Building an Interdisciplinary Career with Christina Wallace, Entrepreneur and HBS Professor

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Thank you, Susan, and welcome everyone to another Walker webcast. It is a real joy for me to have Christina Wallace joining me today. Next week, we're replaying an interview I did with Ezra Klein at the Sun Valley Writers Conference 3 weeks ago, and Ezra and I dived deep on artificial intelligence, homelessness, and a whole bunch of other topics that Ezra focuses on in his extremely entertaining and engaging podcast on a weekly basis for The New York Times. So to those of you who want to tune back in next week, I very much enjoyed that conversation with Ezra, and I hope you do as well. To today's guest, let me do a quick intro on Christina, and then we will dive into our discussion. A self-described human Venn diagram, Christina Wallace has crafted a career at the intersection of business, technology, and the arts. She is a senior lecturer in the Entrepreneurial Management Unit at Harvard Business School, where she She is co-course head for the Entrepreneurial Manager, teaches Launching Tech Ventures, and leads the MBA Startup Bootcamp immersion program. Her latest book, The Portfolio Life, was published earlier this year. Christina holds an undergraduate degree in mathematics and theater studies from Emory University and an MBA from Harvard Business School. She's an active angel investor in early-stage tech startups, as well as commercial theater productions on Broadway. That, that is not usual. We're going to dive into that in a moment. In The Portfolio Life, Christina adapts tried and true practices from the business sector to help you eschew the cult of ambition and experience the freedom of building the flexible, fulfilling, and sustainable life you want. Drawing on research, case studies, and her own experience, she walks you step by step through the process of designing a strategy for the long haul because you deserve rest, relationships, and a rewarding career. Not someday, but today. And after all, you only live once. So, Christina, first of all, welcome. Second of all, I want to start here. You say you wrote the book almost as an autobiography to explain to your mom what you've done with your life, which I love, and that's great. But as I sat there and read it and knew all of my background on you as a person and how you live your life, I sort of felt like I was reading a book like by Michael Jordan, saying, it's just a game, or Kim Kardashian saying, it's just a selfie. In other words, like, it didn't match with what I know about you as being one of the most engaged, hustling, career-focused, trying everything. I mean, I get the fact that you are so talented in multi-disciplines that you have the capability to write this, and yet to sort of write it for others, I sort of sat there and said, this is like MJ saying, Ah, don't worry about it. You don't need to work that hard. It's just a game. Tell me why I should listen to what you said, given what I know about you as a person.

Um, wow, that's very flattering. I don't think I've ever been, uh, compared to Michael Jordan in any, uh, context. Um, you've never seen me on the basketball court. I—

You are 6 foot. You are 6 foot. So everyone watching this should know that Christina—

I'm a complete failure at basketball. Part of this, I think, stems so deeply from— I go after every piece of my career, every piece of my life because I want to. I care deeply about it. It fills me. It brings me joy. There's no element of what I do because I'm driving for prestige or money or something that other people are impressed by. And I remembered when I started my MBA at HBS and I met all of these folks. I came from a very non-traditional background. I'd worked at the Metropolitan Opera before I came to business school. And I asked folks, you know, like, what do you, what do you think you're going to do with your life? Like, why are you here? What are you, are you here to learn? And so many of them said, well, I'm going to be the CEO of a multinational company. And I was like, okay, which, which one? Like, do you have an industry in mind? Do you have a sector that you care about? Do you have any connection to this work, or is this just a certain level of power and cachet and prestige that you aspire to. And I, I really didn't feel a connection to that at all. My ambition is very much from a place of I'm doing things that I care about and that I want to see a difference in. And so part of what I'm trying to espouse in this book and in this sort of model is allow yourself to reconnect to the shit you care about and then figure out the business model for your life and for your work that actually matches to that. And it's probably not going to look like everyone else's. And so it requires a certain amount of entrepreneurialness and creativity in how you're going to put those pieces together and manage it. But that is what I believe is going to fill you and give you the longevity to still hustle 20, 30, 40 years down the line, because it's going to keep changing as you change.

So you talk about that. And when you describe those fellow HBS students who said, I want to be CEO of a multinational company, when Ezra Klein and I had our conversation in Sun Valley a couple of weeks ago, Ezra asked me, what does our society put value on? And my response to him was success and achievement. And there were 2,000 people in the audience, and everybody sits there and nods their head. You state in your book, step back from the cult of ambition. Yet you're teaching at the Harvard Business School, where, at least from my take, that's probably the most ambitious cohort of people you can possibly find on the face of the planet. So help me understand that.

True.

That's a little bit conflicting there. If you were teaching the arts across the river at the college, I could kind of get it. But teaching this of disassociating yourself from the cult of ambition at the Harvard Business School seems a little counter to what I would typically think.

Sure. For one, let me be clear, I am ambitious. I'm incredibly ambitious. But the cult of ambition, the way I think about that, is the world in which every time you achieve a thing, the very next thought in your mind is, okay, what's next? What's bigger? What's higher? What's more impressive? What's next? And it is this, this linear mindset that requires constantly moving up into the right, and usually in only one dimension of your life, your professional life. I am incredibly ambitious right now. I'm ambitious in many dimensions of my life, not just my work, my book, my teaching, also my family. I have a 1-year-old and a 3-year-old. There's a lot of work I'm putting into helping my kids get off to a start where they have emotional control. They have an understanding of how the world works in a way that they fit into and they can be kind and generous. I have ambition for my marriage that it doesn't fall apart at this motion of early children and a career, right? There's a lot of dimensions that I seek ambition. And part of what I'm trying to bring to my students at HBS is that understanding that ambition can be incredibly wonderful. It can drive you for sure, but don't let it be— the, the only God you worship. And in particular, when I think about where I can have the most impact, I don't need to go across the river to the art students and teach them to follow what they love. I need to go to the business school students who are willing to work themselves toward a goal that they might not even want. But they haven't questioned that. because it's so shiny and it's so respected by society. And honestly, if we can have a few less miserable billionaires, I think that has a pretty significant impact on the world.

