Dorie Clark on The Long Game

Dorie Clark on The Long Game
Intro: 00:00
Welcome to Brainfluence, where author and international keynote speaker Roger Dooley shares powerful but practical ideas from world-class experts, and sometimes a few of his own. To learn more about Roger’s books, “BrainFluence” and “Friction”, and to find links to his latest articles and videos, the best place to start is rogerdooley.com. Roger’s keynotes will keep your audience entertained and engaged. At the same time, he will change the way they think about customer and employee experience. To check availability for an in-person or virtual keynote or workshop, visit rogerdooley.com

Roger Dooley: 00:37
Welcome to brain fluence. I’m Roger Dooley. My friend Dorie Clark is an adjunct professor at Duke University’s Fuqua School of Business, and the author of “Entrepreneurial You”, “Reinventing You”, and “Standout”, which was named the number one leadership book of 2015 by Inc Magazine. Dorie is a former presidential campaign spokeswoman, and the New York Times described her as an expert at self-reinvention and helping others make changes in their lives. Dorie’s new book is “The Long Game: How to Be a Long-Term Thinker in a Short-Term World”. Welcome to the show Dorie.Dorie Clark: 01:05
Hey, Roger, so good to be here with you.

Roger Dooley: 01:08
Well, it’s really fun because you’re so full of good advice for people. I loved “Reinventing You”, and all your content about personal branding. And I think that now, your new book, Dorie, addresses another concern, which is long-term thinking. I talk a lot about long-term thinking for businesses. I’ve had Tom Peters on the show, and he is always hammering away at how short-term thinking totally screws businesses, how CEOs are so concerned about this quarter’s earnings, this year’s earnings, that they ended up really not focusing on a customer, not focusing on their people. But here you are focused on long-term thinking for the individual, like all the people in our audience. So, that’s really great. I’m curious Dorie, how did the pandemic influence your thinking on this topic?

Dorie Clark: 01:51
Well, the pandemic obviously shook things up for just about everyone. And ironically, I sold the book, I got an email from my editor at Harvard Business Review Press on February 28, 2020, saying, “Hey, congratulations, we want to buy the book.” And literally, it was the next morning, it was March 1 that the first case of COVID was detected in New York City. And of course, within less than two weeks, the entire city shuts down. And in many ways, the entire country shut down. So, things happened really rapidly. So, I had just sold a book about long-term thinking, and the entire world is screeching to a halt. And not long after that, I actually… there’s a guy that I knew, and we were having a conversation, and I mentioned that I’d sold the book, he asked about what and I said, “Long term thinking.” And he just laughed, and he’s like, “Ah, well, you know, guess the world doesn’t need that anymore.” I thought, oh, no, can this be true? Is the entire premise completely off now? But I have come to the belief over time, that actually, I think that long-term thinking is perhaps even more important now. Because for the past 18 months, we have, like it or not just being forced into reactivity, and having to adapt to circumstances and just taking what has come at us. And you need to be able to do that. That’s obviously an important life skill. But you can’t live your life that way. You have to stake a claim for some long-term thinking and some long-term vision. We have to be moving towards something, otherwise, life becomes pretty unsatisfying. You’re just kind of a jellyfish floating in the ocean. And so, I think it’s time to take back control over our lives to take back control over COVID, and stake our claim for doing some long-term thinking so we can begin to reorient ourselves toward where we want to end up, not what we have to do.

Roger Dooley: 03:46
Start evolving from a jellyfish into a shark perhaps?

Dorie Clark: 03:49
That’s right. That’s right. Or at least a dolphin, that’s maybe a little friendlier. But yes.

Roger Dooley: 03:55
Well, I don’t know. I guess I’m not too into that business thinking mentality of war metaphors, sports metaphors, sharks, and so on. Something that you talk about you I think is really important in the book, Dorie, is that this is not an instantaneous process. It is something that takes time and effort. A past guest on the show is James Clear who wrote “Atomic Habits”, which continues to top the Wall Street Journal bestseller list years after it came out. And he emphasizes the same thing. And I think that his approach is part of the reason that his book has that longevity. He’s not saying this is going to fix you overnight because things don’t happen overnight in the real world. You buy one of those books and after a couple of months, well, I haven’t been fixed so forget this. But he emphasizes continuous improvement, 1% improvement here and there. And you do all these little 1% improvements, and wow, suddenly you’re a whole lot farther than you expected to be or closer to where you want to be. Talk about that a little bit Dore.

