In our short-term world, Dorie Clark is proof positive that there’s incredible power in long-term strategy—and here she riffs on her new book, “The Long Game.”
Transcript:
Debbie Millman:
You may have your dream job, but does your job let you dream? Is keeping up with its day-to-day demands distracting you from actually doing what you love? This is the problem addressed in Dorie Clark’s new book, The Long Game: How to Be a Long-Term Thinker in a Short-Term World. Dorie Clark is an executive education professor at Duke University School of Business. The New York Times described her as, “An expert at self-reinvention and helping others make changes in their lives.” She started as a journalist, so she’s no stranger herself to self-reinvention. Dorie Clark, welcome to Design Matters.
Dorie Clark:
Debbie, I’m so glad to be here. Thank you.
Debbie Millman:
Thank you, Dorie. Dorie, is it true that during the pandemic you started taking weekly ping-pong lessons?
Dorie Clark:
I most definitely did. Yes. I was taking these incredibly long four-hour walks around Manhattan because all of my friends had fled the city and all the gyms were closed. And I was just wandering around in a new neighborhood one day and I came across this oasis, and it was a two-story ping-pong studio and they had signs that they were open 24 hours and they had lessons. And I thought, “OK, it’s God speaking to me, I must do this.”
Debbie Millman:
Did you get any good?
Dorie Clark:
I’m actually decent right now. I’m not ready to be a world champion. They actually do employ literal Olympic champions as coaches. But I would say I have transcended basement player level status.
Debbie Millman:
Nice. I’d like to see that. I understand that you grew up in a self-described “little golf resort” called Pinehurst, NC, population 3,000. So did you grow up playing golf? Are you a sort of natural athlete that only comes out when playing?
Dorie Clark:
No, I really hated my hometown. I thought it was kind of boring and stultifying. And so my adolescent rebellion was refusing to play golf.
Debbie Millman:
Is it true that when you were a little girl, you wanted to be a spy?
Dorie Clark:
Yeah. You’ve been digging. It’s all true. I was really into James Bond when I was growing up, which was saying something, because that was the Roger Moore years, but I just thought it was so sophisticated and so wonderful. So I did want to be a spy. And in fact, my adult catharsis version of that is writing a lesbian spy musical. So that’s one of my COVID projects, as well as the ping-pong.
Debbie Millman:
So [inaudible] sort of meets Daniel Craig’s James Bond.
Dorie Clark:
Something like that. Absolutely.
Debbie Millman:
You mentioned as you were growing up, you felt incredibly frustrated. I know that you felt somewhat curtailed by the opportunities around you, [and] and at some point you wanted to be a lawyer. Then you considered becoming a gay activist, but I also understand you were in a band, and I believe it was called The Unlimited Powers. So let’s talk about your early days as a rock and roller. What instrument did you play? Where did you play? Give us all the details.
Dorie Clark:
Yes. The Unlimited Powers was a very short-lived band. The title was inspired by … I guess, appropriately, by Anthony Robbins’ book Unlimited Power. So I was a little bit of a self-development geek even as a teenager. And I played the guitar kind of badly. I managed to take a couple of years of lessons as a teenager, mostly so that I could sound decently impressive strumming the Indigo Girls by a proverbial fire. We cut our singles by singing into cassette recorders, and that was about it.
Debbie Millman:
Oh, I’m going to spare our listeners from doing our own rendition of an Indigo Girls duet, but I think we have to set up a date to do that.
Dorie Clark:
Absolutely.
Debbie Millman:
Did you become a Tony Robbins fan or go to any of his seminars?
Dorie Clark:
So the reason that we named the band that is that the girl who was in it with me, her mother … actually, I was over at her house, my friend Rosalind, and I was over at her house and her mom was reading Tony Robbins as, I guess, most people were back in that moment in time. And I saw it lying around the house and I picked it up and I was flipping through it. And she, the mother, was just obviously very excited by this development because I think Rosalind was not a wit interested. And she said, “Oh, do you like that book?” And I was like, “I don’t know, what is it?” And so she explained to me the basic outline of what it was. And she said, “If you read this when you’re 13, you will be invincible.” And I thought that was actually a pretty good sales pitch. So she’s like, “Do you want to take it home and borrow it?” I was like, “All right.” So yes, that got me on the Anthony Robbins bandwagon.
Debbie Millman:
I don’t know if it’s a coincidence then, but at 14, so one year later, you went to the Mary Baldwin College Program for the Exceptionally Gifted. So you went to college at 14, one year after reading Anthony Robbins’ Unlimited Power. I think he needs to know that.
Dorie Clark:
It was all the neuro-linguistic programming. Let’s give credit where credit is due.
Debbie Millman:
So you attended Mary Baldwin for two years. Then you transferred to Smith College, where you graduated Phi Beta Kappa, where you majored in philosophy. I love that—you majored in philosophy. Two years later at a mere 20 years old, you received a master’s degree from Harvard Divinity School. So you had a master’s degree at 20.
