The Problem With Your Five-Year Plan

About 1 million years ago, I was wrestling with what I believed (at 23) to be the biggest, most important decision of my life. The weight of it felt crushing. So, naturally, I got on a plane and flew to Florida to talk it through with the two people who knew me best and who also happened to be my biggest cheerleaders: my parents.

We spent the weekend dissecting every angle. Pros, cons, potential consequences, imagined outcomes. I repeated the same thoughts over and over. I had an answer to every question they asked and an objection to every suggestion they made. As always, my parents were insightful and patient. Exceptionally patient. Even as I looped through the same arguments for the fifth or fiftieth time.

Finally, at one point, I threw my hands up and said in frustration, “You don’t understand! This is the biggest decision of my life!”

My mom, often the voice of reason, paused and said, “That’s just not so. You have no idea what the biggest decision of your life will be. It might be walking out of your building and turning right instead of left. You turn right and get hit by a bus. You turn left and meet the love of your life.”

Her comment has stayed with me ever since.

We think we can blueprint our lives. That if we plan carefully enough, do all the right things, control all the variables, we’ll land where we’re supposed to. And sure, planning has its place. Vision matters. But the idea that we can map out our lives with precision? That’s a myth we cling to for comfort—not a reality we can count on.

Just yesterday, a client nearing the end of our coaching engagement told me, “What I really want before we wrap is a six-month, twelve-month, and five-year plan. I need a plan so I know exactly what to do and how to get there.”

I get it. I do. We all crave that sense of certainty. A clear line from here to there. But what I wanted to say (and maybe what I did say, kindly) is: you can’t possibly know that. Not fully. Not now.

It’s not that creating a vision or setting goals is foolish. It’s just that life—beautiful, messy, unpredictable life—rarely honors the plan. I’ve known this since I was 23. And if we hadn’t all learned that by March 2020, surely the years that followed have driven it home.

It is not difficult to predict the future. It is impossible.

And still, this isn’t a call to throw up your hands and drift. I believe in preparation. I believe in hard work. I believe in showing up, every day. But I also believe we need to hold those things lightly. We need to keep our eyes up—on the horizon, on what’s possible—and stay open to the opportunities and pivots that life will inevitably throw in our path.

Take the next step. Then the next. And then the one after that. But do it with a kind of open-handedness, a willingness to adjust course, change your mind, try something new and be surprised.

Very few people actually execute a five-year plan—not because they’re lazy or unmotivated, but because life doesn’t work like that. Life is, by its very nature, an unpredictable experience.

So we build our toolkit. We grow our resilience. We clarify what matters most—knowing that even that might shift.

And I know this isn’t always a welcome message. Clients don’t always love hearing it from me. What we want is a guarantee. A formula. A neat little equation: if I do X, then I’ll get Y.

But life is more art than math.

So plan. Prepare. Dream big.

But keep your eyes up and leave space for the unknown. It’s usually where the most interesting things are hiding.