A letter to my son about his dreams

The other day, before our third snowstorm in two weeks, I went to the supermarket to pick up a few things.

The electric doors slide open and a woman in a black parka and pink galoshes fills her cart with bottles of wine. There were 6 bottles in the cart and a 7th in her hand.

Our eyes, full moons fixed above our respective face-masks, meet. She must have known I was taking inventory and became suddenly self-conscious, because she snapped, “It’s not all for me. I swear.”

I don’t have to tell you life is hard. And life, in 2020 and 2021, has been a lot harder than any other years in recent history. No wonder research shows in the first six months of the pandemic retail wine sales grew 19.3%.

Life, with all of its annoying and painful and heartbreaking experiences, pressures us, gets us drunk, and attempts to derail our ambitions. These hard experiences quickly overwhelm us, break our spirit, and inspire us, with shaky hands, to reach for another bottle of fermented spirits.

Please know, I am not condemning shopping-cart-full-of-wine-lady or anyone else who drinks to escape their problems. I am NOT holier-than-thou. When I was in better health and stressed, I often resorted to drinking for release. But alcohol and my brain do not mix now, and I must find a sober way to deal with stress.

For me, letter writing is a stress release that does not require yoga pants or concludes with a hangover. Letter writing is a constructive way to articulate thoughts and get lost in meaningful, restorative work. It’s a way to slow down, think clearly, and discover intentionality in an often unintentional world.

This week, stress got to me. I boiled. I was moody. Rude. Impatient. Ungrateful. To simmer, I wrote a letter to my son about his dream of being a professional baseball player.

I liked the letter so much I’ve put the letter in the book I’m working on. (And have since begun drafting a letter to Haley and Dylan.)

Writing the letter below slowed me down. Gifted me control, a minute to breathe, and kept me grounded and sane during a physically, mentally, and emotionally stressful week. I hope, if you’re having a stressful week, you consider letter writing and save the wine for later.

Be well,


Dear Chase,

It’s 2021 and you’re 10. Based on your current detestation of books and reading, and given this letter is stitched in the middle of this book, you probably will not read this book or this letter soon. Even if they were written by your dad.

Knowing this, I wrote this letter to the 18-year-old you, hoping you have developed a slight tolerance for reading by 2029.

In 2029 you will, unofficially, be a man. Certainly, you will feel the squeeze of adulthood. The pressure to assign yourself to a profession. I don’t know what you will dream of being in 2029. Maybe a gym teacher or a professional Tick-Tocker. But now, in 2021, you dreamed of becoming a professional baseball player.

You talked about playing shortstop in big league stadiums, maybe for the Phillies or the Angels, being on TV, and making millions of dollars. You even promised me a good seat behind home plate with all-you-can-eat hotdogs.

When you were 10, you impressed your coaches with how well you listened, how focused you were, and how you played baseball with a Labrador-playing-fetch joy in your heart. And I want you to know watching you stretch a single into a double on a perfect summer evening made your dad feel like a kid again.

But you’re 18 now and it’s time you heard the hard truth: dreams don’t always come true.

Life, like baseball, gets increasingly difficult. A lot has to go right for you to turn pro. Your body must remain injury free. Your mind must remain level and humble. You must be wary of praise. You must keep your enthusiasm. Ability and fate and luck must synchronize their watches. And amid the distractions of adolescence you must commit to the daily grind of improving your swing, your footwork, your fielding, your agility, your strength, and your hand-eye coordination.

I hope when you read this in 2029, my delusions of you having already been drafted and featured in Sports Illustrated are true. And maybe you’re reading this on a chartered flight to the Phillies spring training facility in Florida. Or maybe you’re in a swanky New York City steakhouse, sitting on a red-leather couch, awaiting a shiny-shoed agent attempting to woo you and your.305 batting average.

But what if my delusions are just delusions? What if your baseball dream doesn’t come true?

What if, in 2029, you’re just a B+ high school kid trying on tuxedos for prom? What if you just received another college rejection letter? What if you stock shelves at the local supermarket and play slow-pitch softball on Sundays?

If this happens, promise me before you graduate high school, you will have the courage to dream a new dream.

The ugly side of adulthood is that after an adult realizes their childhood dream will not happen, they cannot dream a new dream. Therefore donuts, sports gambling, tax evasion, and Oxycodone will always have an adult audience. Failing to dream a new dream is deadly. It’s a surefire way to get lost in a life that you do not want. Maybe your new dream will not have the pinstripe romance of a big league ballplayer. So what? There is a real cost of not chasing your dream, no matter how unromantic, how ordinary the new dream is.

Whether it’s hitting a baseball or selling insurance or hanging drywall, you must chase a dream that fulfills the mysterious parts of yourself. You must have the courage to do what’s in your heart. In that hidden place where hope and joy wait like prom dates for the music to play, for the dancing to begin.

I also wanted to be a baseball player when I was 10. And then, at 14, I was cut from my high school baseball team. I spent years wondering what to do next. In college, maybe I was 20 or 21, I dreamed of becoming a writer who sold millions of books world-wide. And then, when I realized writing was hard work and most writers are lucky if they even sell a few dozen books, let alone millions, I became a high school teacher. Yet while I busied myself with teaching, the writing dream, like a stubborn update notification on your iPhone, remained. It wasn’t until I got sick, turned 40, and retired from teaching that I accepted that notification. Maybe it was facing my mortality or the sudden gray stubble on my chin, but I realized we have little time to chase our dreams. And it makes little sense not to spend your life chasing your dreams.

I want you to know, if the baseball dream doesn’t work out, it’s okay. I will not love you any less, even though it would be nice to watch a game behind home plate and stuff my face with hot dogs.

Listen, figure out your dream, not my dream or your girlfriend’s dream or whatever dream is trending on Twitter, and chase it with your Labrador heart. If you chase anything in this life, chase the dream that brings you joy. Live up to your name and chase the dream that can make possibilities starched realities. Chase the dream with dogged persistence and boundless energy. That makes your heart thump and flutter. Chase the dream that keeps you awake at night. Chase the dream you can share with others. The dream you will one day tell your children about. Chase the authentic dream. The worthy dream. The hard dream. The dream that will paralyze you with doubt and fear. Chase the dream that will soothe your soul. Chase the dream that will inspire others to chase their dream.



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Need some encouragement? Some perspective? This hardworking, almost-handsome, suburban soccer dad can help. Subscribe and, like a pizza, get my posts delivered to your door (your email inbox). No spam. Just posts.


Jay Armstrong is a writer, blogger, speaker, and an award-winning high school English teacher. Despite being diagnosed with a rare neurological disease, that impairs his movement, balance, eyesight, and speech–Jay presses on. He hopes to help you find joy, peace, and meaning in life. For Jay, a good day consists of 5 things:

1. Reading
2. Writing 
3. Exercising
4. Hearing his three children laugh
5. Hugging his wife
(Bonus points for a dinner with his parents and a beer with his friends)

Jay hasn’t had a bad day in quite a long time. 

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