The Portfolio Life with Harvard Business School Professor | Christina Wallace

Welcome to the Beyond Harvard podcast. I'm your host, Roshana Weersinghe, and today we are joined by Professor Christina Wallace, the definition of a modern-day Renaissance woman. Christina is a senior lecturer at Harvard Business School, Tony-nominated Broadway producer, and the author of The Portfolio Life. Christina describes herself as a human Venn diagram, having crafted a career at the intersection of technology, business, and the arts. Christina, welcome to the podcast.

Thank you for having me.

I'm delighted to have you, Christina, and I want to start this conversation the same way you started your book.

Okay.

You, you describe yourself as someone who's trilingual, fluent in 3 languages: English, math, Yes. What age did you discover you were a multi-hyphenate? I—

it's, it's so funny. It's less that I discovered I was a multi-hyphenate and more that I discovered that that was not what everyone was, right? There's sort of like— there's a moment as you are growing up where you finally have the self-awareness to realize that you are a thing and that like there are other people and they are not necessarily the same as you, right? There becomes this kind of self-awareness piece. And so I started piano lessons, I can't even tell you, I was so young, like I don't remember a before. I think I must have been 4 and a half, 5. And I obviously don't remember before I was speaking. And math was just always part of my life. I remember doing math in preschool, in kindergarten, like it's just been a thing I've always loved.

Yeah.

And so all 3 kind of coexisted as each equally interesting and equally important in what I did, how I expressed myself, and equally part of how people saw me, right? There's an identity piece of this. And I think early on, you know, I have an older sister, Stephanie.

Right.

She's 2 years older. And early on, we both demonstrated excellence in piano and math. And so we became the Wallace sisters, who were those girls who are great at piano and math, right? It became this like package deal.

Okay. Like a duo.

Yeah. And everywhere we went, they were like, oh, they're the math geniuses, they're the pianists. And we went to a very small school. And so all the teachers who had her had me and every— all the piano teachers who had her had me. Like everywhere we went, we were this. So as the younger sister, obviously I loved this.

Yeah.

As the older sister, obviously she hated this, but it was— this was just who we were.

Yeah.

And it, it just sort of was. And it wasn't really until, I think it was probably the 4th grade, when someone was like, who do you want to be when you grow up? Right? Like the typical question some adult asks a child because they don't know what else to talk to you about. And I said, well, you know, obviously I'm going to be a professor. an author, an astronaut, and the president.

Oh.

All at the same time. Like, crucially, they must be simultaneous activities. I got 2 out of the 4.

Yeah.

And I did apply to be an astronaut. NASA didn't want me. And they were like, oh, well, that's not possible. And that was the first time that I was like, what do you mean? What do you mean that's not possible? And then they sort of like broke down that not only are those 4 very different jobs and 4 very different paths, but that to do things at the same time would be impossible for— and then they just kept talking. I sort of tuned them out. But that was the first time that I was like, what do you mean it's impossible to do them at the same time? I do all things at the same time right now. Like, I'm playing piano and winning trophies at competitions, and I am 3 grades ahead in math class, and I am doing all— like, What do you mean? You know? But even then I was like, well, I think you're wrong.

Yeah.

Classic cocky little 4th grader. And I think all the way through, even, you know, through high school, even into college, when adults would challenge me on this idea of like, but which one will you choose? I still was like, I don't think you get it. I'm not going to choose. And I was still somehow very confident that I would find a way to make this all fit. And I don't really know where that overconfidence came from. It could be because I'm tall. I don't know. Tall people just figure things out. Unclear. Um, but I just, I really had this identity that was tied to being both, being an artist and being a mathematician. And I could not imagine a world where I only had one.

Mm-hmm.

And so it just felt like an inability on their part to be creative enough to see how I was gonna do this, as opposed to an inability for me to Pull it off.

It's like, it's a you problem, not a me problem.

Yeah, I was just like, you're just not interesting enough. I'll figure it out. I'll report back.

I— what I love about that, Christine, is you chose not to choose.

Yeah.

When it— when you were kind of sitting in between these worlds that people were trying to box you into.

For sure. I mean, in college they were kind of like, well, you don't have enough time to do all these things. And I was like, yes I do, watch. And so I was like, how many credits can I take in a semester? Like 23. And I was like, great, here's the math. I can do a double major and a triple minor taking 23 credits a semester over 4 years.

Boom.

Like the math works.

Yeah.

You have to be strategic.

Yeah.

You have to use every credit intentionally.

Yeah.

But the math works. Watch me do it.

Yeah.

And they're like, but you're gonna crash and burn. I was like, hmm. But you don't know how I manage my time. I have color-coded schedules. I, I have a list, you know?

Yeah.

I am excellent at my systems. And I think that's the other piece of it. I've created systems to stay on top of this, and I've had them from a very early stage. So you don't get to like dream big and then sort of hope for the best. If you're gonna make your life complicated, You gotta figure out how to manage it. But I've had these systems and I've made that work. And as a result, it works. And I think, again, your failure of imagination is a you problem.

Yeah. And I'm curious there, Christina, because I think what I love about your work and your book in particular, which we'll get into, is you've been able to turn your interests into a Brand and almost a differentiation factor. And is that a gift? Is that a strategy? Or is it both?

