I began High School as David Letterman began his show, The Late Show with David Letterman, on CBS. It was at this time that my parents either thought I was old enough to stay up late enough to watch Letterman or my parents themselves became so old they no longer knew what time I was going to bed. Either way, I watched Letterman every night.

Twenty-one years later, Letterman is wrapping up his run as the host of The Late Show. A lot has changed over those two decades. As a teenager I idolized the man; as an adult I feel a great deal of empathy for him. While his career has been legendary, his success seems tainted by a serious sadness.

I don’t know the man and I would never claim to speak in much certainty about him. But here are a few observations which I think are true about his life. In Letterman-style, these are the Top Ten Lessons from the life of David Letterman:

1. Money might be good, but it’s not everything.

Who wouldn’t want the money of David Letterman? It’s estimated he is worth $400 million. My assumption is that if I had that much money, I would automatically be happy. Yet I’ve never had the sense while watching Letterman that he is happy. While he has long entertained millions every night, his own life has long seemed to have a deep sense of sadness. (See: Money Can Make You Happy)

We don’t have to turn down money, but we are fools if we think money is the key to happiness.

2. Fame often results in the opposite of what it promises.

Like money, fame is often assumed to be a key to life satisfaction. Yet fame, maybe more than anything else in life, gives the opposite of what we expect. With fame comes loneliness. While everyone wants a picture with Letterman and would love to know him, Letterman has always appeared to be very lonely. Rightfully so. With every relationship, Letterman has to wonder if the person really wants to be his friend or actually just desires some of his fame, money, or influence.

Fame might seem appealing, but there is no reason to desire fame because it doesn’t provide what we think it promises.

3. We rarely know what we need the most.

While Letterman has long seemed lonely and unhappy, he appeared most satisfied with life in his later years. What has changed over this past decade was the birth of his son. Letterman has said he never thought he could have children because of the demands of his television show. After having his son, he realized the value of family and the unmatched meaning that comes from marriage and fatherhood. (See: What Down Syndrome Teaches Us All)

While we know a lot, humanity rarely knows what will bring true satisfaction in life.

4. Our private lives can have very public ramifications.

I was a fan of Letterman until his very public sex scandal.  While I appreciate how he handled the aftermath, I was finished with being a fan when he abused his power and had inappropriate relationships with a female staff members.

We like to think our private lives are private, but they are not. They have very public ramifications and we must be very wise in all of our decisions because personal/private decisions can hurt very many people.

5. When you make mistakes, own them.

While the scandal disappointed me, the way Letterman handled the aftermath was brilliant. He was being extorted and instead of allowing others to profit off his mistakes, he took the situation public. He took personal responsibility for his actions and made amends. (See: Remember This When You Make a Mistake)

We all make mistakes. When we do, we would do well to follow the example of Letterman.

6. Appreciate who you are more than regretting who you aren’t.

While Letterman was fiercely competitive, a time came in his battle with Jay Leno in which Letterman realized he was not going to win the ratings war. Instead of getting desperate or changing his identity, Letterman simply accepted his role as number two and enjoyed his opportunity.

It’s easy for all of us to desire more. We want to be the best salesperson or have our children be the top of their class, but we can’t win everything. Instead of regretting what we can’t accomplish, we should appreciate the opportunities we have.

7. When you don’t get what you want, make your own way.

Long before the ratings war with Jay Leno, there was an ugly battle over who would replace Johnny Carson on The Tonight Show. Letterman was the obvious choice and the one Carson wanted to replace him. But Leno got the job. Imagine having your life-long dream stolen from you by your best friend. It could have sent Letterman into a tail-spin. Instead, he mourned his loss and made his own way. He developed his own show, found a new network, and cemented the legacy he had built.

Life will rarely go exactly as we hope or desire. When something doesn’t go our way, we are right in mourning our loss, but we should not stop striving. (See: 7 Leadership Lessons from Gus Malzahn)

8. Never forget where you came from.

Everyone knows David Letterman is from Indiana. While he has lived in the greater New York area for decades, he is an Indiana boy. He never overlooks an opportunity to remind people where he is from, brag about his home state, or use his resources to assist those at home. It would be easy to move to New York and forget small-town Indiana but Letterman has not.

Wherever we go in life, we all should have a deep sense of gratitude for where our lives began and the people who made our success possible.

9. Always remember the power of humor.

Few things have the ability to change a situation, influence a person, or deflate a tension like humor. Letterman is funny. His humor doesn’t relate like it use to. There are many comedians (most of which he influenced) that I now prefer. But he still has the ability to find the humor in most situations and point it out. He is, perhaps, best at making fun of himself. (See: Try Not to Curse During the Baby Dedication)

Most people are not naturally funny, but we all can recognize and highlight the small ironies or inconsistencies at life. And laughing at one’s self is the most humanizing of all acts.

10. When you think life is over, it has sometimes just begun.

This seems to be a lesson Letterman learned after his heart-attack and I hope it is another lesson he realizes in retirement. Letterman nearly died several years ago after a heart condition created the need for major surgery. He has spoken at length that he feared he would never work again. Not only did he come back from that experience, but it seemed to greatly influence him for the good. Since his heart surgery, Letterman seems happier with himself, others, and life. My hope is that retirement brings the same experience for him.

We all go through many experiences which seem to be the end of life as we know it. Yet often those moments are simply transitions which can usher us into a better season of life if we embrace what is to come.

This list is a lot like life–it’s full of good and bad. This is not a critique of David Letterman; it is simply a list of the lessons which I consider as I look at his life.