I never watched Conan, at 12:30 or 11:30, until the last show. And I have to say that I was impressed with the energy and the feeling of it; it reminded me of Letterman in the old days. Obviously this loose, fun tone was driven by the situation, and the fact that he had nothing to lose.
Having that responsibility lifted from your shoulders can be an amazing creative enabler. I once got into theatre school at York after doing a kickass audition piece as Lenny from Pinter's Homecoming. The problem was, it was only kickass because about five minutes before going before the judges, I had decided that I didn't want to spend the next four years with a bunch of hams-in-training. I literally had to be sitting outside that room to figure out that in my heart I knew I wasn't an actor. That freedom was only one reason that I was decent enough (that one and only time) to get accepted, and it was absolutely impossible to replicate that.
I guess the question for us regular employment-type agency folk is, how do you keep that lightness, that fun, in your work over the long term? There are a whole bunch of MBA-ese qualities that help set that stage, like respect, good communication, and other noble corporate virtues.
More than anything, I think it's about tone. Of course you take the job and the client's business seriously, but you don't take yourself or The Advertising Business too seriously. I'm not standing around pontificating or pushing marketing ideology, and neither is anyone else here. Being part of the reality-based community means that you value the time and experience of the people around you. In other words, you listen. And our team is loose enough that when someone (for example, me) fucks up, no one is afraid to say so.
Having a tendency to self-deprecation is also a real plus, in my eyes. Most of the best people I've ever worked with tend to play down their abilities on a day-to-day basis. They love their work and their craft, but they don't boast about their skills or victories.
Because you probably don't want to spend your days at work with someone who's looking to, as another Conan said, "crush your enemies, to see them driven before you, and to hear the lamentations of their women."
Slightly unthematic but related follow-up: In baseball, apparently, other players will say of a really good player, "He can play a little." That feels right.