Help Me Improve My Ability to Plan

Building time into my day/life for strategic planning and futuristic thinking is something that I really struggle with. As a person and leader I am always running forward with a try-and-see approach. For most things I am nimble enough to adjust on the fly or deal with problems as they arise. However I think I could save myself time, energy and stress by predicting some of the roadblocks and detouring long before I ever even reach them.

How do you handle planning and thinking as it relates to your work/life?