The Portfolio Life: From Failure To Flourishing With Christina Wallace
Your existence is not a linear path but an ongoing exploration. There are still so much to learn and ways to grow, but that’s the beauty of our journey. Christina Wallace, the author of The Portfolio Life says growth comes from getting comfortable with being uncomfortable. Today, she shares how her biggest failure became a powerful lesson and why she calls herself the "Human Venn Diagram." Tune in and peek into the portfolio of Christina's life!
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The Portfolio Life: From Failure To Flourishing With Christina Wallace
It is my honor to introduce you to my guest, Christina Wallace. She is a self-described human Venn diagram. I love that Christina has crafted a career at the intersection of business, technology, and the arts. She’s a Senior Lecturer of Entrepreneurship at Harvard Business School, an active angel investor, and a co-producer of Broadway musicals.
Her latest book, which has been out for a little bit, is The Portfolio Life: How to Future-Proof Your Career, Avoid Burnout, and Build a Life Bigger Than Your Business Card. A serial entrepreneur, Christina has built businesses in eCommerce, EdTech, and Media. She also co-authored New To Big, which is a book about how companies can create like entrepreneurs and invest like startups, and was the co-host of The Limit Does Not Exist in the iHeart podcast, which was fantastic. I remember listening to that back in the day. In her free time, she sings with various chamber choirs, embarks on adventure travel, and is a mediocre endurance athlete. She lives in Cambridge with her husband and their two children.
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It is wonderful to have you. I’m so honored to welcome you to the show.
Thank you for having me. Thank you for being true to my description as a mediocre endurance athlete. Some people always want to take that out. I am very proud about the fact that I’m not great at it but I do it anyway. That’s a crucial part of my hobby.
It’s part of the portfolio, so you include it.
Exactly.
It’s about also continuing to show up even when you’re not great at it.
That is something I had to learn how to do, which is how to be bad at something and still find the joy and the reason to do it. As an overachiever, it was not something that I came to naturally.
100%. I know that feeling too well. I’m thrilled to have this conversation. I feel like it’s long overdue because I know your book came out some time ago.
The paperback is coming out soon. We’re at the one-year anniversary. It’s crazy.
It was a fantastic book. I remember reading it. It hit a lot of nerves because it resonated with a lot of things that I think about myself. I’m thrilled about the work you do. I’m looking forward to uncovering your journey to getting where you are. We do that through what’s called flashpoints, these points in our journey that have ignited our gifts into the world. I’m going to do that, and I’m going to give that turn-over to you in a moment. You’ll share what you’re called to share, and along the way, we’ll stop and see what kind of themes show up and dig a little deeper. Does that sound good?
I love it.
Please take it away.
The Outsider
There are probably two things that have really been formative to who I am and the work that I have chosen to do. The first is that I have always been an outsider, a weirdo, or someone who doesn’t fit in. I finally found the joy in it. It was not something I took great delight in as a child, but I’ve been an outsider in a lot of different ways. One is I’m 6 feet tall, and I’ve been 6 feet tall since I was about 13 years old. I could not blend in a room if I tried. I am also a theater-trained actress, so I’m very loud. There’s no version of the world where you need to ask me to speak up.
I take up space. I have opinions. I find quite a bit of pleasure in the fact that I was raised by my grandmother, who didn’t have a job. She hardly graduated from high school and was raised in a very conservative religious family. Yet, I was raised in a way that I equate to the confidence of a straight White man. I was taught to go out there, claim my space, and be who I was, even if no one liked it. My grandmother passed away years ago. I didn’t ever get a chance to quite dig into how or why she insisted on that mindset for my sister and me, but I’m very grateful for that.
Since I never fit in, I never felt the pressure to conform because fitting in was never going to be on the table. It wasn’t an option. At every step along the way, when I came to business school and when I was debating what to do afterward, the follow-everyone-else path was never appealing. I never had to fight against the, “If I do that, then at least people will understand what I’m doing.” No one understands me, and that’s fine.
