You Can't Be Relentless About Nothing

When I was 18, a small group of friends got together at my parents' house for dinner. It was a warm June night, high school was coming to an end, and we were all feeling some combination of excitement and nerves about what came next.

We sat out in the backyard. The air was warm, someone had snuck a couple bottles of wine, and my friend Brian and I made lobster tails for everyone.
I know, I know. Lobster tails and wine at 18 sounds ridiculous. Apparently, we had expensive taste from a young age.
It felt like the kind of night we were all going to remember, and it was. While the lobster tails were delicious, and this was the last time I remember seeing this group of people in one place, those aren't the details that made it memorable. It was a conversation we had.

My friend Brian asked me if I was afraid of what was going to happen next. I was, and I remember telling him that. He felt the same way.

Neither of us had any idea what we'd do after school, or how (or if) we'd ever earn a living, let alone buy a car, a house... anything really. It all felt overwhelming. Impossible.

So I did what a lot of scared people do. I spent years trying to out-work the fear.

Through business school and into my career, I put in the hustle of someone who was terrified of being left behind. I'd put in 60-80 hour weeks, get 4-5 hours of sleep and miss meals regularly. The work I did was always interesting to me, but I let others make a lot of decisions for me, and didn't have a clear sense of direction. I figured I could work my way into purpose, and that eventually lightning would strike and I'd stumble onto my path.

Looking back on this time, I think I would have told you I was relentless; or at least I would have told you that I aspired to be.

Fast-forward two decades later, and I had a car of my own, a house, and had even started a family with RSPs, RESPs, and TFSAs too. 18-year-old me would have been thrilled; I MADE IT!!! But... I still felt like something was missing. I'd look around and see other people who I felt were 'relentless' too, but who seemed to be making a different type of progress. They seemed to be doing something that mattered to them in a deeper way than anything I'd done. I felt like there was some secret ingredient those other people had that I didn't.

I couldn’t put my finger on what that was until this year, at Waypoint Retreat.

Nancy and John Corcoran own Whispering Springs, where we host Waypoint every year. As we've both written about before, the space they've created is spectacular, with care and attention given to the smallest details. It feels personal from the moment you step onto the property.

Last year (and on our podcast), Nancy shared her story with our group about the work she's doing to support her granddaughter who suffered a life-changing injury during her delivery. Her tireless advocacy to change our healthcare system earned her a label from her mayor as being 'fucking relentless'. That label became a theme for us at Waypoint.

This year at Waypoint, Nancy spent some time with a small group of us, and shared another story with us.

Years ago, she and John found a property they fell in love with. 80 acres, with a waterfall and a river running through it. It was available for $80,000 - a total steal.

But, there was a catch. Getting onto the property required a bridge more than 120 feet long. A bridge like that could cost millions to build and service, and it had turned away buyer after buyer.

Not Nancy. She got on the phone, calling around until she reached a scrap yard, and found out that Ontario Place was removing a 120-foot bridge and was going to have to pay thousands to get rid of it. They offered to sell it to her for $7K, and had it shipped to the property in pieces. They built their dream home the next year.

Nancy IS fucking relentless. And hearing her tell that story was a lightbulb moment for me.

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; when I look back on that now, that was mostly me reacting to my own fear of trying something myself, getting left behind.

I was relentless about the WORK. Nancy is relentless about the THING.

When Nancy hits an obstacle, she doesn't put her head down and grind harder. She gets thoughtful. She gets creative. She gets intentional about the thing that she wants, and finds a way to get it.

The realization I've had is that you can't be relentless about nothing, and you can’t be relentless about everything. If you’re going to be relentless, it’s got to be about something.

Once I saw it in Nancy, I started seeing it everywhere.

I LOVE reading biographies, and learning about what some of the great people in history and of our time have achieved and how they did it. With this as my lens, I couldn't STOP seeing this same theme come through.

Abraham Lincoln grew up in a dirt-floored cabin in the wilderness. He taught himself to read, and eventually to practice law, all while battling a depression that followed him his whole life.

Tara Westover grew up in a survivalist Mormon family in Idaho, with almost no formal education. Against her family's wishes, she taught herself enough to get into BYU, went on to earn a doctorate, and wrote a bestselling book (Educated) about the whole experience.

Steve Martin wanted to be in show business, and by his own account, he wasn't very good at it. So he performed. Constantly. For years, he'd put on 3-4 shows a day with a goal to become so good no one could ignore him. Well done, Steve.

The list goes on, and the theme is loud and clear. Each of them was relentless about a specific thing. Reading. An education. Being undeniable. Their obstacles were massive, but they were obstacles in the way of something that meant something to them.

The bigger the thing you want, the bigger the obstacle will be. That part doesn't change, and it doesn't get easier. But I don't think more hours are the answer anymore.

It's a privilege to have the house, the family, the RESPs (and so on) that I thought was impossible when I was 18. But if I were to tell 18-year-old me that this was all I'd achieved, I think he'd be disappointed. I think he'd want it to be about something. I think he'd want to see me being fucking relentless.

So, that’s what I'm working on now. Finding the thing, defining it, and then doing the work to get after it.

Maybe you've already found your thing and you've been sitting on it. Maybe you're still figuring out what it is. Either way, it's got to be about SOMETHING. So what's YOUR thing? And what would it look like to be fucking relentless about it?