Executive Coaching At The Crossroads Of Creativity And Leadership With Jessica Wan

Executive coaching takes on a new dimension as Jessica Wan — executive coach, classically trained soprano, and former marketing leader at Apple, Smule, Magoosh, and the San Francisco Opera — shares how she’s built a career at the intersection of business and creativity. In this conversation she reveals her formative “flashpoints,” from growing up in immigrant communities to earning her MBA at Berkeley Haas, and how those experiences shaped her Ampersand Manifesto podcast and upcoming Ampersand Summit. Jessica offers fresh insights on integrating multiple identities, leading with authenticity, and using diverse experiences to elevate leadership, spark innovation, and sustain long-term success.

---

Listen to the podcast here

Executive Coaching At The Crossroads Of Creativity And Leadership With Jessica Wan

It's truly my honor to introduce you to my guest, Jessica Wan. Jessica is an executive coach and former marketing executive with twenty years of leadership experience at Apple, Smule, Magoosh, and the San Francisco Opera. Quite a combination. A classically trained soprano, Jessica has led a dual career for the past two decades, performing opera and musical theater in the San Francisco Bay Area.

She's the creator and host of The Ampersand Manifesto podcast, where she interviews leaders who straddle the corporate and creative worlds. She holds an MBA from UC Berkeley Haas School of Business and earned dual degrees in music and product design from Stanford. Her third ampersand is mom to a nine-year-old.

---

It's truly a pleasure to welcome you to the virtual campfire.

Thank you, Tony. It's a pleasure to be here.

I am so aligned with what you speak on, the things that you're passionate about. I'm just thrilled that we have this opportunity to connect here. We're going to have a lot of fun. We also had the pleasure of collaborating on an article for Fast Company that we both really had a lot of fun doing. That was cool.

It was such a joy. Thank you for inviting me to do that with you.

Childhood Flashpoints & Ampersand Roots

Of course, and more please. We'll do some more of that. As we do on the show, we explore people's journeys through what we call flash points. Flash points are the moments in your journey that have revealed your gifts to the world. In a moment, I'm going to turn over to you, and I'm going to have you share what you're called to share. You can start wherever you'd like, and we'll pause along the way and see what themes are showing up. How's that sound?

That sounds great.

I'm so thrilled. I cannot wait to hear all of the different, interesting, and present moments along the way that we're going to explore. Take it away, my friend.

I'll start with a flash point that really is a flashback. I'm maybe 5 or 6 years old with my parents. I was an only child. I was with my parents a lot. They were my best friends. I grew up in Canada and in central Ohio, where, at the time in the ‘80s and ‘90s, there actually weren't that many immigrants from China or Taiwan. We're all ethnically Chinese, and they grew up in Taiwan. When they came to North America, like many immigrant families do, we found the people who had made the same journey.

This flashback is in a community room of maybe a church or a school, and it's a Sunday night, and there's ballroom dancing. This Chinese American community of central Ohio did ballroom dancing, karaoke, Chinese choir, and line dancing. Since I was an only child, I just went along for the ride. When I got to be a teenager, if on the ballroom dancing night, some uncle's wife was sick or something, I would sub in, and that's how I learned how to ballroom dance. When I think back to my childhood, the seeds and sparks of ampersand were absolutely there already.

My mom was a stay-at-home mom, but later got into the retail business. She sold jewelry, and that was very much her day job, but she was such an artist and a culture maker within her community. Whether that meant hosting parties or making sure that we were all learning about Chinese culture and arts. My dad was a chemist, or still is a chemist. He was the principal of the Chinese school. He also sang in the choir. They were just very active in not just building their careers, but building a life for our family and also for the community.

From Instruments To Opera: A Musical Revelation

It seems an amazing container to grow up in, if you know what I mean. It's a sense of passion for their particular crafts, but also this idea of wanting to see that you're exposed to many things. I just love that story that you shared because oftentimes we don't get that experience of getting out and spending time with adults as kids and seeing what they're like, but also engaging with them. You get to grow up fast, but also, you get an experience of what it's like to be in those circles. As always, the seeds are planted early for who we are in the future. I love that you went in those early days to find those seeds. Thank you for sharing that. What happened next?

