Finding meaning within and outside of our work

Q&A with Christopher Wong Michaelson and Jennifer Tosti-Kharas, coauthors of the new book, Is Your Work Worth It? How to Think About Meaningful Work.

Christopher Wong Michaelson is a philosopher with 25 years of experience advising business leaders pursuing meaning and providing work with a purpose. He is the Opus Distinguished Professor and Academic Director of the Melrose and The Toro Company Center for Principled Leadership at the University of St. Thomas and on the Business and Society faculty at NYU’s Stern School of Business.

Jennifer Tosti-Kharas is the Camilla Latino Spinelli Endowed Term Chair and Professor of Management at Babson College. She teaches, researches, and coaches others about what it means to craft a meaningful career, and appreciate the risks and rewards of work as a calling.

Chris and Jennifer are the perfect pair to co-author Is Your Work Worth It? How to Think About Meaningful Work, released in May 2024. We had an awesome and educational conversation about the individual and societal pressures that shape our overall attitudes about work, whether “follow your passion” is good advice, if you have to love your work to be happy, and so much more.

Love what you do .... Don’t settle?

“Don’t lose faith. I’m convinced that the only thing that kept me going was that I loved what I did. You’ve got to find what you love. And that is as true for your work as it is for your lovers. Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do. If you haven’t found it yet, keep looking. Don’t settle.”

– Steve Jobs, Commencement Address at Stanford, June 12, 2005.

Annie: The advice about work that I hear all the time is, “Don't work for the money. Go find what you're passionate about and then you'll be happy, and the money will come.” I can say, in my case, that worked great. But I've always struggled with that advice because some people don’t have that luxury. I would love to hear, just to start, big picture, as we think about what the purpose of your work should be, whether my skepticism is unwarranted.

Jennifer: Nope. Your skepticism is totally warranted. Even though we, like you, deeply love our work and followed a passion that’s worked out well, it is by no means a surefire route to success or happiness. Our book does not pretend to offer it as “one size fits all.” But you're absolutely right, that this is so ingrained in the dominant cultural discourse. We tell people all the time, in ways explicit and implicit, that they should do what they love, follow their passion, or find their calling. There are lots of ways to have a happy and productive life apart from finding your passion.

A lot of people are happy and fulfilled doing work that primarily serves to fund their enjoyment and calling and passion outside of work. We would never want to advise against that. Similarly, there are people who are doing what they love. I study some of these people, notably musicians, who do what they love almost to the detriment of their lives as a whole. They are pursuing unbelievably challenging career paths and not making a lot of money. The starving artist mentality. I'm not sure, for some of them, that they're better off following their passions than they would be if they did something else.

Annie: Just following up on that, I want to take a cognitive scientist’s eye to it as well as a probabilistic approach. As a cognitive scientist, one of the things I worry about with this idea of “follow your passion” is that there's a lot of survivorship bias built into that. You hear about the people who famously succeeded following their passion. But we definitely don't hear about the people who don't succeed following their passion.

Christopher: Yeah, I would say that, at one end of the spectrum is “Do what you love and the money will follow.” Way at the other end, there’s an excellent recent book, Work Won't Love You Back by Sarah Jaffe. We are at neither end of that spectrum. We are at both ends and all the space in between. There's not one simple answer for everybody. Our book encourages people to think about all the reasons that make work worth doing, including love for the work itself, love for the beneficiaries of the work in the form of the family you support, love for your community, and even the comradery that you get from being a part of an organization and being part of an enterprise that makes something bigger than you could do on your own. Those are more realistic goals than finding work that you love and getting rich doing it because that's only going to happen for very few people.

Annie: I love the idea of reorienting to all the things work is giving you. I want circle back to that, but first I want to come back to what Jen said about studying musicians. I lived in LA for a while, and everybody was an actor. All your waiters were actors. Only once did I meet somebody who put a deadline on it and said, “If I'm not getting success by this time, then I ought to go do something else.” Partly to your point, Christopher, I think it’s okay for people to put a deadline on pursuing their passion as work. If they go on to something else, they can fund other things they love, whether it's their family or rock climbing or whatever else it is.

