Christina Wallace : Author of The Portfolio Life

Episode 429

On today’s episode, Christina Wallace, Author of the terrific new book The Portfolio Life, sits down with Kara Goldin to discuss her journey as a self-described "human Venn diagram." After a decade as a serial entrepreneur, Christina joined the faculty of Harvard Business School where she is the course head of the first-year entrepreneurship class and runs the HBS Startup Bootcamp. Whether you’re looking for a career change, a side hustle or a way to express your creativity, her latest book The Portfolio Life, is packed with practical tips and inspiring stories that will help you rethink your career and life choices. This is a not-to-be-missed episode in entrepreneurship and life choices that will have you thinking about the opportunity of a portfolio life too. You don’t want to miss this episode. Now on #TheKaraGoldinShow.

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Kara Goldin 0:00
I am unwilling to give up that I will start over from scratch as many times as it takes to get where I want to be I want to be, you just want to make sure you will get knocked down. But just make sure you don’t get knocked down knocked out. So your only choice should be go focus on what you can control control control. Hi, everyone and welcome to the Kara Goldin show. Join me each week for inspiring conversations with some of the world’s greatest leaders. We’ll talk with founders, entrepreneurs, CEOs, and really some of the most interesting people of our time. Can’t wait to get started. Let’s go. Let’s go. Hi, everybody, it’s Kara Goldin from the Kara Goldin show. And I’m so excited to have my next guest. Here. We have Christina Wallace, who is, amongst other things, the new author will actually she’s a previous offer author as well. But the new book that she has authored is called the portfolio life. And you must get your hands on this. It is so so good. And Christina is a self described human Venn diagram. And after a decade as a serial entrepreneur, Christina joined the faculty of Harvard Business School where she is the course head of the first year entrepreneurship class and runs the HBS startup bootcamp. And what a dream job on so many levels. So her latest book, The portfolio, life is terrific and packed with practical tips and inspiring stories that will help you rethink your career and life choices. Similar to what she has done. She is just a wealth of information, having operated companies, which I’m such a big fan of when people are actually telling you that the road to stardom to to success definitely is, is one that Christina knows quite a bit about. And I think it’s really great that she’s decided to write a book about career choices and changing things around a little bit and her own journey. She will share with us today. So welcome, Christina,

Christina Wallace 2:14
thank you so much for having me. I’m so excited to be here. Absolutely. I

Kara Goldin 2:17
should also mention that I’ve known Christina for a while. So actually, like over a decade. Yeah, pre Harvard Business School teaching and pre kids and marriage and all that kind of stuff. So I’m super, super excited to see and hear everything that she is doing. So what inspired you to write the portfolio life.

Christina Wallace 2:39
So there were a couple of reasons that I wrote the book. I started with this, this feeling that I had, I’ve been writing about many of these ideas in small ways over many, many years. As a columnist for Forbes, I had had a podcast for several years, called the limit does not exist. And I’ve been doing some public speaking around this idea that you can have chapters of your life go through seasons, you can diversify the components of your portfolio, and crucially rebalance that portfolio for each of these seasons. As you go through these transitions, you can rethink how you build the business model for your life. But equally, so I wanted to write this book to explain to my mother what it is I’ve been doing with my career. She’s kind of like, what are you doing now? And I think there’s a lot of people that I’ve met over the years who have sent me emails saying I am so inspired by how you have managed to put all of the things that you are together in a life. Yeah, that works for you. That makes sense that doesn’t feel like you’re a dilettante, like you’re a flake, but also is completely unique to you. And how do I get permission to do that? So I wrote the book as part permission, as though I have the ability to give anyone permission, but also part process, here’s a really tactical way to think through the steps of building that business model for your life that is sustainable, that is balanced, that is future proofed against the constant disruptions we’re dealing with. And that allows you to be bigger than just how you monetize your time today.