As you talk about the students that you teach at HBS, I had sort of 2 comments and sort of a question for you, which is that you teach entrepreneurial marketing and entrepreneurial management. And I'm sure I'm sure that you have students come up to you all the time and say to you, like, I heard you say once that someone walked up to you and said, what hobby should I pick up? And you were sort of like, that ain't for me to determine what hobby you ought to pick up. This is expressing your own interest, not what Christina Wallace says you ought to go do, which I loved.

Right.

It was great. But I can only imagine that you see a lot of business plans and you have a lot of students who come up to you and say, like, oh, I'm excited to be an entrepreneur in this or that. Do you ever sit there and look at that student and say, you know what, from my knowledge of you, you actually aren't built up to be an entrepreneur and you actually ought to go take that job at McKinsey?

I have never said it in those words. Um, I've thought it a couple of times. The closest I have come to it is saying, I wonder if this is the right move for you next, as you think about the experiences, the network, the mindset, the resources you need to be a successful entrepreneur. Do you feel like you have those yet, or you have access to them yet? Or is there some experience you might want to gain, maybe as the chief of staff to an early-stage CEO, so you can see what these, uh, these environments feel like, right? That the roller coaster, the constant change, the uncertainty that comes in the earliest stages, you might find that's not the best fit for you. Maybe you are a better fit in the later stages of company building, or once it's already up and running and you're thinking about the scaling of a company. So not everyone has to be that founder that they're on day zero to be entrepreneurial and to build things. And part of this work is to figure out where you fit. I write in the book that one of my great joys was finally embracing that I'm a very strangely shaped puzzle piece. I embrace that I'm a weirdo, and I would argue that everyone is a strangely shaped puzzle piece, and your work is to figure out what shape you are. So that when you go into rooms, whether it's jobs or relationships or anything else, you have an understanding of where you fit. And it's not a question of, do you, do you like me? It's just like, Do I, do I fit the puzzle? Like, the space that's available, do I fit or not? And if I don't, rather than like shave off parts of my puzzle piece to try to like jam it in, maybe I should just find the rooms that want me.

So when you finished Emory, you say that you were fluent in 3 languages: math, music, and English.

Yes.

Take us on a quick journey from that young woman who was fluent in 3 languages of math, music, and English to getting to the Harvard Business School. What was that journey like that ended up putting you in Boston, Massachusetts a couple years later?

So when I graduated, I had a really hard time deciding if I was going to get a PhD in math or if I was going to pursue a career in the arts. I really did love both. I have loved both my entire life. And so I applied to a bunch of PhD programs, and then I applied to a bunch of jobs in the arts. And I basically said the universe will tell me which way I should go. And I got into a couple of PhD programs and I went to visit and it became very clear this was not my path. You know, I spoke with a couple of professors and they said, I gotta be honest, in all of my years of reading applications, I've never had a candidate with a recommendation letter from a theater professor before. So that's a little odd. And they said, you know, it's not that you can't do this work, I just wonder if you are going to want to focus for the next 6 or 7 years on one tiny little problem in mathematics that maybe a dozen people in the world care about. And when they put it that way, I was like, you're right, I don't. Like, that's not the fit for me. Thank you for helping me figure that out. And so I moved to New York and I sent my resume everywhere. There was a website at the time called the New York Foundation for the Arts job board, and I just sent out like 50 resumes. This is back in the era where you still printed them out and sent them. My students don't believe that that ever happened now, and I got exactly one interview, and I was at the Metropolitan Opera. I had applied for their director of children and supernumeraries, which are the extras in operas. I was literally 20, 21. I had no work experience, but I applied to a director-level job because apparently I have some chutzpah. And the HR director called and said, you know, he's like laughing. He's like, yes, so you're not a director level. candidate, but we filled that job internally and now we have another opening as a rehearsal associate. Are you interested? And I was like, obviously yes. And he's like, do you know what that means? And I said, no, but I have $600 in my pocket and like, this is the only job lead I have. I did not tell him that, but I went in to interview and as part of the process, they, they really wondered if I'd be a fit there. They said, we talked to your references and they said you like to come in and change things. And we're not interested in that. We are the Metropolitan Opera. We've been doing things for 100-plus years this way. And so as part of me accepting the offer, they made me handwrite on the bottom of my contract, I, Christina Wallace, promise not to ask to change a single thing in my first year here. I was so broke. I was like, whatever, I'll take it. Neon flashing red lights. I didn't care. I took the job, and for a year I kept my mouth shut. And I took a lot of notes. And after a year, I showed up in my manager's office and I said, I have some ideas. She's like, oh dear. And I said, in particular, I have this one idea. You know, we're doing all of these by hand. Rehearsal associate, it's a very high level. It's operations and contract management. I was like, we're doing all these things by hand. I think we can turn this into a computer program. I did some programming as part of my math major. I can't code the whole thing, but like, find me an engineer. I can work with them and we can automate a ton of this stuff. And, you know, I looked at our financial situation. We're a little bit over budget every year. And I think because so much of our budget is people, if we can find some efficiencies here in how we schedule rehearsals and performances, like, we could probably get closer to breaking even. And she looked at me just absolutely bemused and was like, get the fuck out of my office. I didn't like that answer. So I went to her boss and he kicked me out. I went to his boss and she kicked me out. So I finally went all the way to the top, to Peter Gelb. And he basically is like, look, this is, this is not a place where we're going to change things quickly. This is not a place for someone who's young and ambitious. Like, there's nowhere to go until someone dies or retires. And I looked above me and everyone was healthy and in their 50s. And I was like, okay. And he's like, I think you should go to grad school. Everyone smart goes to grad school. I was like, okay. So I went home and I Googled MBA programs. I didn't know anyone who went to business school, but I figured that's where the people who run the world Go to school. I took the GMAT 2 weeks later and then got in quite luckily, like the year before the financial crisis, which is when everyone decided to go to business school. So there was a ton of luck involved, but showed up to business school thinking, I don't know the difference between a stock and a bond, but I'm going to figure it out because these are the skills that the people who get to make the decisions build. And I want to be in the room, the room where it happens, as they say in Hamilton.

