How Today’s Top Business Thinkers View Leadership - Dorie Clark

In today’s episode, I chat with Dorie Clark, the Wall Street Journal bestselling author of The Long Game, Entrepreneurial You, Reinventing You, and the award-winning Stand Out, named the #1 Leadership Book of the Year by Inc. magazine.


She’s one of the Top 50 business thinkers in the world according to Thinkers50, was honored as the #1 Communication Coach in the world by the Marshall Goldsmith Leading Global Coaches Awards, and is one of the Top 5 Communication Professionals in the World, as graded by Global Gurus.

Dorie has always left an impression. Born in Pinehurst, North Carolina, she left high school at age 14 to attend the Program for the Exceptionally Gifted at Mary Baldwin College (now University) in Staunton, Virginia. Going on to teach at a number of prestigious academic institutions, herself - Duke University, Columbia Business School, HEC Paris - Dorie has unique insights on the next generation of business leaders.  

Her journey, experiences, and those of her students were the basis of a really fun discussion that covered education, leadership and the timeless lessons that inform success. This was a bucket-list conversation and, one I hope you enjoy as much as I did recording it.

Dorie Clark

Dorie Clark helps individuals and companies get their best ideas heard in a crowded, noisy world. She has been named one of the Top 50 business thinkers in the world by Thinkers50.

She was honored as the #1 Communication Coach in the world by the Marshall Goldsmith Leading Global Coaches Awards, and one of the Top 5 Communication Professionals in the World by Global Gurus.

She is a keynote speaker and teaches executive education for Columbia Business School. She is the Wall Street Journal bestselling author of The Long Game, Entrepreneurial You, Reinventing You, and Stand Out, which was named the #1 Leadership Book of the Year by Inc. magazine.

Clark has been described by the New York Times as an “expert at self-reinvention and helping others make changes in their lives.”

She is a frequent contributor to the Harvard Business Review, and you can download her free Long Game Strategic Thinking Self-Assessment

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Matt Burns

Matt Burns is an award-winning executive, social entrepreneur and speaker. He believes in the power of community, simplicity & technology.

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Transcript

Dorie Clark: It. I, uh, like to think of it like an iceberg because there's the part of the iceberg which is above the waterline, and so everybody can see that. And it's like, oh, you know why I'm not doing it? It's because I have too many meetings. It's because I have too many emails. That's why. And it's not that that's not true. I mean, it is true. We all have too many emails and too many meetings. That's fine, that's legitimate. But what is also true, what is additionally true, is the whole entity of the iceberg underneath the surface, which is that oftentimes we are systematically making choices that are in direct contravention to what we say that we want.

Matt Burns: Constraints drive innovation. Hey, everyone, it's Matt, here for another episode of Thinking Inside the Box, a show where we discuss the innovative ways organizations and their leaders overcome complex issues at work. If you're interested in checking out our other content, you can find us at our shiny new website insidetheboxpodcast.com and on all of your favorite podcast platforms by searching Thinking Inside the Box. And if you enjoy the work we're doing here, consider leaving us a five star rating, a comment and subscribing. It ensures you get updated whenever we release new content and really helps amplify our message. In today's episode, I chat with Dory Clark, the Wall Street Journal bestselling author of the long game entrepreneurial you reinventing you. And the award winning standout named the number one leadership book of the year by Ink magazine. She's one of the top 50 business thinkers in the world. According to Thinkers, 50 was honored as the number one communication coach in the world by Marshall Goldsmith, leading Global Coaches Awards, and is one of the top five communication professionals in the world as graded by global gurus, dory has always left an impression. Born in Pinehurst, North Carolina, she left high school at age 14 to attend a program for the exceptionally gifted at Mary Baldwin College, Now University in Stoughton, Virginia, going on to teach at a number of prestigious academic institutions herself. From Duke University to Columbia Business School and HEC Paris, dory has a unique insight on the next generation of business leaders. And so her unique perspective experiences and now those of her students were the basis of a really cool conversation that covered everything from education to leadership and the timeless lessons that inform success. Dory's connected to a number of people that I really respect, and what she's done with her gifts, frankly, is remarkable, and it's a pleasure to bring you.

Dorie Clark: Dory Clark.

Matt Burns: Dory Clark I don't want to put too much pressure on you, but I have had this date circled on my calendar now for at least a few weeks. Thank you for finding time amongst your busy travel schedule overseas, doing lots of speaking, and thanks for joining me today.

