Planning vs. Serendipity

If you ask my friends, they will readily admit that one of my faults is that I am an "overthinker".  Given a theoretical situation, I will spend hours figuring out the outcome, what it means to me, and what the odds are that it will occur.  I also happen to be a card-carrying pessimist, so you can imagine that my expected outcome will rarely be positive and my belief is that odds are never in my favor. 

I wasn't always this way, for better or for worse.  Not long ago, I took individuals at face value and believed in the best of people. Fast forward through a scarring divorce plus a few personal/professional betrayals and I came out the other side determined to be 1) prepared and 2) protected.  What I *really* wanted, deep down, was never to be hurt again.  It's quite the internal conflict: wanting to go after something (a relationship, a job position, etc) but being so damn SCARED about potential pain that I'd end up sabotaging myself at the very beginning, because at least then I could control the depth/length of the pain.

A close friend recently pointed out that I was really being quite arrogant - believing that I could foresee the future and all it's outcomes. Quite the power I have, eh? Initially I tried to defend (to her and myself) what I was doing, after all - what's wrong with planning and being prepared?  It wasn't until just recently that I realized I was preventing myself from experiencing something I used to believe in deeply: serendipity. Serendipity is described in the dictionary as: good luck in discovering unexpected things.  To me it has always meant finding something valuable or delightful when you are not looking for it.  Kind of the the same, but different.

If I'm too busy worrying about the future, I'm missing opportunities in the *now*. I need to let the story play itself out without reading the last page first.  Another friend opened up to me that they sensed a change in me when it appeared that I had an "oh, what the hell - might as well take the chance" moment.  And they were right.  When I gave up trying to micro-manage my life and just let it be... I found serendipity.