So you get to HBS, and second year you take Clay Christensen's course. To those whose name Clay Christensen might not be a household name, Clay wrote a legendary business book called The Innovator's Dilemma, which was built— written in 1997 and has been reprinted thousands of times. And talk for a moment, Christina, about Clay's impact on you? Because I've read enough of what you've written, I've heard enough of what you've said, that of all the people who had a big impact on you at HBS, it was Clay. Why? What did Clay either do, teach, or say that captured your imagination?

Clay was just an amazing, amazing man. And he made me realize the impact that professors at HBS can have at scale, right? Not just in the writing and sharing it with the world, but also on the people who sit in the seats in those classrooms. And so I took this course with him, Building and Sustaining a Successful Enterprise. It's a terrible title for a class, but it's about how to stay innovative, how big organizations can use these theories around disruption to continue to innovate and find new businesses and basically disrupt themselves. And, you know, he taught this incredibly fascinating class with this very academic style, which is not typically the style at HBS. It's much more practical in most other classes. And this required us to formulate theory and sort of extrapolate into higher-level thinking. And then on the last day, he came in and said, you know, I'm going to take the turn toward the personal today. And in that moment, you know, he had shared with us he had just been diagnosed diagnosed with brain cancer, and it was, it was quite possible— many of us thought in, in the moment, as did he— that this might be his last semester teaching. And so he, he used that last class as a way to talk about our lives and the responsibility that managers had because of the impact they had on all the people that worked for them, right? You, you have a bad day, you take it out on someone, they go home, that's how they show up for their family, that's how they show up for their team, right? It becomes this huge cascading effect. And And so he talked, you know, quite extensively about the ideas that ended up becoming his book, How Will You Manage Your Life? But it was this notion that we could take the tools that he'd been teaching us for managing businesses and we could apply them to our lives. And maybe that feels really wonky to take frameworks from the business world and, you know, set up your life and give it kind of a balanced scorecard or whatever else. But for us in the room, it made a lot of sense, right? It connected with how we thought about priorities and resource management. And he gave us permission to care about our professional life, yes, but to care very deeply about our personal life. And I think it was the first time that I'd ever heard, certainly at HBS, but even beyond, people say, you know, it matters if you're happy. That's not just like a silly little you know, thing that people who don't aspire too much get to have. Like, it matters. Unhappy people who are hugely ambitious can wreak havoc on the world. It matters that you're happy. It matters that you invest in your family and in the communities that you serve. And that impact is as important as the professional ambitions that you might have.

So it's interesting that your first 2 books are basically on those 2 themes. So your first book, New to Big, is all about how large companies can be more entrepreneurial and scale new ideas. And so I want to focus on that first. And then The Portfolio Life is very much on that other piece that you took so much out of that last class with Clay, which I— when I asked you about that, I didn't know you were going to come right, you know, that you hit that softball right down, down the middle of the field in the sense that I didn't know that there were those 2 things. But let's talk for a moment, Christina, about New to Big, because—

Sure.

In that book, you talk about a growth operating system. And you basically say to larger companies that this isn't kind of a one-off moonshot of, let's figure out what the new entrepreneurial idea is today, put resources to it, and enter that market. This is more about building a permanent ladder to the moon, where you've got a culture inside of the company, you've got the systems inside of the company. And I think most importantly, what you underscore is the risk-taking and ability to fail culture that is so lacking in many large corporations that must be there for large corporations to be able to pursue these innovative ideas?

Yeah, yeah, it's, it's a challenge. I mean, this is when, um, I wrote that book with, uh, the CEO of the last company I worked with, uh, Bionic, um, David Kidder. We were working with these huge Fortune 500s, and, you know, they could, they could build these sort of one-off innovation successes, but they required almost like an act of God. Like, it required the CEO picking up the phone every third day and being like, just do it. Like, break the rules. Go ahead. Like, I know legal, you don't like doing this. Just do it. And it showed that, like, you can be innovative in these one-off efforts through these acts of God, but that is not a sustainable, repeatable innovation strategy. And so if you really want to build that culture of innovation where you can disrupt your own business rather than waiting for the startups to do it and then acquiring them so that they don't. For you to do this, you have to build effectively an internal entrepreneurial ecosystem. And entrepreneurship has at its core this high failure rate. You're trying many, many things. with a high failure rate in the effort of getting faster, closer to what is going to be successful. You're searching for the truth. You're not planning the truth. You're not writing out a 3-year product launch over something that you have absolutely no evidence the market wants, which is often how large company innovation is planned. And so it requires this sort of injection of an entire entrepreneurial system. So it's not just the workers being more entrepreneurial as they run experiments, look for evidence, chase down new trends or new behaviors that they think might be interesting. It also requires the senior leadership to take off that executive operational hat and to put on a venture capital hat that says, we're going to make lots of bets, and we expect that most of them will fail, but in their failure, they will teach us something. And out of that portfolio of bets, a few will survive. And that we are okay with failure as long as it is in search of the commercial truth. And that's just an entirely different way of operating that requires a bit of like a truth-telling that doesn't exist in some companies. And we saw this, you know, as we worked with not just the folks on the ground doing the entrepreneurial work, but as part of our work, we, we coached, we worked with the senior leadership to help build that venture capital mindset, that way of showing up in the room, of asking questions rather than, you know, offering dicta. And, um, and we showed them in many cases how afraid their, their company was to tell them the truth. And, and in those moments where the company could say, you know, we invalidated that, you really liked that idea, the hack Turns out we did a little bit of research. It didn't actually require that much work to find out no one wants that. Literally no one wants that. It's a great idea. No one wants it. And certainly no one's going to pay for it. And to be able to tell the CEO that, in this one case that we did it, the CEO literally went back and told that story at his next all-hands as a way of not just showing the people doing the work that he valued the truth, But showing the entire company that the truth is the only thing that is going to get them closer to what that next big opportunity for growth will be. And that, that requires really this mindset shift from the top down.