Dorie Clark: Thank you, Matt. I've been looking forward to it as well. So this is going to be great.

Matt Burns: Yeah, we have a lot of friends in common, and it's rare that I come across somebody that all of my friends consistently say, dory's amazing. You have to have a chat with her. She's going to be one of your best podcast guests. So, again, I'm not trying to set the bar too high here, and I have expectations for a good conversation. So I think it's going to be a really interesting chat. I also think it's particularly cool, um, about your background and just the path that you got to get to today before we get there. I don't want to get too far ahead of myself. For those who don't know, Dory Clark, may a bit about your background, your experiences and what's led you to today.

Dorie Clark: Oh, my goodness. Well, I will be brief, but, uh, the quick version of what I do now, what I do today, which is, um, I write and speak. My most recent book is The Long Game how to Be a Long Term Thinker in the Short Term World. So I do some executive education teaching at Columbia and talk to a lot of folks about professional reinvention and being, uh, a long term thinker. But the way that I got there, I originally thought I was going to, uh, be an academic. I got a master's degree in theology. I then wanted to go on and become an English literature professor. But I got turned down by all the doctoral programs I applied to. So I needed a plan B. I became a journalist and did that for a while, after which I got laid off. And so I needed another plan. So I went to work on first the governor's race as a press secretary, then on a presidential campaign, uh, as a communications director for the first in the nation primary in New Hampshire. Uh, and it was an exciting run, but we lost, so I, uh, had to come up with another plan eventually. I ran a small nonprofit and that is where I got the germ of the idea to start working for myself. And I became a, uh, consultant and an executive coach and have had my business since 2006.

Matt Burns: Well, let me be the first to say that plan E is working out for you very well.

Dorie Clark: I appreciate it. Thank you so much. Yeah, it took a while to get there, but eventually you find something that clicks. Right.

Matt Burns: But I think it makes sense in the context of your latest book because in this world that we're in now, things are so disruptive and the days of you being able to settle into a 20 or 30 year career trajectory, they're just gone now. You have to consistently reinvent yourself and you have to consistently find the intersection of the value that you can bring to a broader society, but also what you're passionate about. And I think as you talk through your story, I can hear the passion in each of those chapters of your life where you've clearly pursued opportunities that are interesting to you, that you're passionate in. I think that's admirable in a world where a lot of people play it safe because they're afraid of taking a chance. They're afraid of, um, betting on themselves. And I think it's very clear to me that you've obviously done a lot of that. I'm just curious, where does that come from? I mean, as somebody who's reinvented themselves multiple times, where does that drive to do something different, pursue a new path come from?

Dorie Clark: Well, I think that one of the things that I've picked up over time, and in fact, my first book, Reinventing You, sort of emerged from this, uh, because I was forced to reinvent myself repeatedly. Uh, and I feel like I was kind of dragging my feet and kicking and screaming a little bit. I wasn't that enthusiastic about it at the time. I mean, now they've all been good experiences, but I think probably like a lot of people, I had a thing I wanted to do, and I just wanted to do that thing. And so being, uh, prevented was extremely frustrating. So I was not really enthusiastically going into my reinvention. Sometimes people are, but a lot of the time, it's something that you have to do and you have to kind of make peace with. So I wanted to write a book, hopefully to make it easier for people than it was for me. But, uh, yeah, I think a lot of my doing these things really just emerged from, like, all right, okay, guess that's not going to work. What else do we got? And, uh, I needed to support myself. I came from a position where, thankfully, uh, I knew I was not going to be sleeping under a bridge. Like, worst case scenario, I would be sleeping in my childhood bedroom. But that seemed bad enough, and I really didn't want to do that. Uh, I was very passionate about needing to find a new revenue source for myself, and so it prompted me to, uh, put some wheels on, uh, when it came to trying to find the next endeavor.

Matt Burns: Well, it fits in well with this podcast. Our tagline is Constraints drive innovation. And I firmly believe that, to your point, when you're forced to make a decision, you'll make a decision. And a lot of times people are reluctant to do that. I want to spend more time talking about this subject, but I want to set some context around it. And I want to go back to 14 year old Dory Clark, if that's okay. Because when I was reading your bio and doing some research for this interview, one thing that stood out to me was you were born in Pinehurst, North Carolina, and you left high school at age 14 to join a program for the exceptionally gifted. If that wasn't enough pressure for you, at Mary Baldwin College, now University in Stanton, Virginia. I'm just curious, what was life like for 14 year old Dory Clark?