Sometimes it's okay to settle, and maybe we shouldn't call it settling at all. There are so many things that you can get out of work, even if you don’t become the equivalent of Natalie Portman or Robert Downey, Jr. It feels like we’re discounting that meaning in favor of this world of wealth and fame when we know what the odds are. I think the problem is, in the face of those kinds of odds, people still say, “You should keep trying. You should keep following your passion.” Then they'll tell you about somebody who didn't make it until they were 45.

“The American dream” vs. other meaning we get from work

Annie: What would happen if people really understood what Christopher said about the other types of meaning and connection that you can get from work?

Jennifer: I think we’re all drawn to this American dream based on rugged individualism. Everyone wants to feel like if I work my hardest and I put my all into it, I’ll succeed. If someone else succeeded, then why not me? That’s not probabilistic, statistical thinking. It's the opposite. It's a myth, a fantasy. It may not be uniquely American, but it’s certainly a predominant American view. Why not me? Then, everyone who makes it, of course, says, “I could have given up. I almost gave up here. But I kept going. It was my rugged persistence.” Then, you think to yourself, “I have that. I'm persistent.”

And then things just perpetuate. You keep going.

The downside of that is if we don't make it, then it's on us. “I wasn't good enough.” Within each industry, there are such random odds about who gets whose attention, who's a gatekeeper at the right time, who gets that one audition. There are elements of these “winner take all” markets, as they've been described, in just about every type of work. Who makes law partner at a big firm? We write a lot about in the book our own former lives as management consultants. Who makes consulting partner?

The Music Man

Christopher: I want to pick up on what you said, Annie, questioning the term “settling.” One of my favorite stories in the book is about Dennis, a guy that I went to college with. He was hoping to become an opera singer. We both went to Northwestern University, which has an amazing theater program. I think David Schwimmer graduated the year ahead of us. Brian D’Arcy James, who played King George III in Hamilton on Broadway, graduated in our year. They were the markers of success for somebody in Dennis's position. When he didn't get the auditions out of college that he was hoping to get, he actually did what you described. He put a time limit on chasing his calling, and he did settle. He settled for becoming a paralegal, which was something that he could do mindlessly, earn a decent living, and pursue happiness outside of work. In some sense, this reinforces this idea that we shouldn't give everything to chasing work that we love.

Dennis's story is also interesting because, while he was a paralegal, he started dreaming about music again and he ended up auditioning for a part in a show in Minneapolis. He got the part and ultimately had to choose between continuing as a paralegal or doing the show, which would mean low pay, no guarantee of continued income, no health insurance, and no long-term security.

He decided to give it one more shot.

Today, he makes his living as a freelance musician. He performs in churches. He does a John Denver tribute show. He just opened a Jimmy Buffett tribute show. He estimates that he has sung YMCA at least 700 times, and Sweet Caroline more than 1000 times. And he says, “I'm a success because I always wanted to be a musician and I am a musician.” I think we can redefine settling and redefine what success really is.

Annie: We think that becoming wildly, famously successful at something we love is a prerequisite to happiness. I think we feel like we're not allowed to be super happy being a freelance musician doing a Jimmy Buffet tribute show. If you would be okay with that, something’s wrong with you. Why can't you love that?  And why can’t you be happy in a random 9-to-5 job that pays the bills and gives you a chance to spend time with your family and develop your interest in things you love away from work? It feels like this is something we just, as a society, struggle with so much.

A less famous commencement speech

Christopher: Steve Jobs made his famous statement during a commencement speech at Stanford. To your point about survivorship bias, it's people like Steve Jobs who get invited to give commencement speeches. But we were sent a YouTube video of a commencement speech given by a guy named Chad Sokol who we ended up interviewing for the book. Chad's commencement speech was not at Stanford, but it was near Stanford, at Modesto Community College. That’s where he had begun his schooling after he left what he describes as a religious cult that he was raised in resulting in his being disowned by his family.

He left to pursue an education because he thought that there might be more to life than the manual labor that he'd been trained to believe was the only work that he should do because the end times were near. Of course, he also now needed to plan for further ahead than a few years.