It's so funny. I'm delighted this book got out in the world, got to be published, got in the world. I never intended to write a book, to write this book, although I did say I was going to be an author in the 4th grade. I ended up writing this book because I've been calling myself a human Venn diagram simply to help other people understand what to do with me. I have been using it as a way to introduce myself since like 2010. It's just, it's an easier opening line than like, I'm a this and a this and a this and a this. It sounds more strategic than flaky. And when I had my podcast, The Limit Does Not Exist— Check it out.

Slight plug.

It was a phrase we used a lot, and we interviewed a lot of people who lived at this intersection, mostly of STEM and the creative worlds, and they really connected to it, and a lot of our listeners really connected to it, and so it sort of took on a life of its own, and as we were out in the world, and I was writing a lot about the systems that I had put in place to make this life work, I was a columnist for Forbes for a while, and so I was publishing there, more and more people found their way to my inbox saying, this is me too. I just didn't have a name for it. And once it has a name, it feels legitimate. It feels like it's a thing now.

Mm-hmm.

And so now I don't feel like the weirdo in the corner. I don't feel like the flake or the dilettante or the person who can't make up their mind. Now that you've given it a name, like, I feel like I have permission to keep doing what I want to be doing. And so then I felt like I had to write the book. And so a lot of people who want to criticize are kind of like, you didn't make this up. Charles Handy wrote a book. And I was like, I know. I literally say that in the introduction. It's called The Age of Unreason. He literally wrote about the portfolio life. And I give him that credit. I just named the thing, the trend, which is actually becoming even more of a movement now that AI is disrupting everything.

Yeah.

And I put it out in the world with a bit of a platform underneath it. And because of that, it's helping a lot of people feel like what they're doing is a legitimate thing. And so I didn't intend to become a brand. It just— I have a loud voice. I'm tall and I'm loud. And I take up a lot of space in the room. And because of that, I've been able to share a model that I think is really powerful for a lot of people. And that brings me a lot of joy.

That's exactly what I felt reading the book, Christina, because I think I'm someone who's sort of had this idea of a portfolio life. And it's something that I subscribe to because it felt congruent with my values. But until I picked up your book, I didn't know it was really a thing. thing. And to use your words, it gives you permission to sort of pursue it a little bit more intently. Um, so I think that's the perfect transition into, into the book segment of the episode. Um, Kristen, in 2023, you, you released The Portfolio Life, which is a practical playbook on how to future-proof one's, one's life. And you cover different parts of having a portfolio career, from the why, the what, the how. And I want you to start, Christina, maybe just by defining what a portfolio career is. And I have the book here.

Just in case I need it.

Just in—

yeah. Luckily, I've been talking about this nonstop because it came out in English in 2023. But then it came out in Taiwan in complex Chinese in 2024. And now it's coming out in simplified Chinese in 2026. And now it's going to come out in Spanish in 2027 and Korean. Oh, that's exciting. It's going all over. It's so fun. So the portfolio life, and there's a reason I use the term portfolio life and not just career.

Yeah.

Although you can hear the portfolio career, and I do want to kind of define both.

Yeah.

This idea of a portfolio at all, I had never heard the term before I became a student at Harvard Business School. I came from the arts. I was an opera girly. I had worked in nonprofits. Lord knows my family did not have portfolios. Like, we were not talking about personal financial planning around the dinner table. We were working class. So I got to business school. I took first semester finance, or finance, as they say.

Oh, great.

And I was introduced to this tool called a portfolio. And this idea is that you have a group of resources, and then you allocate those resources across different assets, in the case of a financial portfolio. And those assets have a profile. And we typically look at those assets in terms of 2 dimensions, risk and return or reward.

Hmm.

So if you're looking at a financial portfolio, you might say, well, stocks might have a higher return, but they also have higher risk than something like bonds. Bonds have lower return, lower risk. Cash has the lowest risk of all, but has like no return. In fact, it could have negative return in a period of inflation. Then you have really high-risk investments like crypto or maybe an early-stage startup, a Broadway production. And then you could have other things, real estate, I don't know, more stable businesses, but that are privately held, right?

Yeah.

So you have all these different types of assets, and then you're going to design your investments according to what you need for that period of your life. So if you're early in your career, you might say, we're going to take more risk because we have a longer time horizon to retirement, to when we need these assets to pay out. So we can, we can take losses if we have a down year or two, but we need the money to work for us. So we're going to take a higher risk because we need a higher reward. And if you're at a different stage of your life, maybe you're closer to retirement or you're just closer to needing the cash. Maybe you're like, we're going to go buy a house soon, so we need to make sure our down payment is not in super risky assets. Let's put it in cash or bonds for a while or Treasuries. Then you want lower risk, and so you're going to take a lower return. So you're designing your allocations based on your needs for that season of life.

Whew.

Right? Amazing. I was like, this is insane. And then you learn all sorts of other things, like how different assets have correlations.

Ooh.

Oh my gosh. So they talk about, I'm going so deep now. We can have a whole separate podcast on just personal finance. I'm obsessed. But they, different assets can have a positive or a negative correlation. And so as you're designing your portfolio, like, 2 assets in the same industry might be positively correlated. If something happens to the industry, they might move in the same direction because they're influenced by the same input, right? Like there's a drought, 2 things in agriculture are going to both take a dive.

Yeah.

Negatively correlated assets are because of some outside force. If one goes up, the other would go down. So if you can think about your house and your home insurance, when your house is doing great, you're losing money on your home insurance because you're paying into it and getting nothing back.

Yeah.

When your house has a fire, your house goes to zero, but your home insurance pays back. So your house and your home insurance are negatively correlated. Okay, we've got the basics.