I started piano lessons around age five, and this is pretty common, especially in Asian families, to play the piano. I think that music really was my first channel for being an achiever. I think academics as well, but music in particular. When I think back as a child, I did enjoy it, but I think what I enjoyed the most was actually the achievement and the positive progression and the moving on from book one to book two to book three, and doing some competitions and things like that.

I started playing the violin in fourth grade and then the oboe in sixth grade. It was like the more instruments you accumulate, the more that your musical knowledge and breadth just builds on itself so much that when I got to college and I got placed with a roommate who was already an opera singer, we would do these musical theater duets with each other, and we both played piano. I think she was self-taught, and I had played for many years.

We'd sing these duets, and she introduced me to this whole canon of musical theater. One day, she said, “I think you should audition for my teacher and take classical voice lessons.” I thought, “Sure, why not? That sounds fun.” Little did I know, I went into college thinking, “I'll probably find what I should major in, and I'll minor in music.

That'll be easy because I want to take all the classes anyway.” I ended up majoring in music. I came in thinking oboe would be my primary instrument. I did play all four years, but voice became my primary instrument. My parents, who had nurtured so much of the arts in me. They were pretty surprised because they didn't really know about Western classical vocal music.

I remember at my senior recital, my mom said she drank 4 or 5 cups of coffee because she thought she would fall asleep. She was on the edge of her seat and riveted. It's so interesting because a lot of parents, and even I as a parent now, want to expose their kids to so many different things and see what sticks, and you really cannot predict. I don't think my parents could have predicted how much this music thing would stick with me.

I love that they actually foster that because again, I think there's something that's challenging about the thought of going into the arts or having them even go into music. Most people are afraid of what a business, what a career will I have? How will I make a living and all that? I'm just so fascinated that this is the path that you are following.

When you had the safety path of the oboe, it was the one that you were more inclined to, but then the voice became something that you leaned into. I do have a question around this range of musical instruments and leaning into voice. Is it easy to add new instruments to the portfolio, or does each instrument have like a different language that it has to play with?

It's absolutely both. I think because I was already pretty proficient on piano and violin, they basically handed me the oboe and said, “This is a really hard instrument, but you already have a background, so please play this.” In David Epstein's book, Range, there is a whole chapter about these women. I think they are nuns who are trained in three or more instruments, and how that really prepares them to pick up any other instruments.

In high school, I also played bass drum in the marching band, because oboes don't march. I picked up ukulele and guitar. I think having it really is music is a language. When I was a kid, it was really a channel for achieving and then also building a network of friends and community, and band and orchestra, being very social.

I think it was really in college where I discovered how much I loved singing because it is language, it's poetry, lyrics, and music. My path to becoming a classical singer is actually pretty different from most of the singers I know. A lot of the singers I know came in through the church tradition or sang in choirs. I was fully playing instruments. I'm really grateful for first being an instrumentalist who then discovered singing as an instrument.

Singing is a language: poetry, lyrics, and music.

I'm sure there were some advantages to that because of the idea of the range of tones that needed to be put in place. Opera is like a whole different beast, I think. There's singing and then there's opera. I think of that as just something that people train most of their lives to get into this space. The discipline that it takes to get really good at opera is a lot. Talk to me a little bit about that for a moment.

I've now been studying with my voice teacher, Susan Gundunas, for over twenty years. I go to lessons. It's every other week. I am constantly learning, and I'm constantly humbled, and I'm constantly working on things. I do think that my technique and skill are better than they once were, but it's also, like you said, a lifelong journey. It's a lifelong endeavor. There is no point at which you're like, “I'm done.”

I've gotten to the end.

I've learned everything about music. I possibly could. Because your instrument is your body, that changes when I was pregnant with a baby. When I hit my 40s, that changed. The technique that I learn is very much about really healthy aging. How do you keep your instrument healthy? How do you keep singing so you can sing well into your ‘80s or ‘90s? Little did I know when I started in my twenties that it would really be so sustainable and such a lifelong companion.

Well said. I want to shift gears in a moment, but before we do, I just think there's something about this, which is like how much that is a mirror of life. This idea that like taking care of your instrument, much like being a coach, like you have to continue to think about, “I am the body of work and I have to make sure that I'm taking care of and honing my instrument all the time so that I can show up with the power and energy that's going to be serving the people I work with,” right?

