Reimagine Your Work

Episode 231 - A Harvard Expert Is Asking You to Reimagine Your Career and Your Relationship to Work

Guest: Christina Wallace

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Christina Wallace is a veteran when it comes to following a diverse career path. Starting in the arts, she learned early on the necessity of juggling multiple roles – musician, theatre artist, and, later, various roles in theatre production. This experience laid the foundation for her career philosophy: versatility as a survival and success strategy.

In our conversation, she shared her insights on the emerging trend of leading a portfolio life and career. This interview unearthed valuable insights into how a diversified career path offers resilience in an unpredictable job market and caters to the multifaceted aspirations of today’s professionals.

As the job market evolves, employees and employers are re-evaluating their values and purposes. The concept of a single, lifelong career is becoming increasingly obsolete, replaced by a multifaceted approach to professional life. This approach aligns well with today’s dynamic job market, where adaptability and a diverse skill set are increasingly valued.

The Portfolio Approach in Practice

A portfolio career is characterised by a combination of different professional activities, including part-time jobs, temporary positions, freelancing, and side gigs. Christina’s career trajectory, from working in theatre to roles in tech and business, illustrates the richness and diversity of a portfolio career. This approach offers varied income streams and a way to continuously develop and apply skills in different contexts.

A central theme in Christina’s discussion is the role of identity in career development. She emphasises the need for individuals to move beyond a narrow definition of their professional self. This expansion of identity allows for greater flexibility and openness to diverse career opportunities.

She also reinforces the importance of adaptability in a portfolio career. She shares her experiences of learning from failures and realigning goals, illustrating the importance of resilience and flexibility in today’s job market.

Advice for Aspiring Portfolio Professionals

Those best suited to a portfolio career are typically adaptable, enjoy variety, and can manage multiple projects effectively. Christina highlights the significance of seeing the whole picture – understanding the beginning, middle, and end of each project and enjoying the process of continual learning and challenge.

For those considering this path, she recommends a deep exploration of personal identity and goals. This understanding helps in selecting the right mix of roles and projects, contributing to both professional fulfilment and security.

Christina Wallace’s insights offer a compelling argument for the portfolio lifestyle and career as a response to the changing dynamics of the job market. For professionals navigating these shifts, the portfolio approach provides a path for survival and thriving in a world where change is the only constant.

This approach reflects the growing trend of professionals seeking variety, flexibility, and fulfilment in their work lives. As traditional career paths become less prevalent, the portfolio career emerges as a viable and necessary strategy for success in the 21st-century job market.

If you’re interested in investigating this further, we have several episodes of The Job Hunting Podcast dedicated to this theme.

Please check out these two Categories: “Portfolio Career” and “New World of Work” to learn more.

About Our Guest, Christina Wallace

A self-described “human Venn diagram”, Christina Wallace has crafted a career at the intersection of business, technology, and the arts. She is currently a Senior Lecturer of entrepreneurship Harvard Business School, an active angel investor, and a co-producer of Broadway musicals. Her latest book is The Portfolio Life: How to Future-Proof Your Career, Avoid Burnout, and Build A Life Bigger Than Your Business Card (Hachette, 2023). A serial entrepreneur, Christina has built businesses in ecommerce, edtech, and media. She also co-authored New To Big: How Companies Can Create Like Entrepreneurs, Invest Like VCs, and Install a Permanent Operating System for Growth (Penguin Random House, 2019) and was the co-host of The Limit Does Not Exist, an iHeart podcast with millions of downloads over 3 seasons and 125 episodes. In her free time, she sings with various chamber choirs, embarks on adventure travel, and is a mediocre endurance athlete. She lives in Cambridge with her husband and their two children.
Renata Bernarde

About the Host, Renata Bernarde

Hello, I’m Renata Bernarde, the Host of The Job Hunting Podcast. I’m also an executive coach, job hunting expert, and career strategist. I teach professionals (corporate, non-profit, and public) the steps and frameworks to help them find great jobs, change, and advance their careers with confidence and less stress.


If you are an ambitious professional who is keen to develop a robust career plan, if you are looking to find your next job or promotion, or if you want to keep a finger on the pulse of the job market so that when you are ready, and an opportunity arises, you can hit the ground running, then this podcast is for you.


In addition to The Job Hunting Podcast, on my website, I have developed a range of courses and services for professionals in career or job transition. And, of course, I also coach private clients

What is a portfolio career?

A portfolio career involves diversifying your professional life across various streams of income, interests, and roles, rather than focusing on a single career path.

Who can benefit from a portfolio career?

Individuals who value flexibility, variety, and autonomy in their work, and those who wish to leverage diverse skill sets across different sectors or industries.

How does one transition to a portfolio career?

Start by identifying your core skills and interests, network in your desired fields, and seek out varied opportunities that align with your abilities and passions. Gradual transitioning is key.

What are the challenges of a portfolio career?

Balancing multiple roles and responsibilities, maintaining a steady income, and managing time effectively can be challenging in a portfolio career.

How does a portfolio career offer job security?

By diversifying income sources and skill sets, a portfolio career can provide more stability in times of economic uncertainty, as opposed to relying on a single job or industry.