The other thing that really contributes to who I am is the fact that I have been this person who loves lots of different things. I’ve been this person my entire life. I cannot remember a moment before I was a math nerd and a musician. They’ve been equal presences in my entire life. Being that math weirdo who also loves playing classical piano, cello, and opera and letting that translate into the arts that I discovered in college, doing theater, writing poetry, and all of those things, I have to have all of these pieces in my day or in my life to feel like me. It’s not an option. I tried very briefly. I spent eleven and a half months in management consulting.
A professional services job is one where you have no control over your calendar. You jump when the client says, “Jump.” It wasn’t about how much I had to work because I worked hard. It was about not having control over my calendar that made it impossible for me to have all of these different things and I realized this was never going to be happy. It didn’t work for me. Those two themes of, “I can’t fit in, so don’t try,” and, “I have to have these multiple worlds in my day to feel like me,” have helped me root and stay true to what I need even when my path looks very strange to any outsider looking at my LinkedIn, trying to make sense of what on earth I’m doing.
We’re off to an amazing start. It’s remarkable. I often hear these stories of people who come in and they say, “I knew I was different, but people try to force me to fit into the box.” It sounds like you were supported in this path of being that trailblazer, which is really great. The word that came to mind, and I’m sure you’ve heard this before, is the idea of the tall poppies. Tall fits the bill, but the idea of the tall poppy syndrome is that if you’re standing out, people want to cut you down or if you want to fit in. That probably was something you, at some point, had to have faced.
It’s very true. I find it so fascinating about my entire education. I went to a very small religious, not really accredited school with actual teachers all the way through the ninth grade. As a result, they cared more about the religious side than the actual education side. It was so small. My class had 14 or 15 entire students in the grade.
Since I was advanced in every subject, like in Math, I was three years ahead of everyone else, I effectively was sent off to the corner with textbooks to learn at my own pace or teach myself. I was homeschooled in a school setting. What I love about that is that it was not a normal setting and I was not a normal person. There was no version of the world where they could convince me to be the god-fearing future wife who stays home, has babies, and respects her husband. That’s not who I was ever going to be.
As a result, I dropped out of high school after ninth grade. I was like, “This isn’t serving me at all.” I convinced my grandmother to let me go to community college for a year. I was 14 or 15, going off to community college. I took all these classes and did great at them. I aced them, but I was like, “I need friends. I need socialization at some point.” I was fifteen and I had never really had a friend. Even I was like, “That’s not normal.”
I ended up finding the opportunity to go to boarding school at Interlochen Arts Academy for my last two years of high school. Truly, if I’m thinking about flashpoints, going off to Interlochen was one of them. I finally had teachers. I had my first Math teacher in the eleventh grade. I had a roommate who was so unlike me. She was this Japanese socialist lesbian. I was like, “What is happening here?”
I got this huge dump of all of this newness. The outside world was so different from this tiny little community that I’d been part of that it forced me to be like, “I don’t know anything about the world. I don’t know anything about what my opportunities are.” Instead of that being scary, it was more like, “Game on. How do I learn more? Where do I go from here?” Since I was never attached to that idea of fitting in, going home, being comfortable, or peaking at fifteen the way some people are, I was like, “I don’t know what I’m doing. I’m really uncomfortable and awkward about it, and I still am not sure how to be friends with my peers, but let’s go learn.”
Something about what you shared has me thinking about so many people who are probably in the same predicament as you but they weren’t in the right environment to be able to explore that. They weren’t able to explore their curiosities and challenge themselves to start to blossom into the people that they were meant to be because of the fact that there’s like, “Get back in the box,” or, “Do your job. Do the work you’re doing because that’s what we expect of you.”
When you are given the opportunity to enter an environment that starts to challenge you, rise to the challenge, and pique your curiosity, that is wonderful. However, many people don’t get that opportunity. We need to look for those people and give them the chance so we can help them explore their brilliance. Do you agree?