Thank you for drawing this parallel. I think it is in many ways similar to coaching and similar to other practices or disciplines that people have.

The MBA Accelerant: A Transformative Flashpoint

I think that's when you think about multidimensional thinking or people who are ampersands, it's a lot of things that we need to be able to pull from one end of our lives into others. I think having that ability to say, “I've gone deep in this area, but what I've been able to do is take that depth in here and bring it to another part of my life.” I think that's where the true power of having multiple passions and multiple identities is really powerful. It allows you to bridge between two different worlds. Which is where we're going to go next. I'm sure of it, but I want to hear what the next flash point is that you want to share.

There have been years in my life where those particular years felt like accelerants for me. One of those years was 2007. To set the scene, I was working at the San Francisco Opera. I had done marketing for a few years at a design firm. My other side, my ampersand in undergrad, was product design. That's mechanical engineering. I call it mechanical engineering with a twist. Mechanical engineering with art and psychology.

Music: it's a lifelong journey, a lifelong endeavor. There is no point at which you're like, "I'm done.”

I had to take improv for the major, which was awesome. After that, I worked at a design firm and then fell into marketing. I was really good with the people side, identifying needs, and also communicating with the constituents along the way when we were coming up with our designs. After that, I saw that a marketing job had opened up at the San Francisco Opera, and I jumped on it because I wanted to just see the inner workings of this world-class opera company. I was there.

I had been there for a couple of years at that point. At the end of 2006, I got a phone call, and my mom was diagnosed with pancreatic cancer. I flew home, and I was 25 at the time, and that spring was an accelerant in my life. I spent a lot of time with her. I remember calling my then-boyfriend from the hospital, saying, “If we were going to get married anytime, we should just do it.” We did. We planned a wedding.

My mom made it to the wedding. We had a reception in Ohio with all of her friends, and she died on June 1st. Also, at the time, remember being in the hospital in one of those last few days and seeing the US News and World Report magazine and picking it up and flipping to business schools and seeing Berkeley Haas and thinking, “Maybe I should go to business school. I'd love to.”

What a weird thing to have that juxtaposition of the most beautiful relationship of my life ending in a way. Also starting this new path on getting an MBA, where I had never even taken Econ one. I had no business in business school. I think actually this ampersand of music and product design was a great foundation for then learning about all that breadth, learning about how the world works. All of this was just happening at the same time when I was 25.

It's a good time. When I think about it, like when you're at an earlier stage in life and you start to realize, “There is an expiration on life. Although I still have a long runway to go. I still want to make sure that I'm capturing all I can from the time I have on this planet.” You start to make bold moves, and you start to do things that, for most people, may not make sense. For the folks who are, you wired like you are and myself, you start to make these choices that are about, it's about the collecting of dots.

It's not about worrying too much about, “This is how it's all going to map out. I know that the intuition I'm following right now is that these things are going to make sense somehow.” Everything up to that point was also like testing this out, doing this, and these all made sense. They all were following a light that you had, a passion you had. Now it's like how the next thing is going to be something that I feel, just have a spark for. I think that there's something about it that we need to see what happens, and so you do.

The Enduring Value Of Connection & Community

Getting my MBA has given me gifts that are still being given now. The amazing people that I met, the friends I made who I otherwise just wouldn't have known, folks who were focusing on real estate or climate tech. It's just incredible now, being on the other side of it fifteen years out and seeing where people have gone with their careers, really industries that did not exist when we were in school. They are leading those industries and lots of folks who have really lived into their ampersand that maybe they wouldn't have guessed. It's been just amazing to see where people have gone and the journey that they've taken.

It's something that's the endorsement we need to have for, like, going to a master's program, things like that. Don't worry too much about the specifics of what you're studying, but it's really about the ability to create a good connection with other people in the network you build, the ability to start, challenge your thinking.

When you leave these programs, the wonderful thing is that you're able to see the world a little differently. You have a network of people who've gone on the journey with you, who then become part of that exploration path with you. It's really an interesting thing. Whenever people ask me, “What did you learn in your MBA?” I'm like, “I learned a lot of things.” The most valuable thing is that it's about the importance of connecting and building relationships that last.

