Morning, Greg here!
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Now please enjoy this special Father's Day Issue!
Why Father’s Day Cuts Both Ways for Me
Father’s Day is one of my favorite and least favorite days of the year. There’s no other way to put it. It’s a double-edged sword.
I love being a dad more than anything. There are no two people on this planet I love more than my sons. And there’s no one I miss more than my own father.
That’s the tension I live with every year on this day.
The Missing Piece
My boys are 18 and 21 now—the exact age window I was in when I lost my dad. I was 17.
We’re walking through milestones together that I never got to share with him.
Graduations. College decisions. Career talk. Life lessons. I have no personal blueprint for what this time is supposed to look like with a father. I’m figuring it out as I go. Trying to be the dad I wish I had. Trying to be fully present. Sometimes, maybe too much so.
And if I’m honest, sometimes I catch myself living through them a little. I don’t know if that’s fair to them.
What I Wish I Had
I think a lot about the conversations I never got to have. The moments I wish we’d shared. The guidance I needed but never got.
And then I look at my boys. If my dad hadn’t gotten sick—if he were still around and healthy—I’d probably be just like them. Carefree. Focused on fun, friends, the future. Not thinking about loss or time running out. Not wondering what life would be like without a father. And they shouldn’t have to.
They should believe their parents will live forever. That’s the way it’s supposed to be.
The Tension I Carry
So I try not to push too hard. Try not to get hurt when they don’t come to me for everything. When they don’t want to do everything I want to do. When they don’t text back right away or invite me to visit as often as I’d like.
That’s part of the work. Holding space without crowding it. Letting go without disappearing. Giving love without conditions.
And I’m grateful for the perspective. I wish I never had to earn it this way, but I did. It’s shaped how I live. It’s why I value time more than anything. Why I believe pressure is a privilege. Why I don’t take a single day for granted.
A Tribute in Progress
This Father’s Day, I went back through what I’ve written—about my boys, about my dad, about fatherhood. I wanted to see if I could share some of that. Create something meaningful. A tribute to fathers and sons. And yes, to mothers, too—because we wouldn’t be fathers without them.
It’s always been a dream of mine to write a book and dedicate it to my dad. To show his picture on stage. To carry his name with pride. To honor the legacy of being his son.
That responsibility has brought me joy—and pain. I know I have high expectations of others. Probably unfair ones. But it’s how I’m wired. It’s how I love. And it’s how I see it.
Please enjoy my personal selection of essays below and read our Editor-in-Chief, Jon Finkel’s, award winning short story on fathers, sons and driveway hoops, free to download for Father’s Day.
In Health,
Greg
The Greatest, True Story You’ll Ever Read on Fathers, Sons, Driveway Hoops & a Magical Moment You Won’t Believe
The guy on the left is my dad. The young guy in the middle is my little brother (now two inches taller than me) and the goofball on the right is me, Jon, your Editor-in-Chief here at Midlife Male. This photo was taken around 1999, a few years before the events in this story, The Night the Legend of the Driveway was Born, take place.
Everyone who knows me personally says this is the best thing I’ve ever written. Better than my Macho Man biography. Better than 1996. Better than all eleven of my books. Even better than my column on classic ESPN that’s been read by over 10M people. Of the thousands and thousands of pages I’ve written, these dozen or so stand alone. It was even given a notable mention in the hallowed pages of the Best American Sports Writing Anthology.
And the thing is, I think I agree with everyone.
There are a few reasons:
1) This is a TRUE STORY. Every single word of it. I promise. As you read it, you may not believe that because it is such a magical event, but I give you my word, every bit of it is true.
2) This story is about three people: my father, my brother and me. It’s simple. It’s timeless. It’s about a bond between a father and his sons.
3) It’s relatable. If you’ve ever shot hoops in your driveway with your dad, you will understand the magnitude of this story and why it matters. You’ll get it. You’ll feel it in your bones.
4) The athletic feat that I chronicle in this story is genuinely extraordinary – a once-in-a-lifetime event that I still can’t believe happened.
It’s the perfect father/son/dad Father’s Day read and it’s yours, free to download, here. I 100% guarantee you’ll love it. And let me know what you think. – Jon
Download the ebook here:
Happy Father’s Day from Midlife Male!
In Health,
Greg
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“You either define midlife, or it’ll define you.” – Greg
MLM Editor-in-Chief: Jon Finkel / Follow Jon on Twitter/X and Instagram
“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming.” – Teddy Roosevelt
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