Absolutely. I’ve got 2 children who are 2 and 4. I think a lot about, “It’s not that I’m protecting them, giving them the answers, or making life easy, but how do I raise them to be excited by the idea of, “I don’t know, but I can figure it out.” It is to be excited by the opportunity. If not excited by discomfort, then at least not shying away from discomfort.
Comfortable With Being Uncomfortable
Much of my greatest growth and opportunities have come out of the fact that I am comfortable with being uncomfortable. I’m familiar with it. It doesn’t scare me. It is because of that that I can lean in instead of shy away from things that have made it possible for me to take really big swings often in things that I’m wholly unqualified to do.
I don’t think I’ve ever had a job, including this one as a professor, that I was qualified to do when I got the job. Since I have the confidence of a straight White man, I say, “Let’s figure it out. How hard can it be?” Here we are. It always works out, which is also a classic privilege statement to make. I feel like leaning in in those moments of discomfort or uncertainty instead of being afraid of what could happen has been truly one of my greatest superpowers.
I’d like to know, and maybe this is going to come up eventually anyway if there was a moment you felt like you went too far. You overdid it, maybe. Those are all learnings, too.
I started traveling by myself in my early twenties. I had never gotten to travel growing up. We didn’t have a ton of money. I went off to college, having never been South of the Mason-Dixon line, and I went to college in Atlanta. I was like, “Whatever. We’ll see what happens when I get there.” I graduated from college, I never left the country, and I wanted to go see the world.
I then had the opportunity. My job at the Metropolitan Opera out of college gave me six weeks off in the summer, which no one gets. You can’t take a single day off during the season, but you get these six weeks off in the summer. I said, “I want to see the world, and no one else can go at this time. It’s either I go alone or I don’t go.” I decided to go alone.
This was pre-smartphones. This is in the era of Lonely Planet guidebooks and internet cafes that cost $3 a minute. I tell people this and they’re like, “Connect to the Wi-Fi and you can Google search.” I’m like, “There was not even a Google map. Google was not a thing beyond Gmail at this point. It didn’t exist.” I go to Europe with a backpack and no money. I figured it out the first year, and that goes really well. Next summer, I do Central America, and that goes well. I get to business school and think, “Do you know what I really want to do? I want to go see East Africa. I’ve never been on the continent. I want to go see what this is like.”
I had made plans to meet up with some friends to climb Kilimanjaro at the end of this trek. I was going to spend five weeks backpacking through Kenya, Uganda, Tanzania, and Rwanda. The infrastructure certainly in 2009 for backpackers in East Africa was non-existent. This is not like hopping on the Eurail system in Germany and making friends to go stay at a hostel together. This is at the point where you can’t even pay for airline tickets through the internet. You could make a reservation, but you had to pay once you got there because they couldn’t yet transfer funds across the Internet.
I got there, and at this point, my confidence in discomfort, my cockiness even, had maybe gotten a little too comfortable. I had a series of really stupid choices along the way. One night, I was out in Zanzibar during a power outage. The Darsalam had cut off the island from their electricity supply. I was like,
I’ll go down, get dinner, and find my way back to the hostel.”
I don’t bring a flashlight. What I do bring is my backpack with $2,000 in cash. It was all of the money I had for this whole trip because credit cards were not reliable at that point. I also had a DSLR camera, my passport, my ID, and everything on me that if I had gotten jumped at this moment, the headline on my hometown newspaper would’ve been, “Idiot Girl Makes Stupidest Decision Ever. We Don’t Know Her.” We all could recognize that this was a poor choice.
It’s so dark that I can’t see my hand in front of my face as I’m trying to make my way back, but I get home safely. I’m fine. At that moment, I’m like, “That was stupid. That wasn’t brave. You have to learn your limits.” That was my stupidest moment physically that very luckily turned out fine similarly when I started my first company, Quincy Apparel, with the confidence of an HBS grad who is a straight White man.
