This past week I encountered an experience that on the surface seemed ordinary but my failure to complete, has been at the fore front of my mind ever since. Not because of the actual undertaking, but because in hindsight it turned out to be a metaphor for a lesson in my life.

The adventure occurred on Monday afternoon on the island of Maui. Those of you who know me realize that my ideal vacation includes reading, relaxing, and discovering the best cocktail followed by the ultimate perfect bite. But for some notion on this Monday afternoon I found myself headed shoreline with a friend declaring that I needed to do something fresh and exciting. His grand idea was going to exert more energy in a single activity than I had in last ten years combined. But who I am to back away from a challenge?

The first phase required me to swim. Maybe not in the deepest water, but it was a distance and surely further out in the ocean than my children have every witness me embarking. So off I went among the fish in clear blue refreshing water. Then I reached phased two. The climb. And I mean it was a challenge. The best description is to imagine me as spider man scaling the side of a building. Mind you I am doing this in a bikini with a large audience of strangers of every age shape and size. Barefoot and vertically challenged I climbed, straddled, crawled my way to the top and along to my final destination. Small children and crabs raced by me at great speed and agility. But hey I thought I made it, I overcame two legs of a journey. Good job Jacky!

Finally I was perched on a rock inches from the promise land, the 20 foot plunge into the crystal, vibrant Pacific Ocean below. I took a moment to rest, catch my breath and gather my thoughts. Here is where I met Carly. A spunky13 year old girl who informed me this jump into the water below was nothing. She had done it many times and even accomplished a higher distance in Jamaica. As we all sat there and waited for Carly’s dad to return so she could dive into life, it became apparent it was my turn. I got up, looked out into the horizon viewing one of my most favorite locations in the world. I looked down my destination below where those who have gone before me swam around and I FROOZE. What seemed a juvenile exercise, where the reward out-weighed the risk tenfold; I couldn’t take that final step.

With Carly and company cheering me on all I had to do was fall forward. I had to give up control for 5 seconds and I just couldn’t do it. So in true Jacky fashion I quickly gathered my thoughts scrambled back to a safe place to sit and consider my options. Obviously the most efficient, safest and most honorable move was to get back up and take a leap of faith. But not me, I started problem solving. I let risk outweigh the reward. Needless to say it took another 20 minutes to scale down to a lower point and jumped back into the ocean.

Once back on shore and sitting at the Tiki Bar with Mai Tai in hand it dawned on me. The past hour Hawaiian adventure was a lesson for my life. I worked so hard to get to the finish line. The most difficult and highest risk activities I managed to conquer. I praised myself for tackling obstacles I normally would avoid. I encountered setbacks and suffered some scraps along the way. I had my supporters and some skeptics. I pushed myself beyond my boundary, set milestone goals. But in the end when it came to that moment of truth, the final step, probably the easiest part of the journey I couldn’t seem to find the courage to take the final step.

How many moments have passed me by over the last four decades for the exact same reasons? Why do I work so hard and then end up just short of the finish line?

I have been working on writing a blog post on thoughtfulness. In today’s world of instant gratification and technology I feel the art of thinking before we speak or act is getting lost in translation. But maybe this experience has opened my eyes to the balance between being thoughtful and impulsive. What lesson have I learned? Well I would do anything to go back and leap off that damn rock. But, maybe the next time the metaphorical leap at the finish line presents itself I will just close my eyes and jump.