Letter to My Younger Self

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Dear 12-year-old Derek, 

This letter is for the kid with the Dave Winfield poster on his bedroom wall. 

The kid with the Yankees Starter jacket and Yankees cap and the Yankees chain that his aunt got him for his birthday.

The kid who danced to “P.Y.T.” in the sixth-grade talent show. (Don’t worry, the home movies have been destroyed.)

The kid who watched his dad play shortstop in a corporate softball league and thought: That’s my idol. That’s exactly who I want to grow up to be. 

This letter is for the kid from Kalamazoo with the Ralph Tresvant-inspired New Edition shag and the dream that seemed crazy to everyone else. 

This letter is for the kid with the Dave Winfield poster on his bedroom wall.

- Derek Jeter

Baseball.

Baseball and nothing else. 

That’s just always the way it was. 

At first, it was like you dreamt about the big leagues in black and white. Like it was something from another dimension. The baseball cards and the posters and caps. It was something that was so thrilling that it was almost unreal. But then one day, your parents took you to the old Tiger Stadium when the Yankees were in town. And that was when everything changed. It was like somebody flipped a light switch. Walking through those gates and sitting in the outfield bleachers, it was like all your dreams suddenly were in color. 

It was all, somehow, even better than your wildest dreams. 

How many things in life can you say that about? 

You turned to Mom and Dad in the middle of the game and said, “Someday, you’re going to be watching me out there.”

From that moment at Tiger Stadium, it was baseball and nothing else. You even stood up in front of your fourth-grade class on career day and said, “When I grow up, I want to play shortstop for the New York Yankees.” 

Somehow, someway, that dream will actually come true. 

But that’s not what I want to talk to you about. In a lot of ways, that’s the easy part. That’s the fairy tale. That’s the version that everyone always wants to hear about. What people don’t want to hear about — what you probably don’t even want to hear about — is the failure. 

And, man, believe me, you are going to fail. Spectacularly, as a matter of fact. At the plate. In the field. Everywhere. The first taste you are going to get of minor league ball in the Gulf Coast League will be a nightmare. You are most definitely not in Kalamazoo anymore. 

The first taste you are going to get of minor league ball in the Gulf Coast League will be a nightmare. You are most definitely not in Kalamazoo anymore. 

- Derek Jeter

On your first day, you’ll go a cool 0 for 7 with five strikeouts. Each walk back to the dugout will feel longer than the last. 

You’ll struggle just to keep your head above .200 the whole season.

Most of your nights will be spent sitting out on the balcony of your hotel room at the Radisson, looking out over Tampa Bay, crying your eyes out. It’ll be so embarrassing that you’ll actually ask your mom if you can just give your signing bonus back to Mr. Steinbrenner and come home. 

Thank God for your mom and dad. They’ll be the calming voice on the other end of the line, keeping you from quitting. 

And thank God for that signing bonus, too. Because you’ll rack up about $300 a month in long distance calls home to Kalamazoo. Every night, you’ll tell your parents that you’ve made a terrible mistake. That you should’ve just gone to Michigan and played college ball first. That you can’t handle this level of competition, this loneliness, this failure.

There’s no magic words that they can say. There’s no pep talk. There’s just one simple message: You have to find a way to keep pushing on. You can’t quit. 

So you’ll push on, and in your second season, you’ll do something almost historic. It’s truly incredible to think about, even now. 

You’ll commit a mindblowing 56 errors at shortstop — nearly one every other game for the big-shot first-round pick. 

You’re going to actually feel the older guys in the clubhouse looking at you like, “Man, this kid is our No. 1 pick?”

Looking back on it now, as a 47-year-old man, you can recognize that this was the ultimate test. This was the moment when your life could have turned out a very different way. At the time, you won’t have that kind of perspective. Honestly, it’s just going to be miserable. 

But whatever it takes …  just don’t quit, man. 

You’re going to actually feel the older guys in the clubhouse looking at you like, “Man, this kid is our No. 1 pick?”

- Derek Jeter

Because the funny thing is, you will fail so much in the minors that it will turn into a positive. You’ll learn to convince yourself, truly, that the only thing that exists in the world is the next at bat, the next ground ball, the next moment. 

If there is one key to success that I can give you, it’s to treat every game like you’re still in Little League. When you were completely oblivious to the fear of failure. When it’s all just fun. If you can embrace that mindset even in the majors, then the last at bat won’t exist. There’s no failure. There is only the moment. The pitcher. The ball. The game. The thing that you love more than anything in the world. 

And the beauty of baseball is that every day is a new chance to get it right. 

If you can keep pushing through the failure, you’ll keep building yourself up, and eventually you’ll get a chance to live your dreams in pinstripes. You will wear that famous navy cap. The same one you’re wearing now, on your way to junior high. You will walk out under that giant Kingdome roof in Seattle for your first major league game and spot your father in the stands. He’ll be playing it cool. But you’ll see what it means to him. Everything will seem like it did that first time you walked into Tiger Stadium as a kid. Somehow everything will be bigger. It will be even more colorful and alive. It will seem unreal. 

After the game, you and Dad will meet up, and he’ll say, “I’m proud of you, son.” And you’ll go for a postgame meal together at the first place that comes to mind. 

You’ll go to McDonald’s. 

You’ll sit there having hamburgers and fries as a New York Yankee. You and your dad. Your idol.  The guy who used to sit on the couch with you before afternoon kindergarten and compete — and I mean compete — in playing along with The Price is Right. The guy who you watched in awe, just playing softball in Kalamazoo. 

Nothing will ever take that moment away. 

There are so many memories that I could tell you about from the last 35 years. It all goes so fast. It really does. The time when you were having dinner late after a game on the Upper East Side during your rookie season, and for the first time ever, you saw a random New Yorker walking outside the restaurant wearing that T-shirt….

JETER

2

It won’t even seem real. 

Or the time you parked your Mercury Mountaineer right outside your apartment building on Second Avenue during the ’96 postseason, and you woke up the next morning to find that it had suddenly vanished into thin air.

“Taxi!!! Yankee Stadium, please.”

(Always remember to pay your parking tickets. Nobody is invincible.)

The memories are what count. 

That first World Series win. 

That fifth World Series win. 

That final at bat at Yankee Stadium. 

The truth is that it all goes by so fast. 

You used to always say the same thing in the locker room, after every single game — win or lose. You said it so much the guys got sick of hearing it. But I think it’s only now that you can really understand the true meaning behind the words. 

You’d always say, “O.K., fellas, we got another one tomorrow.” 

Well….

One day, that won’t be true anymore. One day, it will all be a beautiful memory. 

So if you remember anything from this letter, just remember this:

If you don’t quit down there in Tampa, if you don’t give up in that lonely hotel room, if you keep pushing past the failure and the embarrassment of those first few years in the minors, you’re going to be blessed. You’re going to live out your wildest dreams. You’ll be a Yankee. A champion. Even a Hall of Famer. 

Never take it for granted. Remember to savor every at bat. Every ground ball. Every moment that you’re blessed to play this game.

And hey, P.S….

Just a thought. Maybe cut the shag. 

Sincerely, 

Derek