At the beginning of every year, everyone plans. The year. The quarter. Life. The startup. Themselves in five years.

And today something reminded me of a story from a decade ago, when we were sailing in the Exuma Sound, Bahamas. It gave me one of the most valuable lessons about planning I’ve ever received.

Here’s the short version of why it matters: we confuse the goal with the route. We hold onto the plan harder than the purpose behind it. And we end up not where we wanted — but where the stubborn plan dragged us.

The story

We had a perfect seven-day plan. Which islands to visit, where to anchor overnight, which passages to make. Everything was logical, beautiful, optimal. The goal was clear too: see the islands, swim, find beautiful spots, have a great time.

On the third day, we set out on a long passage. And pretty quickly, it became obvious something wasn’t right. Almost no wind — and what little there was blew the wrong direction. The current was fighting us. The motor wasn’t enough.

We had two options:

Option A: Heroically motor through the night, arrive where we’d planned, angry and sleep-deprived at 3 AM.

Option B: There’s a bay nearby. Not the one in the plan, but a decent one.

The captain put the choice to the crew. We debated and — naturally — first voted to push through. We’d planned this! We had a route!

But the captain was experienced. He calmly explained both options one more time.

What happened

We turned into the bay. Dropped anchor. Watched an incredible sunset. Had an excellent dinner. And sitting there with our plates, we replanned the remaining days in fifteen minutes.

We never made it to the island we’d originally targeted. But we visited two others we hadn’t planned for.

The goal — see beautiful islands, swim, have a great time — was fully achieved. Just not on the route we’d drawn.

The lesson that stuck

In projects, work, and life, we do the exact opposite all the time.

We create a rigid route. Break it into stages. Attach deadlines. And at some point, we forget why the whole thing started in the first place.

The wind changes. Conditions shift. We ourselves change. But instead of replanning the route — while still heading toward the goal — we heroically push toward the next waypoint. At night. Without wind.

And when we finally arrive, the next stage doesn’t work anymore. Because resources are burned. Context has shifted. And the enjoyment and purpose have evaporated somewhere along the way.

This is a skill you can train

The ability to systematically change plans is incredibly valuable. I’d love to say it’s easy, but it’s not. It requires accepting that the plan you spent time creating — maybe even defended in front of stakeholders — is no longer the best path to the goal.

But you can get better at it with practice:

  • Regularly compare your plans to your goals and the weather. Maybe the weather has already changed. Maybe the value of reaching the next island isn’t worth the resources it’ll consume.
  • Check if the purpose of the entire journey has shifted while the plan stayed the same. This happens more often than you’d think.
  • Ask the captain’s question: “What are we actually optimizing for right now?”

I review my own routes twice a year — in January and in July. And whenever the weather changes significantly.

The business version

I’ve seen engineering teams push for months to deliver a feature that nobody needs anymore — because it was in the roadmap. I’ve seen founders refuse to pivot because “we told investors we’d do X.” I’ve seen organizations spend entire quarters cleaning up after a plan that should’ve been abandoned in week two.

The goal isn’t the plan. The goal is the goal. The plan is just today’s best guess at the route.

When the wind changes, the good captains adjust course. The great ones do it calmly, over dinner, in fifteen minutes.

I re-plan routes twice a year — January and July. And whenever the weather changes. The sunset in that unplanned bay remains one of the best I’ve ever seen.