When I was in my last course of my undergraduate degree, my professor made the entire class write down a five-year plan in order to get a final grade. We had to discuss what our plans for the future were, and what steps we would take to get what we wanted. I wanted to work in investments then, and I distinctly remember my plan to be an investment advisor by age 27.

Things change, and I’m not an investment advisor. I still remember the plan.

When my professor gave us the assignment, he said, “You may not have any plan yet. But if you have to write one down, and you have to show it to me, your brain is going to make you feel guilty about falling short of what you wrote down. And then you’ll have to take it seriously.” He was right. I wrote one plan down that was half-baked, then realized I would be embarrassed about showing it to someone, so I took the assignment more seriously.

Though I’m not in investments now, the first two years of that plan involved completing my master’s degree in accounting and learning how to analyze financial information. That led me to a Big 4 consulting firm, which led me to where I am today. The plan got me there, even if I didn’t fully follow where the plan led me at first.

The plan is not the point. The point is considering that the future will exist.


With every team I manage, I periodically enforce a 1-2 week vacation period for everyone on the team, including myself. I’m not terribly concerned with what people do with their vacation time - if “silent meditation for a week” sounds amazing to them, great - but I need them to leave. If they don’t leave on their own, we have to force them.

People get sick. People get burned out and quit. People get hit by buses. The team cannot risk a person leaving throwing off the works. And so we have to occasionally road-test their absence. What do they silently do every day or every week that keeps the entire process running without anyone else’s knowledge? Vacations are a way to keep our bus count high.

We vacation-test the manager too. I also leave the scene periodically, with my deputy being the only person who can get in touch with me. This also forces me to constantly delegate and cross-train, such that I am only needed for something that might cause a strategic shift in priorities (and even then, the expectation is that the deputy can probably just confirm things with a text message).

Bus count testing is future-planning. Eventually that team member will get sick, or quit, or retire, no matter what we do. If we aren’t planning for that eventuality, we are not accepting that the future will exist.


Future-planning isn’t just about the negative, it’s about the positive too. Each year, I kick off January by scheduling individual check-ins with the team to discuss New Year’s Resolutions inside and outside of work. It is always revelatory. Sometimes, someone wants to go up for promotion and this is the first time I’ve heard of it. Sometimes, they have an out-of-work goal that may impact work (like training for a marathon where they need to leave every day with enough sunlight to get a run in).

And yet, sometimes, I have team members who haven’t thought of their future beyond maybe the month. Their manager asking about it creates a prompt to force the thought. Now they’re considering “maybe I could run a marathon” or “maybe I will push myself for a promotion.” And then we’re talking about execution plans, not just vague ideas.


We humans are meant to evolve and grow. We are meant to change. We replace all of our cells every 7-10 years and become completely new people, chemically speaking. We have to imagine that the future might exist, and what we will do with it when it gets here. Failing to dwrite down a plan is asking for it to hit us like an unexpected bus.