One of the world’s foremost thinkers on business and social science, Daniel Pink is the author of several bestselling books on business, work, and behavior. He joined Ryan Hawk, the creator and host of The Learning Leader Show, to talk about the critical components of sustaining excellence, what it was like writing speeches for Al Gore, and how Dan left his comfort zone to bring his side hustle front and center.
This conversation has been edited and condensed. To listen to Daniel and Ryan’s full conversation, click here.
Ryan: You’ve been fortunate to spend an immense amount of time around people who’ve sustained excellence over time, whether it’s talking to them, writing about them, interviewing them for books—and you are one of these people yourself. I’m curious, what are a few of the things that those people all seem to share?
Dan: One of them would be curiosity. They follow their noses, they remain interested in stuff, even if they know a lot of stuff—especially if they know a lot of stuff. One of the consequences of knowing a lot of stuff is you realize how little you know, and so, there’s a lot more to be curious about.
The second thing is that, not uniformly, but in many, many cases, there’s an element of generosity to these folks that might surprise you. They’re willing to help other people out, they’re not people who pull up the ladder once they get on the top.
And the third thing is they are extraordinarily hardworking and conscientious. The old-fashioned virtues of persistence and grit and conscientiousness are their hallmarks.
Ryan: I’d love to dive into your story to find how you’ve gotten to where you are today.
Dan: I think that in life, there’s an enormous amount of serendipity and randomness and, to some extent, luck. I grew up in Ohio and had a sort of normal middle-class childhood. Went to Northwestern thinking I would study journalism, but instead studied linguistics, graduated from college, didn’t know what I wanted to do, [had some] dead-end jobs, [did] a little bit of traveling, and then, finally I went to law school. I didn’t really like it very much [and] knew pretty quickly that I didn’t want to be a lawyer. I met my wife in law school, so it was a great move on [that] front, but otherwise, it was just a colossal mistake. Graduated massively in debt and never practiced law.
“My wife finally convinced me that maybe what I was doing on the side is what I should be doing in the center.”
Instead, I started working in politics because I was–emphasis on the past tense–deeply interested in politics. This is where the serendipity and the lack of planning comes in—I became a speechwriter basically because somebody asked me to write a speech. And I did it reasonably well and they asked me to write another one. And I did that reasonably well and they asked me to write another one, and suddenly, that’s what I was doing. [I] became a speechwriter for the labor secretary at the time, Robert Reich. Did that for a few years and then the job as chief speechwriter for then-Vice President Gore came open. Speechwriters are kind of like managers in Major League baseball—there aren’t that many people who can do the job, and so, it’s always the same group of people for every opening.
It just happened to be my turn in the rotation, I guess, and I got that job. And I liked the people I worked with quite a bit. I really liked working for Al Gore, not just because he was Vice President, but he’s a terrific guy. But I ended up realizing that I didn’t like politics very much. It just was so much nonsense, I just couldn’t really stand it. And I also realized I wanted to do my own thing, and I’d always written a lot on the side. I’d written magazine articles and newspaper columns, but never thought I would do it as the center of what I did, but my wife finally convinced me that maybe what I was doing on the side is what I should be doing in the center.
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And so, I left, saying I didn’t want to become a career political hack, and I decided to try to write under my own byline. The house that we lived in at the time had a third-floor attic that became my office. I just tried to follow what I was curious about and do work that I was proud of, but do it in a way that was strategic enough that my kids had winter coats. And then, you know, lather, rinse, repeat.
Ryan: What was the process like in order to make that jump, to say, “You know, I’m not into this politics thing. I can write speeches, I’m a pretty good writer. I’d like to write [under] my own byline”? How long did it take before you were actually making money and making it a career?
Dan: In terms of what I did, which [is] what I would advise people to do: this is one of those areas where you take a small step or two rather than a giant leap. And the small step or two went like this. First of all, I had been doing writing on the side before, so it wasn’t like, “Oh, I’m going to become a ukulele player even though I’ve never picked up a ukulele.” So before I left, I negotiated a very modest contract to do some articles for a magazine.
Now, my wife happened to be a lawyer at the U.S. Department of Justice. She kept her job and her health insurance. So it wasn’t like, “We’re going to go from having an income to having no income.” [It was], “We’re going to go from having two relatively modest incomes to having one relatively modest income for a little while, while we try to bump up the second income.” And so, I think you take a small step and [have] low overhead. I have never had an office that I’ve paid rent for.
Dan: We had one house, I worked on the third floor. Then we moved a mile away, and we converted the garage behind the house and made Pink Inc. world headquarters. I have never paid rent for an office. Indeed, I have always deducted the cost of my office on my taxes.
So, low overhead. Right now, I’m organized as an S corporation. There are two employees at our S corporation: me and my wife. I’ve never had another employee. Et cetera. [Another] small thing: I haven’t had business cards for four or five years. I think frugality and low overhead [is key]. It’s an ethic that is enormously important.
Ryan: I have a background in the profession of sales, the first job I had when I got done playing football. I still think of myself as a sales professional, even though I’ve progressed into other things because I believe, as I know you do, that we’re selling every day and it’s a noble profession. What are some of the qualities you [would] look for to hire in a role that is all sales?
