Chief Change Officer
#335 Waverly Deutsch: Computer, Broadway, and the Beautiful Mess of Career Design
Thu, 1 May 2025
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._________________________Connect with Us:Host: Vince Chan | Guest: Waverly Deutsch --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: Who is Waverly Deutsch and what is her background?
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, Wayfully. Welcome to my show. Good morning, Vince. I am thrilled to be here. Usually, I kick off our interview with a little introduction about my guest. Today, I'd like to switch things up a bit.
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?
Chapter 2: How did Waverly balance her love for theater and computer science?
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 and 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 with 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 something, do a deep dive in 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.
As you indicated, that was late 70s and early 80s. There must be very, very few females in your computer science class. How did you navigate this deeply man-dominated world?
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Chapter 3: What challenges did Waverly face as a woman in computer science?
One of, sorry, you're saying one of three or four women in the advanced computer science class. Like how many students were in that class?
Anywhere from 20 to 35. Oh, okay. Yes. You're a hundred percent correct in thinking that it was very male dominated. I think today in college classes, in computer science, in STEM, you'll have a higher percentage of women, but it still won't exceed. It won't reach 50% in a lot of cases, but it was 5% at best when I was studying computer science.
I was very lucky in that the head of the computer science department at the University of Pittsburgh happened to be a woman. So I at least had visual role models because, of course, in computer science, most of my teachers were also men. So I did have a female role model to look to when I was a computer science student. I got along really well with the nerdy guys.
I've always had nerdy guys as friends. I have my nerdy side. I'm a science fiction fantasy fan. I cut school in high school to go see The Empire Strikes Back on its very first day in release with my friend Michael, who we called Zonar. I am a nerd, and I got along really well with my nerdy, computer science classmates, I also got along really well.
I have, I don't want to brag, but I have what I think is a fairly well-developed EQ from my mother. I got along really well in theater and I got along really well with my much more artsy feeling theater friends. They were two totally different worlds. They did not overlap at all.
The question of gender, I think, is a really important one in the conversation that we're having because you're talking about love and logic. And very often, love gets attributed to the feminine and logic gets attributed to the masculine. And they have always been a blend in my life. And I fundamentally believe that they are a blend in humanity.
that we artificially separate into, have to be honest, and maybe this is a little too much information for your podcast audience, but I do not comply with gender norms. I never have. I was a tomboy growing up. I am... tall for a woman. I wear my hair very short. I have a deep voice. I frequently get mistaken for a man. I identify 100% as a woman, as female. My pronouns are she, her.
But I have always felt this blend of the masculine and feminine in my life. And it goes right to this question of love and logic. So as a woman who had tomboy characteristics, that's what they would have been called in that day.
Even when I grew up, I'm younger than you by about 10 years. Tomboy was still a commonly used term in my generation. Don't forget, we're now in June 2024. The month of June is the month of Pride. So we are proud of our identities.
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Chapter 4: What led Waverly to pursue a career in teaching?
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 Forrester. 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. But 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 Forrest? 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. And so there were no jobs.
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Chapter 5: How did Waverly transition from academia to Forrester Research?
In fact, it's a little bit pre-bubble. It's as the internet is becoming part of our daily life, we're really using dial-up AOL or CompuServe. I'm having a conversation one night with a friend, and we're out to dinner with my partner and her husband, my friend's husband. We're having this conversation and she turns to her husband, she said, she'd be perfect for Forrester Research.
And I said, all right, what's a Forrester Research? I had never been in the business world. I had never thought about careers in business. And turns out he was an analyst for Forrester. They were a tiny little boutique market research company that looked at the impact of technology change on big business. Their tagline was helping companies thrive on technology change.
So why was this an unbelievably opportunistic moment? I call it luck, karma, fate, the world, just throwing open a door when you need one. If there's one thing a PhD proves that you can do, it's research. That is the fundamental thing that you do, right, as a PhD student. And I had a technology background. I knew how computers worked. I knew how to talk that language.
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 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 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.
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Chapter 6: What pivotal moment changed Waverly's approach to emotions at work?
I love that question. And I think that it, 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.
It was a gut feeling that this was an entry back into the world of technology that I wanted to get into. And a real sense that I could learn a ton from the people I met in my interview process. I could learn about business. It's not that I hadn't been working. I had only been doing a PhD. I actually taught for Stanley Kaplan test prep for 15 years. Was it 15 years? Oh, my goodness.
No, I guess it was about 15 years. From about 18 to about 29, so 11 years, teaching people to prepare for the GRE, the GMAT, the SAT exam. I had been working in the office at Stanley Kaplan. So I had been in the world of business education. But this was an entry back into technology. And there was no, is this the right job for me? Let me look at the market size, due diligence on the company.
This was, I am so lucky to have this opportunity presenting itself to me. Fast forward... I leave Full Rooster in 1999 and I take a much more strategic approach, a much more logical, thoughtful approach to what I want to do next. I see a career coach, get some skills assessments done.
I evaluate some jobs and realize that I don't want any of them as full-time jobs, but I enjoy the people that are coming to me. So rather than take another full-time job after recovering from my stint at Forrester, and I say recovering because we were growing so fast. We were working 50, 60 hour weeks. It was very stressful. We had gone through an IPO.
We had reached 200 million in sales and 400 people in the company all in the seven and a half years I was there. So I took a little break after I left Forrester.
Instead of joining any one company, I decided I would create a small consulting company and work with all of these companies, an independent consulting company, work with all of them at some level or other, large companies on their e-commerce strategy, internet companies on their go-to-market, technology companies on raising funding from venture capitalists. I did...
some consulting to see what kind of work I really liked and to see if there was a company that I wanted to throw in with full time. So I went from, as a 29 year old, leaving one field that I had deep experience in, the academic field, and getting into a new field and literally just taking the leap
based on a leap of faith that I had this opportunity to join this company that I really liked these people and knew I could learn a lot. Fast forward 10 years, almost 10 years, and I'm taking a very different approach to what I want to do next.
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