Dorie Clark: 04:50
Yeah, absolutely right. And it’s great that you say James Clear. In fact, in my most recent past book that’s come out, “Entrepreneurial You”, I actually interviewed James and talked to him about his process of how he built his following. And I think his story is useful here, it kind of exemplifies it. Because when I was interviewing him, it was early 2016, my book “Entrepreneurial You” came out in 2017, and this was a guy that had already built up something like, at the time, I’m trying to think, maybe 300,000 email subscribers, something substantial, less than what he has now. But he didn’t even have a book. He had just built this list. He started with no public profile and he built the list on the strength of doing two articles per week, writing them on his blog, and then syndicating them. And that was his plan. And I think it’s an important lesson. Because one of the things that I’ve seen with so many professionals in my coaching work in the online community that I run, called recognized expert, is that oftentimes a problem that a lot of really smart people face is that they want to change strategy too frequently. There’s this constant like, “Well, what else should I be doing? Well, what should I be doing differently? Or “Oh, should I try this? I heard about this.” It’s like you constantly are questing or looking for the magic bullet. What am I not seeing? What am I not doing? And those are good questions to be asking, but not all the time. Because often, the real answer is just, it takes time. The real answer is just to keep doing the thing that you were doing that was the right thing, just do it longer. And James, he was very certain about what had led to his success. He said, “Look, I did an article twice a week on Tuesdays and Fridays, and I just kept doing it.” And I think that many of us can learn from that.

Roger Dooley: 06:41
Right. And of course, he wrote very good articles that people wanted to read. That helped him. He had a robust system for getting subscribers. So, you’ve got to put those pieces together. But I think it’s important, he probably along the way saw that it was working to some degree. In other words, if he’d been doing that for six months, and had only a tiny, tiny number of subscribers, he would have said, okay, maybe I need to try social media instead, or I need to do something different than what I’m doing now because this isn’t working. But as long as you can see that you’re making progress, keep on doing that. Because I think we all can get really distracted by we get every day emails with great articles written by smart people saying, “Wow, I got 100,000 new followers by doing x.” I say, “Wow, that seems like such a good idea. Man, I could do that if I wanted to do that.” And so, we immediately drop whatever you’re doing, and we try and do x. And then two weeks later it’s, “I put weeks’ worth of effort into that and it really didn’t work the way it did for the other person.” So, just focusing on what’s working for you is the key. So, talk about whitespace. I just had Julia Funt on the show, she wrote a book called “A Minute To Think”, and she talked about whitespace too, and about how we’re all too busy. And you echo that. I think your approach is a little bit different. But explain your version of whitespace and why it’s important and how you get there?

Dorie Clark: 07:59
Yeah, absolutely. So, whitespace is important. And to define whitespace, of course, it’s if you think literally about, you’re looking at your calendar, you’re looking at your datebook, is it completely covered in listings from 8 am to 8 pm? Are you meeting-meeting, call meeting, or is there actually literally white space? Are there gaps in your calendar, where you have time to catch up on things, time to think, time to strategize, time to plan or prepare for the next thing? Or are you literally just so back-to-back that you are racing around like a chicken with your head cut off? I think no one thinks that that is an optimal way of being. And yet, for so many of us, that actually is how our lives are. And one of the points that I make in “The Long Game” is that we need to get a little bit more thoughtful about how and when we fight back against that. No one’s going to hand you white space. This is something that we really have to strategize about how to get in to defend it like we’re defending a fort. But it’s valuable. Because ultimately, if we really are going to be long term thinkers, if we believe that that is a valuable goal to strive toward, you just can’t do it if every minute of your day is taken up with having to respond to some crisis or some urgent thing in the moment. It’s not that it takes huge amounts of time to do long-term thinking or strategic thinking. It doesn’t. It’s not like you need some retreat in Tuscany. It’s not like you need hours and hours every week. But you do need some time. And ultimately, the first step, the first logical step is clearing your schedule just enough so that you have that breathing room to be able to ask important questions like, ‘Hey, all these things I’m doing, all these meetings I’m racing around to, all the things that I’m optimizing toward, are they the right things? This is a question that we don’t often ask ourselves, but actually, it’s pretty darn important.