So one thing that you say in the book that I thought was really interesting was focus on what your customers do, not what they say. So there's There are lots and lots and lots of companies out there that sit down with clients, listen intently to what they're saying, and then go back and craft a strategy to meet those needs because the client has said, well, this is what we'd like to do, or this is what we get from other providers, so you need to mimic that, or what have you. How does one go about looking at what the client actually does rather than what the client says?

Yeah, this is crucial because your customers will lie to you. It's not because they're bad people, and sometimes they don't even know they're lying to you, right? Sometimes they're trying to tell you what they know you want to hear, but sometimes it's because they're projecting a version of themselves that they want to be true. It's just not true. I think the perfect example of this: I worked with a large packaged foods company that that kept hearing from their customers they wanted healthier food options, especially healthier things that they could eat on the go. And so they said, oh, we gotta come up with health— healthy options that can, you know, sit at the front of the grocery store. And, you know, we have all these different ideas. Let's see which ones we, we should use. And we said, okay, let's do some ride-alongs with some of your customers. We're just gonna spend the day with them, and we're gonna watch how they eat. And we set up the experiment in 2 ways. One, where we basically paid for what they ate every day. We gave them gift cards to cover that so that it wouldn't come down to, well, I want to eat healthy, but it's too expensive. So we wanted to take that out of the equation. And then the other case, we didn't pay. We just let them do their normal thing, and we just literally like hung out with them for the day. We sat in the car, we rode around, we, we did their errands with them. And we got in, uh, to the car with one customer who had been going on and on all morning about how much she cared about being a healthy eater and, um, how this was really part of her, uh, her identity and, and what She wanted to show her kids. And then we get in the car and the floor of the passenger seat of her car are like 12 Snickers wrappers and like a handful of empty Coke cans. And we're like, interesting. Okay, so what you're telling us, but what you're doing are 2 very different things and we have to unpack that. And so we get into the the real truth of the matter, which is some of it is about convenience, some of it is about form factor and being able to eat on the go, some of it is about perception. I want to be the type of person who is healthy, but also those Snickers bars are really delicious. And so like getting to the root of behavioral experiments and particularly transactive experiments, things that cost your customers something, they say you want this, great. Give me your credit card to pre-order. Sign up. Give me an LOI, a binding LOI for this thing. Like, put a little bit of something on the line so that it's not just, yes, I like that, because that doesn't cost you anything. And once you get into the actual transactions of, uh, of study, of experimentation, you'll start to get to the truth much faster than just asking for what they want.

So as we transition From your first book to your second book and The Portfolio Life, which I want to dive into in a second, I want to touch on the personal side of things for a moment because your TED Talk on how you found your husband, Chaz, is so good and it is so Christina Wallace. It's scary.

Okay.

So I don't want to spend too much time on this because anyone who wants to watch it can go watch it on TED. Just pull up Christina Christina Wallace TED Talk, and it will come right up for you. But talk for a moment about you taking a dating app and turning it into a funnel, and then also the zero date.

Yeah, so I— this, this started, um, as I was approaching turning 30. I, I had been dating in New York City, and anyone who's ever dated in New York City will feel me right now. It's just a terrible place to have to date. Um, I had had a serious boyfriend through business school that didn't work out, and then it was like on my own as an entrepreneur in New York trying to find a partner. And as I was approaching 30, you know, the fake deadline where women are supposed to expire, and I was feeling this pressure, I was like, look, I am really good at business and I am really bad at dating. So I'm just going to treat dating like a business problem and I'm going to apply my business tools and we're going to solve this problem. And so I took myself on an offsite. I went camping by myself in Maine for a week. week and pitched a tent, wore some flannel, drank some whiskey, and did a retro on all of my previous dating situations, my relationships, the situationships, and tried to get to the bottom of where did they go wrong? At what point did they know they went wrong? How long did I stick around after I knew they weren't going to work? And I started to realize in doing this work, I'm like, this is just sales funnel analysis. I literally do this all the time as I'm doing deals. So I just need to set up a sales funnel and I need to really understand my qualifying criteria to move a prospect through the funnel from, you know, potential lead to qualified lead to, to each of these things. Like, what am I gonna do and what am I gonna ask for them? And again, behavior, do not say. What are the— what are they going to do to show that they're interested and that they're committed to this? And then, you know, at what Do they get ejected from the funnel? And I'm just gonna use online dating as a way to source leads, cuz it is a way to meet lots of people that you don't run into on a daily basis. But I'm not gonna use it as a way to qualify leads, cuz I think I was finding I was, I was tending toward using these online profiles like a resume review. And then it turns into like, you look great on paper, but we don't have any chemistry. So I was like, I'll source my leads and then we're going to get offline as quickly as possible. And this was crucial because the things that I had identified that I really cared about in a partner, I couldn't really vet online, but I didn't want to be giving up like 3-hour dinners for people that I had hardly vetted. And so I came up with something in between, which is the zero date. It's not a first date, but it's the zero date and it's one drink, one hour to answer one question. question, which is, do I want to be stuck for 3 hours having dinner with this person? And I would just stack them back to back. I would pick one night a week for dates and I would do 3 a night as a way. And I would tell them ahead of time, I've got a hard stop. I wouldn't tell them I have another date, but tell them I have a hard stop. So we're setting expectations appropriately. And it was just like, do I want to know more? And so I set up this funnel and I started, you know, I had a couple hundred inbounds at the top, and you can watch the TED Talk to see the math of how many make it to the bottom. But going through this process, it's how I met my husband. He loves the story. He thinks it's absolutely hilarious.