In addition to discovering new truths as a student, he developed a love for writing and he's now a published poet, but he is not making a living as a poet. To support his daughter, he also got a job at Costco rounding up carts in the parking lot. When he graduated from Modesto and then got his bachelor's at Berkeley, he got invited by Costco to apply for a buying job. He incrementally worked his way up within Costco. Not only did he find ways to succeed in a conventional way in a career, but he also worked his way up to VP of sourcing for wines and spirits. When I talked with him most recently, he was into candy and dry goods, two of the best jobs in the company. He's also found ways beyond that career to satisfy the more creative side of his life by waking up every day at 5:00 AM, so he can write poetry and get to the office by 7:00 AM.

I guess it's a story about a lot of things. It's a story that you can come from modest beginnings and do amazing things. In his commencement speech, he wasn't exhorting people to do what they love as much as he was advocating for the power of the humanities to help us recognize what makes life worth living. He was sharing a story of hard work and incremental progression from rounding up carts to a high-level executive position.

Annie: If I may, let me add two takeaways that I got from that. The first is, just as you shouldn't be limiting people to work that they have to be passionate about, you also shouldn't limit people to manual labor as the only thing that has meaning. It feels, like depending on what society you're in or what family you're in, or in his case, what cult you're in, we seem to be limiting people's choices. We have our values, and we impose them on other people, which then seems to create great unhappiness. Number two, which I was just thinking about with him working his way up at Costco, I'm sure he is very good at his job, but it may not be his love. Poetry’s his love. And that’s okay. You can succeed at work even if it isn’t your passion, and that can fund your passion.

The distinction between vocation and avocation

Annie: When I was growing up, I remember this distinction between vocation and avocation. I would love to hear you speak to that because it feels like in all we've been talking about, the lines between those two things have become blurred. I don't even know if we have that vocabulary anymore.

Jennifer: Going back to your point number one, Annie, just to briefly respond to that, I think that underscores that work is a big deal in our society, and that's why we try to control it. Work confers so much. It's who you are. When we meet people out in the world, we say, “What do you do?” And we all know what that means. It’s what do you do for work? It's identity. It's status. It's so much more than a job title. Also, for most of us, work consumes so much of our lives. That it's such a big deal and such a zone of control is just reflecting that. Sometimes, I wonder for myself, why have I been for pretty much my whole life, even as a kid, obsessed with what people do for work? And I think it’s because it’s just that big of a deal.

To your second point, I guess the term now would be “side hustle,” though in academia, we still use this demarcation between vocation and avocation. But I'm fascinated by the psychology behind that. At first, the conventional wisdom was if you take something that you love doing or you're intrinsically motivated toward and then introduce an external reward, it reduces your motivation. In other words, by you paying me for it, I want to do it less because now it's work and it's not fun. New studies are coming out that not so much debunk that view as complexify it. You can actually care about both.

You can care about the work and your love and enjoyment of the work and your enjoyment of it are motivators. You can also care about pay and, particularly, in being paid fairly. Being paid to do it doesn’t necessarily totally drain us of love of work or love of a task. In fact, we can hold both of those values at the same time. My own research and that of others has shown that often people who do love their work settle for less pay. On the flip side, people think it's fair to pay them less because they love the work. It just seems right to us if you really love it or if it does good in society or it helps others, that's its own reward. We don't have to worry about extra compensation.

I've been trying, when talking about this topic, to reinforce that it's okay to love what you do and demand fair pay for it. As to whether you just save what you love for what you do outside of work, I think that's what a lot of people do, especially when they've had this early dream for something. At what point does that dream bump up against the reality of the winner-take-all markets? And at what point are you just frankly taking yourself out?

In some way, shape, or form, that happens to a lot of us. I'm thinking back to the example of Dennis, the aspiring musician. There’s this constant renegotiation and readjusting of what I’m doing and how important it is for me to be doing it. And then, am I getting paid enough to maybe keep these different areas of my life active? I have a study where we looked at the difference between full-on professional musicians (they’re getting paid, it’s their primary job) and people who were out of music entirely. The participants all got into the sample because they were talented high school musicians, who were at a famous summer camp for musicians.

