I wanted to share something that helped me visualize my life and the changes I’ve been making in it lately. This is the scene right outside my apartment, looking at a tree across the street. It’s about 7am in late July, and the sun is starting to peek through the leaves.

What I saw in this tree, directly in the center of the photo, is a little hole through the leaves. This little hole gave me the best image of how to answer the dreaded question: “Where do you see yourself in five years?” Now, I tell people I want to be going right through that hole in five years. But what is that hole, and how do you get there?

First off, what defines the hole? Only you can really answer that question. In my example, it might be something like: Divemaster. Fluent Spanish speaker. Brazilian Jiu-Jitsu competitor. Business Partner. Every island in the Caribbean under the belt. Things like that. Pick the things that you want to experience, improve, or become, and roll them up into a ball; or a hole, if you will. More on goal-setting to come later, so let’s move on.

Think of your life as being on a trajectory, slowly but inexorably moving towards that tree. I want it to go right through the dead center of that tiny hole. What this requires is setting the appropriate trajectory now and then protecting it vigorously, because tiny errors along the way will mean missing the mark significantly.

Lately every morning I spend a few minutes staring at that hole before catching my train. I think of all the things I need to do or stop doing in order to make it through that hole by the time I’m 40; this illuminates the adjustments that must be made now now to make that happen. Find your own hole, remove anything that knocks you off the path to it, and double down on things that stabilize & refine the trajectory.

photo: just outside logan square blue line station, chicago
credit: myself

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