Worst Advice Ever: “Be More Aggressive.”

I’m in Antigua.

Been here a little while. Waiting on a weather window to sail away.

It’s well understood in sailing that the boat can often handle more than the crew can. And so to avoid confusion, I have a set of wind and wave parameters I like to sail in. I’m in no rush.

The other day, I overheard two people talking about the weather and leaving. One said, “You need to be more aggressive and just go.”

And I immediately had a flashback.

For years, in boardrooms and offices, I heard the same thing:

“We need to be more aggressive about ______.”

At the time, it never sat right with me.

And it still doesn’t.

Aggression is rarely the right path.

People who know me have heard me say: You have to let the game come to you and then act. The difference between aggressive and decisive is everything.

Aggression doesn’t let a situation unfold. It forces it. It pushes. It tries to bend reality.

Decisive people don’t do that.

Decisive people observe. They gather data. They wait just long enough. They understand timing. And when the moment is right, they move. Completely. Without hesitation.

From the outside, decisiveness can look aggressive. It can feel bold. Fast. Even sharp.

But it’s different.

It’s intentional.

It’s contemplated.

It’s nuanced.

Aggressiveness often lacks those things. And at its worst, it carries a quiet carelessness underneath it.

In sailing, picking a weather window is exactly that balance.

I wait.

I watch.

I let the situation unfold.

But when the opportunity shows itself, I will take it.

It may look aggressive.

It won’t be.

It will be decisive.

So next time someone says, “We need to be more aggressive,” pause and ask:

Aggressive?

Or decisive?