Stephen Colbert on Life as an Improv

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Stephen Colbert is a compelling commencement speaker. If he were to tweet his advice to graduates this year, it might read something like this:

Follow your dreams. Service is love made visible. Life is an improv. And as you walk your path, say “Yes!” as often as you can.

In earlier posts to this blog, I explored Colbert’s thoughts on what it means to follow our dreams and on the notion that service is love made visible. But what is this business about life as an improvisation? And why does Colbert tell graduates to say “yes” as often as they can?

In his address to the graduating class of 2011 at Northwestern University, his alma mater, Colbert said:

After I graduated from here, I moved down to Chicago and did improv. Now there are very few rules to improvisation, but one of the things I was taught early on is that you are not the most important person in the scene. Everybody else is. And if they are the most important people in the scene, you will naturally pay attention to them and serve them. But the good news is you’re in the scene too. So hopefully, to them, you’re the most important person, and they will serve you. No one is leading; you’re all following the follower, serving the servant. You cannot win improv. And life is an improvisation. You have no idea what’s going to happen next, and you are mostly just making things up as you go along.

Colbert is telling the graduates that in life, what’s going to happen next is uncertain and that they’re going to be making up their plans as they go along. But for IT professionals, that idea might push us a little beyond our comfort zone. After all, IT professionals spend a lot of time and money on developing plans, lining up resources, and delivering results. The idea that we’re just winging it is hard to swallow.

Bear with me. Colbert doesn’t mean this literally. He didn’t become a national brand by winging it. For most of us, on most days, we plan—and our plans work out. I go to the dentist for my six-month checkup on the assigned day, at the assigned time, and I come home with gleaming teeth, a new toothbrush, and advice to floss more regularly. This outcome is exactly as I would have predicted based on my plans. Likewise, when I head out for a trip, I board my flight on the assigned day, at the assigned time, and my bags and I arrive at my destination just as I planned. I walk into a routine meeting with a routine agenda and walk out with expected outcomes.

We live most of our lives based on probabilities, not possibilities. If you’re like most people I know, probabilities guide planning. It is possible that I will win the lottery jackpot, but probably not. If I bet all of my resources on the possibility that I will win the lottery, it is probable that I am courting disgrace and financial ruin. Of course, good planning includes considering possibilities, even dire possibilities.  Sometimes the dentist tells me I’ve cracked a molar and will need to discuss options with a specialist. Sometimes I arrive at my flight’s destination in Chicago, but my travel bags containing all my clothing and toiletries are at that moment winging their way to Boise. Sometimes my routine meeting turns upside down because two people with a simmering feud pick that moment to brawl over an issue that’s trivial to everyone but them. Factoring in disastrous possibilities, no matter how small the likelihood, is part of what we call risk management. Most of the time, though, we build our core strategies around probabilities.

Here’s what I take from my reading of Colbert. Some parts of life are, inevitably, an improv. Probability and possibility switch places. I’m unexpectedly required to make room in my life for the cost, discomfort, and inconvenience of specialized dental care. The freshly pressed suit designed to make a great impression during my keynote speech is not in Chicago, and I have to figure out whether I can get away with wearing the frayed travel jeans that I wore on my flight. Angry people in my routine meeting force me to improvise, on the spot, new plans for meeting outcomes.

Most of what Colbert does in public settings is carefully planned by his handlers. But in a moment of complete candor, he might say that his edge, his secret sauce, is his ability to improvise during those parts of his life that are not scripted. Let’s agree with him for now: Life is an improv. But what does that mean? Does he have some advice about how to “do improv” better?

Five years before his address at Northwestern University, Colbert addressed the Knox College class of 2006. He urged the graduates:

Say “yes” as often as you can. When I was starting out in Chicago, doing improvisational theatre with Second City and other places, there was really only one rule I was taught about improv. That was “yes-and.” In this case, “yes-and” is a verb. To “yes-and.” I yes-and, you yes-and, he, she, or it yes-ands. And yes-anding means that when you go onstage to improvise a scene with no script, you have no idea what’s going to happen, maybe with someone you’ve never met before. To build a scene, you have to accept. To build anything onstage, you have to accept what the other improviser initiates on stage. They say you’re doctors—you’re doctors. And then, you add to that: We’re doctors and we’re trapped in an ice cave. That's the “-and.” And then hopefully they “yes-and” you back. You have to keep your eyes open when you do this. You have to be aware of what the other performer is offering you, so that you can agree and add to it. And through these agreements, you can improvise a scene or a one-act play. And because, by following each other’s lead, neither of you are really in control, it’s more of a mutual discovery than a solo adventure. What happens in a scene is often as much a surprise to you as it is to the audience.

Colbert isn’t the first person to point out the limits of planning. In remarks delivered at the National Defense Executive Reserve Conference in 1957, U.S. President Dwight Eisenhower cited lessons learned during his army career:

Plans are worthless, but planning is everything. There is a very great distinction because when you are planning for an emergency, you must start with this one thing: the very definition of “emergency” is that it is unexpected; therefore, it is not going to happen the way you are planning.

So, the first thing you do is to take all the plans off the top shelf and throw them out the window and start once more. But if you haven’t been planning, you can’t start to work, intelligently at least.

That is the reason it is so important to plan, to keep yourselves steeped in the character of the problem that you may one day be called upon to solve—or to help to solve.

Eisenhower and Colbert may seem like strange bedfellows, but aren’t they saying much the same thing? They are advising us that it is essential to plan: schedule that regular dental checkup, press that suit and book that flight to Chicago, and distribute that agenda for that routine meeting. In addition, Eisenhower and Colbert are observing that although plans are necessary, they are not sufficient. Eisenhower might have reminded us that sticking to the plan even as actual conditions deteriorate could be a prescription for disaster in the grim and ugly chaos of battle. And Colbert might be saying something that at first sounds paradoxical: for your plan to succeed, you must plan to improvise.

Planning to improvise requires colleagues, friends, lovers, family, associates, and even new people who enter your world at the very moment that improvisation becomes essential. When Eisenhower was a general in the army, leading the massive Allied invasion of Normandy on D-Day, he might have said: You need your squad, your buddies, the people who have your back—and maybe even the villagers you met only five minutes ago who know the terrain better than you.

Let’s go back to Colbert’s address at Knox College. He reminded us that improv works best when we say yes as often as we can. When I say yes in my everyday work, I am accepting “what the other improviser initiates on stage.” When I say yes-and, I am agreeing and adding to it. When my fellow improvisers say yes-and in return, our improv—our new plan—becomes “more of a mutual discovery and less of a solo adventure.” And that makes all the difference.

I can think of no better way to bring these reflections to a close than to give Stephen Colbert the final word:

Now, will saying “yes” get you in trouble at times? Will saying “yes” lead you to doing some foolish things? Yes it will. But don’t be afraid to be a fool. Remember, you cannot be both young and wise. Young people who pretend to be wise to the ways of the world are mostly just cynics. Cynicism masquerades as wisdom, but it is the farthest thing from it. Because cynics don’t learn anything. Because cynicism is a self-imposed blindness, a rejection of the world because we are afraid it will hurt us or disappoint us. Cynics always say no. But saying “yes” begins things. Saying “yes” is how things grow. Saying “yes” leads to knowledge. . . . So for as long as you have the strength to, say “yes.”