Reset the Compass, When the Wind Changes, So Should You

Momentum without direction leads you adrift. A reflection on an Aruba sailing trip, leadership, and the importance of resetting your compass before the year ends.

Every November, I take a pause, not to plan the following year, but to reset my compass.

It’s easy to confuse momentum with direction. You can be moving fast, chasing goals, and still find yourself completely off course.

A few years ago, I learned that lesson the hard way in Aruba.

My stepdad and I decided to rent an 18-foot Hobie Cat to go sailing. The winds there are always perfect — 20 to 30 mph — and the water that day looked calm and easy. We’d done this before, so we didn’t overthink it. No compass, no captain. Just confidence.

We jumped right in and sailed away from the beach, zigzagging along the coast, maybe 200 yards out. I’ve always loved speed, so naturally, I said, “Let’s bring out the jib sail and really push it.”

Within seconds, the jib filled beautifully, and then everything changed.

The main sail rope had wrapped itself around the rudder.

My stepdad said, “We’ve got a problem.” Before we could fix it, the boat capsized.

I landed hard on the mast and thought I was bleeding. But we didn’t panic. We knew how to right the boat.

We took down the jib, pulled on the lines, and tried flipping it back over, but we forgot two key lessons:

1️⃣ Use the wind to help you, not fight you.

2️⃣ Drop the main sail once the boat is upright.

We didn’t.

So when we finally got it flipped, the tangled rope caught the sail, and the boat took off without us.

We hung on as long as we could, exhausted, gripping the side of the hull while the wind carried us farther out to sea. My arms were shaking. The shoreline looked smaller and smaller.

Then my stepdad said the words I’ll never forget:

“Let go.”

It didn’t feel natural. Letting go never does.

But we did, and watched the boat sail away, flip again miles out.

There we were, floating in open water, the shoreline a thin line in the distance. We had one way back: swim.

That swim taught me something I never forgot, about leadership, rhythm, and life.

Momentum without awareness leads you off course. Speed without direction isn’t strength; it’s chaos.

We eventually made it back, exhausted but safe. But that day, I understood something deeper: sometimes you have to let go of what’s pulling you off course to find your way back.

So as the year winds down, don’t just push to move faster.

Stop. Check your sails. Untangle the ropes. Reset your compass.

Because the wind will always change, but how you steer will decide where you end up.

Coffee Reflection:

Where do you need to pause, untangle, or “let go” before the next season begins?