Dorie Clark: Well, I was super pumped to be able to go to college. I, uh, was feeling very stymied, uh, where, you know, I came from a okay place. I mean, Pinehurst is just small and boring. That's sort of the nature of it. My mother will firmly assert, it's much nicer now. It's much bigger now. And, uh, that's true. That's true. You can actually get things like Indian food now, um, which was not at all a thing or not at all possible. Uh, it was sort of a classic pizza and Chinese type of place. Little small, Americana kind of place. But, yeah, I really wanted to get out. I mean, partly it was because I was just frustrated and didn't have enough friends and wanted to get on with living my life and doing things that were exciting. Um, I sort of fancied myself an intellectual, and I didn't have enough intellectual stimulation there. Uh, partly it was because I was realizing I was gay and I was not going to get a lot of that where I was in that small town. So I thought that even going to a small college, which Mary Baldwin is very small, uh, I thought, okay, it's going to be a better scenario for me. So, uh, I was excited about that. Where did you grow up, Matt?

Matt Burns: Victoria. So we have some parallels. I mean, a small town, not as small as Pinehurst, but a very safe, comfortable place. They call Victoria the land of the newlywed and nearly dead. So that gives you a sense of the kind of the community in there. It's the place that in February, the tulips are coming up. It's beautiful. Um, it's basically a giant greenhouse.

Dorie Clark: Uh, I have been to Victoria.

Matt Burns: Okay. So, you know, it's a wonderful place. And like you, I longed for something bigger and better. And since my mid 20s, I've bounced all around the world, traveling for work and living different places in search of more excitement and more diversity and different ways of thinking, because Victoria can be sometimes a bit insular, bit conservative. Um, I'm curious when it comes to Mary Baldwin and your experience there. You're 14. Are you the only 14 year old at this college? Are all the individuals in this school gifted? What does that look like in terms of the composition of the class, the people that you're going to school with?

Dorie Clark: I, uh, was not the only person, uh, that was in that situation. It was a program within sort of a vertical within Mary Baldwin. So, um, there were about, when I was there, about 50 people who were underage, I guess you could say, who were college students in this program, um, spread throughout the four years. So it was not enormous at all. But there was enough of a community that you didn't feel literally like the only person your age. Um, but it was great. I mean, it was the first time I had at summer camp before met some kind of one off people that I really loved and had become cool friends. But it was the first time that I was in a community where there was like a collection of people, where it's like, oh, there's literally a number. A number that is more than one of really cool, interesting people. Um, because you have to imagine, right, it's a certain type of person that is really keen to go to college early. Um, so they were very interesting people. Welcome.

Matt Burns: Hey everyone, it's Matt here. I hope you're enjoying today's conversation. And before we continue, I want to update you on my latest creative project this Week at Work. Every Friday at 07:00 a.m Pacific Standard Time. That's 10:00 a.m. Eastern and 03:00. P.m GMT. My good friend Chris Rainey of HR Leaders and I discuss the latest trending topics on the minds of executives globally. From organizational culture to technology and the future of work. We cover it all and we invite some of our favorite colleagues to join us, from Dave Ulrich to Whitney Johnson, um, and executives from iconic brands such as NASA, Krispy Kreme and WebMD. What can I say? We like to keep things interesting. And if you've been following us for a while, you'll no doubt recognize the fun partnership chris and I have developed over years podcasting together. We're not afraid to be real, share our own challenges and ask the tough questions. Joining? Well, that part's easy. Follow me on LinkedIn, click the bell icon on the top right of my profile and you'll get notified when we go live. And now back to our discussion. My high school experience similar insofar as I also was in an academically enriched program in Victoria where they pulled students from all over the city and I was really lucky. So at twelve I had to apply and go through a battery of tests, psychological tests and IQ tests, and various leadership tests. And they basically gave you this assessment and said, okay, you can be one of 25 students to go through a five year high school experience with a cohort. So we were all together for five years. So it's similar in terms of your experience.

Dorie Clark: It's m super interesting too, that they gave you like psychological tests and stuff. That's pretty deep, right? They're trying to weed out the psychopaths.

