Keep Your Work
Keep your iterations during the design process, and, when finished, look back and review how you ended up where you did. What decisions didn’t work and why? All failures should produce learnings.
I’m currently doing all my design work in Sketch. Previously, my tool of choice was InDesign. Both are great for me because I like to work iteratively and these tools make that easy. After every quick round of design changes to a comp/artboard, I make a duplicate and continue with my next changes there. Sometimes the changes are small differences on one element or component. Sometimes the changes are more broad and structural. But no matter the scope, I can always read the story of how I came to the final solution.
When it’s time to archive a project, I go through my designs and review. I take a few notes, asking myself, “What did I learn from this?” It’s not always much. Maybe something like, “Call to Actions always feel better to me when placed closer to the bottom right.” Or, “The solution for greater clarity in this component depended on increasing the typographic contrast.” I then often delete many of the interum iterations, keeping ones which most represent my best thinking. Reducing the clutter will make going back to the project later easier to revist.