Dorie Clark:
I did. I did, in theology. I’m not sure how far that gets ya, but yes I did.
Debbie Millman:
So why theology?
Dorie Clark:
I was interested in div school for a couple of reasons.
Debbie Millman:
I love that there’s a little acronym … not an acronym, but a nickname, “div school.”
Dorie Clark:
Yes. So the first reason was that as I was studying philosophy, what I was really interested in was understanding life, was understanding what motivates people and what drives them. And interestingly, if we really want to geek out here, at Mary Baldwin, they taught a form of philosophy that it turns out is very uncommon in American academia, which was continental philosophy. It’s just a different approach to the discipline.
Debbie Millman:
What is continental philosophy?
Dorie Clark:
Continental philosophy is largely focused on, as the name implies, European philosophers, but it’s focused on … you could see these sort of broader issues of metaphysics of, “What is life? What’s life about? What are we doing here?” And I got to Smith and it turned out I did not know this, and I did not know enough to even be asking the question. They didn’t teach philosophy that way. They taught philosophy in a really different way that is much more prevalent in American academia, which is known as Anglo-American, or the Analytic Tradition in Philosophy. And that is much less concerned with European philosophers, much more concerned with … I will say in my deliberately loaded way, trying to turn philosophy into a science. And so they’re focused on logic, they’re focused on math, they’re focused on almost neurobiology, the neurobiology of experience.
And I just was like, “Oh my God, is this what I signed up for? This isn’t what I was wanting to do.” And so I kind of muddled through it to finish my major, but I felt a little dissatisfied. I felt like I was sort of robbed. And so I switched over into religion and theology because I thought, “OK, this is a little bit more where my interests lie.” So I ended up going into theology as a result of that. That was one reason. The other reason was actually because of activist reasons. I was very interested in understanding the psychology of the religious right, and wanted to stop the Christian Coalition, which at the time was agitating very strongly against gay rights and other things that are important to me. And so I wanted to have a better sense of the theological underpinnings of where they were coming from so that I could be more effective.
Debbie Millman:
At that point in your life, you also assumed that your career was going to be in academia, but you ended up getting turned down by every doctoral program you applied to. And what I really didn’t understand was how do you get turned down for doctoral programs after graduating from Harvard at 20?
Dorie Clark:
Well, I appreciate your indignation on my behalf, Debbie, thank you. I wish you were on the admissions committee, but what actually did me in … I kind of have a sense of it. I didn’t really understand that when you were an undergrad, being a Renaissance person is the best thing ever. If you’re applying to undergrad, that’s what they’re looking for. They want diverse interests. When you are applying to a doctoral program, that is actually the last thing they want. They do not want diverse interests, they want one person who will do one extraordinarily narrow thing. And I was not telegraphing that. And I think they saw through me and realized, “Oh, this person might be a liability.” And where I really knew I was in trouble, you have to take the GREs. And I did well in the GREs.
I did quite well, but I was interested in switching over from religion into English literature. I wanted to do the intersection of religion and literature, which was probably not a popular choice. And so I had to take the English subject GRE and I did not do well on that. And I knew, I tried to study for it, but in the middle of the test, I’m like, “Oh God, this isn’t going well.” When I see the question, “Translate this from this passage of Beowulf, from the Old English.” I thought, “Oh yeah, that’s not my area of expertise, now is it?”
Debbie Millman:
Wow. Well, I do know from Roxane, who has a Ph.D., that you do need to be fluent in, I think two other languages when you get a Ph.D., in some sort of English of sorts. But I didn’t know you needed one before. Oh my God.
Dorie Clark:
It’s true. And I even had taken a course and passed an exam in [inaudible], but unfortunately, theological French, not so helpful with the whole Beowulf situation.
Debbie Millman:
And you didn’t think there was a niche there. Dorie, how did you manage the disappointment at that time? When I was thinking about going to get a master’s, I applied to one school—I applied to the Columbia School of Journalism. I didn’t get in and I was just inconsolable. You applied to several doctoral programs, got rejected by all. How did you manage that?
Dorie Clark:
Mostly I panicked because I didn’t have another plan. I was 100% sure, it had literally never occurred to me that I would not get into any of them. I had steeled myself to the fact that I probably wouldn’t get into all of them, but to get into none was literally a possibility that I had not considered. And so I just thought, “Oh my God, what am I going to do?” And so I had to scramble to try to figure things out. So I set up an internship for myself, working at the State House in Massachusetts. And there had been a politician whose campaign I had volunteered on. And I set it up to be an unpaid intern in his basement office in the Massachusetts State House for a semester, which kind of bought me some time and bought me a little experience on my résumé that I figured I could leverage into something afterwards.