Matt Burns: And I think low key kind of categorizing us. So the intention of the program was ah, to create global citizens. And the beauty of it was that the diversity of people in the room, despite the fact that Victoria itself wasn't terribly diverse, was pretty phenomenal. I mean, we had the school I went to was known for two things rugby and jazz. If there couldn't be two more different things so people would come to the school for the academic experience because they also wanted to spend time on the rugby team or in the jazz program. So my program is full of people that were incredible musicians and then people that went on to do incredible things. Scientists, mathematicians, lawyers, doctors, et cetera. And you mentioned these tests at the time I'm twelve. I go through these tests and I remember somebody calling me afterwards being like, okay, we want to give you the results of your test. And at twelve I'm asking myself, am I in or am I not in? I'm not more sophisticated than that. Am I going to go to this program with all these other smart, cool kids or am I going to the program, the school down the road where I'm not that excited about it, I want something different. And I was given a really incredible dose of executive coaching at age twelve where I was told basically this, and I didn't fully appreciate this until much later in life, but at the time I was told, matt, you're not the smartest person we're going to admit this year. In fact, you're not the smartest person we've admitted over any of the last years. However, you're going to be amongst really smart people. But what you bring that's unique to you and why we want to put you into this program is you are a conduit. You are a catalyst. You have the ability to synthesize complex information, to translate it amongst groups of people. You're the glue that holds disparate people together.

Dorie Clark: In 20 years, you will start a thing called a podcast.

Matt Burns: Right? You will pursue a career path called Human Resources. Um, and at the time, I'm like, again, am I in? Am I not in? I'm in.

Dorie Clark: Cool.

Matt Burns: I'll go to school on Monday. I'm going to this program at the time though, again, a program populated by people who were just gifted and brilliant and in their own ways trying to figure out how to be social with other kids. And we were the group of kids that in amongst a program of 800 students. We were 25 kids in this little bubble that hung out together all the time at recess and at lunch and we'd go each other's houses and sit in the kitchen and talk shop and watch Monty Python and just nerd out on weird things because we were the weird kids in this school. Um, and ultimately that experience was really formative insofar as exposing me to different types of people, really smart people, and also people that would challenge me to be the best version of myself. And I'm curious for you, as you look back at your experience at Mary Baldwin, was that similar? Did you find your tribe, as it were, people that would push you and challenge you and lead you to be kind of, if you will, the fullest realization of yourself? What was that experience like?

Dorie Clark: Yeah, it was really great for me in the sense that, um, because I had never had this kind of collection of friends before, it was, uh, a legitimate kind of group that all hung out together that was really exciting. And, I mean, when you're 14, that's kind of like all you want, anyway, is to have a cool group of friends. So to be able to have that was really fantastic. Um, that being said, I got sort of the highs and the lows of it because my friend group was initially centered around this woman, who, in very short order, after arriving on campus, became my first girlfriend. And so it was kind of like her friends. Anyway, then we broke up, and then all the friends went with her. And so then it was, like, super lonely and depressing again. Uh, so you got both sides of it, but, uh, it was, uh, very exciting while it lasted.

Matt Burns: The other thing that stood out for me as you go through the path to get to today is your university experience. After Mary Baldwin, you went on to do a BA in Philosophy, as you mentioned, at Smith College, followed by a Master's of Theology at Harvard Divinity School. At the same time, you were serving as a board member for the Gay and Lesbian Victory Fund, an organization that works to elect openly gay candidates to political office.

Dorie Clark: Wow. You went into the archives, man I.

Matt Burns: Went into the archives because, again, I come from a very strong Catholic background as well. So I'm like, okay, another synergy there as, uh, somebody who was also raised in the Catholic faith. I mean, my great uncle did his master's of Theology at the Vatican. So catholic. Catholic? Two priests in the family, three nuns in the family. We were Catholic. As somebody also raised in that faith, I'm curious how those experiences of, again, in divinity, in theology, Catholic faith, Harvard, how that juxtaposed with Gay and Lesbian Victory Fund, you being openly gay yourself, how you reconciled those two?