Roger Dooley: 09:56
Well, I think you make the point that often our frenetic pace is really our own fault. It is our way of coping perhaps with the modern world. We feel like as long as we’re busy going from meeting to meeting, we’re being productive. And I’ve certainly met people like that, who, they’re in 35 hours of meetings a week and they cancel out. “Man, I don’t have time to get anything done.” But they are opting out of these meetings, because they feel at least like, “Okay, well, hey, I’m busy. I must be productive. I’m in these meetings. And people want me in these meetings because they invited me.” And that’s in certain ways, a crutch for not doing some of the harder work of okay, I’m going sit back and think about some of these strategic issues that my job is supposed to entail, and so on.

Dorie Clark: 10:37
Yeah, that’s exactly right. One of the interesting things that I learned in the course of researching “The Long Game” is there’s some research that’s been done by Sylvia Bledsoe from Columbia Business School and her colleagues. And it’s really about the fact that in most Western cultures, certainly in American culture, busyness is viewed as a form of status. And when we recognize that, when we recognize, “Oh, if I actually give up being busy, in a way, it’s giving up status,” we begin to realize why it’s so hard for some people to do it, even when they say, ‘Oh, gosh, I wish I were less busy. I wish I were less busy.” But they don’t actually make those changes. We all have too many meetings, we all have too many emails, that’s a given. But ultimately, there are sometimes some emotional issues at play that we have to deal with.

Roger Dooley: 11:25
Well, Dorie, you and I probably have more ability to control our schedules than some people you know. We can accept gigs, turn down gigs, we can choose to do things and not do other things. But I’m sure many of our audience members are in a position where they don’t completely control their own schedule, their own activities. They’ve got bosses, maybe multiple layers of bosses, maybe some weird matrix organization, where bosses and other departments are co-opting their time. How do you suggest that if you’re in that situation, how do you deal with that?

Dorie Clark: 11:57
Yeah, so in a very literal sense, if you are finding yourself just almost structurally unable to do the things that you need to do, I think where people worry, and I think justifiably, is that if they say, “Boss, I can’t do this, I’m too busy,” that they’re going to come off looking like a whiner, or they’re going to come off looking like somebody who’s just incapable. Like, well, why can’t you do it? Are you just shirking your duties? And so, in that situation, it’s really important to take a collaborative approach, rather than you deciding into saying, “Well, I can’t do all this.” One of the most important things is to go to your boss. And first of all, there are often structural issues. If your boss is not the only person assigning you work, if other people are assigning you work, it is really useful to get the chain of command straight, so that someone is serving as a filter, so you don’t just have three or four different people pouring things on you without an awareness of what’s going on. So, maybe it’s a group meeting, or maybe there’s a policy change where all the people who give you projects have to report through one person so that they have a sense of how much is coming your way. But ultimately, it’s going to them and saying, “Look, I want to get all these things done. I want to help you help me triage, help me think this through. Let me present, here are all the things that need to happen. Obviously, I can’t do them all at once. Help me understand the level of priority so that I know what to focus on, and I will focus assiduously, and then I will go on to the next thing. But you help me contextualize.” And that way you can really ensure that they feel like they’re on the same team with you in trying to accomplish it.

Roger Dooley: 13:35
Yeah, I think that’s really smart instead of just saying, “Well, I really don’t want to attend that two-hour sales meeting because I know it’s going to be a waste of my time.” You run the risk of sounding just like, “Wow, I don’t feel like doing that.” But saying, “Gee, I can attend this, but I was going to use that time to work on Project X that I know was one of your priorities.” And just putting that content where at that point, at least, the boss or whoever can have some input say, “Well, that sales meeting is really important, and here’s why. And here’s we should try and get out of it or get done with it. Or say, “Well, no, you’re obviously correct. Work on that project, because that’s much more important than the meeting.” But the key thing is to be proactive, to not just say, “Oh, man, here comes another meeting.” And partly, I think Dorie, it’s software-driven. Today’s scheduling software often lets you just sort of pluck time in from people’s calendars where you say, “Oh, well, we need somebody from sales on that. Okay, we need somebody from product management on that.” And so, you grab somebody, and you slap them into the meeting, and often that person doesn’t really know whether their involvement is going to be critical, or whether they’re just there so that this person can say, “Well, yeah, we covered all the bases on it.” And there are software solutions for that too where you can block out time or limit the number of people that can be invited to a meeting. There are all kinds of solutions. And if your organization doesn’t have one of those, probably have a look at one of those.