Yes.

Great. This is important. So I was learning about this in finance, and I was like, this could work as a model for my life. You're like, how? Stay with me here. So instead of thinking about like work-life balance, which is this thing that works for exactly zero people because it puts your work and your life in opposition to each other, I think about my life as a portfolio. And each of my assets are a piece of my life. So work is one of those assets. My hobbies are an asset. My family is an asset. My health is an asset.

Yeah.

My rest is an asset, downtime. Maybe my personal growth that I'm investing in myself. I wanna learn something new. My community, am I involved volunteering or part of like my spiritual community? That's an asset. All of these things are pieces of my life, and my time is my allocation. My time and my intention, my efforts. And I can allocate that across these different assets, and my allocation can only add up to 100%.

Mm-hmm.

I can't be overallocated. Otherwise, you burn out because you've promised the same time to 2 different people. That's when you burn out. So, or that's when you stop sleeping. Or you cut down on your health, right? You think you're investing, but you're not because you've overallocated. Okay, so it has to add up to 100. So that's the first insight. And then secondly, as you think about your allocations of how much you're giving each of those assets, you have to design it based on the stage of life you're in. And so how you design it is going to be based off of, well, what do you need and what do you want, right? That risk and reward.

Yeah.

What are you investing in for this stage? How long are you looking for it to pay off? And what do you need? So you might be in a stage of life, like many of my MBA students when they first graduate, where you got a lot of student loans. You got a lot of student loans.

Yes.

It's not cheap. And as much as you might want to go save the whales, you have to pay back those student loans.

Yeah.

So you might say, Professor Wallace, love this, but like, I need to make some real money and work my tail off for a little bit. I'm like, great. So one of your needs is significant income for a little while, a couple of years. So you're going to craft your portfolio where work is going to be a really big portion of your portfolio because you need that cash flow. But you got to make sure your other needs are covered. Like, your health still exists. You can't ignore it or you're going to have health debt. We talk a lot in tech about technical debt when you sort of do a quick fix on code.

Like a Band-Aid.

Like a Band-Aid on code. And like, it fixes it for today. But if you do too many of those, at some point the whole thing falls apart. It's the same for your health. And like, you're not— 18 forever. This stuff adds up. Yeah, too many sleepless nights, too many takeout orders, too many not working out.

Exactly.

Like, it adds up. So you still have to take care of your health, mental and physical. You still need friends, you need community. And if you're in a place of transition post-school, you need it even more. So how are you going to make sure you have space for that even if you're working 6 and a half days a week? from 8 to midnight? How are you gonna do it? It might just be your group chat, but you gotta make space for it. How are you going to still invest in yourself? What's your creative outlet? What's your moment to feel like yourself and not just the cog?

Mm-hmm.

Right? All of those needs still need to be met. So even if it's a 1% allocation, make sure it's there, because if it's there, you'll remember That once that debt is paid off, or at least paid down, you'll remember, okay, it's time to rebalance. As opposed to what more often happens, you make that short-term choice. I'm going to pay down that debt. And then it becomes a habit. And once you pay down the debt, now you've created this habit of these crazy work hours. And then you sort of stick around because that next promotion is like 6 months away and you paid off the debt. But now you really like that cash flow. That cash flow is going straight to your bank account now.

Yeah.

And you've worked really hard without getting to see any of that cash. And now it's kind of nice. And after that promotion, now, like, bonus season is only 6 months after that. And after that, you're only like a year away from another promotion, right? Like, yeah. And the next thing you know, 9 years later, you're managing director and you hate your life. And you're on your second divorce.

Yeah.

And your kids don't talk to you, right?

Yeah.

I'm being extreme, but this is how you end up living a life that you never wanted, that might look very impressive from the outside, but is not what you want. So you design that portfolio, you make sure that your needs are met, you make sure that you have all of the different assets that you care about, and you put the guardrails around what is the season and when will that season change, and what am I going to do to make sure I keep an eye on that change of season, whether it's I'm going to put something on my calendar, I'm going to pre-schedule my resignation email. No one ever takes me up on that one, but that's my favorite suggestion. Whatever that is, like, be really thoughtful about it and then redesign for the next season. Yeah, that was a very long answer, but that's the portfolio life.

Yeah, no, thanks, thanks for sharing that, Christina, because I think what I loved about your explanation there is it really roots it in intentionality, right? There's like a lot of intention, and it's finding this intersection of intentions and interests. And one of my favorite lines in your book, Christina, is you say Doing one thing is the riskiest career move you can make. Say more.

It is because— there are 2 reasons why. One is in my mother's generation, in my grandfather's generation, that was how you built a life. That was the work path, even if you didn't want it to be. I would have died if I had been born in that generation. Like, I'm so grateful. As annoying as it is to have the world rip out from under me every 3 years, I'm so grateful that I get this life. That was the path. You picked a thing and you did it.

Yeah.

Hope you picked well. Now the world changes. It used to change like every 20 years, and then it changed every 3 years, and now it's changing every—

Hour.

Every hour. Like, it's not even every 3rd Tuesday. It's every time I check your phone. And so when you are doing just one thing, not only are you putting all your eggs in one basket career-wise, and by that I mean all of your professional skills, all of your industry network, all of your job relationships, your individual company political clout, all of that.

Mm-hmm.

You're all in. on one thing, but even more so, you're not looking up and being aware. You think you're safe and you're not. That's the more dangerous thing.

Mm-hmm.