Dorie Clark: Ah, uh, well, thank you. Just to clarify, i, um, was actually not raised Catholic. So, uh, the, um, Harvard Divinity School is, um I mean, people of all faiths go to it. They've got Jewish people and Buddhists and Catholics and Protestants. But, um, interestingly, I find this part really fascinating. Essentially, Harvard itself was founded to train clergy, as you might imagine, in the 16 hundreds. Kind of all of it was for that purpose. But the Puritans I didn't know this until I studied it. You kind of scratch your head now. It's? Hmm? What happened to the puritans? Like, there's not really Puritans around anymore. Um, but the super fascinating thing is that actually where Puritans went, quote unquote, is that that lineage turned into modern day Unitarian Universalists and United Church of Christ, which are the two most liberal Protestant denominations, which is just kind of mind blowing because we think of Puritans as being oh, I don't know, Puritanical, and they end up being super liberal. Um, so that's just kind of a funny, modern irony. But yeah. So I grew up, actually in a family that was not incredibly religious in general, um, although I did go to an Episcopal elementary school. But mostly, I think, that was just because they thought it was a good school. So I didn't have a kind of heavy overhang with that. Actually, my mother, she was raised kind of Catholic and had to go to Catholic Sunday school and stuff like that. And so she has, like, the you kind of go in one or the other direction, so now she's, like, allergic to it, basically. So when I told her that I wanted to go to divinity school, she's like, Why would you do that? She was just really not having it. She wanted me to go to law school. Uh, but I thought it was very interesting. And so, for me, it was not so much to sort of fulfill, uh, a personal longing or quest or whatever, per se. But I was extremely curious from a sociological perspective because having not grown up in an especially religious background, I felt like there were major gaps, frankly, in my cultural literacy, and I wanted to fill them. I wanted to sort of understand a little bit more because, I mean, honestly, half of American culture is sort of biblical references, whether it's something super overt, like these homophobic protesters being like, Sodom and Gomorrah, blah, blah, blah. Or on the other hand, you just have these expressions that, Blah, blah, blah, we're going to separate the wheat from the chaff. And it's like, all right, that's Bible just down the alley right there. So I wanted to get the picture. And so I thought that divinity school would be extremely helpful for me in, uh, filling in those gaps, kind of making me a better informed person, making me a better informed citizen, a better informed activist. Because I did have sort of activist inclinations in terms of, um, things like joining the board of the Victory Fund, et cetera.

Matt Burns: Yeah, I can see that. I can see that in your background and obviously a strong advocate for education. So as we again fast forward another chapter, you've had the opportunity to teach at a number of prestigious academic institutions. So you mentioned Duke, Columbia, HEC, Paris. I'm just curious, from your perspective, as somebody who had their own unique experience through education as a young adult and then now moving into an adult life, what similarities do you see as far as the next generation of business leaders, ah, as it relates to maybe perhaps our generation? Um, and how are they different than what experiences you talk about in terms of your own?

Dorie Clark: You're asking a very good question, Matt. It's a little bit loaded. I'll say, uh, unintentionally because my girlfriend teaches at Harvard. She's, um, a professor at the Graduate School of Education, and her area of specialty is young adult development. And so she has a lot of thoughts about this and, in fact, wrote a book about it called the end of Adolescence. And I, uh, have thoughts and impressions and things like this, but she has actually studied it in depth and something that I find really fascinating. So the premise of her book is that she found this archival this forgotten archival collection of interviews from students from Harvard, from the class of 1975, and they were just, like, basically in an attic or whatever for 50 years. Everybody forgot this research had even been done. And so they went back and they listened to them, they transcribed them, and then they found those people, and so they followed up and did interviews with them 50 years later to sort of track, like, well, what happened? Uh, we got this sort of, like, cliffhanger here when they're 22, what did their lives turn out to be, and what tracked and what didn't? Uh, it's really fascinating to see what kind of came through. But one of the biggest findings is that the things they talked about, the things they worried about, the things they experienced are basically not in any way dissimilar from students. Mean, you know, substitute in the know, Instagram for reading Rolling Stone magazine or whatever it is. But developmentally, it really is almost exactly the same thing. And so her thesis, which I think makes a lot of sense, is that in our lived experience, we tend to sometimes exaggerate the differences. I mean, ten years ago, it was all like, oh, those millennials, and now it's, oh, those gen z. It's like, oh, well, they're lazy. Well, they're honestly, it's like, who isn't lazy when they're, like, a year out of college and they don't know what it's like to be in the workforce? And besides that, because they're young, their circadian rhythms, like, they want to be sleeping till 11:00. You know what? When I was that age, I wanted to sleep until 11:00 too. It's not that I'm more productive now, it's that I'm basically middle aged. And so now my circadian rhythms are like, oh, it's like 06:58 a.m. Ding. I'm not more responsible, I just wake up earlier, because that's what happens when you're in your 40s. So I think that a lot of it is like, you know what? It'll come, it'll come, it'll go. What else? I don't know. What do you think, man?