My cofounder and I went out. We raised money. We started building this thing. There are lots of reasons why we should have failed, and we did fail. We failed so much that Harvard Business School wrote a case study on our failure that we taught for nine years to the MBA students on how not to turn out like me. It was really humbling in this learning moment to see for the first time at 28 the limits of my abilities. There were so many things that I could learn on the job, and I did. I got smart in some areas and figured out how to make deals. I did all these things, and then there were a whole handful of things, particularly around managing people, that I wasn’t getting smart enough on or fast enough on. I couldn’t fake my way through it.
It was an important moment in my work education to realize where I had real gaps, the skills that I needed to build, and the places where you can’t fake it until you make it as a manager. At least you can’t when you don’t have the whole infrastructure of a large company around you to pick up the pieces when you screw up.
It was really important to see there are lots of places where you can show up as an outsider and not know anything. You can ask the stupid questions and that might offer insight that no one else is seeing. There are some places where it does matter that you have the expertise to have the experience and to show up with a couple of reps under your belt before you decide to go it alone.
This is brilliant. I love what you shared. Many entrepreneurs, out of the gate when they don’t have that experience of maybe working in other companies or what have you, feel like they’ve got it all figured out around the people. It’s always the people because it’s something that we feel like, “I’ve been managed before,” or, “I know what it feels like to be managed.” It’s a different story when you’re trying to come into that role, and you start to say, “How do I drive this train and also think about what people need and make sure that they’re included?” It’s a common challenge.
Especially when you realize, and this sounds so obvious, that people are all different. Even if you can backsolve from how you like to be managed to how you should manage someone like you, that’s only one slice of the talent that you’re going to have ideally. You’re not only hiring people like you in best-case scenarios. You are learning the full toolkit of ways to communicate, ways to manage, and ways to help develop people. It is like, “Is this someone who loves being in a little bit over their head and they like the stretch goals, or is this someone who shuts down at that moment because they know that it’s going to be a B-plus at best and they only do A level work?”
Knowing how to read different people, how they respond to feedback, and all of that is 85% of the job. Often, it’s a skill you can’t learn in the classroom. It’s something you learn by apprenticing, hopefully with great managers. Sometimes, you learn what not to do by working with terrible managers. It’s hard to jump over that experience and still be excellent at it yourself.
Knowing how to read different people and how they respond to feedback—all of that— is 80% of the job. It's a skill you can't learn in the classroom. It's something you learn by apprenticing with great managers.
The Journey To Becoming You
It was a humbling experience for you. I hear it and feel it from what you’re sharing. Tell me what happens next, though in the journey to becoming you. You go through this experience and say, “Am I going to do that again?”
What comes next is the slice of humble pie. The company fails and I am dirt broke. I have $0 to my name. I’m paying rent with a cash advance on my credit card. I am single. I do not come from any family money. In fact, I send money home to my family. It’s like, “You have 30 days to get a job or take out more of a cash advance on your credit card. There’s no backup plan here.”
I, at this point, was feeling so lost. This is also quite the first time I have failed at anything in my entire life. The closest thing I had to a failure before this was a B-plus in Differential Geometry my sophomore year as a Math major. That is my closest failure. It’s like identity shaking, this idea that I couldn’t figure it out. Who am I if I’m not the girl who can figure it out?
Also, I have no idea what I’m employable for at this point. I looked at my resume and I’m a Theater and Math major who had 2 years in opera, 11 and a half months in management consulting, and 2 years operating a failed fashion company with an MBA, but honestly, what good is that? I was like, “I don’t know who I am, what I have to offer, or who wants someone like me.”
First, I spent 3 weeks in bed, watching all seven seasons of The West Wing and speaking to no one. It was a wonderful moment of transportation to a different era or a different time. It was lovely. Seasons 5 and 6 sucked, so that was the moment where you were like, “At some point, you have to go back into the world.” You get to the end, and President Bartlet has said, “What’s next?” so many times at this point that you’re like, “What’s next?”
