The Thing You Will Regret the Most

“Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover”

Mark Twain

Of all the ideas of the greatest thinkers I’ve written about, the one that I have the most trouble internalizing is regret. In her book, The Top Five Regrets of the Dying, Bronnie Ware reveals the thing that people regret the most when they’re on their deathbed. This is “I wish I had the courage to live a life true to myself, not the life others expected of me.” To a certain extent, I’m following my dreams. After all, I’m reading and writing every day and I do it without expecting anything in return. Like most people though, I don’t think I follow the quote in every area of my life.

Some things are scary. Taking your dream job that doesn’t pay as well, asking someone out on a date, or moving to another country are some of the possibilities we regularly confront. Those things make us uncomfortable in the short term but have the potential to be life-changing in the long term. Like Freud once said, “One day, in retrospect, the years of struggle will strike you as the most beautiful.”

So why is it so difficult to go from theory to practice? I mean, I’ve read entire books about fear and regret and I still can’t seem to get over them. Well, that’s when emotions come into play. Although we blame emotions for our inability to do certain things, they play an important role. In The Subtle Art of Not Giving a Fuck, Mark Manson says “Emotions are simply biological signals designed to nudge you in the direction of beneficial change.” In other words, emotions allowed our ancestors to survive long enough for us to be here today. We shouldn’t be complaining about our emotions; we should be thanking them.

Although our emotions served our ancestors well back when they were hunting in tribes in the savannah, we need to be able to manage them in the modern context. We all know that some things in life have the potential to change our lives and that’s because they’re the hardest ones to do. In those cases, fear works as a compass. Our job is to recognize those moments as they unfold before us and remember that if we don’t act then, we might take the feeling of regret with us until the day we die. 

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