Most people who say they’re strategic thinkers mean something specific by it. They mean they’re good at high-level thinking — direction-setting, pattern recognition, the occasional insight that makes a room go quiet. Then someone else executes, and the strategic thinker moves on to the next thing, neck safely intact.
That’s not strategy. That’s advice with no skin in the game.
Real strategy has stakes. It’s not a solo performance — it’s a collective effort that guides an organization toward a future that makes it better, faster, stronger. The individual leader’s job isn’t to arrive with the answer. It’s to evaluate where the lines are getting blurred — between what shouldn’t change and what needs to evolve constantly — and to hold up a mirror so everyone in the room can see clearly how things actually look. If it’s ugly, they’d better do something about it.
Seth Godin calls strategy “a philosophy of becoming.” Not a plan, not a roadmap, not a set of frameworks — a commitment to a direction, held loosely enough to adapt but firmly enough to actually mean something. That framing landed differently for me after eleven weeks of sitting inside the fault lines. Because what I kept finding, week after week, was that the organizations and leaders who got strategy wrong weren’t missing a framework. They lacked clarity about what they were actually trying to become — and conflated it with what they’d already built.
That confusion is where strategy dies. The practices that made you successful start to feel like core values. The methods become the mission. And somewhere in that blur, the whole thing stops being a philosophy of becoming and turns into a defense of what already exists.
Strategy is overcrowded as a topic only if you mistake it for a subset of leadership content — another trait, another skill, another mindset to develop. I don’t think it’s any of those things. It’s a field of study. A serious one. And it’s barely been touched by most of the writing that claims to cover it.
What I know after twelve weeks of this is that I’ve scratched the surface. Strategy-aware, not strategy-expert. The difference is that the awareness is now reflexive — it shows up in conversations I’m not having about strategy, in problems I’m not being paid to solve, in the mirror I’m learning to hold up without flinching.
That’s the practice. You don’t need a title to apply it. You just need to keep learning.
P.S. This is week twelve of a twelve-week curriculum exploring the fault lines that run through strategy, leadership, and organizational life. If this landed, start at the beginning — The Fluff Illusion is where it all started. And if you want the weekly essays that go deeper than the blog posts, subscribe to The Blind Spot — they go out every Sunday.