What’s next is that you take a shower, eat some vegetables, and send an email to everyone you know saying, “I need your help. I need coffee. I need your thoughts on who I am and why anyone would want to hire me. I need you. Also, I need you to pay for the coffee because I am broke.” I sent this letter to 100 people. I was desperate at this point. Seventy of them said, “Yes.”
That’s a good return.
It felt very good at the moment. As I’m starting to schedule this, I’m like, “That’s a lot of coffee,” because I did 70 coffee chats in 30 days. That’s more than two cups of coffee a day. It’s a lot of coffee. Some of them I turned into walk-in talks. There’s a point where the caffeine becomes too much. I went on all of these coffee chats and ended up asking them the same three questions. I was like, “Number one, when have you seen me happiest?” It was mostly because, at that moment, I could not remember being happy. I was so far from happy.
It had been a tough time. Not only did my company fail, but my grandmother had died. Six weeks before that, there was a hurricane in New York and everything was cut off. It was a really rough Q4. I was like, “When have you seen me happiest? Help me piece together the dots about why I was happy in those moments. Question number two, what do you come to me for? What’s that moment where you’re like, “I should see what Christina thinks about this.” Where do I stand out against my peers?” In part, it was because I was like, “I feel like I can do a lot of things, but I know not all of them are useful. Not all of them stand out. What are the things that I could really offer to the world?”
Through these conversations, I was able to pull out some of these throughlines around how I’m happy when I’m in control of my calendar, so client services are off the table. What do they come to me for? It’s to find the story, whether it’s their resume, a product launch, or a marketing pitch. What’s the story? Not just the strategy, but what’s the emotional pull of how we’re connecting these dots?
Where do I stand out against my peers? I’m a public speaker through and through. Give me a microphone and 1,000 people staring at me and I am happy as a pig in slop. Apparently, not everyone feels that way about public speaking. I did not realize this. Through this, I was able to suss out like, “Where would I fit? What should I be looking for? Where would I land?” I landed at this startup based in Boston that wanted to open a New York office. They needed someone who knew the ecosystem and someone who loved the 0 to 10 stage of company building.
In entirety, at every step along the way in this process, no one held my failure against me. No one was like, “We were going to hire you, but then it turns out you failed.” What they wanted to know is like, “What’d you learn from it? What are you going to do differently next time? Under what conditions would you try again?” They wanted to see what my reflections were and how I was going to bring that experience into what I did next rather than black hole it and pretend it never happened. I thought that was really interesting.
I can’t say that this is true for every geography or every industry, but at least in the startup world at least in New York, there was this reverence or this awe for someone who took big swings even if they didn’t work out. That surprised me. Also, it was really reassuring that, like, “I can keep taking big swings. I don’t have to now play it safe because I tried once and it didn’t work.”
I love that. It’s such a great message. It’s exactly what we need to have people know. It’s not because it didn’t work out when you took the first swing that it means it’s not ever going to work out. It means you need to get up to bat again and try again. The other part of this which you shared and a lot of people miss is that some of the most successful people in the world are successful because they ask for help. If you’re not confident enough or okay with asking for help, it’s going to be hard for you to be able to have that moment of, “How can I ask other people what is the thing that I do well? What are the things that they see in me?”
Forward Motion Is The Only Way
Oftentimes, we’re going to be stuck in that, “Let’s call the cave of despair, continue to spiral, and say, “I should be doing the same things I’ve always been doing because that’s what I think people expect of me or what I’m expecting of myself.” If you ask them, they will give you the answers that they see. That’s going to lead you to a very different life or a different situation.
I’m grateful I didn’t have a financial safety net at that moment. I’ve seen other founders go through that moment of failure of shutting things down and they have stayed in that cave of despair for 6, 7, or 8 months. The longer you’re there, the harder it is to get back out. I am so lucky. I did not feel this way at the moment, but I am so grateful that I had a ticking clock. It was, “Rent is due in 30 days. How are you going to figure it out?” It forced forward motion at a time when that felt really uncomfortable, unfamiliar, and unwanted. Yet, forward motion is the only way you get new information.