So it's not just that you're all in, it's that you think, you think that it's going to be okay. So you're not networking, you're not getting a sense of which skills you might want to brush up on, you don't know what your market worth is. You're not aware of which jobs are growing in other industries or what other industries might be looking for someone like you and how that job description might be completely different now. You're not doing any of those things. You're like, doo-doo-doo. And you think it's safe. So I do a lot of the admissions events for HBS. I had one memorable applicant last year who came in and goes, tell me why I should do entrepreneurship instead of consulting. And I was like, I don't need to. He's like, it seems so risky. And I said, I don't need to convince you. That's not my job. I'm here to teach entrepreneurship for those who are interested in it. But I will say, if you think consulting is safe, I have bad news for you. Because every consulting firm from the top all the way down to the boutiques are dramatically changing their entire business model from a pyramid to an obelisk.

Mm.

Because AI is able to do so many of the jobs that used to be taken by the entry-level analysts and the post-MBA consultants. And those were the roles that you got your leg in and then apprenticed your way up to partner. Yeah, they don't need as many of you, so they're not going to be hiring. And those of you who have those jobs are not going to be getting promoted as easily as before. And the work that you will be doing is going to be looking very different than what you thought. And so I would just push back on your belief that that's a safe industry.

And that reminds me of—

He didn't like that answer.

I bet. It reminds me of Another one of my favorite lines from your book, Christina, and I think this directly collides with what you're saying. You say, high salary or a good wage guarantees neither security nor freedom.

Yes.

And I think when you talk about— and if we're talking about consulting versus entrepreneurship or having this safety net, I think one of the aha moments for me is we think it's safer.

Yes. In a previous life, it was. 20 years ago, it was. It's not now. And I think it becomes more dangerous the higher you lock in a higher cost of living. One of the pieces, many pieces of advice Clay Christensen gave me as my professor and mentor was how easy it is as you go out and you get promoted and you get raises along the way, how easy it is to let your cost of living creep up to match those increases, that you suddenly get a slightly bigger house and you upgrade the cars, and now the kids are going to private school and the vacations get a little nicer. And, and you don't really notice it at first because it's, you know, they're small raises for the most part. And so you're making small changes.

Yeah.

And we know from psychology that like once you make a change, you notice it at the beginning and then it becomes normal pretty quickly.

Yeah.

But the problem with that is once you— this becomes habit and you've moved all the way up this cost of living scale, it becomes really painful to step out of that level. And the higher you go in your career, the harder it is to find flexibility, to step out and say, I'm gonna go and be an entrepreneur, or I'm gonna go and pick a new industry and maybe go back a few levels. Or right now in the world of AI, I have to go reimagine my value to the industry and maybe completely retool who I am and what I have to offer. And that's not going to be valued economically the same as my current role, but my current role is an iceberg and it's not going to exist— or a glacier, I don't know. Global warming is melting all of them, okay?

Yeah.

Um, and like, it's not going to be here, so the longer I stay stay here, the more dangerous it is. And yet it's painful because you let that creep up along the way. And so that, that nice high salary, that wage that feels safe, just, just isn't. And this is where personal finance becomes really important. Like, really allow yourself that discipline of I don't want to say always believing the rug can get ripped out from under you because it feels like a place of panic and scarcity, but just sort of— I love the entrepreneur mindset, or what I call it, the artist mindset. I think there's a lot they have in common.

Yeah.

I started my life as an artist, and the great thing about being an artist is you never know where the next job is coming from. And as an artist who came from a working-class family, like, you figure out how you're going to pay the rent. Like, This is where the portfolio career piece comes in. This idea of you gotta have multiple irons in the fire. You have, you have, you're always looking for the next piece of work and you're not, you're not gonna be prissy about saying yes. So you've got asks out to people and I was a director, but if you need someone to hang lights, I'll be there this weekend, right?

Yeah.

You want me to do a dramaturgical workshop? Great, I can do research. It'll make me a better director.

Yeah.

Right? I can be a stand-in for Queen Elizabeth for the kids' workshop this weekend. True story, Georgia Shakespeare, there are photos. Right? And so, and then you, those are all highly correlated to each other, by the way. So then you look for some inversely correlated work. Then I go out and teach SAT and LSAT and GRE, did not ever learn the GMAT, for Kaplan. Then I go teach piano lessons. Then you look for like other pieces of work work that's not directly correlated, and you find these income streams that allow you both the agency but also the stability because of the diversification, right? That's the other power of the portfolio. It's not just that you're able to design and that gives you flexibility, it also gives you diversification. And that's the only way to future-proof when you don't know. Right? You can't plan in a world that has no visibility. Right? We, we have like this much visibility. It's like your hand is directly in front of you, right? Like you're in a whiteout. You're not driving with a good mile down the road. And so you can't plan. You can only diversify and hope you've got one bet in the corner that will pan out.

Yeah.

I'm mixing so many metaphors. It's delightful. I hope any of our ESL listeners are like, I sort of understand what's happening. Um, and so that's where the diversification helps you. And that's the same as you think about your portfolio life. The diversification is not just financial, it's also emotional. So I get diversification from an identity standpoint.

Mm-hmm.

If my Broadway work hits a bump, I'm still a professor at Harvard. If my kids tell me I'm the worst mom ever because I won't let them have a 4th cookie— true story— I'm still a Tony-nominated Broadway producer, you know? Like, in every dimension, I have some resilience because I'm not just that. And when I'm thinking about all of the things that I'm investing in, There's even resilience and diversification in my skill set. I can do these things already, and I'm learning about those. And not because I'm being strategic. Sometimes it's just because it's interesting.