Matt Burns: I think similarly, I think, to your point, we do exaggerate generational differences, and we do look at our own generations with a bit of a romantic lens, and there's a tendency to do the US versus them binary conversation, and I think circumstances have changed. Um, and I think to your point, there's an evolutionary, um from a scientific perspective, I agree with you. I mean, circadian rhythms have not evolved materially over 50 years in the human species. The conditions in which we operate obviously have materially shifted. And I'm always curious about the role of, for example, technology and globalization and how that could affect the same conditions. But from a scientific perspective, I think we are who we are, and we do see incremental evolution of our species. But 13 year old children in 1964 are 13 year old children in 2024. Save for the conditions in which they operate and the broader societal context and notion, I think we expect more from 13 year olds in 2024 than perhaps we did in 1964. There was maybe a bit more of a I use the word romantic, but maybe a bit more of a I don't want to say immature. That's probably not a fair term, but maybe a bit more of an idealized version of what being a child was back then, where I think people have to have to grow up and participate in society. Much earlier on. With the advent of social media, where we're now connected to adults in a way that we weren't 50 years ago when my interaction with adults was my family, my teachers, my sports coaches. But now, if I'm 13, I can plug into Instagram or TikTok and I can talk to adults all day long. So it absolutely has a fundamental effect on kids. And, um, at the same time, I think they bring with them a level of sophistication that we need in broader societies. We try and tackle some bigger problems. Um, one thing I know you're passionate about is things like mental health and about practicing the right kind of habits, so that if you put the right kind of fuel in the engine, as it were, you get good results coming out of it. Um, and I love that mantra because I think it deeply resonates with me for a number of reasons. Um, you talked about things like doing a daily jog before you start work, or cutting out your inbox every Friday afternoon to stay organized. A personal favorite of mine. M, I'm just curious for you, as we think about productivity or about being the highest realized version of yourself, where do you think a lot of us go?

Dorie Clark: Astray yeah, I think this is an important question. I mean, I'm always interested in the sort of gap between our stated intentions and our actual behavior. Um, sometimes it's about productivity and habits. Sometimes, frankly, this was in many ways the topic of my most recent book, The Long Game, because everybody's like, yeah, strategic thinking. That's it. That's what we want to do. And then meanwhile, study after study and just our lived experience shows that most people are like, yeah, but I don't have time for strategic thinking, which I just said was the most important thing to do. So there are sometimes some ironies that we have to surface and figure out, like, okay, what's really going on here? What's getting in the way? And so what I've come to understand, both. About strategic thinking and also about cultivating the right habits and things like that. I like to think of it like an iceberg, because there's the part of the iceberg which is above the waterline, and so everybody can see that. And it's like, oh, you know why I'm not doing it? It's because I have too many meetings. It's because I have too many emails, that's why. And it's not that that's not true. I mean, it is true. We all have too many emails and too many meetings. That's fine, that's legitimate. But what is also true, what is additionally true, is the whole entity of the iceberg underneath the surface, which is that oftentimes we are systematically making choices that are in direct contravention to what we say that we want. Some really interesting research comes out of Columbia University, and, um, Sylvia Boletza and her colleagues have shown that busyness, basically in contemporary American society, or North American, let's say, um, has basically become a marker of status. It's a societally approved marker of so, you know, you hear so often, people are like, hey, Matt, how's it going? Oh, I'm so busy. And that's basically this okay, way to be, uh, know, I am so popular, I am so in demand. And people do this all the like, when push comes to shove, we keep making choices that put ourselves in that position because it feels emotionally satisfying. So there's a lot of central ironies that we need to unpack, which are kind of they're a salve in the moment, but they're actually preventing us from the things we claim we want to do.

Matt Burns: Like a degree of social masochism of sorts, where we're just like trying to fit in by doing the most uncomfortable thing. And you go back to 14 year old Dory Clark or 14 year old Matt Burns, and we were guilty of doing the same things, of just trying to fit in and maybe pushing ourselves outside of our comfort zone. But your point is well taken. I think as adults, we absolutely do that now. And there is a badge of going through the grind and going through the hustle. And if somebody's like, well, you know what? I'm taking a sabbatical. It's almost looked as like, uh, are you giving up? Or whereas it probably is, I'm prioritizing mental health or relationships or other parts of, uh, my life that I also find valuable, in addition to the amount of money I make and the jobs that I hold and the schools that I went to, and all the things that are important. Um, let's go back to 2017, because this was my first interaction with you. Now, you weren't there for this, but I feel like you were in sorts because I picked up your book in 2017. I was on a plane doing one of my many cross continent flights and, uh, tired of about 20 years of my own grind and hustle. And I'm so busy. I was every turn of my life at this point in 2017, choosing my professional opportunities ahead of my health, mental health, relationships, all those various things, and I was ready for a different message. I picked up your book based on a recommendation and said, okay, who's this dory clark character, and what does she have to say? And I picked up entrepreneurial you, my first interaction with the great work that you put together. I'm just curious, as somebody who's read your book multiple times, what was the inspiration for that particular, um, chapter of your life, and how did your previous works reinventing you and stand out, influence it?