Well, the thing that I find so interesting— the thing I find so interesting about it, Christina, is this. The first thing is a lot of people use dating apps like a game, and you're very clear in saying it's not a game. Like, this is serious stuff. Use it as the tool that it is. The other thing is that you're very straightforward in saying the access to potential partners is what makes the app so valuable. In other words, hanging out in New York, you can only go to so many bars. You can only meet so many people in a night. You get stuck in a conversation for 4 hours, and that's the end of it. And you might not want to see that person again for the rest of your life. So use it for what it actually is. And I— as I listened to you talk about that, I said, you know, there's so much out there on LinkedIn and Instagram and all these different things are sort of clickbait. They don't, you know, they kind of, they keep us interested, but they don't actually produce anything. And what I found so interesting about what you did with the dating app was you actually understood what the dating app had as far as a benefit to getting you what you wanted to do. You used it as the tool that it is not necessarily intended to be used at, but what you saw as being the ability to get you the outcome. And then you actually were wildly successful because you met Chaz on it. And the The two of you now have two kids, and all the rest is kind of history. But I, as I sit around and think about all the different social media sources that we have, as I think about bankers and brokers at Walker and Dunlop who use our Salesforce database, who use LinkedIn, who go to conferences, and all the kind of the the distance between the lip and the cup to use a golf analogy as it relates to oh, I've got this person. I met them on LinkedIn. I think they're gonna you know I think they're gonna. borrow money from Walker and Dunlop and this is gonna be great. And then it doesn't get converted into something because they're using the tool as just kind of broadcasting who they are rather than really identifying who a real potential client can be and converting that connection into an actual sale.

That's exactly it. Like understanding what the tool can do and what it can't and defining what you need at each stage of the funnel or whatever the process is that you're developing. saying, what is the right tool for that, and how do I piece together, um, the, the, you know, these different steps in order to get to the outcome that I care about? And I think as crucial as that is, um, you know, in understanding both what they can do, it's also what evidence— this gets back to my, my obsession with evidence in experimentation and innovation— what evidence are they offering that they are interested in taking this to the next Are they giving me an email? Are they offering their time? Are they saying yes to a coffee? Am I doing all of the work to show up and it's convenient for them? Or are they in some way showing in good faith that this is something they care about too? And it's looking for that transactional evidence at each stage to help you, uh, have just higher fidelity in, in the process.

So in the portfolio You hate the term work-life balance. So if you hate that term, have you come up with a better one?

Yeah, a portfolio life. No, I mean, I, I hate the term work-life balance because it sounds like, you know, it's like you got a teeter-totter and you've got work on one side and you've got life on the other and you're trying to get them to balance. I mean, that, that's the image that conjures in my head. And I hate that for one reason, they're never going to balance. There are always going to be phases where one is going to be heavier than the other. So I'm not sure balance is the goal. And then 2, I hate it because work is a subset of life. It is not in opposition to life. So when I think about a portfolio life, and I use that term intentionally and not just portfolio career, Portfolio life, you know, you think about your financial portfolio, you, you visualize it as a pie chart, and your work is a piece of that pie chart. And so are your relationships, your community, your hobbies, your rest, the other things that you allocate your time and talents to. They all are a slice of that pie chart, and it adds up to 100%. So your work is in the context of your life, and that cannot be separated because as you think through through these different seasons of your life, these different chapters where you might need very different things, you then are going to have to adjust your work and all of your other allocations to be balanced, balanced in a portfolio sense for that season of life.

So a couple things here. I mentioned to you previously that I now know why at I went back to my HBS 25th reunion a year ago. You didn't present there, but you presented this year. And you were the rave of the reunion. And somebody said, oh, she was amazing. And now that I've done my homework on you, I realize why. Because once you get to my age, HBS has figured out we're not trying to teach you how to manage or how to lead or how to make a financial analysis anymore. You're done with that part of your life. Now you're into kind of like enjoying things. But then you also said to me, no, but they also had me speak to the people who were back for their first reunion and their 5th reunion. reunion and their 10th reunion. So I think about this in, in the following way, Christina. Uh, I'm interviewing 2 people who both went to Emory, and in comes this woman who was a finance major. She interned at an investment bank in the summer and then for a real estate firm, and she says, my dream job is to be a mortgage banker at Walker Dunlop and do big transactions and loans. This is all I want to do. And I meet with her and it's all great and good. And then in comes this young gentleman who also went to Emory and had the same GPA as she But he says, I was pre-med at Emory, took some biology and some other courses, but decided I don't want to be a doc. I'm a big skateboarder, and so I've spent my summers at a skateboard shop. I also play in a band, and I really like reading literature. And doing a job in commercial real estate finance sounds like kind of a cool thing to do. Okay?

Mm-hmm.

So I see these 2 people and I say to myself, okay, who am I hiring? Who am I hiring? I'm hiring the woman, like flat out, I'm hiring the woman because she's walked in saying like why she wants to work at Walker Nellup and all that. Whereas you talk a lot in your book that actually I ought to be hiring the young man, um, because of his diversity of thoughts and experiences and everything else. So help me from 2 perspectives. One, Willie Walker the hirer, Versus Willie Walker the first year out of Emory interviewing for a job.