Debbie Millman:
During that time, you decided to try a career as a print journalist, and you got a job as a political reporter at The Boston Phoenix, and despite winning two awards from the New England Press Association, you were laid off with four days severance on Sept. 10, 2001, which made it nearly impossible to get a job. And I thought that the layoff story was an interesting one to share with our listeners.
Dorie Clark:
The interesting thing for me is, nowadays, if you say, “I was a reporter and I was laid off,” people are like, “Well, duh, what did you expect?” But the truth was the year 2000 was literally the most lucrative year in history for print journalism. And we forget that sometimes, history can change so fast, but The Boston Phoenix was an alternative newsweekly, it was part of the genre—like The Village Voice, it was a cool kid paper. I had loved it so much, I had loved it for years. And to be able to write there was just so exciting for me. It was like I was in the action. I was in this place that I really admired. And unfortunately it was a free paper which was largely subsidized by its classified ads … let’s be honest, its porn ads, but nonetheless, it supported some great journalism. But those were the papers that were the first victims of Craigslist.
And so I was laid off in 2001. And at that time, it was just such a shock that you would be laid off from a journalism job, I absolutely didn’t predict it, I didn’t see it coming. I had an hour to get my desk packed up and out the door and I was unbowed. I was very upset, but I thought, “OK, OK, I’m going to go out and I’m going to find another job.” What I really wanted was a job at the Globe, The Boston Globe, which was the sort of prestigious regional daily in that area. And I thought, “OK, the next morning, I’ll start pounding the pavement.” And of course, the very next morning was not the time to be looking for a job.
Debbie Millman:
You ended up freelancing for The Boston Globe, and I thought it was interesting, especially given the topic of your most recent book. The folks there had a very different response to your work—whereas your previous editor at The Phoenix would tear your work apart, the Globe often published your articles as-is with very little editing. How did you make sense of this, and what has that taught you over the years?
Dorie Clark:
It was enormously satisfying for me. One of the things that I do talk about actually a lot in my work these days is so often we … I say a collective “we,” just professionals, people in general, tend to give, I think, far too much credence to the gatekeepers around us, to the people who are by luck or by title, or what have you, in a position to be able to say, “Well, this is good,” or “this isn’t good,” or “you get in,” or, “no, you don’t get in.” And it was very demoralizing to me when I was working at The Phoenix because I had an editor who just … I really felt like I couldn’t do anything right. I mean, I would get this sea of red ink and I’d try to understand what she wanted, and she just gets so frustrated. She’d just be like, “Well, just make it better.”
I’m like, “That’s really not helpful here.” So it just felt like the Sisyphean task of trying to intuit what she wanted. And it was just so gratifying for me when I sent my first piece in to The Globe, which was considered the more prestigious paper, they didn’t change anything. And it was kind of a light bulb moment for me, because I think what I got out of it was just really understanding one person’s opinion should not matter. I mean, fine, don’t be an idiot, listen to 100 people’s opinion, but one person’s opinion could be wrong. And we’re doing ourselves a disservice to give too much credence to that view, even if that person is in power.
Debbie Millman:
I want to get back to that. It’s a really juicy topic, but continuing on with your origin story—so freelance writing really wasn’t enough to support yourself, and so you pivoted again and made your first big professional reinvention and turned to political campaigning. And I think this is a different experience than what you were referring to about working in the basement for free. Here, you started working with Robert Reich, the former U.S. Labor Secretary who had decided to run for Governor of Massachusetts. Given your sort of bouncing around, shall we say, at the time, what made him decide you could be an effective press secretary?
Dorie Clark:
I think it was largely desperation. There’s nothing like a low bar, Debbie. Bob had entered the governor’s race late and it was a crowded field in the Democratic primary. He was the fifth candidate who was running. And so the honest truth is that the other candidates who had been in the race longer had snapped up all of the usual suspects who were political campaign staff. And Bob was scrambling to try to assemble a team. And unlike some of the other people who were running, there was the Senate president and people who had pre-existing staffs and pre-existing relationships they could tap. Bob hadn’t been back that long from D.C.
And then he was in this academic career. So he didn’t have his “people.” So he turned to a political consultant that he had hired named Michael Goldman. And Michael was someone that I frequently talked to and had quoted as a source when I was a reporter. So we had a nice rapport. I mean, I’d call him all the time. And so when I got laid off, he knew it—I wasn’t calling anymore. And he thought I might be looking for a job. So he reached out to me around that possibility. And because I had worked in media and because I had done a little bit of politics before, they thought I was a decent enough vet, so they brought me on.
Debbie Millman:
Reich lost in the Democratic primary, but you were bitten by politics and began thinking about working on a presidential campaign. The thing that I really love about your career, Dorie, is how sort of undaunted you are and how willing you are to just throw yourself into the biggest possible challenges. Rather than work on another governor or Senator or mayoral campaign, you’re like, “OK, I want to work for somebody who’s running for president.” And you did; you got a job working for Howard Dean in his quest to become president in 2004, but at the same time, you also became the executive director of an organization called The Massachusetts Bicycle Coalition. And you worked with legislature and state agencies to improve transportation planning. So, talk about these sort of different pathways that you were taking at that time and ultimately what made you decide to stop both and start your own company.
