Create a Life that you are Proud to Live

I really like this quote, because it pretty much sums up my way of thinking about life and choices.
I have a recurrent thought in my head whenever I am making big decisions that goes something like this:
- If I could go back in time 5-10 years and tell the Anna from the past what her future is like now - What would she think? Would she be proud? Or would she be disappointed?

I´d like to think that the past Anna would be super-proud of the way some things in my life has turned out. But then of course, regarding some things she´d be like: What the he.. were you thinking?!
And.. She would have a point!