Dorie Clark: Yeah, well, thank you, matt. I appreciate you, uh, diving into the OOH there. Uh, so, entrepreneurial you, I like to think of my first three books as kind of a trilogy in some ways. And so the subtitle for entrepreneurial you, it's monetize your expertise, create multiple income streams, and thrive. And essentially, like all good authors, I was writing a book first and foremost for myself. You're sort of embarking upon this year long or year and a half long research project. And so I was like, what do I want to figure out? And so stand out. Its predecessor was basically trying to answer the question, how do you become a recognized expert in your field? Because that's the problem I was trying to crack at that time. So I interviewed a bunch of people who, in my estimation, had already done it very successfully, and I was like, great, let me figure out what they did, and then I can copy them. That sounds like a great idea. And then I will share these insights with other people so it can be useful. But really, it was like a project for me. And so then entrepreneurial you was kind of the next culmination, which is, okay. Once you achieve some degree of renown or recognition, that's amazing. That's great. It sometimes leads directly to revenue, but not always. And you actually have to sometimes in the modern economy, be a little clever and a little crafty, because recognition and social status is fantastic. But there oftentimes used to be a direct line between that and money. Now it's a little bit more opaque, and so it can definitely get you money, but it's not always clear how. And so I wrote entrepreneurial you, because basically, I had a lot of successful friends that were making a lot of money, and I'm like, this is excellent. I really should figure out what they're doing. And so this was an opportunity for me to interview them, ask them extremely nosy questions about their business model, learn from it. I mean, sort of the goal, first and foremost, was like, all right, great. I'm going to apply this in my business. I'm going to be the guinea pig here. And, uh, then I wrote a book about it so that I could hopefully help other people figure it out as well.

Matt Burns: It's amazing what having a book or a podcast can do in terms of removing the veil of asking nosy questions. It's just like, okay, I'm writing a book, so I'm going to ask you some deeply personal questions that I really want to ask you anyway over coffee. But because I'm writing a book, it's now acceptable. I do the same thing with the podcast as I'm sure you do with yours. As I talked about whether it's the Harvard Business Review, whether it's Fast Company, Business Insider, and then also you're the host of Better, Newsweek's weekly video interview program. You've featured some of my favorite people, seth Godin fellow, uh, Canadian Chester Elton. From, uh, one interviewer to another, as you talk about learning from those conversations, I'm just curious, is there a guest insight that's lingered with you over the years?

Dorie Clark: Oh, that's great. Yeah. In doing the show, one of the kind of interesting elements about it, we recently reformatted the show so that it's recorded. It was sort of like a podcast, but for two and a half years, I ran it as a live stream. And so all the guests were super interesting. It was great, and I learned a lot from them. But I would say rather than a particular guest insight standing out, for me, the biggest thing that I learned was live streaming is kind of its own animal. Right. It's different than podcasting because it's not so much necessarily about interacting with a guest and having a rapport with them, although it certainly is. But on top of it, you have to have this ambient awareness of the audience whom you cannot see. Um, but you're monitoring this stream of comments and questions and trying to draw them out and engage them so that it can be this sort of like, lively experience where you're making people feel included in real time. And so I think probably the biggest thing that I learned from it was just the act and the art of essentially being an MC. That's kind of how I thought about myself. It's partly about being an interviewer, but even more than that, you're kind of like running a show and how do you keep the show moving and how do you keep the guests engaged in the show? And I feel like by the end, I got pretty good at it. And so the act of learning how to live stream specifically was kind of the biggest change or the biggest thing that I learned from that.

