You turn toward the wind, then you’ll be more upwind until later. So you retain optionality by having “more room to go downwind”. (Please if we have a more experienced sailor here, do explain it better!)

What up-front cost are you thinking of?

A non-sailing version might be say you’re on a bicycle, and you can drop down the mountain now and go lateral later, or go lateral now and drop down later, and either way you arrive at your destination after the same time and effort. Going lateral now retains optionality.

Very open to hearing better analogies for the same concept! Perhaps from the world of business?

I interpreted ‘turning towards the wind’ as actually trying to sail against the direction of the wind (very hard/annoying).

So trying to do that first for gains you may never realize is not a great idea.

Like trying to drive your bike uphill so that may easily go downhill at some later point in time.

The biking example makes it clearer what you meant (to me anyhow).

Ah yes I could have been more clear. Edited.