A Letter to My 21-Year-Old Self

Happy Sunday, folks,

I'm writing to you live from beautiful Muskoka, ON, Canada. I bought this lakehouse with my Hush co-founder, Lior, when I was 25. We've been Airbnb-ing it for years, and I never really spent any time up here. Now that it’s the slow season, I’m taking the chance to unwind in nature.

This month’s journal entry is a letter to my 21-year-old self—a practice I enjoy to switch things up. Sometimes, I write to my future self too.

As always, if you're not keen on getting deep with a random 29-year-old founder on the internet who's just figuring it out as he goes… feel free to skip this one. We’ll get back to regular updates next week.

Here we go…

Dear 21-Year-Old Aaron,

Hate to break it to you, but you don’t ever fully figure it out. At least, not yet.

The pain you feel as your hockey career comes to an end—the one you built your identity around—feels all-consuming now, I know. Watching your friends live it up at university while you’re up at dawn, blending smoothies in silence, might feel like a lonely road. But this season, as tough as it is, will somehow be worth it.

That time you and your best friend live together in a cramped 700-square-foot condo? Those moments will be ones you laugh about forever. The inside jokes, the late nights, the struggle to get by—they’ll be memories you wouldn’t trade for anything. Don’t rush out of it.

And yeah, sorry to say… your girlfriend isn’t “the one.” Probably not the next one either. I know it stings to hear, but you’re going to learn so much about love, loyalty, and what you really want. These experiences will deepen who you are, and in time, they’ll make you someone ready for something real.

You will be able to take care of your family. You don’t need to stay up every night talking to the ceiling, praying for something big to happen. It will. But maybe keep up that ceiling thing anyway—it kind of works.

Your connection to God will matter more than you can understand right now. It’s going to carry you through dark moments and bring you closer to people who will change your life in beautiful, surprising ways.

That tightness in your chest? Yeah… it’s called anxiety, brother. It doesn’t just disappear. Who knows, you might even make a product that helps millions of others with it… but never fully solve it for yourself. And sometimes, even the cold plunges and sauna sessions won’t touch it. The only thing that ever helps is sitting with it—learning to let it exist without defining you.

My best advice to you is this:
Sit with the feelings. I know you want to run from them, but trust me, they’re there to teach you.

Have the hard conversations. Be the first to apologize, the first to admit when you’re scared. Lean into the unknown. I know it sounds like a cliché you’re tired of hearing, but leaning into that discomfort will shape you. Every time you do, you’ll come out a little stronger and a lot wiser.

And for God’s sake, be honest. You might think hiding parts of yourself makes it easier, but holding back the truth only feeds the anxiety. Show up as you are, fully. And if someone doesn’t like it? Let them go.

Money? It’ll come. Don’t spend so much time worrying about it. Really… I am not joking. You have some weird blessing where it just comes. Focus on the other things.

And please, Aaron… trust your gut. Every time you ignore it, you’ll pay for it—and it only gets more expensive as you get older.

Follow your gut, and listen to Mom. It’s uncanny, but she’s always right. Always.

Love you, brother,
Your 29-year-old future self