Dorie Clark: 14:58
Definitely. I had a very senior leader as a client, and she was coming to me with a problem. She said, “Oh, you know, so busy. I’m so busy. I have so many meetings.” I said, “Okay, we’ll talk to me about this. Why do you have so many meetings?” She said, “Oh, well, you know, everybody keeps putting me into meetings on my calendar.” And I’m like, ‘What? This is not even a problem that we have to solve, just fix the calendar so they can’t do that. You’re the boss. You don’t get bossed around by other people who tell you to be in a meeting. Come on, let’s pull up the script here. And she was just like, “Whoa, really?” And I’m like, “Yes.” And I think it’s so important, we have to exercise autonomy. Now, of course, for everybody, there are some meetings that we have to attend. But you get to vote, you get to ask questions. You should not just be shanghaied into attending something because somebody without your permission plucked it on your calendar.

Roger Dooley: 15:49
I think saying no is pretty good advice. It’s pretty common advice among people who try and help individuals with their productivity, with getting more done, with not leading a crazy life. You give an example that was surprising, where you had a speech invitation in Grand Cayman, and you decided that maybe that’s something you should say no to. I was looking at that, was that really the right decision? Maybe you could have given up the speech in Peoria, and the other one in Kansas or something. But explain what your rationale was, Dorie, in that?

Dorie Clark: 16:24
Yes, yes. So, as you mentioned, Roger, in “The Long Game”, I tell the story about a speaking engagement that I turned down. And it was an unpaid speaking engagement, but it was essentially an all-expenses-paid trip to Grand Cayman where I would give a speech and then get to spend a week hanging out with a friend that invited me and some cool people. And so, it was very appealing.

Roger Dooley: 16:47
It sounds horrible, Dorie.

Dorie Clark: 16:48
[laughs]. Oh, I know the things, I endure [laughs]. But I actually ended up saying no to it, which was a little stressful for me. I was going back and forth about whether it was the right move. But ultimately, a point that I make in “The Long Game” that I think is important for us as we get busier and busier, as we get more and more professional opportunities is that we need to really understand the complete cost, the total cost of the things that we say yes to. So often for many of us, and this was my initial impulse, the question we ask is, “Well, could I do it? Do I have a conflict in the calendar?” And if the answer is no, then we say, “Oh, well, I should just do that. That’s cool.” But ultimately, what I realized and part of why I said no, was I zoomed out a little bit and I looked at it, I said, “Oh, wait, I could technically do this, but the week before I’m traveling for work, the week after I’m traveling for work, and those are paid engagements. Do I really want to travel three weeks in a row? No, that sounds really exhausting. Do I want to turn down a paid engagement for an unpaid engagement? No.” And part of the major attraction as I peeled it back was, Oh, well, it would be time to spend with my friend. I haven’t seen my friend enough.” And then I realized, it’s like Dorie, you idiot, she lives in Brooklyn, you live in Manhattan, it’s not that hard. You don’t have to go to Grand Cayman to make this happen. And so, that is how I ended up turning down the engagement. But I think for a lot of us, the impulse is literally just does it fit in the calendar? Okay, yes. And we’re not considering the total cost or the opportunity cost of it.

Roger Dooley: 16:50
That’s amusing. But often that’s the case, Dorie, I find. A friend of mine, very close to me in Austin, in fact, he’s moved now just a few blocks away from me, I mainly see him at conferences, and on social media. We interact all the time on social media, but somehow, we can never quite arrange the lunch date or whatever. But we end up meeting in Las Vegas, or Orlando, or someplace like that, which is really bizarre.