I will just put one footnote in here. It's just acknowledging privilege around how the financial decisions are made. I have friends who have student debt still from business school. I think that's a very real part of it. Lots to consider. If it is available to you, I'm a big fan of broad-based education, learning together, and being exposed to lots of different areas and types of people and perspectives, because I think that really can help you find yourself in all of that.

I love that you bring that in because first of all, just the idea that not everyone has that available to them, but also, there are alternative paths we can take. It's like, if you don't have the opportunity to go to something like this, you can create your own path to making this happen. That's what we need to do more of in the world, especially now, is create paths to connection, ways that we can connect with other people like us.

We want to find a sense of belonging with a community of people who see the world not the same way, but who have the desire to explore the world in a similar way. I say that because multi-dimensional people, or the ampersands in the world, want to see. I don't want to just look at finance and the same old, same old. I want to see how we can expand the pie, look at things more multidimensionally.

The Ampersand Manifesto: Normalizing Multi-World Straddling

This is really the goal of The Ampersand Manifesto is to acknowledge that people are living these lives where they straddle multiple worlds. It's not just about the paid work part. Many things could be paid for or not, but it's really where you are spending your time and energy. I think for a long time, these stories just weren't talked about or normalized. Our goal is to really elevate these stories, amplify them, celebrate them, and let people know that you are not alone.

If you are an engineer who is also choreographing dances, like there are other people who are like you and who are invested in left brain, right brain, or just bringing these different fields together and being able to see things from a level up, connect those dots, and find new ways of thinking. This is when we say innovation, this is what we're talking about. You cannot innovate from inside your own container. You can only innovate if you are bringing in ideas, ways of thinking from other disciplines in other areas.

You can't innovate from inside your own container. You can only innovate by bringing in ideas and ways of thinking from other disciplines and areas.

I guess to double click on that is to say, “How do you do that?” You do your best when you're in community with other people. The collective effort. If you're just sitting in front of your computer and having a dialogue with yourself, which I sometimes do, there's an element of, you're going to limit the ability of what you can do on your own. You have to be out in the community with other people who are willing to explore, as I said earlier, but let's get back to your story. I want to hear more about some flashpoint moments that brought you into doing the work. Last we left off, you were exploring this path into the NBA, and what happened after the NBA that got you into more of this work, getting into coaching, and what have you.

The MBA, I went in with a few intentions. I wanted to learn the business stuff. I actually was focused on academics. A lot of MBAs aren't, but I was because I did want to learn the business lingo and the econ and finance and all of that stuff. I wanted to make friends and have people who were from different places and paths than mine. I wanted to validate whether I was doing the right thing for me.

I had fallen into marketing. I had about 5 or 6 years of experience doing marketing communications. First marketing research and then marketing communications, a little bit of business development. I went in thinking, “Have I actually been doing marketing the right way? Is there a right way? I need to learn about this.” I took my first marketing 101 class, and it was actually pretty soon in the first few weeks or months that a couple of alums came from Apple to talk about their jobs. I thought, “I've got it. Eureka, I should go to Apple.”

I did. I put all my energy into getting an internship at Apple. I got the internship, and then I worked a little bit throughout my second year of the MBA. I got the full-time offer, and I went to Apple. It was a wild time to be at Apple. This is 2010. I was marketing the iPhone 5 and the iPad 2. This was before iPhones were in China, so we had been working on that behind the scenes. I think it was really interesting.

It was also the first time that I was in the inner workings of this huge company. I got to learn a lot about that. I also got to discover that my preference was a little smaller. I think it was hard for me to be in this place with thousands of people and own a pretty specific piece of it. While it was very exciting and I learned a lot, I wanted to try the startup thing. That's where I went next. I got to lead the marketing teams at two startups. Smule is a music-making app that very much bridges the ampersand.

Magoosh is an ed tech company. In that time, I started managing teams and leading by having more people than just myself. That was a new depth of experience and knowledge, and I loved it. Pretty soon, I realized that all the stuff I was reading and listening to fell in the field of leadership development, team management, and organizational behavior. That area, and while I was still doing the marketing function, I wasn't that jazzed about it, like I wasn't reading a lot of marketing stuff. I thought, “This is interesting. I want to follow this out further.”