It’s an interesting insight. There’s something about this that is a lesson for a lot of people, not just for entrepreneurs. If you’re ever going through a dark moment, talk to people. It’s almost counterintuitive. We want to retreat. Maybe you retreat for a moment and get your bearings, but don’t be there long. Get out there and talk to people because it’s the only way you’re going to feel better.
You’re not going to find the answer by staring at yourself in the mirror or beating yourself over the head with a pencil as you look at a blank sheet of paper. At a certain point, you need new inputs. That’s where you can go out and get some of the outside-in information rather than thinking about it from an inside-out point of view.
The Book
I’m loving this conversation. There are so many great insights. I want to jump into your book because it’s such a brilliant book. It’s the idea that we’re not just one thing. We’re many things. It’s almost collecting all those different parts of who we are along the way, which I’m not trying to give away the book. I want you to talk about it. It’s also what I’m doing here. I’m trying to figure out how we curate our experiences to a point where we’re here and how we make sense of it all. We connect the dots. Tell me. What do people need to know about your book?
The joke is that I wrote the book to explain to my mother what on Earth I’ve been doing with my life. Somehow, if something has a name, it makes it legitimate, so I’ve come up with a name for my career path. It’s called a portfolio life. It’s a joke, but it’s completely real. I said, “I have to have these multiple things. I cannot go all in in one field, one job, one industry, or anything,” because it’s the intersection of differences that I find the most interesting. It’s what I have to offer in a room.
Having the inability to be one thing has really pushed back against a lot of people’s notion of, “Who are you? What’s your identity? What’s your job title? What’s your thing?” I don’t know how to answer that question. This is why I came up with the phrase I’m a human Venn diagram because I struggled to introduce myself.
What I find so powerful about starting with the question of identity in the model is that I realized in both my own work and the coaching I’ve done with my students and other entrepreneurs that so much of what limits us in our lives is not what other people don’t allow us to do. It’s what we don’t allow ourselves to do because that’s not who we are.
My mediocre endurance athleticism is a great example of this. I was told my entire childhood I wasn’t athletic. How I’m six feet tall and I can’t throw a basketball is an absolute shame. Everyone’s like, “It’s okay. You’re a musician. You’re smart. It’s okay that you’re not pretty and you’re not athletic. You have other things to offer.” I believed them. I was like, “Okay.”
It wasn’t until my company failed and while I was trying to get a job that I also was like, “You need to move your body. You are unhealthy. You are unhappy. You have so much stress. You need to move your body. Also, you’re broke.” What is the only free sport in the world? Running. What do I hate doing? Running. I decided, “We’re going to run anyway.”
What limits us in our lives is not what other people don't allow us to do. It's what we don't allow ourselves to do.
I took up running to the point where I finally realized that the key to being good at running is to practice running. You’re not born a runner or not a runner. It’s either you train your muscles, your lungs, and your body, recover, get stronger, and learn how to do this or you don’t. Once you start and you keep doing it, you get better. I ended up running thirteen half marathons that summer. I was like, “Okay.”
I’m not fast. I still have not broken a two-hour half marathon. I never will because I don’t care enough to try. The point is trying things is often a function of what you believe you are capable of doing. Start with a question of who are you? How do you define your identity? Crucially, is there a way for you to define it that’s not only anchored on how you monetize your time? It is also known as, what job do you have? Many people are like, “I am,” and you’re like, “That’s how you make your money. You are a great many things. You’re a connector. You are someone who challenges the status quo. You’re a storyteller. You’re a caretaker. You’re monetizing your time in this particular way.” You start with identity.
