One of two things typically happens.
We look back and say ‘I went for it. I gave it my best’ or we look back and say, ‘I wish I had at least tried. I wonder what would have happened had I gone after it.’
One reason why we don’t do the things that our hearts feel called to—whether it’s to run a marathon, sculpt, start a business, make more memories as a family, make amends, help others be able to not only survive, but to have a choice or dream at all in their lives—is that we often think we will get to it someday when… fill in the blank. Some people will get to those things, but most won’t. And the reasons why we don’t get to them will seem like skimpy reasons when we look back later in life and see that time and opportunity slipped through all of our todays; someday never came.
I keep returning to this idea that maybe I will participate in a triathlon within the next two or three years. One thing stops me… well, two actually. I can’t really swim (queue gasps). And I’m not much of a runner. So why would I want to do a triathlon? One reason is that I don’t care for sitting on the sidelines simply because self-imposed limitations benched me, although that’s not necessarily a good enough reason to invest myself in such a demanding endeavor. But sometimes it is enough to do it so that I have no regrets; it is hard on the soul to look back and wish one had tried.
And there are other benefits—it is immensely valuable in life to face limitations in oneself, to become a rank beginner, to feel overwhelmed by what one doesn’t know, to go through the learning and to achieve what had felt unlikely or impossible. It nourishes our soul to triumph over fears, lack of faith, loss of hope, apathy, mediocrity. It is the design of the human spirit to believe, to have faith, to face overwhelming challenges, to give our very best in what we do.
So here I am… researching and getting clear on what this really means, the training involved, the commitment it will require. Right now, the thought of swimming a couple kilometers across the choppy cold waters of a sea loch, cycling leg-burning climbs and distances and running mile after endless mile falls into the impossible category for me.
It is good to face the question, ‘Why do it?’ for a someday dream or an item on my bucket list. Will I make room in my life and apply myself or just imagine it in the nice, beautiful future life that seems to lie just ahead, where I have enough time, and my home, my hobbies, my accomplishments and my fulfillment look just like they do on my Pinterest boards? I say things like, ‘Oh, I plan on doing that someday.’ This is such a dangerous statement because it gives me a sense of things being a part of my life that are really just pretty pictures. It makes me believe that I am a triathlete waiting for the right time in my life for it to happen, instead of a dreamer who hasn’t signed up for swimming lessons.
I have learned, from my own experience with lost opportunities and from much older and wiser journeyers, to take quite seriously the bucket list imaginings. There isn’t enough life to do everything I can imagine. And if I wait for someday, there is even less, if I make it to someday at all. I have the strength and health of my body now. It is folly to assume it will always be so, although I hope for it.
Soon it will be time to choose; to sign up for swimming lessons and begin running and cycling training or make a conscious decision to let it go and leave it behind, no regrets. There are many things we cannot control in the world and in our lives. Some things we will never get to know or do for reasons not of our own making. But when we do have a choice, it is good for our soul to face the responsibility of the choice and consciously create the story of our life. We were not meant to allow our dreams to go unanswered.
The things that loom so large as obstacles now will so often look manageable or even insignificant as we look back from a vantage point further down the road, where the wish and wonder return unbidden. May we find the courage and perseverance to understand and face the many choices we do have, to live outrageously alive and to leave everything on the field of our life.
Love this Sugarland song, ‘Wide Open’ to get up and after it!
This is the first in a series of posts about going after one’s dreams, covering the gamut from people and things that are Dream Killers and what to do about them, to how to know when to keep going or when to let go, and once you’ve reached a dream, then what?

I signed up for the Danskin one three years ago, and ended up having emergency gall bladder surgery… Its still a dream of mine…. ready or not, here we go??!!!??
Sad but true, Jim, that sometimes the ones we hope support our dreams the most, support them the least.
Dreamkillers… otherwise known as “family”.
I would do a triathalon with you in a couple years. I am a strong swimmer and cyclist, and can hold my own jogging/running. Just need to practice and build my endurance back up!!!!!
It sounds like a triathlon is right up your alley. I gotta get this sorted in my mind for myself. Will I or won’t I? I’ll figure it out soon.