and think at the same time.”

Waverly recounts the pivotal moment when she stopped hiding her emotions at work—and started integrating her whole self into how she leads.

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Host: Vince Chan | Guest: Waverly Deutsch

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