Kara Goldin 4:19
Well, I can’t think of a better time for this book to come out, as I hear, you know, lots of people getting laid off from their roles, maybe their jobs that they thought they were going to be in for a while, are now being taken over by AI type of applications. And whatever it is, I think that understanding how the portfolio life is possible is super, super great. One of the things that I had read about and as I was doing research was something that is growing in popularity called portfolio career. How does that different firm differ from this? Have you heard About that,

Christina Wallace 5:01
yeah, no, I mean, I originally started running about portfolio careers. That was actually one of my first Forbes posts, everyone in the future should have a portfolio career. And, and the idea there is that you have multiple income streams, you’re thinking about, you know, really diversifying your professional network, as well as thinking about how you put to work your different skills and your interests. It’s, it’s, instead of being like, I am a marketer. So all I will ever do is marketing. Instead of that, you can reframe it as like, I’m a storyteller, I might do that through marketing here, I might choose a journalism course there, I might go and think about becoming an author or a professor, there are so many different avenues for applying what I do. And crucially, I can do several of them at once I can have side hustles or moonlighting projects or small businesses that I think about, in addition to maybe that day job, that’s a portfolio career. And I think that is an important part of this model. But I expanded it from career to portfolio life, because your career is in the context of your life. And as you think about rebalancing your portfolio for different stages, what you need at certain stages of your life is going to determine how much time you have for your work, how much flexibility you might need, or how much income you really have to bring in. And that’s all holistic. And so I really, I chafe at this idea of work life balance, because work is part of life. And so I really want to expand this to say, as you think about your career, you also should be thinking about your family, your relationships, your community, and impact, your hobbies, your health, your your rest, your mental health, all of this is part of one big system. And that really hit home for me when I had my first child, when I went from being able to work 18 hours a day and answer to no one, to suddenly saying I have a very different set of constraints. If I want to be the type of Mother I want to be, I need to be thinking about my work in a very different way and design. All of this for the next chapter. And that’s why I came to Harvard to be a professor for this season have small children.

Kara Goldin 7:26
I love it. No, it’s it’s really great. It’s interesting. I think that having kids definitely changes a lot of people’s focus. You know, not only do you want to how you want to divide your time, but also it forced me to kind of think about what else I was interested in. So I had a career in tech, and prior to starting hint. But I became very interested, I was always interested in health. But I became very interested primarily when I had kids in making sure that I was providing health for them. And that’s when I really started. I think there was a hockey stick for me around health and around sugar and sweeteners, and really getting my curiosity sort of kicked into gear with that. So I think that it’s it really like, as I was reading the book, I mean, it really rang true for me on so many levels. So what are some practical strategies for successfully kind of navigating and balancing this portfolio? Life?

Christina Wallace 8:33
Yeah, I mean, it starts with identity, it starts with understanding who you are and what you bring to the table that is greater than the title on your LinkedIn today. I think particularly the further you get on in your career, especially here in the US, the the the closer we start identifying with our jobs as though that is who we are. And so this requires a little bit of both self reflection to say okay, but I am so much more than that. What are all the things that I love, the the Fascinations the little, you know, things I nerd out about, but also the skills that I used to have that I really might not have had an opportunity to make use of the last 10 or 20 or 30 years. That’s still part of me, you know, I am a classically trained musician, piano, cello and voice I spent the first 17 years of my childhood seriously studying music. And then I put it on the backburner for a little bit but it’s still part of who I am. And and it’s important that I remember that and keep that close. So we start with identity. And this can be self reflection. It also can be about going to the people that know and love you and asking them what they see. When they look at you. You I give you three questions in the book. When have you seen me happiest? What do you come to me for like, what is that moment where you think I should see what Christina thinks about this. And where do I stand? out against my peers. Because that reflection might help you recognize that you are so many other things that you don’t currently understand. So you start with this broader identity. And that’s where my phrase human Venn diagram came from. I did this work myself. And I was like, You know what, I do a lot of different things. But I am this multidisciplinary person who loves to live at the intersections. That’s, that’s who I am. So we start with identity, then we think about how you are building the model for this season of your life. What do you need right now that can be everything from you know how much money you have to earn to right now I need autonomy and flexibility. In my life, I have young children, they get sick all the time, I need the ability to clear my day, and go take care of them. If I have to. I also need an office with the door. As you can see, right now, I don’t do well in open workspaces. So understanding what do I need for this chapter? And then we go to what do you want? What do you wish for your life? I push you to grab a stack of post its and write out 100 wishes for your life. And that number is ridiculously large, because I want you to think beyond career goals, or what do I want for this season? I want you to think broadly on your deathbed, what impact do you want to have had what things do you want to have seen? Who do you want to have loved? What do you want for your life? And then you take those three things, who you are, what you need, what you want. And you craft a combination? And a you know, an allocation of your time and your talents? Across things. You say? How can I meet these needs, and drive closer to those wishes those wants, through my job, my volunteer work, my relationships, my personal time? How do I fit this together? Crucially, in a way that isn’t going to burn me out? I think it’s easy to say yes, yes, yes to all the things and then you’re like I have overcommitted and that’s what leads to burnout. So there’s a structure for this that I provide in the book that really helps you understand your capacity, and then fit these pieces together. And these are the four pillars that will work for this season.

