“Our culture has engaged in a Faustian bargain in which we trade our genius and artistry for stability.” — Seth Godin, Graceful

Some risk is necessary for true reward. This we know to be true. But we also know that there’s reward in being firmly anchored to something of substance when it gets a bit stormy. The trick is to know when to leave the safe harbor and when to stay put. As with everything, life is a balancing act skating the line between order and chaos.

“Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did do. So throw off the bowlines! Sail away from safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover!” — Attributed to, but definitely NOT Mark Twain, rather a quote from H. Jackson Brown

The twenty-year filter is a helpful way to approach decision-making: Will staying in the safe harbor be something I regret in twenty years or ensure I make it another day on my journey to twenty years? Will this work mean anything in twenty years? Will I be healthy enough to do this thing I want to do now in twenty years? Will there be any glaciers to hike in twenty years? And so on. Each question posed reveals a truth to us that guides us. Often the answer is, “Don’t wait!” Sometimes the answer is, “Not this”. And sometimes that answer is, “Not yet”.

When we can see the forest for the trees, we gain perspective, insight and a proper sense of direction. Twenty years is about a quarter of a lifetime, if we’re lucky, and gives us a big enough runway to take off for wherever we want to go. In twenty years one can raise a couple of infants to adulthood, build sustained career momentum through a collected network of trusted business associates, pick up an advanced degree or gain mastery in a desired skill. Or we can fritter it away on the trivial and inconsequential. It’s a good round number that is useful in so many ways.

When I look back on the last twenty years, I’m stunned by how quickly it flew by, but also thrilled with the better decisions I’ve made in that time. The poor decisions weigh on me too, but when we live a life of personal integrity and accountability, the good often outweighs the bad. Those good decisions were often unconsciously made with a long-term view, the bad with a distinctly short-term view. Putting a spotlight on this process with a twenty-year filter often makes our choice even more obvious. What exactly are we trading off later for this choice now?