Somewhere along the way, I developed something of a borderline obsession with Don Rickles. Maybe I’m just a sucker for good timing and put-down comics, but to me, the man was (and is) one of the most naturally funny human beings to walk the earth.

Turns out he was also a teacher.

Now, maybe the whole thing Jeff Ross went through at Don’s memorial was pure coincidence… maybe not. Personally, I’d like to think that somewhere in planning for the end of his life, Rickles decided there was room for one more jab and took it. Partly for the laugh, but partly because from all accounts, he was a warmhearted guy.

But it’s a lesson for everyone, really. You’re really, really good at planning? Great. Don’t stop doing that, but maybe you ought to get out of your comfort zone and do something in the moment with zero prep. Improvise. Make mistakes. Fall flat on your ass. Or maybe succeed. Either way, it’ll be an experience you can learn from. Same goes the other way around. Never plan? Great. Now sit down and try to formulate a plan and follow it through. Get completely confused and frustrated. Probably get tied up in knots.

Doing the same thing the same way can be an incredible tool, but you’ll never learn if there’s a better tool (or one that can be used at specific times) if you never look back inside the box.