From Marketing Executive To Executive Coach: A Career Evolution

I was at Magoosh for over six years, and the company was incredible. We had an incredible company culture, just really, when you think about wanting to go to work every day, wanting to be with the people. It was a really, really fun and impactful place to be. At the same time, I thought, there are so many places that could benefit from some of the inspiration and the magic that we have here. That was a little bit of an impetus. Also, when I left that job, I actually didn't know what was next. I didn't have anything planned.

I had some time to reflect, which turned out to be really great because it took me several months to really get to the realization that what I wanted was to have one-on-ones every day and help people unblock what was blocking them. I thought, “There's a job where you can do this.” It's an executive coach. I can bring my years of experience at different companies and cultures into this work and really provide something of value for a range of leaders in a variety of industries. Even though they are working in different sectors, there's a lot of commonality with the people stuff.

I love that you said it's already cut you off. I just think there's something about being able to work across multiple industries, and also having the lens of seeing the world in many different ways, that makes the ability to be an effective coach really powerful. It's not always like, “I'm going to go deep into being the expert at executive coaching for doctors only,” which is great. There's definitely something about that, but there's also something powerful about being able to work across multiple disciplines and being able to share experiences from very varied experiences that can bring a lot to the table.

I found myself flexing in certain ways. I have a few clients from a more traditional industry. I find that I lean a little bit more into my startup experience, just bringing some ideas into their world that maybe are a little faster, a little more tech-forward. I think that's appreciated. I work with several arts executives. These are executive directors of performing arts organizations.

I know that they value that I understand the performing arts. I'm an artist myself. I've worked in a big performing arts company and also been on the board and volunteered. It's been just wonderful to see how I've been able to have so many roles around the arts. The arts are the core, and I have this many-petaled flower, and now I'm like an executive coach. That's really beautiful.

Navigating Multi-Faceted Leadership In Systems

I love it. You're leaning into so many different things that I think it's now time to really explore them. What is it that you think, as you've coached a lot of different areas, what are some of the biggest challenges people face when they're trying to bring together different identities and things like that? Maybe you want to tap into that for a moment.

No leader is truly independent in terms of all that they can do or say. Everybody reports to somebody. The CEO has the board. The middle management reports up. I think that there is an acknowledgement that you are in a system, and you need to understand what the constraints are, what the freedoms within the system are, and how you are able to affect or instigate change.

For example, if the system's a little bit larger and a lot of the culture is left up to the teams, you might actually have a little bit more room to experiment. Say you're really in a pretty rigid system and culture, then probably that multifaceted leadership has a few more constraints around it. You may need to think about that a little bit more expansively about all the areas in your life that you can live more fully. Just recognizing you're never an island. You're always part of a system.

I want to play with this for a second. I know that you're going to be able to go with this, because it's wired into who you are. This idea that, like, the system, you have to read, how are they playing? Is it how we jazz? Are we classical? How rigid are we sticking to the tempo of where we're going? I may not be using the right terms, but I think there's an element of understanding who you're playing with and how they want to play. Do you have more freedom to improvise, or do you have a little less freedom, and therefore you need to be able to get into the rhythm of what is already being played? Riff off of that for me.

I'm going to push your analogy further. If you think about a symphony orchestra and the conductor's role, as we may think, the conductor is maybe the CEO. I would say a good CEO would play that role. The conductor is there to set the tempo and recognize the interpretation of dynamics and markings that were written by the composer. If everyone in the orchestra starts speeding up, then the conductor has lost control. I think it is a conversation. Leadership is a conversation. There is give and take. Even the conductor does not have the full power to make the sound that they intend because each musician has their own power.

Leadership is a conversation, a give and take. Even the conductor does not have full power to make the sound they intend, because each musician has their own power.

I love that. I think this is something that we have to realize, that no one is fully in control. That's beautiful because in many ways we want to make sure that everyone has a way of guiding the direction where things are going to an extent. We want to make sure that in the end, it sounds good, but we want to make sure that there's some freedom to operate within each role that allows them to craft their own role in the overall orchestra. It does come out sounding good, but ultimately we all can say like, “I did that part,” or I made that particular note or I made that come in, come alive.” I think that's where a really good organization can come out sounding good.

Every voice counts, and if you're playing a wrong note, you can hear that. With an orchestra in particular, if you think about the sound of the strings, it actually doesn't work with one instrument. It works with a section. Lots of musical analogies we can play with.