Can a portfolio career be as financially rewarding as a traditional career?

Yes, it can be. It often depends on how effectively you manage and grow your various income streams and leverage your unique skill sets.

What impact does a portfolio career have on personal and professional growth?

It offers opportunities for continuous learning, personal development, and professional growth by exposing you to a variety of experiences and industries.

How important is networking in a portfolio career?

Networking is crucial. Building a robust professional network helps in finding new opportunities, gaining referrals, and staying informed about industry trends.

Can someone with a traditional career background shift to a portfolio career?

Absolutely. Many professionals transition to portfolio careers by leveraging their existing experience and gradually exploring new avenues.

What role does adaptability play in a portfolio career?

Adaptability is key. Being open to change, willing to learn, and able to adjust to different roles and environments is essential for success in a portfolio career.

Resources Mentioned in This Episode

Timestamps to Guide Your Listening

  • 01:20 The Genesis of a Portfolio Career

  • 03:49 Navigating Work and Identity in a Traditional Family Setting

  • 06:36 Embracing Flexibility and Novelty in Work

  • 11:32 Learning from Failure: The Value of Fast Failures in Business and Life

  • 15:44 Balancing Work, Family, and Personal Goals

  • 25:30 Addressing Career Paralysis and Identity Crises

  • 25:52 Unraveling Identity and Career Choices

  • 26:36 A New Approach to Identity

  • 28:42 Case Studies: From Physics to Origami and Beyond

  • 33:41 Redefining Ambition: Beyond Career Success

  • 36:25 The Power of Long-Term Vision in Career Planning

  • 47:48 Strategies and Insights

Renata Bernarde: When did you realize that the portfolio as a career option was a thing? When did it come to you?

Christina Wallace: So, in some ways, it has always been on my radar because, in the arts, as a theater artist, as a musician, you have to have a portfolio. There is no stable income. So, as I was growing up studying classical piano, cello, and voice, you know, I’d be playing in an orchestra on Tuesday, singing in a concert on Friday, and accompanying a wedding on Saturday, right?

You’re always sort of hustling up the next gig and building those relationships, that network that keeps you top of mind when someone needs your skill set. Then, when I got to college and started working in theater, it became very clear that you could make a life as a theater artist, but you had to be willing to do a lot of things.

So, if I said I’m only going to be a director, well, I couldn’t be a full-time director at 22. But if I said I’ll hang lights, work in the scene shop, install sets, work as a stage manager, be a producer, be a dramaturg, and my preference would be to be a director, then I had full-time work for four years all through college.

I had a professional resume before I graduated that made it possible to sustain myself. So, I think that model that artists have always had was just the way I started thinking about work. So, when I started working a “real job” after college at the Metropolitan Opera on the management side of the arts, it was never a question of, “I’m going to drop everything else now that I have this one job.” It was more a question of, “What do I still have time to make space for? Who do I still want to be connected with, and what leads do I want to put out there?” So that I could start seeding the ground for what might come next. And I kept doing this. I’ve literally never had an easy tax year ever because I always have so many different forms of income, expenses, and projects I’m working on.

But it means that I have always felt confident in my ability to take care of myself, which is really important. I come from a working-class family. I have no trust fund, no family support that I could ever rely on. I was on my own. And this was the way I could build my own financial safety net.

Renata Bernarde: I’m so glad that you mentioned family. I was about to ask you that because, especially if you come from a family that doesn’t have that safety net, you know, they may not understand what you’re trying to do.

Christina Wallace: Yeah.

Renata Bernarde: And I think that especially because, right at the beginning, you started with this portfolio mindset. Even when you had a real job, as you said at the Metropolitan Opera, was it like you were surrounded by other individuals who had a similar mindset, or did you stand out, finding yourself being the odd person out?

Christina Wallace: I mean, the nice thing again, even on the management side at the opera, is that it’s still a bunch of artists. We’re still all being underpaid, if we’re going to be honest, and they all had side hustles. They all had portfolios of projects. Mine just looked very different from theirs. They were all still in the arts.

And I was teaching classes to help people prepare for business school tests and thinking about marketing strategies for various small businesses. So, I think mine have always been a bit broader in terms of a portfolio, but I still had that perspective.

My family was always a little, not concerned, but maybe confused about what the hell I was doing with my life. And I find that funny. You know, my grandmother was a stay-at-home homemaker, a mom, a grandmother. My grandpa built cars for General Motors on the assembly line for over 40 years.

My mom was a secretary. So, they are very much in the kind of old guard, prior generation model of you get a job, you keep it for four decades, you retire with a pension. And that’s it. And these are the same people who took me to piano lessons starting at four years old and really encouraged me to go into the arts.

It makes no sense, honestly, but I’m so grateful they did, because although I didn’t end up going into the arts, I did decide to pursue a life that wasn’t conventional. And if they had been like, “No, you have to be an engineer, a doctor, or a lawyer,” something very straightforward with a linear path, I think it would have been really hard to win them over on what I ended up doing. But because they sort of assumed, you know, even on a good day that I go perform at Carnegie Hall, I’m still going to have to have a way to pay my rent, they were somewhat understanding of my zigs and zags between theater, tech, business, and these different worlds. Everything felt risky to them, but they didn’t have any understanding of one level of risk versus another.

