Why You Don’t Need a Five-Year Plan

“Genuine ambiguity is much more useful than false certainty.”

READ ON TO DISCOVER:

  • What an Adam Sandler movie can teach us about career paths
  • Why a promotion is the last thing some people want
  • Why your professional life should resemble chess mixed with improv theater

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. Award-winning podcaster David Burkus recently hosted him on Radio Free Leader to talk about why curiosity and adaptability, not a rigid five-year plan, will guide you to the job of your dreams.

David: I don’t know if you’ve ever seen Big Daddy, but there’s a running gag about so-and-so has a five-year plan, and he ends up working at a burger joint. People feel like they’re supposed to have that broader career plan, and then when you look at people who are really in their dream job, they’re like, “I don’t know [how I got here]. I followed a bunch of interesting things.”

You have a 19-year-old, a 16-year-old, and a 13-year-old. How do you give [them] career advice in that regard?

Daniel: You don’t. What you do is give them values and life advice, and you try to be a good role model. You don’t say, “You should go into X, Y, or Z.” You say, “What’s really important is to do something you’re genuinely interested in. You’re going to be working really hard, [so] you might as well work really hard at something you find interesting.” And a dirty little secret is that if you do something that you’re interested in, you’re going to be better at it than if you’re doing something you’re not particularly interested in.

To disabuse them of the notion that you have to have this strategic five-year plan, say, “Listen, let me tell you what happened to me. I hopscotched my way around in a somewhat half-assed way, but I was focused on making the next thing interesting and valuable, and dealing with the ambiguity of not knowing precisely where it was gonna lead next. And here’s a life lesson: genuine ambiguity is much more useful than false certainty.”

My best advice to young people is, “Go find someone who’s doing something you’re interested in, someone you look at and say, ‘Wow, I would love to be doing that someday,’ and then ask them how they got there.”

And nine times out of ten, that really interesting person is going to answer that question with, “It’s a long story.” Because they weren’t mapping it out. They were making decisions in the moment that were right for them, that were built on a set of values and inspired by curiosity, and they were able to deal with the ambiguity that accompanies that.

“Genuine ambiguity is much more useful than false certainty.”

David: Do you think that applies at a broader level? So if you’re leading an organization, should we be more reactive?

Daniel: That’s a really good question. If you’re talking about, say, specific career development plans inside of a firm, then I think you want to have some amount of structure. It’s all a balance between loose and tight. Loose is this kind of free-for-all, “I’ll just follow my bliss and do what I want.” Tight is, “I have a set of moves that I have to execute.” I think it’s somewhere in between there. So for career development inside of a firm, you might be able to chart out, “Here are three possible paths.” But not say, “There’s this one path, that leads to this result, and I have to go through it in this sequence.” I think that’s dangerous. I think it’s also dangerous saying, “Oh, we’ll just willy-nilly see what happens.”

And I think that’s true, personally. It’s not as if I get to the end of writing a book, and say, “Jeez, I have no idea what I wanna do with my life. Maybe I should be a professional handball player. Maybe I should go become a lumberjack.” It’s basically saying, “Huh, there is a handful of things that I’m interested in. I can see these different kinds of paths out there, but I haven’t committed to any single one, and I certainly haven’t set out specific turn-by-turn instructions of how to get to a particular point.”

David: Like chess, there’s not one perfect sequence. The best competitors think in four or five different sequences, depending on where you are in the game.

Daniel: The limit of the chess analogy, though, is that in chess, everybody’s aiming for the same outcome. Everybody’s aiming for checkmate. Life isn’t a game [like that]. Your checkmate and my checkmate could be wildly different things.

I think you want to think about it as somewhere between chess and improv theater. Maybe even more toward improv theater, because improv requires preparation, curiosity, and the ability to respond, but you don’t necessarily know what the destination is in advance.

game of chess

David: I like the idea that everybody has a different definition of winning. That’s interesting because when most people plug themselves into a large organization, once there’s a hierarchy, there is a pull to feel like there is a checkmate, and it’s moving up the hierarchy. And I think that explains why so many people are miserable, right? Because they thought they were supposed to go along this route, and in reality it’s not working.

Daniel: You’re totally right. But I put the [responsibility] for that more on the organization than on the individual. In creative and technical fields, if you have somebody who is great at writing software or a great designer, the organization loves them and wants to keep their talent. [So] they might promote them. And a promotion could mean watching other people code or watching other people make great designs.

And [then] they’re no longer doing what they love to do and what they’re great at. Instead, they’re managing people who are doing what they love to do, because that was the only path available to them, and so they exit.

So what you see some places doing, particularly in technical fields, is something like, “Okay this person is a great coder, this person’s a great engineer,” so they’ll create positions like Senior Scientist, Senior Fellow, or something like that.

“If you do something that you’re interested in, you’re going to be better at it than if you’re doing something you’re not particularly interested in.”

Same thing is true with teachers. You have a lot of great teachers, and what we say with many great teachers is, “Let’s make them principals.” But a lot of teachers don’t want to be principals. At some level you either stay as a classroom teacher for 31 years, or you become an administrator. And so some school districts are actually carving out an alternative path, which is Senior Teacher, Mentor Teacher, something like that. Inside of firms, there is a great need for coming up with some of those alternative paths.

David: I totally agree. And [there’s] the fact that the average tenure in one organization is shrinking, [although human lives are] getting longer, which is really odd.

Daniel: Exactly, we have two countervailing trends. You have human longevity going longer and longer, and you have corporate longevity — how long a particular company will be alive — shortening and shortening. The half-life of corporations is shrinking at the same time that the life of human beings is increasing. That makes it impossible for some of us to have lifetime employment if we’re going to be alive longer than the organization we’re working for.

David: And that makes that planned spontaneity we were talking about even more important. Because if you’re going to work for twice as long as your parents worked, and companies are going to last half as long, then you have to be more open to multiple different pathways. It may be the only possible solution for staying sane.

 

This conversation has been edited and condensed.