Dorie Clark:
So I was full-time on the Dean campaign for close to a year. I worked first in Vermont for him, and then as New Hampshire communications director around the New Hampshire primary. And it was a really exciting ride. I mean, Dean was someone who went from almost total obscurity and being at 2% in the polls to, within a few months, essentially emerging as the frontrunner in the race and a prohibitive favorite. And then of course rather tragically, he finished third in Iowa, second in New Hampshire and then quietly dribbled out of the race. But we got to see the entire ride, but I was all-in on that campaign. I thought he would have been a terrific president, but after that ended, I decided it was time for me to go back to Boston where I had put a lot of roots down. And I thought I would either run communications at a large nonprofit or perhaps head up a smaller nonprofit, which is how I ended up getting the job at MassBike, the Massachusetts Bicycle Coalition.
And it was a really good education for me because when you’re running this tiny nonprofit, you sort of have to do everything, you have to be a jack of all trades. And also it was a nice humbling experience for me because what I quickly discovered if you’re running a bicycling advocacy organization … I was a commuter cyclist. I’m like, “Yes, I support the transportation benefits of bicycles; we need fewer cars on the road.” The people who were my board, they were the biggest bicycle zealots you could ever have.
Our board president lived 30 miles outside of Boston and she didn’t own a car and she would bicycle in and out, 60 miles each way, for meetings. We would have a board meeting in the morning and then a group ride in the afternoon. And I was the youngest person and I was also always bringing up the rear. It was just really humiliating when our septuagenarian members would be clocking me. But you dive in and make it happen.
Debbie Millman:
What made you decide to go for broke, start your own company, Clark Strategic Communications, in 2006 with the title CEO?
Dorie Clark:
Well, I think the title is just self-aggrandizement, the CEO of the one-person company. But what I realized in the course of running this nonprofit was it was a three-person tiny, tiny organization, so we were pretty much doing everything. I’d be in charge of marketing and event planning and fundraising and database management and keeping up the website and reconciling the QuickBooks. I mean, literally all the things. And I realized that I had managed to acquire this kind of comprehensive knowledge of how to run a nonprofit. And just at some certain point, I guess it had never really fully occurred to me before, but I thought, “Oh my God, this is the same thing as running a business. This is literally running a business.”
And then it took me one or two beats, and I was like, “Wait a minute, I could run my own business.” And I just had so much stress running this little nonprofit where the board was wonderful, but they were not a super fundraising board. I was really responsible for raising all of the money and keeping this organization and our employees solvent. And I realized it would actually ironically be … for a lot of people that I coach or that I work with now, they might want to work for themselves one day, but they’re like, “Oh, but I’d have to take this salary cut.”
And they’ve got the sort of proverbial golden handcuffs because they’re so successful now, they’re making so much money. I had the opposite problem. I was making 36 grand my first year, then I was making 45. They gave me the raise. I was actually not happy about the raise because I had to raise my raise. It was just misery. And I thought, “You know what? I can for sure figure out somehow how to make that much money. And I could get rid of the stress of running this organization.” And so I actually thought, “Wow, the safe choice for me, the easy choice, is having my own business.” So I dove into it.
Debbie Millman:
That’s a stress-free path to take, running your own business as a way to relax into your life.
Dorie Clark:
That’s right.
Debbie Millman:
Now, you focused initially on public relations and consulting as the centerpiece of your business, but very quickly shifted to marketing strategy. Tell me how that happened.
Dorie Clark:
That was me responding to market conditions, essentially, because at the time that I was doing this—I was starting my business in 2006—in many ways I would say that was the inflection point of two phenomena. One was that social media was starting to take off, and YouTube was founded right around then, Facebook was just starting to become publicly available outside of college campuses, Twitter was hot. So everybody was very interested in social media. And the second issue was that newspapers, as evidenced by my own story, were really starting to go into a freefall. And as a result, their newshole was shrinking. Meaning the newshole is literally the amount of print space that they have available. So there would be situations where I was doing PR for clients and they would do something that the year before, two years before, they had done, they were like, “We’re going to have a press conference.”
And they would expect 10 reporters at their press conference because, “Hey, we’re having a press conference.” And what they didn’t really get is that a quarter of the staff had been laid off and the newspaper had cut dozens of pages. And so there was a higher bar in terms of what would constitute something that the papers would cover. So they’d organize an event. I would kill myself trying to pitch the press, get them out and they wouldn’t come to cover the press conference. And my clients, not all of them, some of them understood, but some of them thought I was an idiot, being like, “Hey, loser, Joe, two years ago, got The Globe here, why can’t you get The Globe?”
