Taking The Plunge; A Flip Flop Philosophy

Life won’t wait.

“If we wait until we are ready, we will be waiting the rest of our lives” –Lemony Snicket


It wasn’t too long ago that I was on St. Thomas and was engaged in a conversation with my good friend Jeff as we gazed out over Red Hook and Vessup Bay during another one of those magical evenings in the Virgin Islands. I was sharing with him my intent to move down island and we were discussing the pros and cons, the hardships and the benefits. Because let’s face it, if you think moving to an island is going to be all cocktails and sunshine you are going to be disappointed. But that doesn’t mean the pleasure won’t be worth all the pain.

I had said that all things considered I know it’s a move I will make one day when I am ready financially, job wise, education wise and so forth. Jeff then said to me something that made all too much sense and I honestly think is true; and more that it applies to many areas of life. He said if you wait until you’re ready then it’ll never happen. You just have to take the chance and roll the dice (paraphrasing here of course).

In reality waiting until I am ready to make such a move, or any move for that matter, is pretty novel for me. My entire life has been spent on the trail less traveled and as anyone who has deviated from the normal life path knows, much of that trail crosses through rivers and over cliffs. So, one has to be ready to take a chance, a leap, the proverbial plunge.

Sometimes it’s scary and you just close your eyes and jump hoping to land in deep water, but sometimes you land shallow and break your ass on the bottom! But, regardless of the path you chose I think all of us take that plunge from time to time and, as is with life, all of us sometimes end up with a bruised tailbone from landing in shallow water… at times water we thought was well deep enough.

But what sets aside the adventurer from the one who goes the safer route is that we are able to roll with the punches and not be deterred from or regret our decisions. Me, I’d rather spend a few days nursing a bruised bottom (ego) knowing I faced that challenge and moved onto the next adventure than looking back and wondering how it would have been.

The truth is there is always a reason, and usually a pretty good one, not to take the leap or make the move.  But, in that there must also be a pretty good reason to make that move; otherwise why are you even considering it?

So don’t wait for that perfect moment or for your trail to naturally take you safely down to your beach. Face the possibility that you may have to jump and forge your own trail straight to where you deep down want to be. But when you come to that inevitable cliff don’t just stand idle with your toes hanging over the edge.  Look out at the blue waters, smile, and take that last step.

And even if you bust your ass… in my book it’s better to tend to your wounds in paradise with a cold drink than stand on the cliff and watch as times passes by. It’s your life after-all…

Two Roads. Robert Frost

Two Roads. Robert Frost

I’ll see you down island.


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