Sure. So I, I say maybe you should hire him, and I say maybe for 2 reasons. Number one, the way you just presented him, he didn't tell me a very compelling story of why this. Even if you do a lot of things, even if you had the pre-med background and the literature and the skateboarding and the whatever else, I still want to know you're intentionally choosing this and you're not just falling into it. So I would tell him, the person interviewing, we gotta work on your story because even if this hasn't been what you've wanted to do your whole life, I at least wanna understand why it's the right fit for this chapter of your life. What do you wanna learn? Who do you wanna learn it from? And why is it a good fit for now? If you can't tell me that, I'm not hiring you. The other thing I'd wanna know from the female candidate is, Because what else do you do? I see this laser focus and that is admirable, but I have to imagine that your business is not going to look the same in 10 years as it does today. And I want to be hiring people who are bringing in fresh perspectives, who are reading things that have nothing to do with your business, who are paying attention to consumer trends or technology developments or things that don't in any way seem related, because at some point they might, right? These intersections, these changes, they come out of nowhere, but people who are paying attention see them coming. And so I want someone who is not just laser-focused, but also has an understanding that she needs to be not well-rounded. I hate that term too, but she needs to be spiky. well lopsided in more than just this industry. So getting a sense of how else she is understanding and learning about the world will tell me what she might be able to bring to this work. So I would probably be like you and lean toward her, but depending on how old she is and what she's interested in, I might spend a lot of time coaching her into developing this other, this other piece of who she is so that this one-sidedness doesn't become a liability 10 years from now. When your business has dramatically changed and she hasn't grown with it.

So double-click on that for a moment as it relates to orthogonal networks. You talk in the book about basically, um, 2 vectors that don't overlap. Talk about that either from either a business strategy standpoint as far as what the need is to have people who can think that way, or the other is as an individual developing those orthogonal networks as it relates to what your interests and what your capabilities are.

Yeah, orthogonal networks. I think these are crucial and they're so valuable to managers when you have, you know, individuals who are really active in developing this. And it's for a couple of reasons. As an individual, an orthogonal network, and by that I mean a perpendicular, a non-redundant network. You could think about this as my theater network and my math network, right? I'm likely the only person that overlaps between those worlds. You want this because you as an individual, you bring value to both worlds by being the node that connects them. And you are able to take ideas and people from one world and introduce them to the other. So you can be this sort of cross-disciplinary seeder of ideas. A perfect example of this, you mentioned I angel invest and I also invest in Broadway. And I just did another investment on Broadway, and I had to fill out all of these papers by hand, and I had to form an LLC in order to do this. And I was like, guys, you do know in the tech world, I just go to AngelList, and I wire them my money to be part of a roll-up vehicle that just flows into the startup, and they manage all of the taxes, and they manage all the investor management. It's all done on the platform. Meanwhile, in theater world, I'm still like hand signing and taking photos of PDFs, and And the producers that I was talking to were like, are you, are you serious? Like, I've, I've never heard that. Like, I've, I've lived my entire life in commercial theater. I've never been exposed to that. Is there an entire other way we could be doing this that might offer efficiencies and, you know, cut down and streamline things? And I'm like, oh, not only is this a new idea I brought, maybe my relationships and my network might be able to, to help me. build something in this space. Maybe this is an opportunity for me to pursue. So, so you as an individual, it gives you ideas, it gives you value to add to both sides, and it gives you optionality. If one thing starts slowing down or you're seeing a recession or you're seeing, you know, some, some lack of growth in one area, you can pivot into another and you've already got those relationships seeded. As a manager, why this is so valuable is that you have employees who are constantly thinking about and having access to completely different worlds, whether that becomes a source of clients or whether that is a source of other talent. I think about one of my friends who works in a computer software company who realized one day that she could tap into actors as a great source of salespeople. Actors make great salespeople. They're wonderful at listening and not just talking all the time. And she had this untapped untapped source of, you know, really affordable talent that wanted to hustle in her ecosystem where she was struggling to find experienced salespeople. So, so you have access to these worlds, but also it ensures that your people are again like staying, staying present and staying active in what is shifting because the, the The truth of the world we are in is that disruption is the new normal, and it is coming faster than ever before. And so anyone who is all in on one thing, heads down, laser focused, they are missing everything that is happening around them. So I don't care what you're paying attention to. I just want you to be paying attention to something other than your day job.

If you— there's so much in there. Let's go here. You talked about the portfolio and that you— the COVID of your book in the UK is a donut and it's broken up into a portfolio. First of all, why does the US one have sticky notes and a Venn diagram and the UK one has a donut broken up like a portfolio?

Yeah.

I have no idea.

The research of who buys what in what area, apparently.

I have to tell you, I would've thought donuts would sell a lot better in the US than they would in the UK, but that's—

I will tell my editor because we get a different cover for the paperback here in the US than I've been—

Yeah, exactly. Well, you also have Adam Grant on the COVID of the book now, so that's kudos to that. But let's go on those 2. Let's, for 2 seconds, on the portfolio and the donut.

Yes.

As I think about that portfolio life, And various characteristics that you need to build up to have a portfolio life. As far as your own personal portfolio, Christina, there's one stock that we all have in our portfolio that we'll never sell. It's like that for whatever reason, it was either— it was your first investment, you think that Warren Buffett is the greatest person on the face of the planet and Berkshire Hathaway, you'll never sell your stock. But in every portfolio, there's something that hell or high water, you're not letting go of. So using the analogy to you, as far as your own portfolio life, what's that one stock you'll never let go of?

