Have you ever sat down and thought really hard about what has truly shaped your life, or at least your career? It is easy to take your current situation, and then retrofit a nice story that makes it make sense. But that isn’t the kind of rigorous process that will offer a useful insight – which is what I’ve been searching for lately.
When I recently looked back at my own professional career, a winding road of seemingly unrelated industries and roles, I see one clear thread that runs throughout. At all of the various stops along the way, from West Point to Iraq, from Special Forces to corporate sales, from boardrooms to nonprofit trenches, I’ve been pushed and supported by amazing people. Controlling for all other variables (to the extent one can in a thought experiment), all of my professional accomplishments have been the result of being with the right people.
At eighteen, I showed up at West Point, and from day one, it demanded my very best. I spent four years alongside 4000 other young people who were up early, on time for class, physically fit, and completely squared away. Every single day. For four years, that was normal. Add to that hundreds of instructors who both expected excellence and supported its pursuit, and you’ve got a pretty incredible place to grow up.
From there, I landed in the 1st Cavalry Division, where the standard was leading by example. I was formally and informally shown “what right looks like” from dozens of officers and NCOs that cared as much about the people and mission as I did – especially during a combat tour to Iraq in 2004. Within weeks of returning from that deployment, I was on my way to Special Forces Assessment and Selection, and spent the next two years in a training pipeline alongside some of the smartest, toughest people on the planet. And that was just the warm-up. Actually serving on a Special Forces team meant living in a closely-knit but intensely competitive environment where being good was never good enough. Again, these situations came with both very high standards and the very best people to help me get there.
When I left the military in 2010, I walked straight into outside sales at Quest Diagnostics. I remember being struck by an immediate realization: the Army doesn't have a monopoly on high-drive, high-accountability people. My colleagues were smart and motivated, and they went into the marketplace every day ready to compete like crazy. It was a different uniform, but the same intensity.
Photo courtesy of Instagram @dean.usma
A few years later, I took on leading Team RWB, and once again found myself surrounded by remarkable people, all working on a vital mission, either for free or well below their market rate. The quality of people never changed, even when the paychecks did.
Here's what I want to explore, because I think it matters: while I've been incredibly fortunate to have these people in my life, I also made choices that put me in those rooms. I chose West Point. I chose Special Forces selection. I chose sales. I chose nonprofit work.
Those weren't accidents. They were decisions to enter environments where a lot would be expected of me.
And I think that's where the real lesson lies. We all have choices to make.
It is worth noting that we don't all start from the same place. Some of us are blessed with tremendous parents, teachers, and coaches who set us up beautifully. Others aren't nearly as fortunate. That's real, and it matters. For many of us, it is easier to take a risk and pursue something big, while many others live in situations that feel more urgent and offer much less opportunity.
But here's what's also real: to varying degrees, we all get to choose whether we want to be in the company of serious, driven people, or whether we'd prefer to stay somewhere more comfortable and less demanding. We can choose to pursue high-expectation, high-support environments—or we can choose not to. And a lot of that comes down to what we believe about ourselves.
The uncomfortable truth is that choosing the harder path requires believing something about yourself first. You have to believe you're worthy of being in good company. You have to believe that even if you're not there yet, you can eventually add something valuable to that group. You have to believe you can become an important member of the community.
That belief doesn't come easy, especially if your early years didn't provide it. But it's essential.
The best environments I've been in, West Point, Special Forces, the teams I've worked with since, all shared something in common: they combined high expectations with high support.
“May your choices reflect your hopes, not your fears. ”
That pairing is critical. High expectations without support is just cruelty. High support without expectations is just comfort. But when you bring them together, you create the conditions for real growth.
These places show you what greatness looks and feels like. They demand a lot from you, but they also invest in you. They push you, but they don't abandon you. They expect you to be better tomorrow than you were today, and they give you the tools, the feedback, and the community to make that possible.
That's the rising tide. Not just being around good people, but being around good people in an environment where everyone contributes, and as a result, everyone is lifted higher.
So here's my challenge to you: look around. Are you in a high-expectation, high-support environment? Are you surrounded by people who make you better? Are you somewhere that demands more from you than you thought you could give, and then helps you give it?
If not, why not?
I get it. It's intimidating. Whether it’s a CrossFit gym, or a graduate program, or a new company, walking into a room full of people who seem smarter, tougher, or more accomplished than you feels risky. You might not measure up. You might fail.
But you also might not. You might find that you're more capable than you thought. You might discover that those people want you to succeed as much as (or more than) you do. You might realize that the version of yourself you're capable of becoming only shows up when the environment demands it.
We all do well to remember that our lives are better for being around great people, and we should seek every opportunity to make that happen. Not because it's comfortable (it usually isn't) but because it's where we become who we're meant to be.
The rising tide lifts all boats. But first, you have to choose to get in the water.
