Chief Change Officer
#123 From Curtain Calls to Business Cases: Waverly Deutsch’s Path from Theatre Historian to Chicago Booth Professor
Thu, 26 Dec 2024
Kicking off our “Love and Logic” series, Part 1 features Waverly Deutsch, who shares how her career and life choices have been shaped by a blend of passion and reason. This episode unpacks her journey, with the following installments focusing on her impact at Chicago Booth and her entrepreneurial coaching with WyseHeart Advisory, driven by “tough love for entrepreneurs.” Why Waverly? Known for her direct approach, Waverly has earned the nickname “the Simon Cowell of Chicago Booth,” but with a key difference—her feedback always comes with actionable solutions. She might point out, “You just talked for ten minutes and we have no idea what you do,” but she’ll also say, “Here’s what we can do to make it crystal clear.” That’s the hallmark of her coaching—honest, constructive, and deeply invested in your success. Key Highlights of Our Interview: A Love for Theater and Logic “I fell in love with theater and acting as a child. My mother and I would go to the theater together—it was a special time for us. At the same time, I was good at math and logic puzzles. I ended up with two majors, one in theater and one in computer science. They were separate disciplines, but in my mind, I was always bringing them together.” The Gut-Driven Leap “At 29, with a fresh PhD, analysis didn’t guide my career move. Joining Forrester was pure gut instinct. I saw it as a chance to dive back into technology, learn from brilliant people, and expand my horizons—no spreadsheets, no market evaluations, just a leap of faith.” Academia or Impact? The Career Crossroads “Graduating with a PhD in theater history during a recession, teaching jobs were scarce. Colleges were cutting back on theater programs, and the research focus in humanities felt too esoteric. I wanted to do something more contemporary, more impactful.” Burnout and Breakthroughs “After nearly eight years at Forrester, experiencing explosive growth, an IPO, and 60-hour weeks, I needed a reset. By 1999, I was ready for a new direction and decided to approach my next move more strategically.” Empathy for Everyone “Emotions aren’t just a ‘women’s thing.’ I’ve sat with many men who’ve cried during challenging discussions. The key is understanding that emotions are human, not a weakness, and they have a place in even the most logic-driven conversations.” _________________________ Connect with Us: Host: Vince Chan | Guest: Waverly Deutsch ______________________ --Chief Change Officer-- Change Ambitiously. Outgrow Yourself. Open a World of Deep Human Intelligence for Growth Progressives, Visionary Underdogs, Transformation Gurus & Bold Hearts. 6 Million+ All-Time Downloads. Reaching 80+ Countries Daily. Global Top 3% Podcast. Top 10 US Business. Top 1 US Careers. >>>100,000+ subscribers are outgrowing. Act Today.<<< --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.18 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 1.5% Podcast.Top 10 US Business.Top 1 US Careers.>>>170,000+ are outgrowing. Act Today.<<<
Chapter 1: What is the focus of Waverly Deutsch's journey?
Hi, everyone. Welcome to our show, Chief Change Officer. I'm Vince Chan, your ambitious human host. Our show is a modernist community for change progressives in organizational and human transformation from around the world. Ten years ago, during the summer term of the Executive MBA program at Chicago Booth, I had the pleasure of meeting today's guest, Waverly Deutsch.
She taught one of the standout courses in the Executive program called Building New Ventures. In just a moment, I'll let Waverly introduce herself. But first, I would like to share a memorable memory that really sets her apart.
Throughout my extensive MBA studies at both Yale and Chicago Booth, where I completed the full-time and executive programs respectively, I've sat through countless lectures taught by highly intelligent scholars and well-experienced practitioners. Yet, Waverly is the only professor I've encountered who dared to use the word love in a business school classroom.
In the field of business education, dominated by discussions of numbers, strategies, formulas, and models, all the logical stuff, the concept of love has never surfaced in any curriculum or textbook I've come across. Yet, she bought it into our discussions on angel investing.