The thing that I will never lose as part of my portfolio is a slice of work where I am creating. What that looks like might change over time though. So growing up, it was as a musician. I was a classically trained musician in piano, cello, and voice. For 17 years, that was my form of creating. When I got to college, that shifted into theater as a director and an actor. And now at this stage of my life, it is as a producer of theater and as a writer. And it looks different in different stages, partially because of what I have access to, partially because of where my efforts might be the most fruitful. But I, I learned long ago, for one very long year of my life, I didn't create anything. All I did was manage. I guess you could say I created PowerPoints and they were very sad. All I did was manage. And I realized the verb at the core of what brings me to life is creating. And so that becomes the stock I can't lose, but I'm very flexible as to how that shows up. In any given portfolio.

So now let's talk about the sticky notes and the 100 ideas, if you will. I read it, I've heard you talk about it. First of all, I'm petrified of it. As someone who's a— somebody who's a real doer, I'm really afraid to move beyond the 6 or 8 things that I can tell you right now kind of define me. But talk for a moment about why you first of all, should have bought stock in 3M because of the number of sticky notes that are going to be sold because of your book. But second of all, why 100?

Man, I should have bought stock in 3M because it turns out sticky notes are at the core of all ideation in my mind. They're so— you can throw them away. You don't feel bad. A whole piece of paper, you crumple it up, you feel bad about it, right? A sticky note, you're like, you throw them everywhere. So—

Just as one quick thing, sorry. But when I interviewed Evan Osnos at the Sun Valley Writers and Evan was talking about systems and about coding and about how rigid the computer systems are in the U.S. government. And one of the things that just absolutely flabbergasted me from Evan's writing was that the U.S. computer system for Immigration and Naturalization Services is so rigid that when, during the Trump administration, they made the decision to separate families—

Mm-hmm.

They have an alien resident database resident number that they give to families previously, and it's just one number for everyone in the family, so that when they separated parents and children, they didn't have the ability to go in and give distinct codes to the kids and the parents. And so at the border, they literally took sticky notes, put the A—

Oh.

—Elliot resident AR number on kids, literally like stapled to their forehead. And then when they had to put them back together, they were literally running around taking sticky notes from one to the other put them back together. And it just, it was so, the whole thing was tragic. But the fact that we didn't have a computer system that could deal with that change and that sticky notes were the solve to it, to your point, sticky notes are everywhere and a huge part of our world. Anyway, I digress completely. But anyway, you said that about sticky notes and I had to throw that in there.

I mean, sticky notes are meant to be disposed of, which means they're the wrong tool for keeping families together. Anyway. Sticky notes, 100 wishes. So, part of one of the steps that I make you do in this book is to write out 100 wishes for your life. And I chose 100 partially because it's a nice round number and partially because it is so far beyond. It's like orders of magnitude beyond what most of us think about as like my goals in any given period. It really forces you out of the box of the 6 or the 8 or the 10 that you might have had as your true north. For your career, and by doing that, it makes you realize you're like, okay, I've got 15, I've got 22, I've got 30. Crap! I gotta have 70 more. It makes you think about, okay, well, what are all the other things that I want? Because your career can only get you so many sticky notes, and then you start thinking about, okay, well, I want to climb all seven of the tallest mountains in the world. I want to. You know, and you start, you come up with, I want to learn to bake the world's best sourdough. You come up with these sort of still very big highlights of things. And even then you only get to maybe 50. And then you start to think about some of the more mundane things. I want to have dinner with my family more nights than not. I want my kids to still like me when they're out of the house. I want to be friends with them as adults. I want my marriage to survive. What does that look like? I want us to be happy and still in love 30 years from now. And you start thinking of much more sort of quotidian wishes for your life, and you realize that like those require your effort too. Those require intention and decisions and ambitions if you want to reach those. And this comes back to Clay and what he talked to us about. He's like, listen, if you have— You know, your marginal hour in any given week, you could put that hour toward the big project at work, and in 6 or, you know, 12 months, you're gonna see the fruits of that hour. You're gonna get that promotion or that raise or that big high five for landing that thing. And if you put that hour toward your kids, you might not know for like 18 or, you know, maybe 25 years whether that hour paid off. If you put that hour into your marriage, you might not know for 40 years. whether that hour paid off. And so it's always going to be easier to put it into the thing that's closer and that has a, a quicker cycle time for showing the fruits of your work. But that doesn't mean it's not important to put it into these longer-term, you know, less clear things if those things matter to you. And if they don't matter to you, then decide right now they don't matter to you. And then we can stop pretending. So part of that 100 wishes is that it forces you to really think about, on, you know, your deathbed, what is the imprint of your life? And I promise it is bigger than just the size of your business card.

I, I love both the sticky note exercise and then also your discussion of the marginal hour. And you just basically summarized it as it relates to, do I put that hour into my kid that I might not understand for another 18 years, or do I put it into the project that gives me immediate feedback? The other piece is long-term health. You've run 3 marathons, 22 half marathons, and 3 triathlons. The response from all that is, yeah, I feel this way today, but the real payback for it, when you go back to your 25th reunion like I did last year, is everyone saying, how are you still in such good shape 25 years after business school? That's the day-to-day investment in that that pays off over time, but you don't see it when you go for that run when you're 32 years old. You outline 3 models in the book, Christina, on sort of the portfolio life, the moonlight, the zigzag, and the multi-hyphenate. Why don't you run through those 3 models? And I find it to be really interesting in the sense that the, you know, the— all of us, when we go see a surgeon, we want that surgeon to be laser-focused on what we do. You go to the surgeon who has has the reps, the person who's done the most cases, because you don't want to go to someone who's sort of like, oh yeah, I did that surgery 3 years ago, but maybe we'll get in there and root around and figure out what it is. And as I think about the 3 models for having a portfolio life, differentiating between somebody who really does need to have a more— I mean, everyone needs to have a well-rounded life and a well-rounded focus on what they do, but I do think that there's a difference between someone who might moonlight at something, and then somebody else who might be in the multi-hyphenate type world. Explain that.