Yeah.

But what interests you helps you get good at it because you stick around. And if you're good at it, I promise at some point it's going to come full circle. And be relevant somewhere. I don't know when, I don't know how, but it's gonna come back and be interesting and relevant.

Yeah. And what I love about what you're alluding to, Christina, is you're saying that, you know, these different identities, they don't retract, but they reinforce each other.

Oh yeah.

In many ways. And that's how you're able to connect these seemingly disconnected worlds.

Well, even if you think about like my Broadway producing.

Yeah.

This has only recently come into my life, like in the last 4 years.

Okay.

So I studied math and theater in college, and I thought I was gonna go move to New York and be a Broadway director.

Yeah.

I moved to New York. I needed a day job because, again, working class, no trust fund. And I got a day job. Bless the economy of 2005. It's the one thing I lucked out on. I got a day job at the Metropolitan Opera on the management side. So I'm doing contracts, I'm doing diva management, I'm doing all sorts of things. But it turns out not a day job. It's a day and night and weekend job. Didn't check that before I said yes. It was my only offer though, and I had $600 to my name, so I had to say yes. But it turned out I really liked it. I liked— well, I liked arts management. Let's not overstate things. I liked arts management. I liked the business side of the arts.

Okay.

And I was like, oh, this is really interesting. It was sort of like the intersection of math And the arts and theater and music. I'd been a classical pianist and cellist and singer before I did theater. And so I was like, this is really interesting. And that's what led me to business school. So I came to Harvard and I was like, I'm gonna go run the Kennedy Center someday. RIP the Kennedy Center. And, uh, and then the financial crisis happened and there were no arts jobs. And that's what led me to entrepreneurship. And I was like, I guess I'm gonna leave behind the arts forever because there are no jobs there, but startups were booming. And building a startup is exactly like building a play. That's a conversation for another time. Uh, and so I like took this left turn into tech startups because I learned how to code, it was part of my math major, and went into entrepreneurship for 10, 12, 15 years and really didn't participate in the theater world at all. except as a patron. As my friends were still in that world, I went to support them. I sort of produced this little, like, 50-state play reading thing, but it was like a fun thing. It wasn't like a serious thing. And then out of nowhere, a few years back, I'd been angel investing in tech companies, and a friend came to me and said, I just had an investor back out of the show. I have $25,000 available. I need it to close in 24 hours. Are you interested? And my first reaction is like, absolutely not. I know nothing about investing in Broadway. And then my second reaction is like, wait, I know theater. I know investing in really risky things. Let me take a look. Let me figure this out. So I take a look at the materials. I start to analyze how the math works. And I realize it has the same investment profile as an early-stage tech company. Like, it literally has the same returns. Like, it follows basically the power law of like 1 out of 10 will return the fund. 9 out of 10 are going to go to zero.

Yeah.

And I was like, oh, I know how to do this. So I grabbed 2 friends. We split the unit. We did this. Turned out, won the Tony and was profitable. Beginner's luck. And then a bunch of our friends were like, hey, we love the arts too. We work in tech, we're angel investors. How can we get involved? And the next thing I know, me and my 2 friends who've— we've loved each other for like 15 years when we've wanted to work together again.

Yeah.

We've spun up a production company.

Yeah.

And now we've been on, I don't know, like 12, 13 shows. We've got over 100 investors. We've got 5 Tony nominations. We will find out on Sunday if one of them turns into an award. And it's because these 2 worlds that had been completely non-intersectional for 15 years suddenly overlapped. And the skills spoke to each other in a way that, like, I could translate.

Hmm.

And I didn't see it coming, and I didn't make it happen. It just happened. And I think those are those moments where, you know, I'm talking to a lot of my students where they're like, oh, I tried so hard and I feel like that was a waste of my time. And I'm like, nothing is a waste of your time. There will be a time at some point in your future where this will circle back and be relevant. I don't know when, I don't know how, but the investment you made in learning that skill or building those relationships or getting smart in this area, is going to be relevant and you're going to be able to pull that out. I promise. Like, everything is connected. I'm not woo-woo, but I do believe that everything is connected. And so, like, just keep it in your back pocket. It's like the allocation might be at zero for right now, but it's still there.

Yeah.

It's like a little sound mixing board.

Yeah.

I like to mix my metaphors. And so Nothing's wasted.

Yeah. And you, you said, Christina, you said you may not be the best producer, you may not be the best entrepreneur, but you're the best entrepreneurial Broadway producer at a business school.

Absolutely.

And I want to know more about this intersection because it seems like that's your, your unique value proposition. And absolutely, if you could speak to a little bit more about what, you know, kind of that intersection, and then also what What have you learned about entrepreneurship and vice versa?

It's, it's so fun because at the very beginning of this I was like, oh, these are completely separate worlds and I'll get to like moonlight here and do this there and it'll just be like my fun fact on my resume. And then it turns out to be really relevant. So on the teaching side, it's become a huge part of actually my my next book, like my next research thread. I'm developing a new course on this around storytelling and the role of narrative leadership in the age of the algorithm.

Mm-hmm.