And it’s like, “It’s because everyone’s fired, that’s why.” But I just hated having to always be on the defensive and explaining that to people who are dissatisfied. So eventually I thought, “OK, I am going to leave the dying industry and go toward what is actually prospering.” So I stopped pitching myself to do PR and instead switched essentially into marketing strategy, which involved social media strategy in a kind of more holistic way of marketing, to take the heat off, in many ways. But also because I realized that was going to be the future if organizations were going to actually be able to get known in the marketplace.
Debbie Millman:
In 2009, you decided that you wanted to write a book. You made it your New Year’s resolution. And in the first six months of the year, you wrote three book proposals, hoping that at least one would resonate with a publisher. And none of them did—not one of the pitches, the proposals, resonated with anyone. And you said you were rejected by publishers because you didn’t have a big enough platform. And so once again, you had to pivot and you had to go back to what you referred to as the proverbial drawing board and create a fan base from nothing. So you started out with zero audience. What gave you the sense that this was worth pursuing, and how did you go about doing this?
Dorie Clark:
I had always wanted to write a book, and I knew intellectually that it would also be a good thing for me in terms of my business and marketing and making people aware of what I did, but at a fundamental level, it just was kind of a bucket list goal that I had admired authors from the time I was a little kid and wanted to do it. And so even though it was extraordinarily frustrating to have to realize, “OK, this is going to take longer than I wanted. This is going to actually literally take years longer than I wanted it to,” I just decided, “OK, well, that’s what it’s going to be.” And so I did start blogging and start the process that turned out to be necessary in order to get published.
Debbie Millman:
In 2011, you wrote an article for the Harvard Business Review titled “How to Invent Your Personal Brand.” And the piece went viral. You were approached, at that point, by several literary agents who finally thought you had a topic for a book, and your first book, Reinventing You: Define Your Brand, Imagine Your Future, was published in 2013 to great fanfare. As I mentioned in the introduction, The New York Times went as far as designating you as an expert at self-reinvention and helping others make change in their lives. So congratulations for that, Dorie. I think that the amount of resilience you’ve shown in sort of facing the unknown or facing rejection is stunning. It really is. A lot of people talk about resilience, a lot of people talk about perseverance, but you walk it. And I think that in a day and age when there’s so many guru books and so much out there that will give you a prescriptive path to success, I think you really show tangibly how to make these kinds of things happen.
Dorie Clark:
Thank you. I appreciate it, it means a lot coming from you, Debbie. Back at you.
Debbie Millman:
Oh, thank you. So now I have a little bit of a bone to pick, maybe. Just a tiny one, just a tiny one, because—
Dorie Clark:
Let’s do it. Bring it.
Debbie Millman:
I think you know that I have issues with the idea of a person being a brand, and as somebody who’s worked in branding for so long, I believe that brands are sort of manufactured entities that people can draw and create with imagination and innovation. They’re not really real in the truest sense of the word real—they don’t have a consciousness, they don’t breathe air. As much as people would like to think that, they really, truly, scientifically, don’t. Brands don’t have living, beating hearts, they don’t bleed, they don’t cry. They don’t have souls or feel pain and pleasure. So I’d like to think that people should develop their reputation or their character as opposed to aspiring to be a brand. And I just wanted to get your sort of perspective on that.
Dorie Clark:
I’m with you, I’m completely with you, you win. I really treat personal brand as an almost interchangeable term. I am terminology agnostic, right? As you know, the term “personal brand” really was coined and came to popular use by Tom Peters in a famous 1997 Fast Company cover story.
Debbie Millman:
I still have that issue, by the way.
Dorie Clark:
Oh my goodness. Oh gee. I like it.
Debbie Millman:
I do. I do.
Dorie Clark:
So the term is 20, 25 years old, but fundamentally, all he’s talking about is something that’s millennial, which is, in fact, your reputation. “What do people think about you? Is it what you want them to be thinking about you? And if not, is there something you can do about it?” Those are really the only three questions that matter. And I don’t really care what people call it. I’m happy to use “personal brand” because it’s a commonly used term of art these days. But fundamentally what I’m interested in is making sure that for people whose talents may have been misunderstood or may have been underestimated, I would like to equip them with a way of fighting back so that they actually can be properly understood and valued and respected the way they should.
Debbie Millman:
I fundamentally agree. And that’s really so much of what I like about your work. I think there is a big difference between aspiring to be a brand and having a brand. I think it’s possible for people to create brands, but to aspire to be a brand I think actually limits our potential and our possibility because it doesn’t give us this opportunity to pivot or reinvent, which I think is so important. Anyway, you’ve since written three other books, the latest of which is my favorite. It is titled The Long Game: How to Be a Long-Term thinker in a Short-Term World, which has already received terrific reviews, so congratulations, Dorie.
Dorie Clark:
Thank you, Debbie. I appreciate it.