And, you know, in many ways, they appreciated that I was diversifying that risk by having all these different irons in the fire.

Renata Bernarde: Yeah, sometimes when I’m talking to executives, they are now doing what we call entering executive gigs. So, they step in if, say, someone gets hit by a bus, and they need a C-level professional or head of function, or they have a project. They step in, stay for eight months, and then step out.

They go to these information sessions, or they listen to a podcast. Information sessions that are run by recruiters, not by me, or they listen to a podcast of mine and they’re like, “Oh, I’ve been doing this for years. I just didn’t realize it had a name. Like, I’ve always felt, I was with a client yesterday and he told me, now having done a few gigs, I feel so much more at ease in this sort of environment than if I was trying to fit in and stay for years on end.” Right, what do you think is different about working in a portfolio format? What sort of characteristics should people listening think, “Oh, I have those characteristics, maybe that’s what I need to give a go”?

Christina Wallace: Yeah. There’s sort of, it’s an interesting question because I think there are two layers to this. One is for people who have portfolio careers, which sounds a bit like what we’re pointing to. It’s certainly what I have always had. And the other is for people who are thinking about a portfolio life where their work fits into the contents of a bunch of other things they do, whether it’s paid or not.

So I’ll answer the portfolio career piece because I think this is really interesting. At one point, I was considering getting a PhD in math, and I double majored in math and theater in undergrad. I was sort of deciding which route to take when I graduated. I applied to this PhD program in math, got into a couple of schools, and went to visit.

When I visited, one of the professors said, “You know, I’m going to be honest. I’ve looked at your transcript, I’ve looked at your application, you clearly can do the work, but my question is, do you want to? To be successful as a PhD in math, you’re going to have to pick one really narrow path, question in the world of an obscure corner of mathematics, and you’re going to have to focus on that for seven years. In the end, you’re going to write this paper that maybe 12 people in the whole world care about.” And I looked at how I have lived my life up to this point and I went home and moved to New York City. So, for people who really like the portfolio career model, for those who enjoy being the interim C-suite or the fractional C-suite, they enjoy having these really discrete projects where they can say, “I’m here for a tour of duty, and I don’t have to come in thinking, ‘Okay, I’m here for the next 10 years.’ It’s like, no, I’m here for a specific amount of time to accomplish a specific thing. I see the beginning, middle, and end. I can structure that, know exactly which tools to bring out to succeed at that. And when I wrap it up, I get the pleasure of figuring out what’s next, right? There’s some novelty to it, a new challenge every time, but in the same vein, you know that you can be successful at it.” And I think there are just some people who thrive on that. I think of it like the academic year, right? This semester, what classes am I taking? Versus this calendar year, do I still have the same job title as last calendar year? Right? Those are two just very different approaches to work. I’m someone who loves to reimagine at the beginning of every semester. And I think people like that are really successful in roles like temporary, fractional leadership as they think, “What are the other pieces I can slot in and slot out?”

Renata Bernarde: That’s interesting about the distinction you mentioned before, the portfolio life. But before we go there, I wanted to ask you if, in addition to that conversation with your potential future supervisor, have you had other situations where you thought, “Maybe, oh, I wish I could spend more time doing this”? I’m thinking about the business. I read a beautiful post you wrote that really, you know, sort of made a lot of sense to me because I do find that entrepreneurial streak as well. I haven’t nurtured it as much as you have, but I am wondering, did you want to stay longer there? Now in hindsight, how do you feel about it?

Christina Wallace: Less than two years into building this company, I experienced a death. And it’s tough. I think of it a lot like I think about ex-boyfriends, which is in the moment, it was gone earlier than I wanted it to be, under circumstances that I did not choose. And that hurt a lot. In the moment, it felt devastating, identity-shaking. It felt like everything I thought I knew I was going to be doing has just been burned to the ground. But if I look back now with the benefit of more than a decade of hindsight, I am really grateful that that Band-Aid got ripped off at that point.

I would have much rather failed at that point than done another three years, only to fail a little bit later. There’s some real joy in failing fast, whether that’s in business, in relationships, or in anything where you say, “I think I want this,” and then you start doing it and you get enough information to realize, “Oh, I don’t. Nope. I don’t want this.” And so, when I look at friends who get divorced a couple of years after getting married, people who move to a city and a year later move back to where they came from, I celebrate those moments because they learned that something was not for them and they took action to do something about it. And I think that is so much more of a success than sticking with something that is not for you.

Renata Bernarde: Yes, I think a lot of listeners will resonate with your story, not so much because they’ve had businesses that didn’t go forward, but because they had wonderful jobs that they wanted, that they loved, that they applied for and nurtured, and built teams or projects for, and then at the end of the year, the company gets restructured. Boom, they’re out the door. They don’t even know or understand why. And there is a grief process that takes a long time to evolve and for you to go through the cycles of that grief process and then in hindsight understand, “Well, you know what? That’s it. What was I thinking? I was going to stay here for 40 years. Nobody does that anymore.”

