Teaching My Son He Can Do Hard Things
"I'm Jack Jack. I'm tough"
For six weeks straight, every single day, the same battle unfolds…
We pull into the parking lot, and my son Jack Jack starts crying.
The crying wails build from slow rumbles, like thunder in the distance, to a crashing storm.
He knows we're at his Survival Swim Lesson.
And he doesn't want to go…
The tears continue as we head into the lobby, change him into his bathing suit, and wait for his lesson to start.
"Ok, we're ready for Jack!" the instructor shouts out.
I walk toward the pool with Jack Jack in my arms as his cries grow louder and his grip on me gets tighter.
His legs start kicking and squirming as he tries to climb higher on me, away from the pool, like a boy climbing a tree with a vicious neighborhood dog nipping at his ankles.
For ten minutes, he’s put in drowning situations—and taught to float to survive.
He’s…
dunked under water
stranded in the middle of the pool
even forced to do it all fully clothed
And he hates every second of it.
The crying never stops.
Every gasp for air feels desperate, like he’s drowning again and again. He wants to quit.
But here’s the thing...
He doesn’t.
Even through the tears, he fights.
He kicks. He reaches. He does the hard thing that will make him better.
This is where he finds his toughness—not in the kitchen, safe with sourdough toast and Babybel cheese.
Jack Jack doesn’t see it yet, but I do…
I see the way every lesson adds a layer of toughness to him, the way he’s learning something far more important than just floating or kicking.
He’s learning that he can Do Hard Things.
And so when the lesson ends and we wrap him in his towel, dripping wet and exhausted, I don’t talk about how much he cried.
I don’t talk about how scared he was or how much he wanted to quit.
I talk about how he did it.
And at just 21 months old, I guide him to speak power over himself.
"I did it."
"That was hard, but I’m tough."
"I’m Jack Jack. I’m tough."
The first time, his little voice was hesitant.
He was sad, defeated, and still crying. The words looked foreign in his mouth.
But I kept prompting him, and soon, he started saying them back with more strength.
Because words matter.
The words we say shape how we see ourselves. They shape how we see challenges, struggle, and growth.
Jack Jack may not love survival swim, but I want him to walk away from it knowing one thing about himself:
He is tough. And he can Do Hard Things.
And if he says it enough, he will believe it.
Just like the rest of us.
I have a video from after yesterday’s lesson where you can see this in action.
You can hear Jack Jack saying the words that shape the way he sees himself.
Watch how his energy shifts…
We’ve all struggled with something hard. We’ve all wanted to quit.
But too few of us have ever tried this:
Pay attention to the words you say to yourself. Then change them.
And keep showing up—again and again.
Just like Jack Jack.
P.S.
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That reminds me of Josh Waitzkin on the Tim Ferriss podcast. His then 5yold was trained to love storms and cold showers. And he tought him to say: daddy its so good!
And he gets excited about storms and bad weather that other kids want to avoid.
I used to call this building a perversion. For example I trained myself to enjoy squats.
I think I need to relearn the lesson. That I can build enjoyment for sth uncomfortable.
I hope your training has a lasting impact on Jack Jack!