There are many questions in life that are considered dangerous. Most are considered so 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 the sake of our own sanity.

There is another question that is more dangerous than all of 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 continually look back at our lives and second guess it. We wonder what would have been. We ponder what could 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, 32 hours in the car. While I drove, I was so focused on getting there because I scheduled the move down to the hour and I 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 rear view to make sure I hadn’t caught the attention of any police. What I missed, was the scenery out the side windows. I was focused on where I was going, and where I had been, that I 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 I do this, I miss opportunities. These missed opportunities, eventually end up in regrets.

We all have regrets, at most stages of our lives, mistakes, missteps, and wrong turns are almost unavoidable. I have spent a long time looking in the rear view mirror, and because of that, I have compiled a pile of regrets. In sharing these regrets with a friend of mine, we were astonished to discover that, many of our regrets were the same.

So . . .off I went to find out what others were feeling about this. I found myself wondering if others had the same regrets, or if we’re so perfectly matched as friends that even our mistakes were the same. As you can imagine, coincidence wasn’t that prevalent.

We are all similar in the way we live our lives, the world has conditioned us to think that there is a path we must follow, playing it safe and avoiding things that risk all we have worked for. However, is what we worked for what we want? Or what the world has conditioned us to believe we need? I have put together a few of the most repeated regrets, and they are surprising.


  1. I wish I would have lived the life I wanted, not the one that others wanted for me.

This seems so obvious when you look at it. Why would we ever let someone else tell us how to live our lives? It is easy to say you live your own life, but when you look deep within yourself, does that claim hold up?

To live a life that is true to yourself is much harder and more complicated than it used to be. The pressure of your parents to go to college, get a degree, and tackle the titans of industry are things that we all face when we are young. Then the influences of our friends to stay with the group and keep up with their successes sets in when we get older. Then, there is the most commonly overlooked, living our lives trying to emulate the lives of those we admire, actors, musicians, sports stars. We live our lives based on what the culture of those people dictate is desirable.

We have such a finite time on this Earth, why spend it doing something we don’t enjoy? Spend your time doing what you love, listen to the voice inside you that keeps whispering that there is a better path-and have the courage to walk in that direction.

Stay tuned for the rest of the list . . .