Harvard Business School’s Christina Wallace on How AI Can Help Us Rebalance Our Lives

MOLLY WOOD: Today, I’m talking to Christina Wallace. She’s an instructor at Harvard Business School, or HBS, as you’ll hear her refer to it. She’s also a serial entrepreneur, and author of the book The Portfolio Life. She believes that in an era of work marked by disruption and rapidly evolving technologies like AI, we all need to, quote, build a life bigger than our business cards. Christina’s book views work and life not in opposition to each other, but more like an array of interconnected pursuits that can be balanced like an investment portfolio. She herself is a self-described human Venn diagram who has built a career at the intersection of business, technology, and the arts. And she insists that we are all actually Venn diagrams with our own unique overlapping spheres of interests and responsibilities. In this episode, Christina and I explore the shifting career landscape and the synergy between work life and personal life. We’ll also talk about AI’s potential to help us be more productive, creative, and to free up more time for serendipity and rest. Here’s my conversation with Christina.

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MOLLY WOOD: Start by telling us what you mean by this phrase, the portfolio life. 

CHRISTINA WALLACE: Yeah, so I took this, I stole this from the world of personal finance and financial portfolio theory, right? It’s this idea that you can diversify your portfolio that allows you to have a certain level of risk and reward that can get you where you’re going and at the same time, protect you from things that you can’t control, whether it’s, you know, market risks, systemic shocks, whatever. There’s a diversification piece at play. And it’s this notion, particularly because I’ve always hated the phrase work-life balance, right, it’s this idea that they’re in opposition to each other. And instead, I’ve always seen work as part of my life. So as I’m designing my portfolio life, work is a huge part of it, of course. But there are a lot of other things that are in that portfolio as well. 

MOLLY WOOD: What are the other pieces of the portfolio? I imagine they’re somewhat specific to the individual constructing that portfolio. But give me some examples. 

CHRISTINA WALLACE: Sure. So, obvious ones, things like family, friends, your community, but also things like hobbies. Or maybe you have a consulting side hustle or something that you are maybe building in a small way, an entrepreneurial venture that you’re doing on the side while you still have that great day job. And then there’s the other things that might matter to you deeply, like taking care of your health, and rest. And all of these things have to add up to no more than a hundred percent of your time. 

MOLLY WOOD: Talk about how that can play out in the workplace, and ideally, how leaders could adopt this philosophy for themselves and their employees. 

CHRISTINA WALLACE: So, I came to this model earlier in life, back when I was a student at HBS, studying under Professor Clayton Christensen, who was my mentor, you all know him as the author of The Innovator’s Dilemma. He sort of coined disruption as we talk about it in the world of technology. We have been talking a lot about designing your life and not just measuring the things that were easy to measure, like your promotions, your income, but all of the things that matter to you. But I really landed on the importance of, especially these moments of rebalancing when I had my first child. And then I knew that in this moment, that was not going to work for the next season of my life. And so I needed to design a completely different work relationship. And everyone is going to have a season or two where they need a different relationship to work. And if they step off this up-and-to-the-right, you know, ambitious trajectory that we’ve always expected of our future leaders. Currently, they’re penalized for that. My argument to everyone is allow these seasons of rebalancing, and then when that worker comes back and says, Okay, I’m ready, then you say, Great, welcome back. Let's design what the next chapter looks like. 

MOLLY WOOD: Okay, so that’s in terms of a personal career trajectory. And now let’s put this more specifically in the context of the workplace and how it’s changing, especially now that we have access to all these new AI tools. Does the portfolio model allow for flexibility and resilience at work in a period of really rapid change? 

CHRISTINA WALLACE: One of the things that I think is really powerful about this model: if you as a manager, or as an executive, if you design a relationship, a contract, with your talent that says, we are okay with you having a side hustle, we are okay with you having classes at night or a family commitment, or whatever these things are, we understand that these moments require flexibility, that workforce is going to have a lot more tolerance for you needing flexibility in return. I talk a lot about identity at the core of a portfolio life, that identity historically in America is very tied to our jobs. But if you can develop an identity that is so much broader than just how you monetize your time today, you have, individually, a ton more optionality and flexibility in how you might need to zig and zag. And as an organization, if you have inculcated this culture, you now have an organization that is able to zig and zag much more fluidly. Because you’re all on the same team, and you’re all rowing in the same direction. 