Debbie Millman:
One of the things that I love so much about the book is how it reinforces something I’ve been really thinking a lot about. And it allowed me to think about it in brand new ways. For a long time, I’ve been saying that we’re living in a 140-character culture. I changed that when Twitter changed their character count to 280, but fundamentally what I mean by that is that we expect things instantly, and I believe—and I think you do too now after reading your book—that most people should expect anything worthwhile to take a long time. And in your new book, you posit that personal goals need a long-term strategy. And I’m wondering if you can talk a little bit about what that means.
Dorie Clark:
Absolutely. And to your point, it makes me think about the famous quote from Peter Thiel, “They promised us flying cars and what we got was 140 characters.” And I think, in many ways, what I would like to see is to find a way back to that. It doesn’t, of course, literally have to be flying cars, but I like the sentiment that … where are the big dreams? Where are the aspirations that are worth fighting for and working toward? One of the folks that I quote in the book is Jeff Bezos. He had a conversation in 2011 with Wired magazine. And even back then, when Amazon was literally a fraction of the size that it is now, it was still very successful. And he was talking about the reasons behind their success. And one of the things he said is that “most of our competitors are only willing to plan on a three-year timeframe.”
And the planning is really because of budgeting. It’s because they’re afraid to take longer-term risks because the longer-term risks … it takes a while to pay off. But he said that Amazon’s secret to their success is that they were willing to plan on a seven-year timeframe, more than double. And because of that, they were able to pursue more ambitious goals than other people. And therefore, as we now see with things like Amazon Prime, with things like Amazon Web Services, it might take a while to build up and to percolate, but it can create a huge competitive advantage. And I think the same thing is true for all of us with our own lives and our own careers. We’re often thinking too small, thinking too short term.
We often imagine, if we’re going to create some grand goal, “Oh, well, I don’t know how I’d do that, so I won’t go there.” But the actually really empowering thing is if you have a long enough term goal, you don’t have to know how you’re going to do it. It would be ridiculous to plan a 10-year strategy because so many things can change between here and there, but it is not at all ridiculous to have a 10-year ambition or vision and to just start taking one step at a time toward it, to move in that direction. And that’s what I’d love to see more of.
Debbie Millman:
One of the centerpieces of your book is the notion of strategic patience. Can you talk a little bit about what that is and how you might use it?
Dorie Clark:
So I have never been a fan of patience.
Debbie Millman:
It’s one of your two least favorite things, I understand, from the book.
Dorie Clark:
That is true. Even as a kid, I would just get so frustrated. I would be watching the news of my parents and hear about elections and I’d be like, “Well, I want to vote.” And my mom’s like, “Well, actually you need to wait another 16 years to vote.” I’m like, “What?” It was so offensive. So I’ve never liked patience, but as I have grown up, I have come to realize that we sort of have to make our peace with it because it is objectively true that many things you have to wait for. And you’re either going to suffer and shake your fist at the sky, or you have to reconcile yourself somehow. But I’ve created my own flavor of patience, I guess you could say, because I still have problems with the way that patience is so often talked about, which I think is a really passive enterprise.
A lot of people, honestly, I think just to shut you up, will be like, “Well, just be patient, just wait, just do your thing, Debbie, just work hard. It’ll all work out, sit back.” And I find that to be glib and really unhelpful. I don’t want to sit back and wait. Now I understand I can’t control the universe, I can’t make it happen faster, even if I want to, but what I have taken up and I hope might be helpful to others is what I call strategic patience, because it is simultaneously understanding that things may take a while, but also creating hypothesis, doing things, taking action, taking note of what is happening and tracking it so that you can pivot if necessary or keep going if things seem to be progressing. And actually just taking a more muscular approach to the fact that, yes, we have to wait, but no, we don’t have to be suckers with vision boards, wishing and hoping.
Debbie Millman:
You write how when you’re in the moment, when you’re trying for something, it’s almost impossible to tell if something isn’t working or it isn’t working yet. How do you know when to fight or when to fold?
Dorie Clark:
That is the ultimate question, and it’s plagued so many people. I mean, I know from people who are my colleagues, people who are my coaching clients, I see this. And even going back in history, there’s a really interesting researcher named David Galenson at the University of Chicago who has studied artists. He’s an economist and so he studies the lens of economics and art. And he talked about how somebody like Picasso, pretty much from day one, everyone’s like, “This guy’s a genius.” And fantastic, yay for Picasso, his work sold for a lot of money. He got tons of positive affirmation. It’s easy to be a Picasso in the world, but there are other artists, Cezanne was one example, where it was not like that. And he had been literally working for decades. He was in his late 40s before he pretty much got any acclamation at all.