Kara Goldin 12:25
And these are the four pillars. Do you want to go over those?

Christina Wallace 12:29
Sure. I mean, it’s it’s identity, optionality, diversification, and flexibility. And, and you know, we already covered identity optionality is really understanding that no matter where you are in your life, I don’t care if you are like 92, you are not stuck. You are not on a straight path that can only go in one direction, you may have closed off doors along the way, but there are always still doors available. So many times people feel like well, I chose that major, I followed this path, I’ve been doing it for too long to make a change. This is who I am now, and I disagree with that. You always have the ability, but you have to see it first. So we have that optionality, then flexibility is really understanding that there’s especially today, there’s so many different models. And this is where I get into later some of the different business models, maybe you have a day job where you’re Moonlighting, maybe you are zigzagging from one full time thing to another full time thing. Maybe you’re cobbling together multiple projects at the same time as a true portfolio career. So you have these simultaneous work streams, there are lots of different ways you can design your work based on what you need right now. And then the last one. Sorry, that was flexibility. The third one was diversification, which is about this is how you future proof in a world that is this volatile, that is not slowing down its rate of change. The only way to future proof is through diversification. And that means not just multiple income streams. But how are you thinking about your network? How are you thinking about, you know, who is going to show up and help you if you get laid off here? Do you have other resources there? If this whole industry gets uprooted by AI? Can you take a pivot and go hard left and take your skills to a whole different world? It’s going to be easier to do that if you’re not starting from scratch. So how can you build some of that diversification in before you need it?

Kara Goldin 14:35
No, I love it. I think that this is also as you start to reflect on all of those pillars to it. You’re gonna be a little uncomfortable, right? I mean, you’re sort of kind of going back down to the bottom to figure out the learnings, the skills that you need, maybe but also maybe, you know, what do you have in your toolbox that you can actually The US in, you know, this next iteration of you. So it’s a fun process. It can be daunting probably at times, but but I think that it’s it’s absolutely something that is. That is, so many people are reflecting on that right now or or maybe being forced to reflect on it and shouldn’t be reflecting on it. But I think it’s it’s so key. So can you share any personal experiences or stories that kind of have shaped your own understanding and appreciation for living a portfolio life?

Christina Wallace 15:34
Yeah, I mean, I think one of the key stories and I lean into this hard in the book, it’s the third chapter, which is all about failure. And it’s that my first startup failed, like straight up, ran out of money before we could figure out the business model. And it was the first time in my entire life that I had failed at anything. You know, I had always been high achiever worked hard, smart, sort of, I realized, by that point, I think I was 27 or 28, I realized that I had started opting into things by virtue of saying, like, I think I can be good at that, like, I’m not going to take the risk of trying something that I’m not going to be good at, because success is part of my identity. That is the story I tell myself, failure does not fit that story. And when I had that realization, you know, sort of facing failure. So bluntly, it forced me to reckon with, you know, how many opportunities have I missed because I was afraid to fail. And failure, which feels, especially to young people who have gotten great grades and gone down the high achieving school route. It feels like a moral judgment. And then you realize, like, everyone in history has failed. At some point, marriages fail, people get fired. You know, all of us have faced failure, you realize that as an adult, but I think, especially for younger people, it feels like the end of the world. Yeah. And when you recognize that it’s not, it’s just a moment where you wanted something to happen. And it didn’t it. Yeah, right. And it could have been your fault. Okay, you’ve learned something, it, it might not have been your fault, it might have been the world, you’re in the context, the external environment, whatever that is, you’ve learned something. And now you can move forward, I realized in that moment, I had to get better at being bad at things I had to get, I had to practice. Failing, I had to, like build this muscle, or I would never take risks again. So I decided to start long distance running, I took up like marathons, because I am a terrible runner. I’m like a six hour marathon. I’m a terrible runner. I’ve never been an a natural athlete. But I was like, this is something you are bad at. And you are going to do it over and over and over again, until you can can change that story that you tell yourself. And it’s no longer I’m someone who succeeds. It’s I’m someone who shows up works hard and tries. And that internal monologue changed everything. It gave me the ability to go out and try building another startup after having just failed at doing that exact thing. And without that, you can’t, you can’t build diversification without taking risks. That’s literally the point of a portfolio strategy. Yeah. So getting comfortable with failure is a key part of being able to future proof. You don’t know what’s going to happen, the world is entirely unknown. And if you will only do things that you can predict the outcome of you are going to have a smaller and smaller option set. As we continue on.

