Write Letters to Your Kids

Love letters still matter.

Not the mushy Valentine sort, but the ones with wisdom and the occasional whack of tough love…letters that stay with you.

My dad wrote these to me.

I still have them 25 years later.

His Dad (my grandpa) wrote to him, too.

The actually copies are stored in a dusty cardboard box, but more importantly they are stored where they matter…in my memory, my decisions, my approach to life.

I grabbed a few after a recent house move, and was rereading them.

In 2001 (25 years ago, YIKES), my dad wrote me after a conversation in the car:

"I wanted to talk about the difference between what you've done and who you are."

He went on to distinguish between achievements (which he was proud of) and character – being giving, wise, and optimistic.

Another letter came after a youth baseball meltdown.

I'd given up a home run and thrown a tantrum.

Dad wrote:

"Your teammates all watch you, and are influenced by you. So do the kids in your class. So does your family — and so do I."

He wasn't upset about the home run.

He was disappointed in how I'd responded – how I'd let one bad moment cascade into many.

These weren't casual notes.

They were deliberate.

Intentional.

Important.

Yet how many of us write real letters to our kids?

Not texts.

Not quick emails.

Not Instagram comments.

Actual letters that say:

This matters enough that I'm going to think about it, write it down, and give it to you.

When you write a letter, you think differently.

You have to commit.

You have to mean it.

Kids can tell the difference (I know I could, and I was a little shit).

When something's written down, they know it's important.

They know you took the time.

They know you considered your words carefully.

Our kids are drowning in messages.

Mr. Beast.

TikTok influencers.

Endless streams of people telling them what to think, who to be, what to buy.

But a letter from you?

That's different.

That cuts through.

Write your kids letters when they accomplish something meaningful.

When they disappoint you.

When you notice something about their character developing.

When you want to share wisdom without a lecture.

These don't need to be literary masterpieces.

My dad wasn't trying to win a Pulitzer.

He was trying to turn me into a man.

Write them by hand if you can.

Save them somewhere.

Date them.

In 25 years, your child might be reading them again.

Or perhaps they'll remember the lessons so well they won't need to.

The words will have become part of who they are.

So tonight, grab a pen.

Write:

"Dear [your child's name]."

Then tell them something true, something important, something that matters.

It matters.

Yallah Habibi,

Jon

Dear Jon — 2/12/01

I wanted to say a little more about what your mom and I talked about the other day in the car.

Don’t worry — I’m not going to give you a hard time!

I wanted to talk about the difference between what you’ve done and who you are. I am very proud of everything that you’ve done and accomplished. We probably can’t much influence that (it’s in your DNA to achieve!) and I know you will continue to do very, very well in the future.

But what about who you are? This will ultimately determine whether you are happy and fulfill your potential. Here’s what I think is important in “who you are” —

• Are you a giving person? Do you share yourself and care about others? Are you a good listener?

• Are you a wise person? This is different than a smart or bright person. A wise person has perspective and understands that they are a small part of the world. But a hugely important part of the world and the people around them.

• Are you an optimist? Can you find the good in every person and situation (or at least learn from every one)?

The pressure you feel to achieve will (should) mostly come from inside you. The above 3 things are much more important to me than varsity sports or “A’s.” They’ll help you become a happy young man (and old)!

Love, Dad

Dear Jon:

I want to explain why I was very disappointed with you at last night’s baseball game.

It had nothing to do with giving up a home run. 

Home runs are part of baseball, just like getting pinned is part of wrestling and giving up touchdowns is part of football. 

Andy Pettitte on the Yankees gave up two home runs last night. 

He won the Cy Young last year and may win again this year.

How you reacted is what started my disappointment. 

You threw your glove, then looked like you didn’t care on the next batters. Guess how your teammates reacted when they saw your response? 

They didn’t care either.

 Instead of fighting to win, having fun and acting like young men, they gave up. 

In a lot of ways this is just as bad of sportsmanship as telling the ump to shove it.

Your teammates all watch you, and are influenced by you. So do the kids in your class. So does your family — and so do I.

You are a leader and it is your responsibility to set a good example. You do not have any choice about being a leader — your brains and ability make it that way.

And if you fight it or set a bad example, you’re not a leader — you are a loser.

I don’t think you’re a loser.

My disappointment was in other areas, as well. Right now, you are trying out for the All-Star team. All-Stars aren’t just the best kids in the league — they are representatives of our community. 

How do you think you would have been representing Millburn/Short Hills yesterday?

How much do you think your attitude would have contributed to the team?

Finally, your behavior was disappointing because it was dumb. You knew I was out there by myself, and that I have a responsibility to the team that is very demanding during the game.

Your behavior upset me so much that I ended up letting our team down.

It was a very uncomfortable situation for me — there were eleven kids out there who just wanted to have fun and try to win a ball game. 

Yet here I was, having to deal with a tantrum from the one guy who is the most important player on the team to me (who I can usually count on) — you.

It’s time for you to take a long, hard look at how you think about baseball. 

You don’t have the luxury to be, or act like, a little kid anymore.

I am usually proud of the way you approach sports and the way you conduct yourself. 

I look forward to when I can be proud of you again.

Love,

Dad