Dorie Clark: 18:28
So true.

Roger Dooley: 18:29
Yeah. Dorie, talk about why maybe you should choose to be bad at some things.

Dorie Clark: 18:58
Yes. So, this is a part of the book that I like a lot. Because I think for so many of us, of course, we always try to concentrate on, “Well, Roger, what do you want to be cray? Where do you want to excel?” That’s a fun conversation to have. And of course, we should be asking ourselves that. But what most people are not willing to do. And this is an essential part of strategy. Strategy is equally about what are you going to be great at, and what are you going to sacrifice in order to be great at? And the problem, everybody wants to be great at something, no one wants to make that sacrifice. And so, if you really want to be one of the few that can truly excel, you have to be willing to do both. And if you are, it’s very, very rare. And so, part of the inspiration for this question comes from the work of Francis Frey and Anne Morris. Francis is a professor at Harvard Business School, Anne is an entrepreneur. And they wrote a book several years ago called uncommon service, where they talked about success in service industry businesses. And they really explore this theme about companies. And I read it. I went, oh my god, that’s so true with individuals. What they said is, “Look, you can’t be great. You literally can’t be great if you’re not willing to be bad at something.” And as one example, for instance, you take something like Southwest Airlines. Everybody likes it. “Oh, good. It’s a low-cost airline. That’s nice.” Well, what happens when it’s a low-cost airline? Well, it means that you have really have to hold the line on things like, “You know what, we’re not going to have fancy business lounges. We can’t afford to. We’re not doing that. So, if that’s what’s important to you in an airline, we’re the wrong airline.” Or they cited a bank that stayed open late hours. How did they pay for it? Because they had bad interest rates on their deposits. If you really care about interest rates on your deposits, this is the wrong bank for you. And we have to be willing to make those similar hard choices in our own lives.

Roger Dooley: 21:00
What other focus advice do you have?

Dorie Clark: 21:02
Well, ultimately, when it comes to choosing your area of focus, something that I like to mention is we often put a lot of pressure on ourselves. People understand, right? They want to have a strategy. It’s good to have a strategy. That’s encouraged. But the problem is that people sometimes feel like if they don’t have a strategy, they feel terrible about themselves. They just don’t know and they feel so paralyzed. They often feel like they can’t do anything until they get the strategy. And I really want to drive home a point that increasingly is popular in Silicon Valley, as we think about the process of experimentally developing products in the lean startup methodology, that it’s a lot harder to think your way to action than it is to act your way to thinking. And so, what I mean by that is, and this is a theme we talked about in “The Long Game”, you might not know what your passion in life is, for instance. It’s okay. It doesn’t mean you have to sit still and stay at a terrible job or whatever, until you discover your passion. I have a concept I talk about called optimize for interesting. The basic idea is, look, who knows if something is your passion in life. That’s kind of hard to figure out anyway. Just is it interesting? And if something is interesting, you do a little bit with it, you move a little bit more toward it. If it stays interesting, well, you know what? Keep doing it. And if it doesn’t, you find something else. But if we lower the stakes, it lowers the bar to action. And it is through action, that we can actually discover the strategy, we can actually discover, oh, this is really compelling to me, or oh, the marketplace seems to be really responding to this, let’s do more.

Roger Dooley: 22:40
I like the “optimize for interesting” part. Because so often you run into people who are stuck in careers that they don’t find interesting. Attorneys who spend all day reading contracts, which sounds like punishment to me, but I guess they’re probably some attorneys really like that, tweaking that language, just the right way, and so on. But there are certainly others who find it kind of mind-numbing after a while, but they really have no way out of that without taking massive pay cuts. So, yeah, I think if you start with interesting, hopefully, you can monetize it. Maybe you can’t monetize it, but if it stays interesting, and if you’re able to earn a living doing that, then you’ve really found that sweet spot.