MOLLY WOOD: You talk a lot about the importance of serendipity and actually not, you know, having your portfolio add up to a hundred percent of your time. So you leave some room for magic. [Laughs] And one of the things that’s evident now, like, we’re obviously getting used to what these tools are going to bring, but one of the things that is evident now, is this increase in efficiency, this sort of ability to get a bunch of time back. Talk about how that might introduce serendipity at work in a whole new way. 

CHRISTINA WALLACE: Absolutely. So, one of the key ideas that Professor Christensen sort of drilled into my head as his student was this relationship between the emergent strategy and the deliberate strategy. So classically, corporate strategy, as you’re thinking about five, ten years out in the future—but in a world that is changing, in a world that is unknowable. You can’t see five or ten years down the path, you don’t know where there is yet. And so having a much more emergent, opportunistic strategy is the only way where you can go forward. You might have a sense of where you’re going, but you have to uncover each step—each step will lead to, Okay, what do we do next? And what do we do next? And is that still where we wanted to go? And this is where that serendipity, that space for discovery becomes really useful. So if you can pull out some of the busy work, some of the ridiculous things that somehow have to get done but don’t actually add value to our days—now maybe we can find that hour or two or half a day, in the work week and protect this as our creating time. And that becomes really useful when you have these unplanned, unseen opportunities or insights or, you know, bolts of creativity. We say, I wonder, what if, and then you have the space to go and pursue that. 

MOLLY WOOD: That’s where I feel like it’s going to take some leadership and grace at work to enable that, and a lot of reskilling, right, and education to help your workforce access these real time-saving benefits from AI. Where do you think that starts? 

CHRISTINA WALLACE: So, one of the joys of being a professor and being in the classroom right now, as this new tool has come on with such speed in the last twelve months, is seeing the type of adoption that my students, my colleagues, as we’re all trying to get used to, like, what can we do with AI? And I think at the beginning we all were sort of using it as, like, a glorified search of, instead of searching, I’ll put it in the AI and then it will tell me the answer, you know, microseconds faster than if I searched and clicked. And now I think we’re starting to really unlock the power of using it almost as a partner, as a collaborator. And think, instead of AI as your virtual assistant, it’s more as, AI as your virtual chief of staff, right? There’s these moments where you can actually get to the so what. Don’t just find me all of the search terms and the results—parse them, find the connections, give me the conclusion after having correlated these things together, and then I can use that information to make a judgment call. 

MOLLY WOOD: I kind of want to stay with education for a bit and see what, if anything, you’re hearing about other institutions. It feels, I think we’re all used to a paradigm in which education operates a certain way. [Laughs] There are things you have to memorize, even though we have computers. And now we have, you know, that paradigm times infinity with AI. It’s not just workplaces who respond quickly, who will succeed, it is also the institutions and the teaching models, right? Are you encountering resistance? Are you hearing about institutions that aren’t keeping up as well? 

CHRISTINA WALLACE: Yeah, I mean, there’s certainly the fear. I mean, you said it exactly right. We used to require you to learn things and memorize things, and now you can look them up. In the same way that you used to have to do arithmetic by hand, and then spreadsheets came along, calculators came along. It doesn’t mean we don’t teach arithmetic. It just means once we teach the backbone of it, once you understand the concepts and how the pieces fit together, you can go faster, and then build a spreadsheet, build a financial model off of that, instead of doing it all by hand. And so educators and I think, you know, we all have just felt this incredible—since the pandemic and having to teach remotely and all of that was so overwhelming. And we were all just trying to keep our heads above water. To then come back and be like, Okay, we’re almost back to normal. And then literally be told overnight, every single one of your assignment questions no longer works, because you were asking what, when, how, where. And all of those are things that can be answered by AI. And so, how do you get to, what’s your assessment of, characterize the decision here, make the argument for the trade-offs, and then make a judgment call on which one makes the most sense, understanding the implications of it, right? This requires a second order-level of preparation from educators, a wholesale rewriting of teaching plans, with all of our spare time and all of our extra resources. It’s a lot to ask, all the way up and down the food chain, right, from elementary school all the way up to higher ed. So there are certainly schools that have been on the forefront of this. I think of Wharton and my colleague there, Ethan Mollick, a professor there who’s just absolutely been on the cutting edge of, how do you implement these tools in education? He writes on a regular basis—everything I know I basically learned from reading his writing. And, you know, there’s a handful of us. I have a colleague here at HBS, Mitch Weiss, who’s doing the same where, you know, there’s a few that have the time to dig in, and I’m so appreciative that they’re then like, putting lesson plans, putting out examples of, how do you use AI for different roles? Set it up as a tutor, set it up as a naysayer, right? Make it disagree with you, so that you can make the argument back to it. Have it poke holes in your idea, set it up as a collaborator as you’re ideating for a start-up idea or something, right? So you can assign different roles, you can give it certain different backgrounds, and you can ask it to be a different type of partner. But you have to learn that that’s even possible. I think that’s where everyone could use, like, a pause. And just six months to learn this, and then restart life. [Laughs] It’s like that Saved by the Bell, where they’re like, timeout, and then they talk to the camera. I think we all want one of those. 