Kara Goldin 18:49
I loved your your point in the book, and you just talked about it a minute ago, but the just, you called the just have coffee point in the book. Like I think that that’s perfect, because when I think about steps to move forward, when people are sitting in this position, they’re like, oh, my gosh, what Christina is talking about is me. You know, it’s definitely a, I’ve been through a failure. I, you know, I’m stuck, whatever, this idea of taking that first step and figuring out, okay, who am I going to go have coffee with and say, you know, you’re, you’re somebody that I value your opinion, tell me answer these three questions about, you know, or whatever you like, everyone can do that. Right. And it’s and I think it starts the process for people but how can individuals effectively identify and develop these strengths? What am I missing?

Christina Wallace 19:47
Yeah, I mean, part of it really does require that that excavation of, of who you’ve always been, you know, I look at my children. My kids are one and three and they They are so creative they are so just fearless they are they are all of these things that I look at them. And I’m like, you know how many of my MBA students are convinced they don’t have a creative bone in their body. They’re just like, Oh, I’m not creative. I’m an analyst. I’m a financial person, I am an operator, I’m not creative. And I was like, You were all a three year old once you are creative, you need to reacquaint yourself with that creativity. So whether this requires you to go and try a few crazy things like a comedy improv class or go join some, you know, startup pitch competition that will like put you on stage, whatever that thing is to kind of jumpstart you out of your comfort zone. That is often a great first step. Because once you do that, then you’re like, Oh, well, that wasn’t quite so bad. Let’s see what else I have. And you can go through this, you know, if this isn’t like a squirrel yourself away for a weekend with a notebook and solve all of your, your problems through journaling, right? Like, you have to go out and get some external data points along with these moments of self reflection. And that’s where the coffee chats become really helpful. You can take a look at who am I, what do I bring to the table? When am I my best? And you have a point of view informed by decades of knowing yourself? Sure. But you have to go talk to other people. Yeah, you would be fascinated by how many people I’ve talked to through the course of reporting on this book, that I’ve said, I had no idea that everyone was impressed by this thing I did. It was so natural to me. I just assumed everyone could do it. And you’re like, No, that’s a superpower. How did you not? Are you kidding? Yeah. So it requires these external data points. And once you start doing these coffee chats, it also helps you build that muscle of reaching out and staying connected. I think the other big piece of this is it’s easy to lose the breadth of your network, the further you get into your career, the more responsibilities you have on your plate. If you’re not in a role, where you’re regularly, you know, needing to reach out to people you can start to become really siloed. And silos are what is like going to be a problem in those moments where you are laid off, or you decide you hate your career and want to do something new. So keeping those relationships really strong is going to be a huge catalyst for this life.

Kara Goldin 22:28
Yeah, I think that’s so so key. So what other key messages or insights, if we look at, you know, the book like, what, what do you hope you’re sitting on an airplane and somebody’s like, oh, I read the portfolio life, it was awesome. Or maybe somebody’s thinking, Okay, I want to buy this for somebody like, that I really care about, maybe I want to buy it from my team. That because I really feel like they can start, they could be thinking about this for their team, whatever. What key insights do you want people or I should say key messages that people can take away.

