I am delighted to post another letter in the series, this time by my friend Rob, who I met freshman year when we lived on the same hall. He went on to date and then marry my friend Maia. And now he’s the author of an actual novel that many people have bought, read, and loved. You can find Rob here.

A Letter to My 16-Year Old Self


I have a few things I need to tell you. Some will be really awesome (your wife is hot) and some will be hard (your dad is going to get Alzheimer’s much sooner than you, he, or anyone, is expecting), but these are things I think you would want to know:

Stop Chasing that Girl
You know who I’m talking about and it’s totally cool. There is absolutely nothing to be embarrassed about. You are giving it your best shot, but it isn’t going to work out. Ironically, the strategy you are pursuing is a great one. You are trapped in the “friend” zone. This is a terrible place to be in high school. It is, however, exactly where you want to be later in life. The problem isn’t your approach; it’s just not the right time or person. So don’t be discouraged and don’t worry so much about it.

Buy a Tape Recorder
You don’t know this now, but you are a pretty good reporter. I know, right? You aren’t even interested in journalism and the idea of calling people you don’t know makes you sweat. It’s okay. You are actually surprisingly good at asking the right questions to the right people.
By the time you figure this out, though, you will have lost the chance to interview some crucial sources. You need to buy a tape recorder and interview your grandparents extensively on your next visit to them. You want to learn as much as they can tell you about their lives. This is important for learning who they are, but also for understanding more about where you and your parents came from.

Spend More Time With Your Parents
Your dad is going to be diagnosed with Alzheimer’s in about 15 years. The incredibly intelligent and gregarious guy you see right now? Enjoy him while you can, because he will disappear bit by bit until you have trouble remembering him. I’m sorry, but there isn’t a damn thing you can do about this. What you can do is set aside more time to hang out with him—and your mom. This is going to take a toll on her, too. This is a great time to be around both of them, so please enjoy it.

Stop Listening to Aerosmith
Right now. Later, you will refuse to throw out the 3-CD box set of “Pandora’s Box” because your dad gave it to you as a surprise gift, NOT because you ever want to listen to it.

Apply Early-Admission to William and Mary
I don’t know why you didn’t, but honestly, you never wanted to go anywhere else. Going here is a great choice—might as well lock it in right now.

Dream Bigger
You have a lot of hopes and dreams, but you have a tendency to worry about what’s “realistic.” Please stop. I know people think you want to be an actor—even you may think this—but you don’t. You do, however, want to write, and you’re largely afraid to admit this. You’ve been writing stories since the sixth grade and tucking them away, never showing them to anyone. You spend 50 percent of your time living in your imagination, thinking about novels you never even plan on writing. You have this strange idea that someone will come up to you and offer you a writing contract. I’ve got news for you: you are going to have to do this on your own. Don’t be too worried, though: it’s going to be fine. But you need to stop being intimidated about writing a book. Stephen King started when he was 17 years old. You should get a jump on him. Oh, and don’t worry about getting it published. Technology and a company named after a river in South America are going to solve that problem for you. Just focus on writing.

You Already Know Who You Are
If you ignore everything else in this message, I want you to know this: You are just fine as you are. I know you think you’re a nerd. But believe it or not, nerds are cool now. The last Star Trek movie was a huge hit, people love Lord of the Rings and there is a popular TV show about dorks. Weird, I know. It doesn’t matter anyway. You like to pretend that you don’t care what people think of you. It’s time to stop pretending. You will be much happier.


Your 37-Year-Old Self