Because there's so much that can be given to AI, but there's a lot that can't. AI is terrible at content. It's terrible at stories. It creates this sort of uncanny valley of content that when you look closely at it says nothing. And I think there's so many opportunities for leaders in every industry, in every context, whatever that means to you as a leader, to make meaning to both sort of sense-making and sense-giving, right, to your teams, to your— employees, to the people that you're trying to get resources from, to connect the dots and tell stories. And we don't teach that really at Harvard Business School. And yet I think that's going to be one of the most important skills in the terms of business, right? We do fundraising, we hire, we have to talk to teams when everything's in the dumps and we got to like Get them excited to go into battle and figure this out. We have to get hired ourselves. That's storytelling. We go listen to customers. That's story listening. And we have to understand and sort of pull out what it is they're saying.

Even pitching, right?

Pitching. We talk to the media. We talk to regulators. All of this is using stories really effectively And we got to teach about ethical storytelling and where that line is of like telling a forward-looking optimistic story and telling a lie. That's worth talking about. And that's just the content. Then there's the actual delivery of the story, which my background in acting has prepared me to do. And we really don't teach that at the business school. And so I think there's a lot of opportunity to bring some of this work into what I teach at HBS. And then it's been really fun as Nothing Venture Productions has gotten more and more visibility to be able to have these conversations with the Broadway industry around how we structure investments, how we're thinking about the recoupment model. There's a symposium that Columbia is having I think next week, that is bringing together producers, venture capital investors, academics, looking at like right now, I think that 4 out of 48 musicals have recouped since the pandemic. That's on the low side.

Yeah.

It's 1 out of 12, not even 1 out of 10. And that's recoup. That's not like return the fund. So what do we need to be thinking about in terms of the financials? Like what, how could we be structuring the investments differently? How do we need to be thinking about expenses? I think there's a lot of opportunity for, as an entrepreneur, as an investor, to have a voice at the table, to be thinking about and maybe challenging some of the status quo that has been really insular in how the business has been thinking about the business side.

Yeah.

Which is really fun. It's fun to love this industry deeply from an artistic lens, Yeah. And be able to challenge it from a commercial lens.

Yeah. And I want to get into a little bit of your professorship, Christina. And you're a professor at Harvard Business School, which is the same school you were once a student in.

Yes.

Now, as a lecturer, I'm curious to know, what have you learned on being on the other side of the classroom?

It's funny because I enjoyed my 2 years here as a student, for sure. It was transformative in many ways, and I have become very close with my classmates during our alumni period. Like, as alums, we have become so much closer.

Really?

But during my 2 years here, like, I would have considered myself so much more of an outsider. There's a social element at business school that is quite Important to the experience.

Yeah.

Because that's a big part of what you're getting. Yes, you're getting content and you're learning a lot, but the network, and I don't mean that in a transactional way, but really in the relationship side of things, is also what you're coming to business school for. That's how a lot of business gets done, and that's a big part of what your future value will be. And a lot of that requires money. A lot of that involves travel and dinners and activities and things. And people who come in not having worked in industries that made them a lot of money are at a disadvantage to be able to participate in those things. And I worked in the opera, in the nonprofit arts.

Yeah.

And again, no trust fund. So it was very difficult to be able to participate fully in the social experience. And so between that and the fact that I, I really always sort of felt like, are we doing this? Are we doing another trip? Um, I always sort of felt like the weirdo. I mean, I've always been the weirdo my entire life. I've been the weirdo in every room and in many cases have played that up, right?

Yeah.

In, in my Venn diagram, I'm the math girly in the arts room and I'm the artistic girly in the math room and And like, that's been my—

It's like your superpower.

That's my superpower.

Yeah.

And then in some cases, I'm the weirdo at business school who like doesn't know what a P&L is. It's a profit and loss statement for those of you who also don't know what a P&L is. Um, I had to learn that after I was admitted. Uh, and so I didn't really fit in, or I didn't feel like I fit in at least. And it's so funny that like post being here, I've become closer with a lot of these people in adulthood. Although we were adults when we were here, it did not feel like it.

Yeah.

And now at reunions, so many people have reached out to me or had conversations or even between reunions and have given me a story of my impression on them while at school that does not line up with my experience.

Really?

That have given a story of like, oh, I remember you, you were so— and I was like, really?

Like, are you talking about the same Christina?

Are you, are you sure? Um, so that's been interesting.

Yeah.

Uh, as a professor though, I really enjoy that all of the weirdos find their way to my office hours, and I say that with love. I had one in my office hours just yesterday, the ones who feel like they don't fit in. And what's great about it is there's a lot of them. And I can tell them that, that there's a lot of you. And you feel like you're the only one because the sort of the blob is loud. I'm sure this is probably true at Harvard College too.

Mm-hmm.

Those who come in sort of already knowing the norms, who knew a bunch of people who went here already, their manager, their friends, their dad, whoever, um, and they come in loud and they're already wearing the fleece and they're like, they're like, this is how retreat's gonna go, you know? And you're kind of like, oh, okay. Um, they take up a lot of space in the room and, and so you're kind of like, oh, I must be the only one who's feeling this. And you're not. There's so many. who sort of feel like they're the weirdos. And so I tell them to be like, just be a little bit more visible and you'll find your people. And so it's, it's fun to be on the professor side of things now because I get to be the professor I wish I had had.

Mmm.

And I get to be that voice to be like, first of all, weirdos rock. And second of all, there's lots of you. find your people. Um, and then I get to help some of the, the blob kind of tone it down a bit and realize that they're a lot more interesting than they let themselves come off as.

Ah.

And to, to excavate some of the very interesting parts of themselves that they put away when they went into a very linear path From college to whatever prestigious job recruited them freshman year out of their Ivy League.