And during those times, it’s not just other people saying, “That’s not very good.” If you are that person, if you are Cezanne, even though we know from history that TLDR, he was good, you wonder about yourself, and it’s so dispiriting at times. And so ultimately, what I’ve come to realize is I think there are three key components to being able to help make the judgment about whether it’s not working or whether it’s not working yet. So No. 1 is actually taking the time … and a lot of us, a surprising number of us, don’t do this, but taking the time to scope out in advance what it actually is likely to take to get where you want to go. Many of us make assumptions. We don’t even realize we’re making assumptions, but we do about what to expect or how long it should take.
We think, “Oh, a couple of years.” Well, have you studied it? Have you talked to, have you researched, have you examined people who have done this thing or something quite similar to it before to see how long it took them? Because if it took this person 10 years, you’re probably not going to do it in a year. I mean, God bless if you can, but it’s probably going to be more eight or nine or 11. So grounding ourselves, so we know what to expect, so we don’t somehow get discouraged midway through because we didn’t realize the scope. That’s No. 1. No. 2 is having a group of trusted advisors around you who are both supportive of you and knowledgeable about your field so that they can give you detailed guidance in those moments when you can’t trust yourself, when you’re too emotional, and they can tell you, “Oh, this is really good, keep going.”
Or, “Maybe let’s move on and let’s try something else.” And then the third piece is what I call looking for raindrops. And what I mean by this is that so often a problem that a lot of us have as humans is we are looking for the big score. We’re looking for the big success, the thunder and lightning and the downpour. And we say, “Oh, now, now it’s happening.” But it takes a while before that happens. And so in order to really understand where we are in the process and keep motivated, we need to look for those kind of preliminary raindrops, because usually the way a storm starts is there’s just a few isolated drops coming from the sky.
You might not even know. You might say, “Wait, is that a raindrop? Did you feel that?” But those are the signals, the small kind of weak signals. Maybe more people than usual are starting to friend you on LinkedIn because your name is getting around. Maybe you get a compliment from your boss. Maybe you get invited on a weird random podcast that a person across the world has started and you think, “It’s not a big deal.” But it’s a big deal if you understand that someone you haven’t heard of wants to talk to you. It’s those little signs, and that’s what can help show you you’re moving in the right direction.
Debbie Millman:
One of my favorite topics in your book is the section on learning how to say no. When we’re trying to make it, we tend to think that we have to say yes to everything because we might not ever have this opportunity again or anything is good to get the word out. We’re worried about disappointing people, other things on your list. We’re worried about negative judgments. We don’t want to have hard conversations. It’s easier to avoid them. We like feeling important, that we’re needed. So there’s so many things that really contribute to the sense of no avoidance. First of all, let’s talk a little bit about why it is so hard to say no, aside from those obvious things. What is it about the human condition that kind of keeps us saying yes when we don’t even want to?
Dorie Clark:
It’s a terrible conundrum that most of us find ourselves in, and I think there’s a lot of reasons operating simultaneously. One, we have gotten into, I’ll say in air quotes, “bad habits,” but it’s not really a bad habit. Which is that early in your career when you were first starting out, “yes” actually is the right answer. It’s not like you have this vast queue of people waiting to talk to you, right? “Yes” is actually pretty good because you don’t know who’s going to be important. You don’t know what’s going to be interesting. But the problem is, it’s a great strategy when you’re 22, it’s a terrible strategy when you’re 32 or 42 or 52, because you have grown in stature, you have grown in responsibilities, you have grown in connections. And so if you were literally to continue saying yes to everything, because so many more people want things from you, you would never be able to accomplish what you want.
So I think partly it’s just a failure to understand, “Oh, I’m in a different place now, I need a different strategy.” And the other area, which is sometimes hard to deal with and hard to excavate, is that for many of us, being busy has emotional benefits. And there’s some interesting research by Silvia Bellezza from Columbia Business School and some of her colleagues, about the fact that certainly in the United States and many other Western cultures, being super crazy busy is actually viewed as a mark of status.
Debbie Millman:
Yeah, it’s a badge.
Dorie Clark:
Absolutely. And so people wear that. And if we were to take the steps that we need to actually dispatch some of those responsibilities, it actually calls into question some of our self-worth, which is not incredibly healthy, but is often animating some of our decisions.
Debbie Millman:
You have four questions that you pose that people should ask themselves before saying yes to any opportunity. I’d like to share them. No. 1: “What is the total commitment required?” I think we often forget that, right? No. 2: “What is the opportunity cost?” No. 3: “What is the physical and emotional cost?” And No. 4, I love this one: “Would I feel bad in a year if I didn’t do this?” How did you come up with these four? And how do you use them in your own life?
Dorie Clark:
So I came up with these questions the hard way, because I kept making mistakes about my calendar. I kept falling prey to all of these things that we’re talking about, where I would stuff my schedule, I would over-commit. And really the only question that I was asking myself was, “Well, can I literally do it? Am I double-booked or not? OK, if my calendar’s open, then yes, I can do it.” And unless it was an obviously terrible request, I would pretty much say yes. But over time I realized, “Oh no,” I was making choices about flying this place and that and whatever and I would end up sick. I’d have backaches because I had been on a plane for 17 hours. I was just running myself ragged and not enjoying any of it. And I realized, “This is a problem, I need to come up with a better set of criteria for myself so I can actually enjoy my life.”