Christina Wallace: No. And I think there’s an incredible book coming out soon called “The Setback Cycle” by my friend, Amy Schoenfall, that speaks to this exact thing. There are so many moments in life where things happen to us outside of our control. We did everything right. We followed all of the rules. We did all of the homework and it still didn’t work out, and those moments are really hard.

There is absolutely grief. There’s absolutely this moment of “Well, what’s the point of any of it?” I don’t think I’m any better at those moments than I’ve ever been before. It’s not like I’m suddenly fine when the rug gets pulled out from under me, but I think there’s something really beautiful about recognizing just how much of our lives are not in our control.

We have this false belief that we are in control, and we’re not. And it’s terrifying. I’m a very Type A control freak. I like to know that if I do all the things, it all works out. And there’s a little bit of humility to recognizing there’s a whole bunch going on technologically, ecologically, biologically, geopolitically that I have absolutely no control over or insight into.

Renata Bernarde: Yeah.

Christina Wallace: And so then it takes the personal failing out of the equation. It’s not about if you had just pulled one more weekend shift or cared a little bit more about that one employee, that you would have survived whatever this moment was. It’s like, you could have done all those things and you’d still end up here.

So, given that this was always a potential outcome, are you proud of what you did to this point? Right? Because I would feel so much worse if I had sacrificed those weekends with my family to pull those long hours, only to still get laid off. Right? That’s the moment you’re like, “No, that’s not worth it.”

And I think that brings us to the portfolio life context, right? This idea that your work is in the context of your life, and in any given chapter or season of life, you’re going to need different things. You’re also going to have different things available to you, right? The decade before I had children, I had so much time. It’s almost obscene how much time I used to have. And I made use of it. I had incredible professional opportunities, traveled the world, ran marathons, climbed mountains, sang in a cappella groups, had a podcast. I made good use of that time. It was fabulous. And then I had a baby and thought, “Oh, there goes all of my time.”

Renata Bernarde: Okay.

Christina Wallace: And I realized that if I wanted more children, which I did, that that was going to be true for a while. For a season of life. And so I had to reimagine what I had space for, and given those constraints, what I wanted to prioritize. My work was part of that. I went from a decade as an entrepreneur, a venture-backed entrepreneur working insane hours to build huge outcomes, to someone who needed more control, autonomy, and flexibility than that job would allow.

And so, I decided to become a professor of entrepreneurship for this season of life because I get to stay in that world. I still advise startups, I get to invest in my student startups, but I can turn my brain off and my computer off at the end of the day. And that matters when you have a two-year-old with frequent ear infections like I do. The four-year-old has bronchitis, the two-year-old has ear infections. I was up five times last night. So, this is where you think about, “Well, what season am I in? What’s my relationship to work for this season? What needs is it meeting — financial needs, security needs, health insurance needs if you live in the United States, but also growth, self-expression, community, all of those things your work addresses.”

But there are also lots of things that your work doesn’t do for you, right? And that’s okay. You don’t need one perfect job that does everything. You just need to recognize what’s not there and then find other ways to meet those needs. So maybe you choose a lateral job for a little while to give you a little more flexibility and autonomy like I did.

And you say, “Well, how am I going to get growth if it’s not through my day job? Is it through a new class I want to take, or a hobby I want to try, or a coaching practice I want to start? Is there a community that I still want to be a part of, or a network that I want to get access to, that I might do as more of a moonlighting opportunity, or a volunteer role? Is there something else, like my health, that I need to prioritize right now, and how do I make space for that on my calendar, just like I would for anything else?” It’s choosing the mix of what goes in your portfolio for this season of life, so that no matter what the outcome, no matter which rug gets pulled out from under you, you are proud of how you used your time.

Renata Bernarde: Yes, from time to time. How do you do this? I’ve seen your Excel spreadsheet online as well.

Christina Wallace: I love an Excel spreadsheet.

Renata Bernarde: That Excel spreadsheet, and I love the fact that you tried to—so, the Excel spreadsheet, you can explain it better. But what you tried to do was to practice cello weekly, and you practiced it twice a year.

Christina Wallace: Yes.

Renata Bernarde: I think you said in the document that I saw, and I…

Christina Wallace: No, it’s a perfect example. So, I created this personal balanced scorecard. It’s absolutely a riff off of a classic balanced scorecard that a lot of corporate managers use, where you start with what are my priorities, my strategic goals for the year? What are some of the activities that I’m going to choose to spend my time on that will get me closer to those strategic priorities?

And then, what are the tactics or the metrics that I will evaluate to know whether or not I succeeded at that goal? And so, in this particular year that I ended up publishing, I had a personal goal to get back into playing the cello. I played it very seriously as a child, was in orchestras all the way through college, and then I hung it up one day and have moved it now to 15 different apartments and haven’t opened the case in years.

And I was like, well, that’s ridiculous. If you’re going to keep moving your cello, if you’re going to keep it in your house, you should play it again. And so, I set a goal to practice three times a week. And at the end of the year, I had practiced twice, the whole year. And I thought, huh, okay, that’s really interesting.