Dan: Conscientiousness [is] incredibly important in every realm, but certainly in sales. Do you say what you’re going to do? Do you follow up? I would [also] look for the willingness to develop expertise. Today in sales, expertise matters more than ever before. If your customer, your prospect, knows exactly what they need, they don’t need you very much. Let’s take B2B. If you’re in B2B, you have to understand your prospect’s business better than they do in some cases.
One thing that I think is a little counterintuitive for people, but comes out of the research, which I wrote about in To Sell is Human, is what’s called ambiversion. There’s a methodology out there that strong extroverts make the best salespeople. There’s absolutely no proof of that. But that doesn’t mean that strong introverts are better. There’s some great research from Adam Grant showing that the best salespeople are what are called ambiverts. They are not strong extroverts, they are not strong introverts, they’re kind of in the middle. They’re a little bit of both. So, I would look for conscientious person who’s ambiverted and willing to develop expertise.
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Ryan: Let’s take it back to 2009. You’re preparing for your TED talk, “The Puzzle of Motivation.” Did you have any grand thoughts that this could blow you up, make you go viral all throughout the internet and really put your name on the map? What was your thought process preparing for the speech, and what did you hope would happen when it was published?
Dan: I mean, I just wanted to do a good job. I wasn’t even thinking about the virality of it. If you’re aiming for [virality], you’re going to miss much more often than you’re going to hit. So, you’re best off doing something that’s meaningful, that helps the audience, and that you’re proud of.
“If you’re aiming for [virality], you’re going to miss much more often than you’re going to hit. So, you’re best off doing something that’s meaningful, that helps the audience, and that you’re proud of. ”
Ryan: In your TED talk, [you talk about] a mismatch between what science knows and what business does: how we reward people, how we incentivize them, how we think we motivate people. Now that some time has passed, have you developed that more?
Dan: If you look at the totality of the research that’s embodied in Drive, there’s a considerable amount of nuance. But basically, 50 years of social science tells us that if/then rewards are extremely effective for simple algorithmic, short-term, routine tasks. If you’re following a recipe, you know exactly what you need to do, the finish line is pretty close, those kinds of rewards are pretty effective.
But the same body of evidence tells us that those kinds of rewards are far less effective for more complex, creative work with longer time horizons. And the mistake we make is that we use if/then rewards for everything, rather than the area where we know that they work. And when we apply them in areas where they don’t work, instead of saying, “Oh, let’s try something new,” we say, “Oh, let’s double down on that outdated approach.” And so what I was doing in the book and what I tried to do in that short talk was try to take this very large body of research, which was scattered all over the place but was saying some extraordinarily important things, and try to channel that, distill that so that it was understandable and actionable for people outside of the academy.
“The mistake we make is that we use if/then rewards for everything, rather than the area where we know that they work.”
Ryan: People that listen to podcasts, that read books, that know all your work, these are types who typically give themselves better odds and better chances to achieve levels of success over longer periods of time. They’re learners, they’re trying to improve, trying to get better. But when it comes to implementation and execution we fall apart. Why do you think that is, and what is something that we could do to help fix that?
Dan: It’s a great question. We’re taking on too much. If you read a book, and say, “Great, I’m going to go back and, on the basis of this book, can I change everything in my life?” Or, “Can I change everything in my organization?” The answer is no, you can’t. I don’t care what book you read. Because the world doesn’t work that way.
To my mind, you’re asking the wrong question. The question you should be asking is, “Can I do one small thing tomorrow to make things a little bit better?” And the answer is almost always yes.
I really think that we have given short shrift to the concept of small wins, both in terms of personal development and organizational performance. We want big, audacious goals, we want moon shots, we want giant transformations—and that’s cool sometimes. Sometimes that’s the approach. But most times, the more practical, realistic, and ultimately effective way is to go for a small win.
“The question you should be asking is, “Can I do one small thing tomorrow to make things a little bit better?” And the answer is almost always yes.”
Ryan: It’s really interesting you say that. It brought me back to when I was in college. I sent an email to Drew Brees, quarterback now of the Saints. Drew was still in college at the time and I told him I admired him and maybe he could give me some pointers to help me. And he wrote me back and said, “Focus on moving the chains, man.”
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“You move the chains and everything usually works out.” Which, to non-football people, that means just getting the first down, because if you do that enough, you’re going to be successful.
Dan: I love that. And I think that’s true in so many different realms.
That’s true in the realm of organization development. That’s something Jim Collins has researched. Even though Jim has talked about big, hairy, audacious goals, he also talks about the concept of the flywheel, where you’re pushed [to] getting that momentum going.
If you talk about personal development in terms of habit formation or even something like getting in better physical shape, you don’t say, “Okay, I’m going to start running and I’m going to start swimming and I’m going to become a vegan.” What you say is, “Okay, I haven’t run before, so I’m going to take a mile walk every day for a week. And then, the next week, I’m going to take a two-mile walk every day. And then, the next week, I’m going to maybe try a one-mile jog.”
And that’s how you do it. You just move the chains.