This really resonated with me.
One of the "problems" with over thinking things and "figuring out all the potential problems" is that when presenting the ideas/concepts/solutions one doesn't leave enough room for response by the target audience. You end up with responses like "well - you're really smart - you seem to have thought of everything". Often we really do want and need the audience to have a chance to respond, poke holes, describe what they find to be useful / not useful.