What I say I want is to play my cello. But every time I had an incremental hour available, I used it elsewhere. Where is the disconnect? Is it that I don’t actually want to practice the cello and I need to unpack a little bit why I think I do, or is it that I do really want to practice the cello, but I have too many things going on and there never was an incremental hour available?

And so, I really need to think about my capacity utilization, right? Am I just overbooked? Or is there something else going on? And I realized upon some further reflection there that it was the wrong goal for the year. What I actually wanted was to make music again. I had been consuming music, going to concerts, and listening to records, but I hadn’t been performing and making music in a year or two.

And I missed that.

Renata Bernarde: Okay.

Christina Wallace: This all-tech acapella group of all these tech nerds, we all sang together. We rewrote lyrics to Lady Gaga songs to be about startups. And we sang them at VC dinners for expensive wine. And I did make music all year long and we practiced twice a week and we performed. It just wasn’t playing etudes on my cello. And so, I realized that like the goal was there and I met the goal, I just didn’t quite have the right articulation of the goal. But as you think about when and how you rebalance your portfolio, the big signal for me is when new friction arises. So, having my first child, this is a perfect example.

I sort of had a great portfolio that was kind of chugging along. I had enough time for everything I wanted. I had a great team. I knew what I was doing. And then once I had a kid, I was like, Oh, whoa, I literally just don’t have the capacity for all of this. I can’t go run a marathon. I don’t have the time to train that requires a babysitter now.

And I, I don’t know if I have anything else to say on the podcast that I had been producing for the last three years. Like, I think I’m ready for a break on that. And so the friction was, you know, what used to work is now not working. I’m stressed out, I’m overbooked, I’m crying more than usual, which is, you know, a fair amount.

Whatever the thing is, it’s not working anymore. And that’s why at the bottom of my balanced scorecard, I had one key question, which is, are you happy? Because knowing me as an overachiever, I can achieve anything I set my mind to, and I feared that I would end up acing this test, but be really unhappy.

And maybe this portfolio isn’t the right mix. And you need to go back and revisit it.

Renata Bernarde: Yeah, that’s such a cool way of thinking about it. You know, the revisiting of the portfolio and the goals. I will tell you what I see happening sometimes with some people that reach out to me for assistance with their careers. They think they want to want another job, right? They want to really want to. It’s like wanting to—it’s like me going to the gym. I really want to go to the gym,

Christina Wallace: Yes.

Renata Bernarde: So I set it as a goal. I’m going twice a week, but I don’t actually want it. I just think I need it. And that can come from extrinsic motivators. So, you know, people may think something’s wrong with my career because I’ve been stuck here for so long, or I actually do hate my job.

I don’t know. I don’t have the energy to go out. So, I’m just going to hire this woman and she’s going to sprinkle some fairy dust on me.

Christina Wallace: Huh.

Renata Bernarde: It will happen. That’s not how it happens, right? So the investment is not just financially to get a coach like myself. It’s the investment is carving out the time, you know, and all of that.

And sometimes people want that. And they just don’t move the needle to achieve it. I’m, I’m, you’ve positioned yourself as an overachiever, so I don’t know if you can relate to this. And it’s, I don’t know that it’s procrastination. It’s more like paralysis. Like, I don’t want to, I don’t know how to do this without it affecting my personal brand, the way that people perceive me out there. Have you encountered…

Christina Wallace: You’ve hit on the exact problem, right? This is an identity problem, an internal narrative problem. Because you’re hitting on the exact thing. When you want to want something, but you don’t actually want that thing, you’re experiencing friction between who you are and who you believe you should be, who you believe other people think you are, who you believe other people will respect.

And there’s usually a certain amount of shame attached to that, which is like, “But I don’t want that.” So, you half-heartedly do things like hiring a coach without doing the real work, which is not “What am I running away from?” but “What do I actually want to run to?” And if that’s different from what I have been doing, what people think I do, what I somehow think I should be doing, why is there friction in that gap?

And a lot of this comes down to, this is why I based this entire portfolio life model. It starts with identity because so much of what we think is possible about our lives, our opportunities, the options that we even consider, starts from what we’re able to see based on who we think we are. And when we tell ourselves this narrative about our identity that’s rooted in our jobs—this is a very common problem in America, where we see ourselves as our jobs. And the longer we’re in the workforce, the more narrowly we define that. It’s not just marketing; it’s consumer packaged goods brand marketing at an SVP level or above, right? We start to forget that that’s a piece of us.

But the bigger picture is, we’re storytellers, we like to connect with customers, we understand how to bridge a gap where someone says, “I need this and nothing exists.” We like to ideate about new things, but also we love art history and playing lacrosse and all these other things that are true about ourselves. Part of this work starts with what I call my human Venn diagram. I say I’ve built my career at the intersection of business, technology, and the arts. And if you look at my very zigzaggy career path through that lens, it suddenly looks really strategic. And you’re like, “Aha, I see what she was doing there.”