MOLLY WOOD: We need a little baby sabbatical? 

CHRISTINA WALLACE: Exactly. 

MOLLY WOOD: So with that in mind, though, how can we, let’s sort of keep imagining this in the context of a portfolio, right? How can we think about leveraging AI to be more productive and efficient in our jobs, and then reconstructing our portfolio accordingly? 

CHRISTINA WALLACE: I can imagine a version of the world that I would want to live in, where, because of this new generation of technology, I could choose to work three days a week, or four days a week. One of the joys of being a professor is that they do expect you to do other things—write books, speak, teach, consult. And I have a stranger portfolio than other professors. I produce on Broadway, I sing, I do other things that might not look like they have anything to do with my day job, but I am so appreciative of the flexibility because it allows me to get the things I need to feel whole. And I think there’s a lot certainly—my generation of millennials that are sort of hitting middle age right now, and Gen Z coming up behind us that are saying, that is the relationship that I’m looking for with work. I’m ambitious, I care about doing important things, and there’s a lot of other pieces of me that need attention too. 

MOLLY WOOD: It is interesting to me that this AI transformation is coming in the context of these ongoing conversations about the future of work, and what it looks like and the different ways that people want to have relationships with work. And you have to assume that that includes some managers and leaders, even though some are not in that same boat, but it does raise this kind of question about the mindset that it takes to extract maximum value from AI tools in a way that does not burn out employees, when that message is coming from employees pretty loud and clear. 

CHRISTINA WALLACE: Yeah, I think that is going to be one of the needles to thread in this conversation as leaders go through this. But if you can see the opportunity and frame it as such that says, Yes, we are going to reap benefits as employers in productivity, in the bottom line, of course, and US workers will also reap the benefits, right? We are splitting this value that is being created by this leap in technology., It’s not only accumulating in one direction, I think you’re going to see a lot more willingness to explore what that future looks like. 

MOLLY WOOD: It is, it’s like a positive provocation to business leaders to say, It’s an abundance story for everyone. 

CHRISTINA WALLACE: Exactly. 

MOLLY WOOD: Can you contrast and compare as you look at the history of tech revolutions that have come along? And certainly from your perch as a professor. Technologies come along that change a lot of things fairly often. But can you compare and contrast this moment to what you’ve seen in the past? 

CHRISTINA WALLACE: Yeah, I mean, I think there’s sort of a general consensus that there are these, you know, incremental technology improvements. And then there are these paradigm-shifting technology improvements. Certainly, the adoption of the personal computer is one of those paradigm-shifting technology improvements: just switch from a typewriter to something that you can backspace on, save on, have this ability to run multiple different programs on, was a paradigm-shifting moment. There was a lot that obviously we didn’t see in the moment that we had to learn by implementing this technology, there were a lot of questions and fears and naysayers. And then we figured it out, and I think AI falls within that same portfolio of these truly, specifically changing moments that are going to rewrite how work looks. I think the difference this time around is just the speed of adoption, that it’s going to be just a dramatically different learning curve. Given, this is, in some ways, a UX layer or application layer on top of this technology that has existed, for highly technical folks, for many, many years. And suddenly, it’s being presented and packaged in a way that the average person can use it. And it’s all just being rolled out at once. It’s going to be a much shorter growth curve on this one. And so I think that’s the big question mark that everyone has in their minds now of, how much time do we have to experiment and learn before it’s at a scale that is overwhelming? 