For sure. So moonlighting, you know, some people call it the side hustle. I don't like that term for lots of reasons, but particularly because it connotes monetizing the thing you do on the side. And I don't think you have to monetize everything you do to make it be worth your time. So if you think about moonlighting, you've got the day job, the primary thing it is you do, and then you the thing on the side, evenings, weekends, sabbaticals, whatever. And that thing could be a consulting business, it could be writing a book, it could be something that you make money off of, but it could be a really serious hobby that you invest in and that you care deeply about and that you develop a skill in. And, you know, we talk about this surgeon, we want them to be excellent at surgery for sure, but I give you the flip side, which is often you see later in life people continuing on in their career past the point where they might, should, could have retired because they have nothing else. They have nothing else. And if they were to retire, they would be sitting home, I don't know, playing bridge, and they can't fathom that. And so they stay at it longer. And I don't want the surgeon who worked and did surgery 10 years longer than they should have because they had nothing else that brought them joy. I want them to quit the day that they decide that they're done. So, I want them to love origami or golf or underwater basket weaving, whatever that thing is that says, this brings me joy in a really meaningful way and often helps me kind of turn off my brain that does the day job and gives me something in a different way. Often, this might be a very tactical thing. I know very intellectual people who love throwing, making ceramics on a wheel because it gets your hands physically dirty and it makes you focus. So that's moonlighting. The second one, zigzagging, is often where you have the primary thing and then it switches to a new primary thing. And from the surface, people are like, that makes no sense. You're zigzagging from opera to entrepreneurship. But what they don't see is under the surface. Often a moonlighting thing turns into the zigzag. Maybe you did it on the side for a very long time, and in doing so, you realized maybe you de-risked the business idea. Maybe you saw that there was a bigger opportunity there. Maybe you were just ready for another chapter. And so you kind of dial down the day job and you dial up the moonlighting thing to become your new primary focus. And that is, it's zigging and zagging. From one primary thing at a time, but they do have a connection. The last one, the multi-hyphenate, is often where you see people who are truly on like the vanguard of building new things. And this is where they're living in these multiple worlds at once, sort of equally visibly. You'll see this in some industries very obviously, like the writer-producer-director or the author-speaker-professor. Those are very common. But, you know, I give examples in my book of, uh, of someone who was a computer programmer and a playwright, and she did both equally at the same time. And in doing so, ended up in a position where the TED residency invited her to come in and start writing about and doing research on the intersection of technology and AI and art. And what does it mean if technology makes something creative? Is it art if there's no intention behind How do we make sense of this? She was in a position to do that because she lived in both worlds equally. So those are the 3— those are 3 of the models. There can be many other models as well, but those are 3 that I find very common.

So the final question to bring it all back to the beginning of sort of, if you will, the— what I felt was the disconnect between you as a person and then what the book is espousing. Give it 85%. I love that you went and researched the best manufacturing lines in the world and found out that they run at 85%, because as you write, a planned downtime is cheaper than an unplanned downtime. I find that, Christina, to be so valuable to think about in all of our lives as it relates to your career, your personal life, your investment in kids, and your relationship. That running with 15% reserve to some degree, having the planned downtime rather than the emergency downtime, is really so much— as far as longevity on anything, it seems to make so much sense when you read it in the way that you described it in your book.

And it's one of the hardest to do. I do not make light of how difficult this is. I am still working on this. But, but it is crucial, right? And you pointed out this exact thing. It's like you are going to have downtime. Like, life is complicated and messy and there are mistakes and there are screw-ups. You will have downtime. The only question is whether you have left space for it. And so you have room for maintenance, for do-overs, for serendipity, for really amazing opportunities you hadn't planned for, whether you have space for that already or whether you have to cancel a bunch of stuff in order to squeeze that in or burn out in order to make it happen, but it's going to happen one way or another. And so, part of it is retraining how we think about what is at capacity for our lives. And I do this in total, I think through my entire portfolio, all the things that I've committed to, including my family, my hobbies, my community, my job, that total has to do 85% of my total capacity, so I still have downtime. But within each category, I try to only max out within my work week 85% of my time. And that includes my working blocks. You know, I block them out. I think about everything that I'm doing has a shape. You know, it's not just a to-do list of lines. They have a shape. You can think about it like Tetris. They have a shape and they either fit or they don't. And so as I think through the week and 2 and 3 weeks ahead, I put everything on my calendar calendar to see the shape of my week. And I can see, is there slack in the system or not? And if there's not, I need to either push things out, cancel them, or shrink them. But in some way or another, I have to build in slack because otherwise, if I'm running at 100%, every minute I'm doing anything, I'm not just in the work, I'm also hovering above Monitoring. Are we still on track? Is anything coming down that's going to disrupt it? I understand how rigid the whole thing is and how prone it will be to breakage. And so I can't actually be focused on anything because I'm also conscientious of everything breaking. And so to give yourself slack also allows that sense of flow because you can get into the work and say, I have already— past me already planned for there to be space if something goes wrong. So I'm not going to care about that right now. Right now, I'm just going to focus on this thing I'm doing.

So I'm super appreciative that you brought 100% for the hour that we had together. It's been a real joy. Congratulations on the book. To everyone who has joined us for this hour, which is lots and lots of people by the count at the bottom of the screen, The Portfolio Life is a great read. Thank you, Christina. It's great to have had you on today with me, and I hope everyone has a great day. And next week is Ezra Klein. I hope those of you who joined us today can join us again next week. Thanks very much, Christina. Have a great day.

Thanks so much, Willie.

See ya.