Then, many years later, they're either in it, not in it, or they're amateurs. They're still doing music, but it's not their primary job or primary source of income. We thought the amateurs, in terms of their overall wellbeing, they would be just like the people who were in it professionally. By that measure, they were more like the people who were out of music completely. I guess there's nothing magical about doing something just to say that you're doing it. In our sample, there was something meaningful about getting a salary and being a professional. If you weren't, it didn't necessarily mean your life was over, but it wasn't a way to pretend you were still John Bon Jovi or something like that.

911: Lessons from working lives tragically cut short

Annie: Do people ever feel trapped in that, when you mix vocation and avocation? The people who end up, “I'm a paralegal, but I'm also a musician,” there's a choice implied in there. But let's say that you've chosen to be a professional musician. Isn't there a lack of flexibility to that? What do you do if that's not what you want to do anymore, but that's your source of income? I know that's true for people in other types of work. Isn't it the case that you can get trapped in work, because that's the way that you make money, and it interferes with being able to do something else?

Christopher: Our research together began when we were studying 9/11 victims and the stories that their close relations told about their lives, including the place of work in their lives. There were 2,977 victims. We studied over 2,300 portraits of these victims. The stories were many and varied, but there were many of them that suggested not only an unfinished life – they were all tragically, prematurely taken – but also an unfinished working life. For example, there was the administrative assistant who performed in a band at night. Being an administrative assistant was a way to fund that aspiration.

There were a lot of people who were working in finance, but the brother of a woman who followed him (and their father) into bond trading said she had her eye on becoming a social worker because she realized that there was more to life than making money. There was the person who planned become a professor as soon as they made enough money to buy their parents a house. We studied these stories to understand how we idealize the place of work in life.

There was one more story, about a guy who was working his way up the ladder to become a CEO of a company someday. At the same time, he was getting his MBA at night and his wife said, “All this achievement, all this success, what's it for after all this? He's gone.” Some of these stories had a similar pattern and what we came away with was this: We might look at our work today as an investment in a better future, but sometimes, tragically, that future will never come.

Sometimes we don't live long enough. Sometimes our working life is shorter because of circumstances beyond our control. Sometimes the luck just doesn't break our way. I think one lesson to take away from stories like this is that even though it makes good sense to look at the work we do as an investment in a better life in the future, there's also nothing wrong with doing work today that we will never regret having done. There's a famous story about a bond trader who allegedly left behind a half-finished application to the fire department of New York because he'd always dreamed of being a firefighter, but he was doing the conventional thing, doing what was expected, being a bond trader. And instead of running down the stairs to save himself, he led several other people to safety while working alongside firefighters and dying for the work that he'd always wanted to do. That was unimpeachably worth doing.

Annie: That’s such a poignant story about the bond trader who died basically being a firefighter, which is what he wanted to do. It's so incredibly tragic and so sad, but at the same time, there's something beautiful about that.

Reassessing the meaning of work during Covid

Annie: Another thing that comes to mind about studying all these people and learning all these stories is that many had other things in mind, whether it was an application to be a firefighter, or they wanted to be a social worker, or they were planning to pay off their parents’ house and become a professor. Then, they all had those dreams tragically interrupted. My question to you is how many of them would've actually done it? You're catching them at a point where they're mid-dream. If you had somehow been able to rewind clock and run the counterfactual where those people didn't die, but you still had access to their hopes and dreams, how many of them would have actually done it?

Jennifer: Obviously, we can't know. I think there are some interesting data points though from post 9/11 and then again in Covid that can inform an answer. Following those events, we experienced a lot of people reconsidering their lives. The Great Resignation during Covid, I think, is one indicator that when our mortality is that salient – and again, not everyone has the luxury and the privilege to do so –a lot of people say, “I don't even know what I'm doing next, but I know that I don't want to keep doing what I'm doing now.” Part of what Christopher and I intended with this book is that we can't walk around waiting for tragedy to strike so that we can ask big questions about why I am doing what I’m doing.