Christina Wallace 23:09
There’s, I would say there’s three. One is, as we think about burnout, there’s some research I point to in the last third of the book that I continue to find resonates so strongly with everyone. And so it’s become one of my big talking points around how you think about managing your capacity. And the research I point to is from manufacturing lines, the best in the world that operate at 85% capacity, not 100%, not 110%, they they max out at 85% capacity, because they recognize you need to have time for maintenance, you need time for do overs, you need time for if your best customer comes and says can you do a rush order, you want to be able to help them so you have to leave space for, for serendipity and for for rest for you know, downtime. And and they say the reason is planned downtime is cheaper than unplanned downtime, right. And anyone who has had that moment of burnout, as I have had, finds out, you can either take the nap or you can end up in bed with mono and pneumonia at the same time, like one way or another your body is going to find itself in your own way. So, so really be intentional about how you allocate your time and draw that hard line on. I’ve maxed out my capacity right now. And I’m going to start really saying no, because I cannot run ragged and not think it’s going to catch up with me that 85% is both you as an individual, but it’s also a way that you can think about your team. You know, I can’t tell you how many people I know who say like I’m in meetings all day long. What am I supposed to do my work? Like, like you’re in, you’re ensuring that I have to work nights On weekends and, and holidays in order to catch up. And so as you think about how can we max out at 85%, to leave space for downtime, and for serendipity, this also becomes relevant from a team’s point of view, as you’re thinking about how do I future proof my company? How do I future proof, my my talent, because there’s going to be a lot of changes to jobs in the next few years. And if you as a manager can walk the walk, and show your teams, how you have a portfolio life, you have hobbies, you have new things you are constantly learning, you make space for family, and you are flexible with how those things fit into the day, your team will feel permission to do that, too. The reason this will help you future proof your your talent is that if and when you get to a point where you say I need to lay off 90% of my marketing team AI can do this for me. Now, I don’t need that anymore. But those people say, Well, I’m more than just a marketer. I’ve also been learning to code. I’ve also fallen in love with customer service, I’ve also been doing all these other things. And I am perfectly happy to rotate into an entirely different division here. And it’s not just that I have this in the back of my head, you gave me a stretch assignment two years ago on this, you allowed me to moonlight in that other department and understand how that works. You don’t have to lay them off, you can redeploy them. So having that flexibility in your own team and your own company will give you the ability to match talent with needs rather than holding on to an outdated talent model simply because you don’t want to fire a whole bunch of people.

Kara Goldin 26:40
Exactly. No, I think that those are excellent, excellent messages and key takeaways for sure. So Well, thank you so much, Christina, this is so great. We’ll have all the info in the show notes too. But everybody needs to pick up a copy of the portfolio life. And are you also doing an audio version of the book?

Christina Wallace 27:01
I did. You can listen to my sweet sweet voice. Yeah,

Kara Goldin 27:05
awesome. And also hear more from Christina that way, but but also I’ll put all the info for Christina too, if you want to learn more about her and her terrific journey and what she’s doing today, etc. So thank you so much, Christina for all of your wisdom. And thanks, everyone for listening. Thanks again for listening to the Kara Goldin show. If you would, please give us a review and feel free to share this podcast with others who would benefit and of course, feel free to subscribe so you don’t miss a single episode of our podcast. Just a reminder that I can be found on all platforms at Kara Goldin. And if you want to hear more about my journey, I hope you will have a listen. Or pick up a copy of my book on daunted which I share my journey, including founding and building hint. We are here every Monday, Wednesday and Friday. And thanks everyone for listening. Have a great rest of the week, and 2023 and good bye for now. Before we sign off, I want to talk to you about fear. People like to talk about fearless leaders. But achieving big goals isn’t about fearlessness. Successful leaders recognize their fears and decide to deal with them head on in order to move forward. This is where my new book undaunted comes in. This book is designed for anyone who wants to succeed in the face of fear, overcome doubts and live a little undaunted. Order your copy today at undaunted, the and learn how to look your doubts and doubters in the eye and achieve your dreams. For a limited time. You’ll also receive a free case of hint water. Do you have a question for me or want to nominate an innovator to spotlight send me a tweet at Kara Goldin and let me know. And if you liked what you heard, please leave me a review on Apple podcasts. You can also follow along with me on Facebook, Instagram, Twitter and LinkedIn at Kara Goldin. Thanks for listening