I think there's a balance to be struck. My wife's family has an expression they like to use: "If you want to see God laugh, make a plan."
Not that making a plan is a bad idea. But you can spend weeks planning for every contingency of a situation, when in reality stumbling along the one path that works out might have been more efficient.
In cases where you just keep doing the same dumb thing over and over, I agree with you. There, you know there's a better way - and there's a lot less variables between now and the goal.
But there are also cases where we'd be better served embracing serendipity and letting the universe surprise us.