That strategy was not obvious in the moment, but I encourage people to really excavate what’s in their Venn diagram. What are the things that you bring to the table, the things that make you, you? Because then you can start to identify maybe what you’re going through in this moment is that this piece of you is a little tapped out and you want to go explore this other piece. I have some great case studies in the book of one particular guy, Robert Lang, who was a physicist for 20 some years, and one day woke up and said, “I don’t want to do this anymore,” and went and became a professional origami artist. Now, you might think, “What on earth is that about? That’s a midlife crisis.” It’s not. He had been an amateur origami lover his entire life, since he was six years old. And he realized a lot of his skills from laser and optical physics, he could apply to writing computer programs to help figure out the intricate folds of origami. And that origami, as you and I are thinking about it, you’re like, “Those silly little paper cranes that you have on your dinner napkins.” No, he was thinking about it like, “How do you fold up satellites for launch so that you can open them up in space? How do you fold airbags in cars so they can be more efficient and yet hurt people less? How do you fold up medical devices so they can go in the body and then expand?” This is all the same idea; it’s just under the guise of origami, right? And so it comes back to how you see yourself and the permission you give yourself to look at what to do next. And the narrower that identity, the more you’re going to feel this friction between what I think I should want, because this is who I am ostensibly, and what I actually want, because there’s a piece of me that has not been feeling expressed.

Renata Bernarde: Yeah, I love that so much, and I think that example is so perfect. The amalgamation of so many things that create something completely different. And that, you know, speaks to your personality as well, of merging art, science, creativity, and logic.

So I love that. I find that sometimes you can take things in a completely different direction. I mentioned in my group coaching the other day that I knew somebody who was a CEO at the time I was a CEO of a not-for-profit foundation. She was a CEO of a not-for-profit foundation. I found her a few years later, and she had gone back to trade school and become, I kid you not, a construction worker.

Christina Wallace: Mm.

Renata Bernarde: And I’m like, “What?” And the other day I hired a landscape guy, and I said, “Tell me, how did you decide to be a landscape designer?” And he said, “Oh, I was in tech. I was a DevOps guy. And I decided I’ve had enough of sitting behind a desk and I just want to go to nature.” And I’m like, “This is fantastic.”

So I want people to think about different ways that this can come to you and speak your language, whatever language that is. It could be nature, it could be art, it could be, I don’t know, whatever it is, right?

Christina Wallace: Well, and I love those examples because there are a couple of threads there to pull out. One is you have to decouple your identity from your power, your status. And for people who see themselves as a CEO, and that is part of their identity, it’s almost impossible to step away from that and go be a construction worker,

Renata Bernarde: Yeah.

Christina Wallace: And so if that is how you understand what you are, your value in a room, it limits—no judgment—it just does. It limits what you are allowed to do next. And the other piece of that is a lot of times we feel that status piece is required. That our life is always improving, success is going up and to the right because it’s a function of what we’re afraid other people will think of us. And the great joy of falling flat on my ass with my first company that failed is that I realized how little other people think of me—how infrequently, not how lowly they think of me, but just how infrequently they think of me. That’s actually really freeing. I ran into a couple of classmates from business school, like three years later, and the first thing out of their mouth was like, “Hey, how’s Quincy going?” I was like, “I shut that company down three years ago. I had a whole big, like, big press splash about how I failed on this,” and they’re like, “Oh, really? I missed that.” You know? So allowing yourself the freedom to say, “I don’t really care if I’m impressive; if it makes me happy, that’s what matters.” No one is thinking about you truly. So what is actually impressive is pursuing joy rather than status.

The other way to express this, because I actually had a male colleague once ask me if an alternative title for this book might be called ‘Lean Out.’ Because I was proposing that you don’t have to be excessively ambitious at all times. And I said, “Okay, that’s an interesting read on it.” Here’s what I would say in response: I have always been and remain an incredibly ambitious person. What is different is that my ambition is no longer just about my career. I am ambitious for my family, that my kids are going to grow up healthy and happy with positive relationships to each other and to me. I’m ambitious for my marriage, that we will have a relationship that’s not just about the logistics of child rearing for the next two decades.

Christina Wallace: I’m ambitious for my health because I just turned 40 and you do not get to take for granted that your back won’t hurt every day. Like, there comes a point where you have to actually take care of these things. And my ambition is just distributed across my portfolio in a different way. I’m still ambitious for my work. I’m doing a lot of things, but it’s not the only place that my ambition is expressed now. And the great thing about that is if I have a crappy day, literally in any dimension, my toddler thinks I’m an idiot, it doesn’t matter, I rock at work. If I bomb a meeting at work, it doesn’t matter. I had a great workout. I had a personal best on my run today. Right? When you distribute your ambition, you can fall short in one area and still feel really good about yourself because you’ve diversified. And that’s true not just internally, but also externally. When you get laid off, that’s not everything that you are or have. You’ve got other things, relationships, networks, hobbies, income streams that you can fall back on.

Renata Bernarde: I think the definition of ambition that you have is the true definition of ambition. I also find that that’s very true in Eastern philosophy, whereas in the Western world, we tend to align it completely with career, achievement, and leadership. So, there is a very cringe moment in Australian TV where there’s a journalist interviewing the Dalai Lama, and he mentions the word ambition, and she says something along the lines of, “I think you’re mixing up the words,” trying to correct the Dalai Lama.