It makes you wonder, how does love fit into building a business, advancing a business career, and fulfilling our life's legacy? With that in mind, I've put together a three-part series called Love & Logic, featuring Waverly as our special guest. She will be sharing and exploring from three perspectives how the intricate balance of love and logic shapes our career decisions and life choices.
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Chapter 2: How does love intertwine with business education?
Today's episode zooms in on Waverly's personal journey, the love and logic that have guided her career path and experiences. In our next episode, which is about her being a teacher and expert guide, we'll dive into a major chapter of her career, 22 years at Chicago Booth.
There, she taught and coached a sharply focused group of highly logical talents, all deeply engaged in the passion for innovation, change, and entrepreneurship. From that structured academic environment, she has transitioned to her current role as a coach for a more diverse group of entrepreneurs. In the third part of our series, we'll come full circle and focus back on Waverly herself.
She's now more than a coach. She's an entrepreneur herself, actively building her own new venture. is a fascinating mix of her ever-changing experiences. Good morning, Wavefully. Welcome to my show. Good morning, Vince. I'm thrilled to be here. Usually, I kick off an interview with a little introduction about my guest. Today, I'd like to switch things up a bit.
Chapter 3: What unique combination shaped Waverly's career?
I was browsing through the website of your new venture, Wiseheart, and a specific sentence really stood out to me. It said, as a young person, I had an enormous love for the theater and a passion for logic. Love and logic, what a fascinating combination. So Waverly, can you unpack that for us? Tell us, who are you really at the intersection of these two worlds?
Wow, what an interesting question to start with. I think a lot of people gravitate towards one or the other. And what I mean by that is we are taught that we have a right brain and a left brain. Our right brain is rational and our left brain is emotional. But people have both sides of their brain and they're using both sides of their brain. So for me, the way this manifested as a child
I fell in love with theater. I fell in love with performance. I fell in love with acting. I fell in love with theater. My mother and I would go to the theater together. It was a very special time for us. But at the same time, I was good at math and logic puzzles. And people would say, were you good at computer science? You have to remember, I'm fairly old.
We didn't have computers when I was growing up. As I was approaching my college years, And really thinking about what I wanted to do in college. I had done so much in high school with theater and so much in high school with many other subjects, economics, psychology, math. I went to an excellent high school. And I was approaching my college years thinking I still want to do theater.
But I recognize in myself that I don't necessarily want to have the kind of career where you have a job and then you don't, and then you have a job and then you don't. That I wanted something that would create stability for me. So I approached college saying I'm going to do a dual major in theater and business.
And ultimately what happened was I had a conversation with a guidance counselor in my freshman year of college. He said, don't do an undergraduate business degree. Companies want MBAs and MBA programs want to teach you their methodology. Do a deep dive into something that's related to business that you can leverage in the business world, but would also be
a good foundation for going to business school so I said okay I will take the computer science class for computer science majors instead of the one for business majors and I will check out computer science and again being a child of the 70s and 80s this is the very early 80s I had not been exposed to computers before and I fell in love with the logic of computers
and how it was incumbent on a programmer to break something down into its fundamental elements to teach a computer how to do it. That's programming. I ended up with two majors, one in theater and one in computer science. Computer science was starting to have an impact on theater. I had to learn how to program a lighting board, for example.
But they were really very separate disciplines that I was bringing together in my own life and in my own mind.
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Chapter 4: How did Waverly navigate a male-dominated field?
I was accepted by my male colleagues and I thrived. I did very well. You asked a follow-up question, what then took you back to theater? Yep. So I loved computer science and I loved programming, but I'm not a solitary person. I'm a social person. When I was thinking about what I wanted to do after college, I was pursuing a couple of different tracks.
I had the good fortune during college to be awarded twice the Provost Scholarship to teach. And one of the times I taught in the theater department and one of the times I taught in the computer science department, I knew that what I wanted to do was teach. That was truly my calling. And if you think about a marriage of love and logic, if you think about a marriage of theater and computer science,
being able to structure a subject in a way to present it to people, but then to present it with a little bit of theatricality, a little bit of entertainment, a little bit of humor to make it more interesting, more intriguing, more engaging as a subject for learning. This is where these two things came together in me. So as a senior in college, I was applying for graduate degrees.
