You Can't Be Relentless About Nothing
“I'd spent years thinking hustle and relentlessness were the same thing. They're not. I was hooked on the idea that I could work my way into a direction.”
Borrowing courage
“But she said one more thing about their partnership that stood out. She talked about how important it was for them as co-founders to lean on each other for collective courage and belief in what they were building. This goes beyond skill-sharing. This is about borrowing courage from one another.”
Care Gives You An Edge
“CARE is invisible, but it’s a currency, or a form of capital. It underpins every interaction we have, and in business, it’s not subtle. It’s explicit.”
What Are You Encoded For?
When we do things we’re encoded for, that’s when time evaporates and we’re energized, even after hours spent at it. An encoding typically isn’t an activity. It sits underneath.
You Always Have a Choice
“You push yourself as hard and as far as you can (within reason), and sometimes that means you get a bit banged up. I wear those scars, chipped teeth and crooked bones as badges of honour.
Every time I crash, though, one person comes to mind.
Luke.”
More Than A Retreat
“The first time we hosted Waypoint in September 2025, I had absolutely no idea what I was doing. I'd never even been to a retreat. I'd always thought of them as a little too ‘kumbaya’, full of circles and feelings, which has never really been my thing.”
The Backwards Hat Effect
“Some Waypointers had profound reflections ("I'm not afraid anymore!!") and others were less so ("I really need to do this more") - all were memorable and valuable in their own respects, but one in particular stood out for me.
"I want to get to a place where I can go to work wearing a backwards hat like you, Greg."
Staying on the Bike
“As we get older, we collect an enormous number of good, reasonable, responsible-sounding excuses not to do the things that used to light us up. We're busier. Our bodies don't bounce back the way they used to. We've got people depending on us.”
How To Build Your Perspective
"What has stayed with me about watching this movie is how powerful it is to have an experience that makes your 'normal' feel or look completely absurd. When that happens, it changes how you think, and it helps you grow."
What’s Your Number?
“We've got a personal question for you:
How much money do you need each month to live your optimal lifestyle?”
What Are You Built For?
“Kids express their encodings without even thinking about it. Adults are a different story.”
To The Moms Who "Step" In
“I didn’t know her. I didn’t know if I could trust her. And yet I was handing over the most important person in my life.”
Breaking the Script
“Breaking the script means letting go of the version of you everyone else is still expecting.”
The Reality of Being a Parent, Entrepreneur, and an Essentialist
“Some weeks, there aren’t just a few essential things… there are a lot of essential things, and they all show up at once.”
You Can’t Build on Dysfunction
“With the help of Brené Brown, and a very real experience at the hockey rink this past weekend, I’ve been thinking about change and HOW to make change happen.
Here’s the simplest way I can put it: You can’t build on dysfunction.”
When Is the Obstacle the Way? And When Is It a Sign to Stop?
“Maybe this obstacle isn’t something I’m supposed to conquer.
Maybe this obstacle was the way of showing me that I’m just not meant to do that particular work in our business.
Maybe it was pointing me toward something else.”
Easy Is A Bad Signal
“I’d planned to sip champagne to celebrate at the airport on the way home. I wound up downing three pints of Bud Light at O’Hare in shocked silence.”
Grief Is Not an Event
“One of the biggest lessons we continue to relearn as the kids grow up is that grief is not an event. Once you have it, it’s a chronic condition that you carry with you always. It becomes a part of who you are.”
All. By. Myself.
“I don’t need this time away because I’m unhappy. And not because I don’t love the people in my life. I need it because when my patience with myself and others wears thin, silence is how I reset. Being alone with myself is how I remember who I am underneath all the noise.”