I think most of us feel that way. So how I’ve applied it in my own life. In The Long Game, I actually tell a story about this heartrending decision, where I got invited to give a speech in the Caribbean by a friend to speak to her conference that she was helping to organize. And I ended up turning it down because I realized it would just have been too much, too hard. And frankly, once I was peeling it back, logically, I realized, “Oh, wait a minute. What I really want is to see my friend. She lives in Brooklyn. I could do that this week if I actually was organized and wanted to.” But I’ve tried to get smarter and to get better about controlling our time. Because when we do that, we have to have white space if we are going to actually be long-term thinkers. It’s not that we need an infinite amount of time or some huge amount of time, but you need a little time, you need a little space, and saying “no,” and creating that white space for yourself, is really an essential first ingredient.
Debbie Millman:
In The Long Game, you write about something that you learned after reading Frances Frei and Anne Morriss’ wonderful book Uncommon Service. And they state, “Choosing to be bad is your only shot at achieving greatness, and resisting it is a recipe for mediocrity.” I loved being reminded of that. You go on to recommend that in order to be great at anything, you must decide what to be bad at. Tell us why you need to decide that.
Dorie Clark:
So the essence of strategy at a really fundamental level is making choices. And the problem that a lot of us fall into is we are fine with the idea of, “OK, I can be great at some things and not great at others.” But when they think “not great at others,” what’s in their head is like, “Oh, I’ll be great at some things, and then just average at the rest.” That is not how it works. We have limited time, limited bandwidth. And so the truth is if we’re really being honest with ourselves, being great at something, over indexing in a big way, means that with a world of finite time and energy, you’re probably going to be bad at other things.
And in refusing to make that choice, everybody gets zeroed out, everything’s average, everything’s meh. And so it’s hard to face the idea that we would be bad at something, but we’ve got to let some of it go. I mean, I don’t cook pretty much, period. I just don’t do it.
Debbie Millman:
I was going to ask you, what are you bad at, Dorie?
Dorie Clark:
I’m bad at that. I’m pretty bad at responding to email. I’ll do it eventually, but it takes a long time, but I’ve made my peace with it because when there’s things that I want to be great at, I really try to emphasize that.
Debbie Millman:
Dorie, my last question for you today is this. You include a great quote by Longfellow in The Long Game. You state, “We measure ourselves by what we feel capable of doing while others measure us based on what we’ve done.” And you go on to write about how this makes sense, but it’s awfully frustrating when there’s a gap between what we know we can accomplish and what we’ve done up to that point. And you go on to state that, “Everything takes longer than we want it to—everything.” And I can also underline that in bold italics, everything. For those of us that are slugging away at something and still have big hopes and dreams that haven’t manifested yet, what is one thing people can do to improve their odds?
Dorie Clark:
As we’re thinking about how to play the long game and how to accomplish our long-term goals, it can feel overwhelming sometimes to look out into the horizon and wonder how we’re going to accomplish something. Especially if it’s a big enough goal that we can’t see through the fog. We don’t know what the steps are. They might even change between here and there, but ultimately the question for all of us—and I think this is the essence of strategic thinking—is, “What is one thing that I can do today that will make tomorrow easier?” Because if we can consistently make those choices about ways to learn more, ways to connect with people, ways to become just slightly better or more informed and move the ball forward, we don’t have to know the answer. We don’t have to have it figured out 10 or 20 years or even a year into the future.
We need to be directionally correct and to recognize that things might not … in fact, they probably won’t work out precisely the way that you’re mapping out, but there are a lot of ways to get to your goals. I got turned down by every doctoral program I applied to, but within a few years, I was actually teaching at a university and I continue now to teach at some of the top business schools in the world because when the door was closed, I climbed in a window. And I think all of us can do that, as long as we keep in mind that it’s not about tackling the whole problem, it’s about taking small, consistent steps. And just like a stock portfolio is able to grow because of compounding, it’s like that in the investments that we make in our own lives, in our own careers.
Debbie Millman:
Dorie, thank you for creating such soul-enriching work. And thank you for joining me today on Design Matters.
Dorie Clark:
Thank you, Debbie
Debbie Millman:
Dorie’s latest book is titled The Long Game: How to Be a Long-Term Thinker in a Short-Term World, and you can see more about all of her many incredible endeavors at dorieclark.com. This is the 17th year we’ve been podcasting Design Matters, and I’d like to thank you for listening. And remember, we can talk about making a difference, we can make a difference, or we can do both. I’m Debbie Millman, and I look forward to talking with you again soon.