I’m of the Letterman generation. I began college the same year Late Night debuted on NBC.

Better observers of television and comedy have better summed up why Letterman is significant. (I love Jimmy Kimmel’s take.) But to me he was just real. He didn’t treat television like it was a big deal, and he didn’t treat people who thought they were a big deal like they were a big deal.

His show was irreverent and unpredictable and fun. His timing and self-deprecating humor and wry asides influenced the way I communicate and attempt humor and the way I respond to others. I’ve realized even some of my facial expressions are Letterman inspired.

I listened to Jason Snell’s The Incomparable podcast about Letterman yesterday on a long drive home from the holiday weekend. The podcast was really well done and right in the wheelhouse of someone who would regularly stay up late in the dorm lobby to catch at least a portion of Late Night.

The podcast reminded me that when Letterman got the Late Night gig airing immediately following The Tonight Show, Johnny Carson’s team at NBC put some restrictions on what Letterman could do on his show. He could have no more than four band members and could tell only four jokes in his monologue. They wanted to protect their turf at The Tonight Show and not risk some young upstart stealing their stuff.

But Letterman used those restrictions to reinvent the talk show and to come up with something unique to him. Bizarre, wacky, occasionally cringe-inducing, but so refreshingly unique.

Years later when Carson retired, everyone assumed The Tonight Show would go to Letterman. It was Letterman’s dream, and Carson saw him as his natural successor. But the suits at NBC gave the job to Jay Leno instead.

Again, though, Letterman ended up embracing this setback and used that disappointment to do something better. He moved to CBS, started The Late Show, and competed head-to-head with The Tonight Show.

But he got to stay in New York and keep doing his unique version of a talk show, just on a bigger stage and an hour earlier. He’s even said that if he had been given The Tonight Show, he probably would have just followed Carson’s formula out of respect for the institutions that The Tonight Show and Carson were.

It was the restrictions and the disappointment and the obstacles that Letterman used to shape himself and his show into the cultural forces they became. He didn’t end up winning the ratings war, but his influence resonates as no other television personality’s has since Carson.

Heartbreak? Disappointment? Obstacles in the way? Dream job falls through? Accept a bad turn of events as if you had chosen it to happen that way. Then get busy transforming that setback into previously unimagined possibilities. Turn your obstacles into fuel to propel you further and higher.