Some decisions look massive from the outside. Inside, they don’t always feel that way.
In my conversation with Mark Chipman, he talked about “measured risk” in the context of building things like the arena and True North Square. It wasn’t about instinct or being especially bold. It came down to something much simpler.
He had people who could actually execute those projects.
He had the financial flexibility to move when the opportunity showed up.
And he had a way to break big investments into stages instead of going all in at once.
So what looked like a big bet to everyone else just felt like the next logical step. What this really points to is that confidence in decisions rarely comes from courage. It comes from preparation.
If something feels unusually risky, there is usually something missing underneath. The team might not be ready yet. The numbers might not hold up. Or the path is still too all or nothing.
Most of the time, the goal is not to take bigger risks. It is to make them smaller and more understandable.
Take something on your plate right now that feels like a big bet and ask what would need to be true for it to feel obvious. That is usually where the real work is.
Where are you relying on confidence when you actually need better structure?
What’s one thing you’re working on that feels bigger than it probably should?