Dorie Clark: 23:18
Oh, my gosh, absolutely. And in another section of “The Long Game” I actually talk about the importance of applying in our own lives, Google’s 20% Time policy. And for folks who are not familiar with it, Google encourages its employees to spend up to 20% of their time on these more speculative activities outside their typical job description. It’s how Google News was developed; it’s how Gmail was developed. And I want to argue that we should do it as well. Because the beauty of 20% time is if it turns out it doesn’t pan out, if it’s sort of a “failed experiment”, it’s okay. 20% of your time, your energy is not going to bankrupt anybody. You have plenty of your time and attention on other things that are much more secure. But if it actually turns out that that 20% is allocated to something that kind of is interesting, it could be a thing, it is enough time, that if you compound it, you spend a few months, you spend a year, a few years on it, all of a sudden, you have built up an amazing side gig, an amazing side career, an amazing new direction that you can potentially transition into, that gives you access to the kind of new opportunities that can be genuinely exciting and lucrative.

Roger Dooley: 24:25
Now that sounds actually very reminiscent of my own career, those parts of my own career where I’ve always tried to have some weird little hobby thing going, maybe more than one sometimes. When digital marketing began to be a thing, I started up a bunch of little websites and whatnot that didn’t really know where they were going to go, but they were all about things that I found interesting. One of them turned out to be neuromarketing. That ended up becoming part of my full-time gig here, even today. Another was I had an interest in college admissions. I’d helped my kids through the process and found that it was an incredibly probably confusing process for most normal people, particularly if they did not have their child at a school that offers tremendous college counseling. If your kid is going to Andover something, chances are, they’re going to get a lot of help with the college process. If your kid is going to the number seven High School in your city, chances are, they’re going to get zero help with their college process or zero useful help. So, that ended up growing and growing, and ultimately we sold the business to Daily Mail group, it became the biggest website for college-bound students and parents. But these were all things that were initially sort of interest projects. They’re kind of fun. They grew, and they got traction. And then of course, once something gets traction, they can say, “Okay, this is worth pouring more time, more effort, more occasionally money into.” But the interest part is really important. The last part of the book is all about keeping the faith Early in the book you talked about… I forget who you quote, but basically paraphrasing, things always take longer than you expect. And I think that’d be true of anybody who’s ever been involved in software development, or these days in any kind of construction project here in Texas. But explain a little bit about that, and how you keep going through all this?

Dorie Clark: 26:17
Yeah, well, it’s, it’s certainly it’s true. Who wouldn’t like an overnight success? We all would, right? But it’s just so rare that it actually happens. And so, one of the reasons that I wrote: “The Long Game” was to hopefully serve as a form of encouragement for people who many of them are like my coaching clients that I work with, or people in my recognized expert community, which is an online course of community that I’ve been running for the past five years, where they’re smart, talented people, they have great ideas that they want to share on a wider stage but it can be a really hard and frustrating process to get there. And what I don’t want to happen is for someone with something really valuable and useful to share to give up too soon because “This will never work.” They try it for a little bit and then they say, “No, no, it’s not going to happen.” Ultimately, because things do take a long time, I wanted to create a book with a long game that helps people really think through and understand the process of what it takes to get your ideas known and heard. And hopefully, to provide some ammunition so that in those dark times when you are not sure, you’re legitimately not sure if something is not working, or if something’s not working yet, that you will be able to better tell the difference and make that judgment so that you can persevere when it is the right choice and get through to the other side to get where you need to go.

Roger Dooley: 27:40
I know that you have a self-assessment that our audience members can become part of. Why don’t you tell folks where they can find that, how they can find you and interact with you?

Dorie Clark: 27:51
Yeah, absolutely, Roger. Thank you so much. So, I do have a free self-assessment. It’s the long game strategic thinking self-assessment and folks who are interested can get it for free at dorieclark.com/thelonggame.

Roger Dooley: 28:05
Okay, we will link there, and to any other resources we mentioned on the show notes page at rogerdooley.com/podcast. We’ll have audio, video, and text versions there as well. Dorie, it’s been great to connect with you again. Maybe someday we’ll be able to connect in person, hopefully not before too long.

Dorie Clark: 28:22
Yes, Roger, thank you so much. Great to get to spend the time with you.

Outro: 28:25
Thank you for tuning in to Brainfluence. To find more episodes like this one, and to access all of Roger’s books, articles, videos, and resources, the best starting point is rogerdooley.com. To check availability for a game-changing Keynote or workshop in person or virtual visit rogerdooley.com.