The cottage I used to hate

Hello friends,

This past weekend, we went up to the cottage to spend time with my mother, which is always a special time for us. The cottage matters to me because it is one of the places that I really took for granted growing up. We had to go every weekend, rain, sun, or snow, and I detested it lol. I wasn't much of an outdoors gal.

My parents both had regular jobs. My mom was a letter carrier, and my dad worked with his hands. They saved up in their early twenties and bought this land for almost no money, a beautiful lakefront property in cottage country in Ontario. If you have never been to Muskoka, I highly recommend you put it on your list because it is Canadian beauty in its truest form. My parents couldn't afford a home in Toronto, so they rented, but they wanted to ensure they had land for my brother and me. How special it is that they did that over 30 years ago.

I always use my time at the cottage to read and reflect on how I have grown. A few years ago, I had a moment where I saw how much I had taken the cottage for granted, how much I had been chasing the rest of the world and thinking that what I was searching for was somewhere out there, when really the most beautiful and special place had been in front of me the whole time. I have come to believe that sometimes chasing is exactly what you need in order to understand that what you already have might be the most special thing you will find. I hope to one day write a children's book on this.

A Book Named Winning

That is why the book I read this weekend felt so relevant, i.e. Winning by Tim Grover, who is best known as Michael Jordan's trainer. The argument is simple, and it is powerful because of it, which is that winning is not a zero-sum game. It's not an outcome, but a mindset that you carry into everything you do. When you are in that mindset, you are focused on the destination, and you begin to see your whole life as a game you are playing differently than the people around you.

Winning Is a Constant State, Not a Series of Wins and Losses

The reframe that mattered most to me, and the one I most want to pass to the business owners reading this, is that I stopped treating a win as a single event, i.e. signing a new client, having a post go viral, or closing one strong month. Those are the moments we are all trained to keep score by, whereas the shift for me was to stop keeping score that way at all because the minute you define yourself by individual wins, you have also agreed to be defined by individual losses, and you hand your sense of progress to whichever one happened most recently.

What I hold onto now is that I am in a constant state of winning, and that the small wins are not the prize in themselves. They are compounding, each one adding to a state of winningness that does not rise and fall with any single result. For anyone building something, that is the more useful way to carry it because a business is not won or lost in one launch or one quarter. It is built in the accumulation, and the founders who last are the ones who stopped needing each individual outcome to justify the whole.

Marketing and Branding Is Warfare, and the Only Advantage Is a Mindset

Every industry is saturated, and every industry is competitive, so marketing and branding is warfare, and getting ahead inside it is simple without being easy. The simplicity is the trap because, when the right move is obvious, the only thing standing between you and it is a mindset reframe, which is far harder to make than learning any new tactic.

There will always be voices, whether family, friends, or people who care about you, telling you that you are doing too much and that you should slow down, and I understand the instinct. But I have come to see each milestone as the gift itself, and each one as a stepping stone to the next rather than a place to finally stop and rest.

This crystallized for me when I watched Steven Bartlett interview James Clear, author of Atomic Habits (linked here), where James shares the idea of being an oak tree, the notion that an oak lives in a permanent state of growth and that this is simply what it is. The goal is to be present in whatever state you are in, while realizing you are in a state of growth and that you won't always stay an acorn, a sprout, or a small tree because you live in a constant state of growth.

Winning works the same way. When you are winning, you are reaching new milestones, and you are focused on forward growth. Each milestone is an opportunity to be present, enjoy the journey, and enjoy the success of what you've achieved, but with the understanding that you are constantly moving forward.

It's why I live to read and hear feedback from you on our content, conversations, etc. because I am a branding oak tree, and I want to grow with you. So, if you are looking for some summer motivation, read Winning, and let's keep sprouting together. 🌱

This week I sat down with the founder behind two cult sunglasses brands (Quay & Otra), and it turned into one of the most practical conversations we've had on how brands get built. She started with $165 at a market stall, never took on debt, and sold the first company to private equity. Now she's building the second like a startup again, running lean and keeping her own money out of it, and letting us watch it happen in real time.

On the episode:

● Why she said no to gifting, until the Kardashians demanded ten pairs at a time
● The launch that did $7M in 12 minutes and made Shopify beg her to stop
● Why every model wears Zara, and what most brands get wrong about looking expensive
● The style she'd given up on, until one creator turned it into a bestseller
● Why selling her brand felt like a death she could only undo by building it all again

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