“If I was lying on my deathbed and I had kept this secret and never ever did anything about it, I would be lying there saying, ‘You just blew your entire life. You never dealt with yourself’, and I don’t want that to happen.”    ~ Caitlyn Jenner

When I was in high school, one of my classmates became the first girl to play on the varsity boys’ football team. Our school wasn’t huge, but we usually had a pretty good team and had just won a state championship the previous year. So a girl named Mary making the varsity team – and even playing in some of the games – was a big deal. So much so that Olympic Medalist Bruce Jenner came to our school to celebrate her athletic achievement. For a small city in the Midwest that really was a big deal – camera crews everywhere and both TV and newspaper reporters lined up for interviews. After all, Bruce Jenner had set the world record for the Decathlon just two years earlier and still held the title of the “world’s greatest athlete” for his feat.

That high school memory was in my mind last summer every time I saw yet another mention of Bruce Jenner’s recent public transition to becoming Caitlyn Jenner. Because all I can wonder is how much his gender identity must have pained him, even as long as 35 years ago. Hearing his story now made me wonder about that young decathlete, honoring a girl who was only 17 but still brave enough to step outside her expected gender role to do what she loved. And it made me respect the courage it took as a man with a lot more years of life behind him deciding to live his truth as a woman.

So far I’ve changed my life’s direction drastically twice – once when I was only twenty and then thirty years later — and it’s a lot harder when you’re older, less flexible, more set in your expectations of what your life should look like. But when I finally figured out that more of my years were behind me than in front of me, for a while I began to spend more time looking backwards than forwards – not always with the happiest of thoughts.

All the mistakes… The job I stayed in too long and the one I didn’t get. The relationship I couldn’t get free of and the one that got away. The hours spent with my laptop open when I could have been crawling around on the floor with my son. The trips not taken and some of the disastrous ones that were. Worst of all, days and weeks and years spent settling for the familiar over the truly desired.

Socrates said that the unexamined life is not worth living. In my life, most of the regrets I have are tied to times when I was not examining my choices, not looking too closely at my actions, failing to pay attention to my own internal guide. It’s in those moments that I was most likely to fall back on taking the path of least resistance, or doing what I thought I should or worse, what someone else thought was best for me.

The year I turned 50, I must have said – to myself and to anyone who would listen – “I should have turned 50 a long time ago!” That was the year I left the corporate job that was killing me, and began to make a lot of other choices that people around me thought were crazy. But that year, and every year since, I’ve continued on that path. The path that pushes me to say no even when it makes someone else angry. The path that allows every ‘yes’ to be a “hell yes!” The path that scares me to pieces even as it exhilarates my soul.

The path that is not always fun and definitely not easy but the one that will lead me to conclude some day that I definitely did not blow my life.