Tonight, David Letterman will sign off for the last time. Now you may say, “Everyone is gushing about Letterman, the last thing the internet needs is another ‘Thanks, Dave’ post.”

Well, that’s too damn bad for you, Paco, because this is my blog and I get to write about whatever the hell I want. Go start your own blog. It’s free.

Watching the retrospectives over the past few months, the reason it’s so sad that Letterman is leaving is that it is so clearly time. Even if he reversed course tonight and said, “Nah! I’m coming back!” he couldn’t recapture the edge he had from his earlier days.

I’ve watched Letterman regularly since the early 1990s, starting out when A&E ran reruns of Late Night at 7:00 p.m. For Christmas 1993, I got a portable, broadcast-signal-only TV. The station that came in clearest was the CBS affiliate out of Philadelphia – and that was all I needed as I watched the Late Show every night. In 1995 I moved to Massachusetts (and got a normal-sized TV); even as many things in my life changed, Letterman was there. One of the best compliments I ever received was during sophomore year of high school, when a classmate turned to me and said, “You know, you remind me a lot of David Letterman.” We weren’t even talking about Letterman at the time.

Not to romanticize the man – Lord knows, he’s had flaws aplenty. But watching his shows, I have taken away some pretty valuable lessons – things that apply to politics, careers, relationships, or anything else you’re getting into these days. If only there was a thematically appropriate way to present these lessons in an ordered fashion…

TOP TEN LESSONS FROM DAVID LETTERMAN

10. Build your own road. There’s room. In 1991, when Letterman was passed over for the Tonight Show, there was Johnny Carson on at night and not much else. Arsenio Hall targeted younger demographics and black audiences, and Nightline was there for the news junkies, but there was only one late night talk show. Now there are at least five. Letterman may not have topped Leno in the ratings after 1995; but by striking out from the safety of his 12:30 Late Night time slot in 1993 – and creating his own show – he found more success.  In the process, he’s become the cornerstone for two late night franchises. Not even Carson could say that.

9. Don’t take yourself too seriously. From goofy hair to the gap between his front teeth, Letterman has never been shy about cracking jokes at his own expense. The occasional rough edge is much easier for others to stomach when you make yourself the target now and then.

8. Everyone has a story (and a joke) to tell. With non-celebrity guests – from audience members to kids who won science contests – Letterman really shined, showing genuine interest in what they had to say. He turned his neighbors around the Ed Sullivan Theater into stars. Being generous with the spotlight made Dave look better in the end.

7. Don’t be intimidated by anyone. …And when the person sharing the spotlight thought too much of themselves, Letterman was never afraid to knock them down a peg or two. (Even big stars like Madonna and Cher.)

6. There is such a thing as good-natured cynicism. Each week, Family Guy does a send-up of the sitcom family trope. The characters assault each other verbally, emotionally, and physically. It’s funny, but you wouldn’t say it’s rewarding. Letterman may have been caustic and sarcastic, but at least you knew there was always a smile on the other side of it.

5. Be respectful. When Letterman left NBC, he also left the blazers-and-sneakers look behind; he understood the investment CBS made in him (a $14 million per year contract) and wanted to at least look nice. That shows a level of respect that isn’t readily apparent in the irreverance. It extended to the audience, too. Daniel Kellison, the segment producer for the infamous 1994 Madonna interview wrote about Letterman’s real problem with the Material Girl’s f-bombs: “He always understood the privilege that came with the ability to broadcast, and the responsibility that accompanied it. Ratings and press were less a consideration.”

4. Rely on your team. Paul Shaffer said that Letterman told him from the beginning to jump in with comments anytime – whether it was during the monologue, during an interview, anywhere. Stage hands, producers, directors, writers, and staff all found themselves on the air. Letterman understood what he did was nothing special, and that talent was everywhere around him.

3. Great things can come from heartbreak. As mentioned above, Letterman is a late night legacy on two different networks, and at two different time slots. None of it could have happened without the crushing disappointment of losing his dream job. Sometimes the bad breaks work out. Everything happens for a reason.

2. Remember how lucky you are. As Letterman himself said, “I cannot sing, dance, or act. What else would I be but a talk show host?”

1. Have fun. I couldn’t tell you exactly when it happened, but my all-time favorite memory came when Letterman, in the middle of a monologue or a bit, called out to no one in particular, “Who has more fun than we do?” Dutifully, Shaffer enthusiastically hollered from off camera, “Nobody, Dave!” It was a small, throw-away moment that didn’t seem rehearsed. Few people probably gave a second thought to it two minutes after it happened, let alone in the decades since.

Yet it always stuck with me as the epitome of Letterman’s attitude toward his own show. Even when the jokes were bombing or the guests were lame, it seemed like Dave and Company understood that there would always be another show. At least until tonight.

This may be the most important lasting lesson of the David Letterman era. In every office I have ever worked at in my professional life, I have, at some particularly tense or busy time, called out loudly, “Who has more fun than we do?” The answer has always come back (from folks I’m certain weren’t avid Letterman fans): “Nobody!” Without fail.

Johnny Carson might have invented late night television as we know it. Jay Leno might have bested him in the ratings. Jimmy Fallon might have merged the TV and internet age better than anyone.

But who had more fun than David Letterman?