I was applying for fellowships and I was applying for jobs. And I was offered jobs in the computer science department of ExxonMobil, in the leadership training program of what was then MetLife Insurance, in the computer science departments of Digital Equipment Corporation. But I won a Mellon Fellowship in the Humanities to pursue my PhD so that I could teach. That's what took me back to theater.
I really wanted to teach. And I thought that the way to be able to teach was to do a PhD. And I ended up doing a PhD in theater history.
Teaching has always been your calling. But I was wondering, during this journey from PhD to teaching, there's something called forestry. I believe you joined this firm and helped it grow from a boutique into a major institution over a couple of years. You joined as employee 20-something, 27, I believe that's what you told me. So with your calling for teaching, with your PhD degree,
You could have stayed in the university, building your academic career from assistant professor to associate to a tenure professor, a very well-predicted career path. Then what happened in between? We'll talk about Chicago, your teaching career, 22 years teaching careers in Chicago. But before that, let's talk about what happened in the 90s.
Yeah, my career is nothing but an example for twists and turns. It's an excellent question. How do I end up at Forrester? Graduating with my PhD, we were at the height of the late 80s, early 90s recession, and the Baby Boomers kids hadn't reached college age. College enrollments were plummeting. I was a theater historian. That's what my PhD was in, theater history.
And colleges were cutting theater programs. You had to maintain your acting program. That's what students came for. But you could shave down classes like theater history and allow the English department to teach Shakespeare. You could use the English department to cover some of the theater curriculum. There were no jobs.
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Chapter 5: What led Waverly to leave academia for technology?
I could very quickly learn the modern technologies. And I joined Forrester as the first research associate that they had. hired directly. The woman who preceded me had created the position. She had been an admin on the sales side. She created the position of research associate. I was the first person they hired into that job.
I went on to experience a growth company with the entrepreneur, founder, CEO still in place. We were less than $10 million in revenue. We were 20 people. I was employee number 27. There had been a little bit of modest churn, and we went on our rocket ship.
We had hired a new VP of sales out of IBM, and he revolutionized the approach to go to market and sales, and the company took off, and we were the first company to tell people Fortune 1000 chief technology officers, chief information officers, you have to pay attention to the internet. And that was what put us on the map.
We were working in the early days that I joined with their transition from big mainframe computing to client server computing and the PC and the role that the PC would play. And we were establishing ourselves as a leader in technology market research, but it was really our call around the internet that led took Forrester to the public company that it became and is today.
The founder CEO, still the CEO, personal friend, lifelong relationship. But I got to work very closely with him, see his journey, see what it means to scale a company, see what it means to take a product idea and turn it into reality. And that's where I fell in love with the entrepreneurial process.
While listening to you, I felt like we were having coffee together. Your story had me nodding, laughing, and utterly fascinated. You present this blend of strong analytical thinking with a very human social side. Considering your career shifts and external pressures you faced, you mentioned some kind of luck or perhaps karma. It got me thinking.
How aware are you when it comes to making what you call calculated decisions? This ties into our theme of love and logic, the heart and the head. When you reach a critical point in your career path, how much do you lean on your analytical side? I'm not just talking about money or job titles, but evaluating the broader prospects of a position, diving deep into the industry,
How much of it is a calculated assessment? Or perhaps, is it more about a gut feeling that tells you, hey, this is the right move? So, do you consider yourself primarily analytical when making career decisions? Or do you tend to go with the flow? Or maybe you have your own unique approach or system for navigating these decisions. How does that work with you?
I love that question and I think that for me it changed very much over time. The moment in my life, I was 29 years old when I graduated with my PhD, the moment in my life where I had the opportunity to join Forrester, no analysis was involved. No examination of the job, the market size, the career potential, no analysis.
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