And he said, “No, no, it’s ambition. I am ambitious,” and you just couldn’t believe, you know, that the Dalai Lama was saying that. And it’s hard to watch. You don’t want to watch that scene. It’s not good. All right. So, thinking in this sort of portfolio life mindset in a sort of expansive way, do you think about it, okay, 10 years from now, 20 years from now? I’ll tell you why I ask you this. The beginning of my coaching process is usually, “Tell me how you see yourself 40 years from now.” And that really makes people pause. And I have tried, I’ve used this framework forever. I’ve used this framework since I was the MBA career manager here at an Australian university back in 2008.

And I’ve just incrementally updated it throughout the years. It’s worth it. So, I’m like, “I’ll keep this.” Maybe it’s kind of that dilemma of ethical marketing where you want to sell something that people, you know, that people would relate to more and meet them where they’re at. But in the end, I’m like, “Okay, I’m going to have the best clients because the ones that sign up for this and endure this module, they’re the best clients to have.”

So, tell me how you work on yourself and maybe even with your students at Harvard or people you meet in thinking about the long term.

Christina Wallace: I love this question because it is, it’s like one of these “two things can be true” moments, right? On the one hand, you say, “How on earth am I supposed to imagine what 40 years from now looks like when I think back that the iPhone didn’t exist when I started my MBA program? Like, what? This thing that I can live my entire life now with just the phone in my pocket. Yeah. Because it’s everything, it’s not a phone.” And that didn’t exist when I started graduate school, which was not that long ago. So this notion of, “I have no idea what the world looks like, and so how am I supposed to know where I’m going to be in that period?” is really paralyzing in some ways.

Christina Wallace: But I find it freeing, because you can’t draw a straight line between here and there. You don’t know where there is, right? And so, it forces you to recognize that there is no straight line. It’s what Clay Christensen, one of my professors and mentors when I was a student, calls emergent strategy rather than deliberate strategy.

Deliberate strategy is what corporations used to do when they thought about innovation and growth, which is like, “We’re here, we want to be there. How do we put the steps in place? Let’s go.” I don’t know why I use that as my corporate innovation voice, but it’s there. Emergent strategy says, “I don’t know where there is, but I have roughly a direction that I think there is.” And then I’m going to take a few steps and then I’m going to look up and check. “Is there still where I think there is?” And if not, I’ll redirect. And then I’ll take a few more steps and take in new information, right? Like you become opportunistic and iterative in the process.

So, I say this as a very long preamble—you can cut the whole thing in your editing room. I say this because I love the question, not “Where are you going to be in 40 years?” but “What are the hundred wishes that you have for your life?”

Renata Bernarde: Yeah.

Christina Wallace: When you are on your deathbed, as morbid as that is to think about, what imprint do you want to have left on the world? Who do you want to have loved? What do you want to have seen and experienced? What artifacts do you want to leave behind as your legacy? What do you want to have to show for your time on earth?

And I think that is so delightfully existential as a question that when I force my students, the people I coach, anyone—I have people do this in the book—to write out the hundred wishes for your life.

Usually, you can get about 20, 25 pretty easily. And then you sort of limp to about 30 and then you say, “Okay, I don’t have anything else. I must just not be that interesting of a person.” I’m like, “No, I refuse to hear that.” Because the first 20 are usually professional, and then the next 10 are like, “Yeah, oh yeah, I want a family. I mean, I guess someday I want to go to Antarctica. And, you know, I want to be there for my parents when they’re getting older.” You’re like, “Great, keep going. You got 70 more. What else?” And you start forcing yourself to recognize all of these things that you do dream about, but you’ve decided are impractical because you have to be an adult now.

And this is the stuff you have to do. And as you start kind of allowing that impracticality to run away for a bit and just focus on what you actually want, what you care about, what you want to see, you uncover things like, “Oh, I have this total adventure travel streak that I’ve literally never made time for. I’ve never put aside money for, I’ve never in any way prioritized. But I want to see the world before I die.” Or, “I want a family and yet I am 42 and don’t have time for first dates.” You’re like, “Okay, it probably feels weird to make this a project, but like, if you want it, you gotta make space for it.”

I give the story in the book. I’ve done this Ted talk. It’s on the internet. Anyone can watch it on how I met my husband through online dating, by creating a sales funnel and treating it like a sales process because I was really, really good at sales and business development and customer acquisition. And I was really, really bad at dating. And so I just treated it like a process. I did a whole retro on my previous dating. I went off to the woods by myself camping for a week and kind of did this deep dive. And then I came up with a process and I said, “Here’s how I’m going to run the process to meet as many people as I can.” And then allow myself to unshackle what I think I want in a partner because, Lord knows, 10 years of dating them did not work out well, and force myself to just have some deal flow to make it a priority because I wanted a family and I hadn’t made space for one.

Renata Bernarde: I love that. You know why? Because I often use analogies about dating in the recruitment side of corporate life. So many people have dreams about what their career should look like and what sort of jobs they want without ever going out and asking people, “So tell me about your job,” which is something I want to do as well.

