Fear, Regret and the What If

This story originally appeared on the Gents Cafe Newsletter. You can subscribe here.

Many questions in life are considered dangerous because the answer is one we typically don’t want to hear. For instance, when your wife asks, “Does this dress make me look fat?” Or, “Do you like my parents?” Some are dangerous to the heart. “Do you love me,” “Will you marry me,” “Do you want a divorce?” As fearful as we are of the answers, we need them for our sanity. There is another question that is more dangerous than all the others, one that is the most terrifying of all simply because we have to ask it. “What if?” 

What if I would have taken that opportunity? What if I told them I loved them before they married someone else? What if I resolved that conflict before they passed away? “What if” is the kind of question that can haunt you for the rest of your life, but only if you give it a chance.

Regret is one of the most destructive emotions we feel. We keep looking back at our lives and second-guess them. We wonder what would have been. While we think about what could have been, what is passes us by.

I was recently driving across the country in a move to the West Coast. It was a long drive, thirty-two hours in the car. While I drove, I was so focused on getting there because I scheduled the move to the hour and had to start my new job that I missed something. I spent the entire drive staring out the windshield to see what was ahead and checking my rearview. 

What I missed was the scenery out the side windows. I focused on where I was going and where I had been and missed where I was. Life is the same way. I notice myself working so hard for tomorrow, to make up for yesterday, that I forget about today. 

When we do this, we miss opportunities that become regrets: and over the next few editions, we will discuss the most common regrets stemming from “What If?”. We’re going to lose the regret and focus on today. 

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