If you can find a way to describe it larger than your job, it allows you to see all of the options that are in front of you. We have no problem looking at our past, realizing how many paths we could have taken, and thinking, “I could have been an astronaut, but here I am today.” We see the multiverse of our past. How do we not understand there’s a multiverse of our future, too? Much of this is what you are allowing yourself to see as an option and what you are willing to make changes for. What are you willing to follow down the road? Unless you’re dead, you still have options. It is seeing that and saying, “I’ve been this for twenty years. I can make a change.”
Ultimately, what I love about the portfolio life model is that the principle is to design the portfolio. In the mix of activities, some are monetized, like your income and your job, and some are not, like hobbies, relationships, or health. Design that mix for what you need in this chapter of life. When that chapter of life changes, rebalance the portfolio. Redesign it. It gives you that flexibility.
I’ve got 2 littles, a 2-year-old and a 4-year-old. If daycare decided to be canceled, I’d be like, “Okay.” I have a very different set of needs than I did a few years ago. It won’t be forever. It’s for now. I am prioritizing autonomy, flexibility, independence, and a stable income with great health insurance because daycare ain’t cheap. Those are things that weren’t a priority before. They might not be a priority later, but now, I have to design for that.
As a result, there are things that used to be in my portfolio, like climbing mountains and traveling the world, that are on the back burner. They don’t get an allocation. I don’t even have time to sing in a choir because I don’t have rehearsal time. I don’t have a consistent night every week I can give three hours to. Even singing has taken a back burner. That’s why I’ve spent more of my time producing Broadway. It turns out I can do that remotely, asynchronously, and in little pockets of time. That’s a good fit to meet my creative needs for my portfolio. When my needs change, I change it.
There’s something in what you’re sharing, which is really cool. It’s not because you’re not actively doing all of them at once, which you can’t really do them all at once, that it means you have to detach yourself from that identity or judge yourself for it. You still can be the artist, the traveler, or the explorer, if you will. That’s how I look at it myself.
You Get To Decide Your Identity
You’re still who you are, even if you’re not doing it now.
You get to decide what identity you want to own, not let other people decide what that looks like for you because you are a choice.
I write about my friend Carla Stickler in the book, who was a Broadway actress for twenty years. At one point, she decided to start looking into other hobbies. She was dabbling and thinking about what might come next professionally. She reached a little bit of an endpoint of what she saw for her Broadway career. She learned to code. Not a moment too soon, because the pandemic hits, Broadway closes. She ends up successfully pivoting to become an engineer at a tech startup.
In that transition, she struggled because, in some ways, it felt like she was no longer an actress, a singer, a creator, or a performer. She almost felt she had to hide it because she was worried about not being taken seriously in this new identity. What I love about her story without giving too much of it away is that she has an opportunity to come back to Broadway to save the day when they needed her back, and she did.
At that moment, she was like, “I didn’t stop being an artist. I stopped making money to pay my mortgage as an artist. I’m still a singer. I’m still a creative.” She has leaned into an identity that allows her to be both a coder and a creative in a visible way that also allows her to be an activist and a representative for the inclusion of artists in the tech world. It’s so powerful to remember that you’re the one that defines your identity. If you still are that person at heart, you’re still that person even if you haven’t picked up your guitar in a while or you haven’t written a journalism piece in ten years. Journalism is a way of life. It’s a mindset. It’s not just the job.
You're the one that defines your identity. If you still are that person at heart, you're still that person even if you haven't picked up your guitar in a while or you haven't written a journalism piece in 10 years.
Coming back to this idea of a dancer who loses her legs, you are still a dancer. You can’t dance with your legs the way they used to, but you still have the mindset. You still have those dance moves in your mind. That still makes you who you are. Your identity’s there.
I could go off on this forever. Dancing is your posture. It’s about grace. It’s about your fingers as much as your toes. There’s so much that is still true about how you show up in the world even if you are, in this example, losing the ability to go on point or do the steps that you used to do.
To be honest with you, it’s inspiring in many ways for people to hear this so they can feel like, “Which identity do I want to own?” That’s what your message is. I feel like this viscerally expresses the need for people to own their identities more fully, not just one, but whatever identities they feel connected to.