So having that network without an agenda, without a transactional approach, and just going out and talking to people just for the sake of learning about them, not for the sake of doing anything about you. You just want to learn about them first.

Christina Wallace: I love that strategy. Yes.

Renata Bernarde: It’s entrepreneurial. It’s like doing that research that every entrepreneur needs to do, and corporate professionals don’t think about. They have been told that the best thing they can do is sit alone at their homes and never tell anybody that they want to change jobs or they’re applying for jobs. They’re very secretive about it and they don’t learn.

Christina Wallace: Yeah. No, what I love about that approach—I mean, to continue our dating analogy here—one of the things that I really struggled with in dating was that I would fall in love with the idea of the person. I had a few data points, and I would sketch out in my head the rest of the outline, and then I would fill it in and sort of make up this whole backstory and sort of project out how we were going to be the perfect fit for each other, right?

We all do this. And the problem with that was that then when the evidence started to pile up that the reality was not actually consistent with the drawing in my head, I favored the image in my head over the data. And then I would get three, four, six months into a relationship, and I’m like, “Why am I so unhappy?” And when I would go back and look, I’m like, “They have been utterly consistent with who they are this whole time.” And I have ignored each data point as an outlier, rather than accepting that it was filling in the picture for me. And I think we do this a lot with jobs. Certainly, younger people…

Renata Bernarde: …in the recruitment and selection process, the red flags, the red…

Christina Wallace: …you know this. I once had a job where six hours into the first day, I realized I had made a mistake.

Renata Bernarde: Yeah.

Christina Wallace: I knew it. And when I thought back, I was like, “Yep, red flag, red flag, red flag.” I stayed two and a half years. It was miserable. It was miserable, but you don’t trust yourself to read the signals because you’ve put together the sketch of what you think this job will be or what you want this job to be, rather than paying attention to reality.

And so, what I love about your process of just going out and interviewing people and getting to know them is so much about happiness in our work. It’s really about the day-to-day of what that job is like, who you work with, what your pace is, and how much autonomy you have. You know, all of the things that we all have very different priorities for what brings out the best in us. But none of that gets discussed at university. None of that is really ever put out there, like, “What is it like day in and day out as a surgeon? And how is that different from being a physical therapist?” Right? And there’s no right or wrong answer, but having a little more understanding of the experience, and not just the outcomes, I think would help people be a little less judgmental on themselves when they say, “I’m not happy here.”

Renata Bernarde: Yeah. Oh, I love that, and I see that all the time. One of the things that I used to do back in the day, when I was working with people coming into professions, was to make sure that if they came from blue-collar backgrounds or Indigenous backgrounds here in Australia—we care a lot about diversity and inclusion—is to give them the opportunity to connect with professionals. They didn’t have anybody in their families; their parents were blue-collar workers. Making sure that they were ready for recruitment, that they even had the right attire. That was like 10 years ago, to dress a certain way. I think things have eased a bit in the dress code. There’s the post-pandemic dress code and the pre-pandemic dress code.

Christina Wallace: Very much so.

Renata Bernarde: But look, it was such a lovely chat. I could go on forever, but I know you have other things to do in your portfolio life, and I don’t want to encroach on your time or time with your students. What would be your key message as we finish this chat to people that are interested in learning more about having a portfolio life? What would be the first step, above and beyond buying the book? We’ll have a link to your book below. What do you start doing from day one?

Christina Wallace: Probably three things. The first is, in addition to the book, I’m about to launch a free workbook that’s a little bit of a guided step-by-step through all of the action that I do in the book. I’ve heard from so many folks, they just want a little more scaffolding. So if you want that, join my mailing list on my book website, portfoliolife dot com. And I will send that to everyone who signs up; it’s free when it comes out in April. So that’s number one. Number two, I’d say, is really to go back to that excavation of your identity and whether you think of it as uncovering who you’ve always been but you’ve lost touch with, or whether it’s more about expiring the data of like, “That was true. Is it still true? What’s true now?” Right? You can figure out whatever perspective speaks to you, but really take that time to both internally reflect and to go out and talk to the people who see you, who know you, who love you, and ask them what they see. I give three questions in the book that I did when I literally did this exact experience with a bunch of coffee chats: “When have you seen me happiest? What do you come to me for? Like, what is that moment where you think, ‘You know what, I should see what Christina thinks about this.’ And where do I stand out against my peers?” So go out and get some information, whether it’s inside-out, outside-in, on who you are. And then the last piece is to just remember this tiny little mantra, which is, if you’re not dead, you still have options.

No matter where you are in life, you might think, well, I’ve made my bed and now I have to lie in it. And I just don’t think that’s true anymore. If you’re not dead, you still have options. Whether you’re on the face of retirement or whether you’ve finished your university degree and you want to do nothing with that professionally, nothing is locked in.

Renata Bernarde: I will put a link to the sunk cost episode so that people can go back to that episode and think about it a little bit more. Thank you so much, Christina. It’s been a pleasure talking to you.

Christina Wallace: Thank you for having me. It is an absolute joy, and I love what you’re doing with this show.

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