One of my favorite approach is doing things to see what may not work and why- instead of chasing what would work.
It’s like, dismissing the wrong way first, when walking thorough the process- up to certain point- is done and the reason why it won’t work has been grasped. It could be “costly” in terms of effort, time, and hitting the wall might seems like a “loss” or “waste”.
The worthy part is that, you either get to one step closer to the correct resolution in a fashion that Thomas Alva Edison suggested- or even better, you would discover another way of doing things that you wouldn’t see otherwise.
The best is that, the habit helps to think broadly, and eventually you start to not limiting yourself to boundary. Other side-effect is, you get to know a lot about the wrong ways better than most folks. ;)
I frequently practice this, specially when designing stuff. However, I find, this could be very fatal when you’re enjoying this process too much, and practicing this habit in times when you do not have enough resource to burn away!
BTW it’s not that you want to do what is very obvious failure- we’re talking about things that may have possibility of success, or failure- which you do not know for sure, including the mindset and expectation for the outcome.