MOLLY WOOD: Quick lightning round: what is the latest thing that AI helped you with at work, and not at work? 

CHRISTINA WALLACE: At work, it is the thing that every writer fears, which is the blank page—when you go to write something and you just have to stare at the blank page. So I have been using ChatGPT to generate really bad first drafts, only because I’m not putting much effort into it. But having something to start from is so much better than starting from nothing. At home, I found a tool online that has a freemium version of creating brand identities from scratch—you give them a couple of, obviously the name that you’re trying to make a brand out of, and a couple of attributes, maybe what world it might live in, you give it some color ideas. And then it pulls together an entire brand identity for you. And as a producer on Broadway, I’ve got my own little production company. And we just signed on to do another big project. And I was like, I think it’s time that we have a logo, we have a brand. 

MOLLY WOOD: Okay, wait, back up. What are you producing on Broadway?

CHRISTINA WALLACE: [Laughs] I just signed on, I have a producing team, and we just signed on to be a part of Water for Elephants, which opens in the spring. We were part of Parade this past year that won the Tony. And we’re also early in on Smash, which is in development, probably not going to hit the stage until 2025. So a fun little slate of projects right now. 

MOLLY WOOD: Oh my goodness. When do you do this? 

CHRISTINA WALLACE: In all of my free time? [Laughs] Unclear. It’s the magic time that you just sort of make happen for the things that you care deeply about. I was a theater major in my first world, theater and math, and directed and produced before I decided to go in the direction of technology and entrepreneurship. And I’ve always had the desire to find a way back to it. And a few years ago, an opportunity presented itself, and I’d been a tech angel investor for a while, and so I started out by being a Broadway investor, and then sort of made it very clear I wanted to do more. So, serendipity, man. It works. 

MOLLY WOOD: Wow. Okay, so thinking a little bit ahead to when these new AI tools are more widely available, and when we’ve all kind of collectively grasped their real potential and incorporated them into our lives. What do you hope will be the most profound change to the way we work? 

CHRISTINA WALLACE: You know what, I don’t know if this is the most profound, but this is the use case, I can’t wait to stop having. When I am trying to find that thing, that message, that attachment, that thing. You’re like, I know I have it. But which inbox? Which social media platform did they DM it to me on? Which cloud platform did I save it to? I know it’s there. And I want to ask my chief of staff, find that thing. And connect the dots between that thing and the thing I have coming up, and go grab some context of what’s going on in the market today. Or that person I’m meeting with, what their current profile is on, you know, LinkedIn or whatever. Pull all the pieces together so that I can stop wasting hours backtracking, and instead just do the work that I set out to do that morning. 

MOLLY WOOD: I also want that so badly. And that tech is here, actually. We'll be able to do that soon. Ah, excellent. [Laughs] Christina Wallace is a Harvard Business School instructor, serial entrepreneur, and author of the book The Portfolio Life. Thanks so much for your time. 

CHRISTINA WALLACE: Thank you for having me.

MOLLY WOOD: And that’s it for this episode of WorkLab, the podcast from Microsoft. Please subscribe and check back for the next episode, where I’ll be talking to Aneesh Raman, a vice president at LinkedIn and head of the company’s Opportunity Project, on how AI has the potential to expand opportunities for everyone, including people without what we think of as traditional career paths and educational backgrounds. If you’ve got a question or a comment, please drop us an email at [email protected]. And check out Microsoft’s Work Trend Indexes and the WorkLab digital publication, where you’ll find all of our episodes along with thoughtful stories that explore how business leaders are thriving in today’s digital world. You can find all of that at microsoft.com/worklab. As for this podcast, please rate us, leave us a review, and follow us wherever you listen. It helps us out a ton. WorkLab is produced by Microsoft and Godfrey Dadich Partners and Reasonable Volume. I’m your host, Molly Wood. Sharon Kallander and Matthew Duncan produced this podcast. Jessica Voelker is the WorkLab editor. Thanks for listening.