"If I was more effective, what would be I doing right now?"
"If I was more intelligent, how would I approach this problem?"
Sometimes I ask myself these questions, and oftentimes I get good answers.
"If I achieve everything I set out to achieve, what would I have done? How would I have done it? What would I have done right now at this moment?"
I like that last one. Very very useful sometimes.
Something I wrestle with from time to time is whether to focus on my strengths or my weaknesses. On one hand, weaknesses often represent the lowest hanging fruit. If I'm really bad at, say, programming, a small amount of effort can radically increase my abilities. If I was excellent at programming, that same amount of effort would produce negligible results. On the other hand, time spent by a skilled programmer will create usable work, whereas time spent as a poor programmer probably won't produce anything useful.
An interesting thing to consider is that where you spend your time will define who you are as a person. A person who spends all of his time on his strengths will be a very narrowly focused person. He gets good at something and keeps hammering away at it until he's an expert. He who spends time focusing on his weaknesses will have a very broad focus. He'll be fairly good at lots of little things, but not a true expert in any.
So which is better? Well, despite the impression I give in a lot of my writing, not everything has to be extreme. This is one of those cases where an optimal path may lie somewhere in the middle.
For most of my life I've been way on the side of working on my weaknesses. I was terrible with girls, so I became a pickup artist (but quit before I got as good as people like Mystery, Style, Tyler, etc.). I made no money, so I became a professional gambler. Even though I spoke passable Spanish and Chinese, I switched to learning Japanese. I had never traveled, so I spent a year going everywhere. Whenever I saw a big weakness, I would dive into it head on. Once I cross that "decent" threshhold, I'd back off and start something new.