You Can’t Choose a Future You Can’t Picture

I graduated from high school in 1988 with a 1.2 GPA and no plan. College was not part of the conversation. I was not sitting there deciding between universities or weighing careers. I was not thinking about becoming a business owner, an executive, or anything like that. Those were not careers I had looked at and decided were not right for me. They were not real options in my mind.

That is an important difference. Sometimes we think we made a choice when the truth is we never saw the other choices. You cannot choose something you do not believe belongs on your list. At eighteen, I did not believe I was limiting myself. I did not think I had an invisible fence around my future. I thought I was just being realistic.

After high school I worked as a busboy. The restaurant had a better name for it: dining room technician. A busboy clears dirty dishes and resets tables. A dining room technician sounds like somebody who went to a technical school and got certified in forks and water glasses. I liked the job. I made good money for my age, I worked hard, and the schedule left room for the life I wanted — work, friends, family, and surfing on Kauai. I was not miserable. That matters, because this is not a story about hating my life. My life was good. The issue was not that I hated what I was doing. The issue was that I could not picture myself doing much else.

Nobody had to tell me, “JD, you cannot become a doctor.” I never considered becoming one. Nobody had to tell me I could not own a business. I never pictured myself owning one. Nobody had to reject me from college. I had already decided college was not for somebody like me. That is how some invisible fences work. They do not always show up as a person standing in front of you saying no. Sometimes the possibility never enters your mind. You do not feel stopped, because you never started walking toward it.

Then one day in early 1989, I was sitting on my surfboard waiting for waves that were not very good. When the waves are good, you are paying attention. When they are bad, you have time to think. My mind wandered to getting older. I pictured having kids one day, and those kids having kids, and my grandchildren asking about me. “What did Grandpa do?” In my head, I heard the answer: “Your grandfather was a professional busboy.” Actually — a dining room technician. That sounded better. It made me laugh, and then it bothered me. I was not ashamed of the work. There is nothing wrong with honest work, and I respected the people I worked alongside. The problem was that I had never asked myself whether I wanted anything else. Sitting on that board, I realized I wanted stories. I wanted to go somewhere I had never been and do something I had never done. I did not think, “I need to discover my full potential.” I would not have talked like that. I thought, “Man, I need some stories.”

That one thought — not a plan, not a five-year vision, just a thought — is what eventually put me on a path I could not have imagined: thirty years in the Army, rising to Command Sergeant Major, college degrees, businesses, a family, and this work. I did not tear down every fence at once. I stepped outside one and lived inside five others. I could be fearless in one part of my life and completely limited in another. That is how it went for years, one fence at a time.

Here is the part that still gets me. The evidence that a bigger future was possible was never far away. A graduate of my own high school — the same Kauai High School — became a four-star general and Chief of Staff of the Army. My best friend’s father, a man whose house I slept at, had pitched for the Boston Red Sox alongside Ted Williams. The examples were close enough that I knew their kids. I just never looked at their lives and thought they said anything about mine. I saw his life as his life, and mine as mine.

You cannot seriously pursue a future you cannot picture. That does not mean you need the whole plan before you take the first step. I had no plan beyond leaving. My first step came from a joke on a surfboard and the decision not to cancel the plan when fear finally showed up.

So if you cannot picture what comes next — if every option feels like it belongs to somebody else — it is worth asking whether the wall in front of you is real, or whether it is a fence you were trained to stop at. Is this actually true? Or am I doing it again?

That question is where clarity starts. And clarity is a lot easier to find out loud than it is alone in your own head. And you do not need a title for any of this. Leaders, business owners, investors, CEOs — they call. So do parents, privates, teachers, and anybody else standing in front of a move that matters. The weight of a decision is not measured in zeros. It is measured by the person making it.