Fill in prestigious name here.

Exactly.

That's fascinating to hear, Christina. And before we get into our wrap-up segment, I wanted to ask you a question on failure because you have an entire chapter—

I do.

—in your book dedicated to failure. I'm curious to know, you spoke a bit to your own entrepreneurial journey. You launched a fashion startup, which you then had to shut down. I'm curious to know, what did that experience teach you about failure?

So I included a whole chapter on failure in this book because one of the things they teach us about portfolios is you have to have risk if you want return.

Yeah.

A risk-free portfolio does nothing. And in fact, you will lose money in a risk-free portfolio because inflation will devalue your assets. And I think it's the same thing. It's the same idea here. If you pick one thing and you do only that, that is a risk-free path, you will lose value in that path. And so this notion of you have to take risk, but with risk comes failure. This is why we diversify.

Yeah.

Not every investment is going to pay off.

Yeah.

And so for high-achieving people, failure is a very scary word.

Yeah.

I had never failed in my life until my company shut down. 28 years old. I got a B- in differential geometry. Nearly. I mean, that's not a Harvard B-. That's like a— Harvard B- is basically like, go drop out.

Yeah.

B- at Emory is like, yeah, you didn't know some of the material.

Yeah.

Um, but still, I never had a B-. I never had a B. I, I tried to drop my math major and my advisor was like, absolutely not. He like refused to sign the form. Thank goodness.

Good on that advisor.

Um, that was the closest I had Wow. Come to failure. So at 28 years old, I was like, this is the end. Like, I've just failed. What is this even? Like, my identity is someone who doesn't fail.

Yeah.

Like, I've just met antimatter. So it was interesting to then wake up the next morning and still be here as someone who had failed. So it's important. that I talk about this. I'm actually talking about this at Harvard Alumni Day this Friday.

Oh.

Because you have to practice failing small. And if you fail small, you can avoid failing big. I talk about this a lot in entrepreneurship. To run experiments that may not work out can increase the chances that your startup will not fail. Fail small so you don't fail big. But you have to be willing to do things that could fail. And I talk about Quincy failing very publicly. We actually wrote a case study on it—

Yes.

—for HBS. Because when I was a student, we studied entrepreneurship, and we only studied successes. And I complained about it. And my professor, who ended up investing in my company, Quincy Apparel, said, you know, the reason is no one will let us write about their failures. And we write case studies with the permission of the people.

Yeah.

He's like, no one wants to let us write about their failures. No one wants to be honest about them. And I said, well, that's a shame because if the majority of companies fail and you learn more from failure than from success, then we're missing a lot of learning here. And he goes, I agree. So after Quincy Apparel shut down and after I spent 3 weeks in bed watching all 7 seasons of The West Wing— an excellent way to recuperate—

Yeah.

And after I took a shower and ate some vegetables and got a job, Professor Eisenman called me up and said, remember how you complained about not having any failure cases? Would you like to be the face of failure for Harvard Business School? And I felt so bad that I had lost him money that I said yes. And so he wrote the case study on our failure, and we ended up teaching it for like 8 years. And I came back every year, sat in on classes, spoke to the students about that failure. And I was so insistent that I be in the classroom for this because I think the second year we taught it, I was in the classroom and one of the students who got to class early because the case ends at the boardroom.

Okay.

Where we're making the decision, should we shut down? So they don't know that we've failed. They're discussing at this like critical decision moment, and then I reveal that we have failed.

Yeah.

And so one of the students says to his buddy, he's like, oh well, if she's here, obviously they didn't fail. Like, she wouldn't be here if they had had to shut down. And so I was like, I have to come every year because they They believe that failure is the end of their lives.

Right, and almost something you should hide from, right?

Something that you would never show up for. Yeah. Yeah. And so coming and talking about it for 8 straight years, and it's the reason I ended up joining the faculty, because I, I was able to develop that relationship with the school in this teaching context and in this coaching context for students, um, that they were able to see how I would be able to add so much on the faculty side. So again, you invest in things you don't know, and then they come full circle.

Yeah.

And the world pulls out of you what it needs from you. So I think being open about your failure, and I think this is important, I talk about this too, and being open about like what is on you and what isn't. Professor Eisenman went on to write a whole book on this, Why Startups Fail. I inspired him. I'm the opening chapter. And he did a bunch of research about this. This became like the next chapter of his career. And a lot of his research showed that there are some entrepreneurs that take on all of the blame. They're like, everything was my fault. And then there are some entrepreneurs that take none of the blame. They're like, it was all the world. It was outside forces. None of this was my fault. You can guess which gender. Might align with each of the two. And neither of those two are correct.

Yeah.

Right? And it's the entrepreneurs who accurately assess which of this is on me and which of this was out of my control that have the best success when they try again, the highest rate of actually succeeding on take 2. And the highest rate of doing a take 2. So I think it's important to be able to have that clarity. And everyone I talked to when I went out to get that job asked not like, why did you fail? What did you screw up? They asked, what did you learn? And under what circumstances will you try again?

Mm. You're not penalized for your failure, right? And I think that's what we imagine is going to happen.

For sure. And I think in the context of entrepreneurship— and this is probably true in a lot of other contexts as well— trying something that was a stretch for me, right? I was not CEO material when I hired myself to be the CEO of this company. But putting myself into this role and really having to grow into it even though I failed, it accelerated my career by a good 5 years.

Wow.