We always should in some way be checking in with that. It’s not to say that everyone faced with tragedy or mortality chucks their work and does their fantasy. I mean, I think most of us carry around these fantasies or dream jobs. That's a healthy thing to keep active in the imagination, but that data indicates that a lot of us just get caught up in the day-to-day. There's always a next thing to do, whether it's life or work, so we don't always stop and just say, “Is this working for me? Is this something I want to continue?” The fact that we have these blips when tragedy strikes and when people are acutely aware that it could all end tomorrow, that's really telling. Maybe we're not living our fullest potential or our fullest ambition in the day-to-day. And I think that's probably because most of us aren't.

Annie: Don't have someone force it upon you. Don't rely on a near miss before you’re willing to switch.

The value of work in the age of AI

Annie: I read some research that if you look at people's level of happiness when they've earned money versus when you give them the same amount of money, they are much happier when they've earned it. I think this goes back to the kinds of things you’ve both been saying. It feels like we'd be better off as a society, at least in America, if we viewed work as having meaning in and of itself. It's a huge luxury to be able to make your money at your passion, but work is worthwhile on its own, when you compare what you’re getting out of work in terms of the money earned versus if I just gave you the money. I'd love to hear you talk about that. I think it's relevant to AI and what's happening right now.

Jennifer: I immediately thought about AI when you started that because Christopher and I often find ourselves saying that we as a society need to think about what we're doing when potentially a significant amount of the population's work as they know it today goes away.

Annie: It seems like AI is going to be better at the stuff that people would be passionate about. Ironically, we used to think that we'll have robots doing repetitive tasks, digging our ditches, and cleaning out our septic tanks. But right now, it seems like we're going to have robots writing and painting. Steve Jobs said you should do what you love, but AI is doing this stuff that we as humans tend to love.

Jennifer: I remain cautiously optimistic that the stuff that's truly human – the caring professions, the helping, the artistic and creative – will remain the domain of actual humans. It's obviously all very scary, but we find ourselves saying things like, we need to think about a universal basic income. How do we take earning money off the table if it's going to be taken off the table? How do we quell that base level fear? How do we think about a safety net, especially in our deeply individualistic society that doesn’t like to offer a lot of safety nets? To your point, if a universal basic income is seen as a gift and not earned, what will that do to my self-worth and sense of who I am? I do think this is something we're going to have to grapple with. Christopher, I'll let you weigh in.

Christopher: I want to weigh in with a question, Annie. You've had a really interesting career. I'm guessing that you worked hard as a poker player, and I can see that you work hard now as a book author. But in terms of social esteem for those two kinds of careers, do you feel like there’s higher esteem for being an author and a higher sense that you've earned your money rather than, as some people think, disparagingly, “lucking into it” at a poker table?

Annie: First of all, a little bit. It’s also partly because of luck that I’ve had a couple of bestsellers. You have to get lucky with who reads it. What’s interesting with poker is that when I started playing, it wasn't on television, so everybody thought that you just were gambling. I knew it wasn't, in the same sense that investing like your bond trader was more than gambling or relying on luck. There's skill and luck in that. But the external viewpoint was certainly that you were lucky.

Once poker ended up on television, people better understood that it was a game of skill, and there was enough prestige to what I did that it allowed me to then write the books that I wanted to. That is also very lucky. I've had a lot of lucky things happen in my life, as well as some unlucky things. I think I've made the most out of the good luck that I've been given. I loved playing poker until I felt trapped in it. And part of the reason that I felt trapped in it was because it was on television.

I had a brand and I could make passive income from your brand, and it just felt like, how am I ever going to switch away from this? I'm supporting my family. And that was hard because the last many years of my poker career, I didn't necessarily have the huge passion for it. I mean, I loved it, but I wanted to do other things. I overlapped doing management consulting with poker to build up that career enough so that I could exit when I did. I had to weave it together. But if you ask me what I'm the proudest of, it's definitely the writing, by a lot. This is going to sound very weird but it is because it feels more like my work. Nobody else wrote those books. They were my ideas and I was weaving together things that I had done, in my academic career, in poker, and in my consulting career, to communicate difficult-to-understand science to somebody who is not a scientist. I feel a lot more ownership over that than I do the poker. I'm not exactly sure why, but I do.

