Is it a negative thing in weight lifting if you do it every session you lift?

In cycling, I'd think it'd be a good thing to do certain segments till you blow up. But not for every segment and not for the majority of every ride.

Your example of #1 isn't unlike my saying that you just shift to a lower gear ratio and/or just go slower with less power. So I guess we sorta disagree on what failure is. If you make it up the hill or to the finish line of your ride, that's not a failure. Just maybe not a winner. Losers didn't fail, they just didn't cross the line first.