And this was true of my co-founder as well. And we see this in the research too. Even failed founders end up pushing themselves. We see the next job they're hired for and the role after that, they accelerate versus those who take a job. And then take another job and go forward because the learning curve of the stretch, even with the failure, the learning curve is so much higher. So stretch yourself because the risk of failure is outweighed by the learning.

I love that reframe. That's a perfect segue, Christina, to our little wrap-up segment here. We're going to do a little rapid fire with Prashana. Are you ready?

I'm ready. Let me get a little sip of water here.

Yeah, go for it.

Okay.

All right, Christina.

I'll try to be rapid-fire. You know I talk in paragraphs.

We know you're a singer. Go-to karaoke song? Very important question.

Mm, Carrie Underwood, Before He Cheats.

Oh, good one. Favorite Broadway show?

Oh, that's not fair. I, I can't pick. It's like asking— it's Sophie's Choice. Like, pick your favorite show. You can't.

Give me 2.

No, there's like what's on right now versus what I have produced versus things I love. You don't have like a top 5? Okay, I'm just going with my gut. Suffs.

Okay. But also—

Only because you made me. Two Strangers Carry a Cake Across New York. Currently on Broadway, Tony nominated.

Christina, you mentioned you like to play the piano and cello. Favorite piece to play on the piano?

Ooh, um, there's a Chopin Nocturne in C-sharp minor that I adore.

Oh, you're a Chopin person.

Yeah, that, or there's a Liszt sonetto. I forgot the key it's in. I played it for my senior recital, and it's like the most impressive thing that I can still play by memory. It's my like when I'm drunk and I want to impress people, but they also have to be drunk because I can't quite get all the notes in the cadenza. But they don't know, right? It's Liszt.

I recently got into playing ABBA on the piano. Oh, and there's nothing like playing Slipping Through My Finger when your fingers are slightly— you're like, this feels like—

My husband is very much like a McCartney kind of like he can sit down and play and sing along. He's so much more fun at parties. I'm like a, please sit and you are now going to listen to classical music. I hope you are ready for some etudes, you know.

All right, 'cause we talked a little bit about failure. Favorite failure to date?

Favorite failure to date? Um, every relationship I had before I met my husband. Thank God. Particularly my first in college, because I would have married him and followed him to the ends of the earth, and he treated me like shit. And I am so grateful. I'm so grateful that that never went anywhere. Thank you.

We talked a little bit about this, I think, Christina. You hinted to it. But if you had to create another course at HBS, what would you teach and why?

I mean, obviously storytelling all over the map, storytelling in every version of it. But after that, probably an ideation course. I think our students really struggle with— coming up with new ideas. And we've had a couple of attempts at ideation classes, and I think we're really good at coming at it from an analysis standpoint, from like a let's survey the market, let's get a good sense of the, the white space, let's like understand how big the market are. And I would do it probably as a half course from a purely Creative standpoint. Like, I would make them read The Artist's Way.

Assign read. Oh, I love that.

And we would be doing like artist dates. We would be going to the art museum. We would be doing improv. We would be taking dance classes.

We need a manifesting course.

Like, we would be reconnecting to our creative childhood in order to like reignite our own ability to find ideas. Because I think our students are— have, have like carved off the creative muscles.

Like suppressed it.

They've suppressed it. They've like buried them in a box under the floor, and we need to Edgar Allan Poe them, you know, out.

Yeah, I hope we can like speak this into To reality. Um, you also slightly hinted to this earlier as well, but if you had to write a sequel to The Portfolio Life, what would it be about?

Well, I've already written a Portfolio Life workbook that I offer for free on my website. I really do a bad job of, of telling people about it. Um, what would I do? I mean, honestly, I would probably do a, uh, the sequel of like So AI, huh? Um, with like, how does that— how do you, how do you, um, extend these ideas in the age of the algorithm?

Okay.

Um, what I, I think everything that I've written is still accurate, but I think there's some ideas that really could be extended. Um, tools, absolutely, especially as I get into the how, the last part of the book. I think there's a lot of tools that I've even just like vibe coded for myself that I could really expand on, like building the operating system for your portfolio life.

Yeah. And it wouldn't be 2026 if it was something about AI, right?

I mean, I'm like a little bit sick of saying in the age of AI.

Yeah, I know. AI fatigue is beginning.

It's like saying on the internet in like 2001. Or social mobile local in 2011.

Yeah. All right, Christina, you've been a faculty member at Harvard Business School for 6 years. What's one word your students would use to describe you?

Energetic.

Ooh, that's a good word.

Every single class—

Really?

Every single class that I've taught, I always ask about 4 sessions in for feedback of like, what's working? What should I keep doing? What should I stop doing? What could I, you know, start doing to help your learning? And every class, every semester for 6 straight years, the, the one thing that is keep doing is love the energy. And I'm like, great, because I only have one way of physically being in this classroom.

Mm-hmm.

So there's no way I could do anything different. Thank God it's like not on the stop doing. But I'm also like, how is everyone else showing up? So apparently I'm high energy.

And it's maybe also like the performer, right?

I'm pretty sure. It all goes back together. It all goes back together, yeah. No, I mean, I'm loud and I take up space in the room. It's, uh, so yeah.

Yeah. Well, Christina's book is called The Portfolio Life. And it's a good reminder that portfolio is not just useful in finance, but in crafting your own life as well. Christina, thank you for opening us up to and helping us reimagine this new world of possibilities. Thank you for coming. Thank you for having me.