To feel the freedom to reinvent the expression of that identity. I feel like this is a book for people in transition, truly, whether it’s coming out of college, on the verge of retirement, or anywhere in between. There are so many moments that I’ve seen where folks are like, “Whatever I was doing, it used to really work. Now, I’m feeling friction. Now, I’m burnt out. I’m unhappy. I’m not growing. I can’t make it work like I used to. I have to do elder care. I have to do other things. It doesn’t work anymore.” They’re trying to jam a puzzle piece into a puzzle that doesn’t fit.
Instead of feeling broken, if they feel the permission to, it is the opportunity to say, “That was great for that chapter, but it’s not serving me anymore. What do I need next?” Go and reinvent what the next iteration is. That next expression of that identity is where I’m hopeful that this model can unlock flexibility, fulfillment, and joy for a lot of people because we were never meant to be 1 thing for 80 years.
It would be a boring life.
On the one hand, we no longer have the security that our parents and grandparents had in their careers, but on the other hand, we are freed from the straight jacket that used to be, “Graduate from high school and pick a college major. That’s who you are until you die.”
If there’s any reason why people should be scared of AI like, “AI is going to take our jobs,” that should be a fantastic thing. I’ll let AI take my jobs, and then I can find ways to own something else. I can take on another identity and do something else. I could talk to you all day because this is fantastic, but I do want to respect your time. I have one last question to ask you. What are 1 or 2 books that have had an impact on you and why?
For the first one, anyone who knows me will know why I’m saying this. It is by Clay Christensen, How Will You Measure Your Life? He was my professor at HBS. That book was based on a talk he gave to my class at the end of the semester when he had brain cancer and I was concerned that this might be the end for him. Luckily, we got him for another ten years after that.
This is an incredible book from a leader in the business world who takes a very personal turn towards saying all the things that we’ve been thinking about, like measuring and managing businesses, the world, and organizations. How do you apply them to thinking through what matters in your life? What you measure is what you manage. Peter Drucker said this. How do you put that same intentionality and design thinking into your life and make sure that you’re not acing a test that you don’t care about? I love that book.
The other one is left field. It is by Julia Cameron, The Artist’s Way. There’s something delightful about a ritual of morning pages, getting up, and getting things out of your head. I suffer from anxiety. I take medication for it. It’s delightful. Also, sometimes, getting things out of my head and onto paper frees up the space for me to use that brainpower elsewhere.
There’s the artist date and some of the other concepts of how you go out and make sure you’re refilling your creative well and getting new ideas. I find for anyone who’s trying to innovate, build the future, or imagine something new. You have to feed that machine with new ideas, new conversations, and new relationships if you’re going to be able to see something that does not yet exist.
For anyone who's trying to innovate, build the future, or imagine something new, you need to feed that machine with new ideas, conversations, and relationships if you're really going to see something that doesn't yet exist.
You’re like a kindred spirit here. Both of those books are two of my favorite books. I see myself as a curator. I’m always out there trying to learn and uncover new things because I feel like it feeds my soul, but it also allows me to do better work. I also like to do morning pages because it’s such a great way to see what’s really present for me and get it out of my head. Thank you so much for coming on the show and sharing all your brilliance. Before you go, I want to make sure I share where people can find you.
You can head to PortfolioLife.com. That’s where everything about the book is. I am releasing a guide or a free workbook, a companion to go along with the book. If anyone wants to sign up for it, I won’t spam you, but you could get it through my mailing list. You can find me on LinkedIn or on Instagram. I don’t post very often, but when I do, I would love to see you, make friends, and hear your thoughts on my work. Find me there.
Thanks again. Thanks to the audience for coming on this journey. I know you’re leaving so inspired, ready to take on the world, and excited for what’s next in your chapter of your career or so in your life. Thanks for the journey.
Thank you so much.
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