Holly,
Thanks for your openness and honesty as you write. You have a way of writing that makes me think I'm sitting down for coffee with my girlfriend and hearing her share from her heart.
I really like your question, "What am I looking forward to today?" In a way, that IS looking at things from an optimistic perspective because it implies there are things to look forward to.
Your "matching game" is a great reminder for me to go ahead and do my "dream board". It is pretty much the same thing as you explained, except I love how you've added pictures that portray an emotion or experience. I've had the pictures in my head for a long time and I practice visualization, but this would be good for me to do. I have a cork board in my office just waiting for its pictures.
Thanks for the inspiration