Happy Sunday,On November 30th, 2023, I officially joined Late Checkout. Two years ago today. When the official offer came through, it felt surreal. I didn’t feel ready. I didn’t feel qualified. But something was happening, and I wasn’t about to look away. I’d spent months in the trenches. Writing posts, sending cold emails, chasing opportunities I hoped might lead somewhere (they didn’t). I didn’t know what the role would turn into. I only knew I wanted a life built on writing, thinking, and creating. Two years later, I’ve written hundreds of emails and posts, built funnels, redesigned systems, strategized, sat on calls I never imagined I’d be part of, and realized (slowly) that no one else knew better in my domain. I learned expertise comes from doing the work long enough that people mistake your persistence for mastery. I thought becoming a “writer” and a “growth operator” would change something fundamental inside me. I thought I’d wake up different. More immune to doubt. It didn’t work like that. I still have bad days. I still second-guess myself. But the difference now is simple and earned: I have two years of evidence. Proof that I can figure things out and deliver. I’m steadier, calmer, and more capable than I give myself credit for. Two years ago, all of this was hypothetical. Today, it’s real. I can build, fix, adapt, and hold my own when it counts. And whatever mountain comes next, I’ll meet it the same way I met this one By showing up, over and over again. I’m proud of that.
November in 3 snapshots 🐕 Dog walk with Dad — My parents stayed over for a night, and I took my dad and Trooper for a long walk through Upper Mount Royal. Big houses, quiet streets, easy conversation. I walk that neighborhood all the time, but doing it with my dad made it feel new again. Great morning walk. 🤖 Peeling back layers with ChatGPT — I used ChatGPT to brainstorm Christmas gift ideas. One minute I’m talking stocking stuffers. An hour later, I’m unpacking emotional blind spots I didn’t know were bothering me. Not what I signed on for, but surprisingly helpful. 🏒 Late night hockey — I played two ~11pm games. Skating that late feels like exercising inside a nightmare sequence. My cardio expires halfway through my second shift. But getting out of the house, chasing the puck with the boys, and pretending I’m still 25 is worth the wheezing.
3 Lessons Learned I. Embarrassment is an underexplored emotion. It’s easier to stay small than risk looking foolish. But if you let yourself feel it long enough to survive the sting, you’ll realize the stakes aren’t what you thought. On the other side is a version of life that’s wider, freer, fuller. The discomfort is the doorway. II. Worry is a byproduct of inaction. We loop hypothetical futures, stack outcomes, replay scenarios that haven’t happened (and won’t) because nothing in the real world has changed. The moment we say something, do something, make even the smallest move, worry wanes. Action is the antidote, always. III. Our bodies atrophy quietly. When we’re young, effort is optional, extra. As we age, effort becomes essential maintenance. Strength wears down in whispers, one unchallenged day at a time. It’s easy to coast, but coasting has a cost. Straining today saves us from collapsing tomorrow.
3 fun things to check out
I’ll leave you with a quote 🤔 “We are all faced with a series of great opportunities brilliantly disguised as impossible situations.” — Charles Swindoll Until next time, Scotty
PS Ice is so crispy |