Christopher: I think that's really interesting, and maybe we can bring it back to the conversation about AI doing our dirty work for us, but also our creative work. I think part of the reason that it feels especially threatening that AI might write books and make art for us is that those are the things that make us uniquely human, those creative endeavors. I would like to believe that intelligence that's artificial will never be able to replicate some of the human creativity that we possess. I would find that human life had a lot less meaning if it were able to do that. I'm terrified of the day that I read what seems to be the next great novel, and then to find out that it was written by AI. That would devastate me.

Annie: Luckily, AI at the moment is telling you to eat rocks and smoke cigarettes when you're pregnant.

But I just had a revelation. Poker felt like my job, and writing books does not. Maybe that's why I'm obsessed with this vocation-versus-avocation issue. Poker felt like my job. It felt like work, and I was good at it. I certainly love the game, and I could talk to you for a long time about poker, but the books don't feel like work. They feel like an expression of my ideas in some different way. I think it's an interesting question.

Christopher Wong Michaelson: I was so curious to ask that of you, and I hope it didn't sound presumptuous.

Annie: No, not in any way. One of the reasons why I left academia was because it felt like a thing that I was supposed to do. I was on that path, and I did well in graduate school, and I spoke at conferences, and I did all that stuff. I just felt like I hadn't made the choice, that the choice was being made for me in a lot of ways. Then, I made the choice to play poker. I gave my kids a good life doing that, but when I felt trapped in that, I escaped, and now I'm good.

Final thoughts

Annie: What should I be asking you to tie it up? I have some thoughts, but I think it's probably more productive if you tell me what I should ask you.

Christopher: I don't know if this is what you should ask us, but picking up on what you were just saying about giving your children a good life, I think that a next logical question might be, would you want your children to give their children a good life playing poker? I see that you’re shaking your head. In many ways, that's a similar question that we were trying to get at in our 9/11 research. As you said, not everybody whose family said they were going to become a social worker was actually going to become a social worker. But that's what their parents, their spouses, their loved ones wished for them. I guess it's important to reflect on our ideals of what really matters in the end, and then to let that inform our choices about the place and priority of work in our lives today.

Annie: Going back to the societal thing, let's imagine that I do allow that to inform my choices. That's going to give me a lot of internal validity. But isn't there an external validity problem? My dad absolutely defined himself through his work. He just turned 86, and he’s still working and loving it. Those values definitely got passed on to me as a point of view about work. “What do you do? What you want to be when you grow up?” Every kid knows that means, “What's your job?”

If that's the case, then it seems like that's hard to disentangle. If you do say, my dream is to do something completely different, but I have this work that people think that I’m good at, or I'm getting paid a lot of money, or that's making me feel worthwhile, you have to overcome a lot of external pressure. If I go do this other thing, people are going to be, “You were a bond trader and now you want to quit to devote yourself to your band?” First, how do you grapple with that? Then, second, in a world where AI starts taking things over, you have to grapple with that.

Jennifer: That's one of many things that's so scary about AI. A lot of us don't even know what we would do if we weren't working so hard. What else would we do with our time? Workaholism can become its own trap, where you don't need to make decisions about what to do if you had infinite possibilities. And, of course, we never escape that social judgment, the feeling that, “Geez, you’re now going to do that?” Partly, we can know it's a societal construction and ultimately meaningless, but that doesn't mean we can escape it entirely. When I think about our kids collectively, they’re also going to be facing pressures like rising student debt and unaffordable housing prices.

I think part of these fixes are individual rationalizations, and partly our thinking as a society. Hopefully, we will think about how to preserve people's wellbeing and dignity even with these potentially scary changes or seemingly intractable problems. I talk a lot, with my students and with the book, about tradeoffs. No one has it all. It's hard not to pick one path without giving something up. It’s important to be aware of those trade-offs and being more intentional about what you're choosing at a given time and why.

Christopher Wong Michaelson: I'll try to conclude with something quippy. We all know that success isn't measured in money, and yet it is our only common currency to measure success. So, we give it outsized importance in our society when we all know that the most important things about wellbeing and generosity and creativity are unmeasurable.

Annie: That's a beautiful note to end on. This has been totally lovely. Thank you so much.