I appreciate you playing with me on that because that is just a great exploration, because there's a lot that people don't understand about what's really going on in the system. I think the more that we can sit back and look at what's going on, the better off we're going to be.

In my experience, people who are not “in charge” assume that the C-suite folks have it all figured out when they don't, because nobody has it all figured out. Nobody can predict the future. Also, a funny thing that I find sometimes is that leaders may forget that they are in charge. I'll just give a very quick example here.

When I hear a client come to me and they're like, “I have so many meetings on my calendar.” I'm like, “What is your role?” “CEO.” “You can change this today. You can figure out how this impacts the rest of your team if you're complaining about it and you're the leader. I guarantee that other people also feel the same way.” I think that you shouldn't underestimate your own agency. Also, don't assume that anyone has it all figured out because they don't.

Don't underestimate your own agency. 

Lifelong Learning & Embracing The Unfolding Journey

I couldn't agree more. Time has flown by. I feel like all of a sudden, we blink and we're like coming up on time. I want to leave a little space for two things. Number one, what is a lesson you've learned about yourself on this journey that you want to share? Maybe start with that real quick.

As I think about all the places that we have gone today in our campfire talk, one reflection that I have is that I couldn't have figured it out sooner. I don't think I would have known that I would be an opera singer before that flash point. I don't think I would have gone to business school before that flash point. I don't think I would have become an executive coach before that flashpoint. Hopefully, life is long, which means your career is long. Your careers are long, and you don't have to figure it out right away because sometimes it just takes time, experience, and bringing it all together to see what's next.

Staying open to what's around that corner and seeing how the different things will intersect. Now for the last question, which I ask every guest. What are one or two books or more that have had an impact on you and why?

I'll start with nonfiction. The Four Agreements. It has been one that I returned to time and time again. Four Thousand Weeks. I made a huge impact on myself. Big magic. A coworker gave me Big Magic when I was leaving Magoosh and said that it reminded her of the little speech I had given upon my departure. It really helped me. I will say that I am a voracious fiction reader. I love fiction. Remarkably Bright Creatures was one I read this past year.

Who’s the author? Did you happen to know?

Shelby Van Pelt. Remarkably Bright Creatures. I don't want to spoil the plot point, but one of the main characters is not human and is wonderful. I have a thing for books where they're not human. Project Hail Mary by Andy Weir was incredible.

That's a wonderful book.

I read a lot of fiction. I read a lot of multi-generational family dramas, a lot of immigrant stories. That's a full circle from where we started.

It's lovely to hear that. Especially when you think about some of the books where you bring in an element of non-human character, because it allows you to be able to almost reflect humanity back at you and play with that. That's a powerful thing for us to learn from because we're only human.

Actually, there's a great book called The Humans by Matt Haig. I've read everything that he's written.

Midnight Library. That's cool. I just want to start by saying thank you so much for all that you shared. I feel like we're just touching the surface, but thank you so much for sharing your insights, your stories, and just being you. You're just a wonderful human being who is doing great work in the world. Keep doing it.

Thank you, Tony. I enjoyed our conversation and our riffing and jamming together.

More jamming to be had, that's for sure. Before I let you go, I want to make sure that people know where they can find out more about you and your work.

I'm active on LinkedIn. You can find me there, Jessica M. Wan. My website is JessicaWan.com. You can find The Ampersand Manifesto at TheAmpersandManifesto.com. I will put a plug in. We are having an Ampersand Summit on October 19 in San Francisco, bringing together people who straddle multiple worlds for candid conversation and community building, and also a Works in Progress Show. Definitely come join us if you're interested.

Thanks again. Thanks, listeners, for coming on the journey and for leaving feeling so inspired and so connected to what Jessica is creating in the world. Let's keep this going. Thank you for listening.

Important Links

• Jessica Wan
• Jessica Wan on LinkedIn
• The Ampersand Manifesto
• Range
• The Four Agreements
• Four Thousand Weeks
• Big Magic
• Remarkably Bright Creatures
• Project Hail Mary
• The Humans
• The Midnight Library

Love the show? Subscribe, rate, review, and share! https://www.ipurposepartners.com/podcast