Matt Burns: Yeah, I couldn't agree with you more as somebody who does both. There's definitely more of a performative element on a live stream because you get that instant feedback from the audience. They're sending comments in the comment section. You get to see your view count, go up or go down. There's absolutely this feedback loop that is real time. Whereas the podcast will record this conversation. I'm going to give it off to much smarter people than myself who are going to edit this and make this amazing, and they're going to put this out several weeks from now. But by that point, I'll have moved on to another conversation with another incredible person. And to suspend that, um, empathy while we're having this conversation, always being mindful of the audience, I think is an underreported or underrepresented skill in podcasting, which I think is a really key point that you've made. And I just want to thank you for bringing that to the surface. I think that's something that I haven't thought about, but I definitely know that I'll show up with a different persona here than if I'm on a live stream on Fridays on LinkedIn with my colleague Chris Rainey. We're having a conversation about with an HR leader. It's real time. It's that level of flying without a net, as it were. Um, that adds a bit more risk, but it also changes the social dynamic ever so slightly and does give the audience something a little bit different. We've gone through a lot of your background. I went deep into the archives, as you mentioned. I really wanted to understand the journey to get to this point. So thank you for indulging all those various questions. Let's talk a bit about the book. So your most recent release, The Long Game, is absolutely a blueprint for individuals to think about their big picture plans, as you pointed out in an increasingly short term now world. Why, in your opinion, should we strive for long term thinking? And how do we create space for it in a world that seemingly doesn't reinforce that way of thinking?

Dorie Clark: So the reason I'm a fan of long term thinking, and obviously people don't have to do it if they don't want to, but ultimately, the way that I think about it is it is the difference between being a jellyfish in the ocean and being like a motorboat in the ocean. Because if you don't actually have any long term goals, if it just really doesn't make much difference to you, uh, whatever, things will happen. It's cool to be a jellyfish, right? Like kind of why expend effort. If anything's cool, you could just float on the waves. Things will happen, you'll end up somewhere. Okay, great. Um, not a problem if you're cool with that. But the issue is that, frankly, most of us do have goals. We do have ambitions, we do have things. We'd like our career to get to a certain place. We'd like our companies to be able to succeed and get to a certain place, whatever it is. And so because of that, it is a very risky bet to be the jellyfish that is just responding to external stimuli because you have no control. You don't know which way the tide is going. It just happens. Whereas if you were the motorboat, meaning if you have a kind of engine of volition and choice. You're consciously saying, no, I'm going to steer it over here. Now, it's not a guarantee that you're going to get to your destination because things can happen, major storms or what have you, but it is a heck of a lot more likely that you are going to end up in your destination or at least reasonably close to it. And so, um, that's the reason. Long term thinking is the vehicle through which you are able to get the best shot that you possibly can at achieving the outcomes that you say that you want.

Matt Burns: I couldn't agree with you more, and I think you would agree that it's not a binary question. Rather, you want to find a balance between each of them. You want to have that long term vision and intention, but be flexible to things that come up along the way. That may take you off course. But to your point, just floating through life is unlikely to get you to the place where you could have got to if you are achievement oriented. I have people in my community that are not achievement oriented. In that case, a jellyfish analogy is a wonderful analogy. I have lots of friends who are jellyfishes and they're wonderful people. And I have lots of friends who are motorboats. I think I ultimately aspire to be a jellyfish attached to a motorboat. That's what I'm going for in terms of my life. So thank you for providing that, uh, vision. Uh, Dory, this has been a wonderful conversation. Thank you so much for joining me today. For folks who want to get a hold of you, learn more about you, the book, where's the best place to find you?

Dorie Clark: Matt, I appreciate it's. Been great talking with you. Um, so thank you. Yeah, the book. It's, uh, the long game. And, uh, you can certainly pick it up at Amazon or Indigo or any of those lovely places, Barnes and Noble. Um, but additionally, for folks who are interested, I have a free Long Game strategic thinking, self assessment, uh, with a series of questions to help you reflect more and step up and be just a little bit more of a long term thinker. And for anyone who'd like to get it for free, it's at Doryclark.com slash the Long Game.

Matt Burns: Very cool. We will link all of those details in the podcast show notes so folks can get to that directly. Dory, thank you so much for your time today. Looking forward to keeping in touch.

Dorie Clark: Thanks, matt.

Matt Burns: Bento HR is a digital transformation consultancy working at the intersection of strategy, technology and people operations. We partner with organizations, private equity and venture capital firms to accelerate value creation and identify the organization's highest leverage initiatives. And this can take place in many forms, from strategic planning and alignment to technology procurement, implementation and integration, along with organizational design, process reengineering, and change management. With our proven track record of working with complex high growth organizations. We provide a Ah lens that goes beyond the balance sheet, increasing enterprise readiness, resilience and value. For more information, check us out@bentohr.com.