“Do everything, regret nothing.” — Unknown

There are thousands of movies, memes, and quotes that revolve around the theme of regret – about avoiding regret by embracing everything you’ve done in your past; or regretting the things you didn’t do. Films that follow protagonists that go back in time to relive a life that was otherwise bypassed, or stories about antiheroes that came to terms with their mistakes – mistakes that caused great havoc in their lives or in the greater realm of society.

I had the pleasure of getting sucked into a long-winded conversation with my coworker. Gregarious, warm, and effusive, this guy doesn’t stop when it comes to complimenting.

Today, he shared his past with me. When he was 19, he started his model/runway production company in Florence, Italy, which took him deep into the seedy underbelly of sex, models, drugs, and chaos within the dog-eat-dog world of the fashion industry. But after two decades, he decided to throw the towel in and sell his company. Like a prodigal son, he returned to his family and took a year to soul-search and pick up water skiing. Through the course of events that followed, he met and married his wife, had a child, and transitioned over to where I work now.

What I was most struck by was James’s attitude towards regret. He had none. Even though he danced and flirted with an exhaustive list of leggy models, cutthroat people in the industry, the excess of superficiality, his experience of the world remained blasé and blissfully ignorant to its ugliness. To me, being the “prodigal son” coming home to search for truth, family, meaning, and what mattered most, he should have looked back in dismay at what he had run from.

He then encouraged me to go out in the world and experience as many things as possible, meet as many people as possible, expand my horizons, and open my mind before I get married. “You’ll regret it if you don’t,” he advised me. “Most people who hit their mid-life crisis and haven’t experienced everything end up regretting it. I have no regrets.”

My takeaway, however, was different. While I was challenged to take him up on the offer of travelling to destinations I’ve never been – cool spots in California, Boston, Asia, more parts of Europe – trying the finer culinary treasures of the world, meeting extraordinary people of all walks of life, expanding my cultural appetite, and even taking up new hobbies and getting involved in activities outside of greater DC, I couldn’t help but struggle with the idea of “trying everything” and not being left with an immutable jadedness. Losing your innocence, in a sense. With every experience comes a little bit of losing your naivete to a world prior. Repeated exposure to stimuli dulls and desensitizes. Some experiences can lead to suffering the pangs of painful encounters or turning over leaves better left turned over.

I couldn’t buy the fact that he never experienced regret. I get his modern philosophy about embracing his past; our culture is rampant with self-acceptance and channeling all our mistakes into making better, more complete selves. His past makes up who he is and allows him to appreciate his Greek wife, his precocious three-year-old toddler, and a home in the suburbs. But I believe that regret is not an act of hating or rejecting your past. It’s a brutal and honest evaluation of less than ideal actions you’ve taken up in the past – actions that caused hurt to others, yourself, your career, your life, relationships, etc. Regret doesn’t just come from what you haven’t done. But if you’re a self-evaluating human, you must accept, internalize, and learn from actions that were less than favorable. Take, for instance, the case of a drunk driver who crashes into an 80-year-old-woman crossing the street – shattering her left hip entirely, causing her a hip replacement and thousands of dollars lost on physical therapy. It would be unreasonably calloused to look back on that experience without insurmountable regret – probably enough to cripple a man from ever driving again. Maybe he could have had two drinks instead of 15? Maybe he could have handed his keys over to his sober friend to drive him home?

Regret is a healthy form of self-evaluation. It prompts wisdom and discernment; and it is shrewd preparation for your future actions. It teaches you what mistakes not to make or repeat over again. It provides disclosure into the implications of your actions, and how they can gravely hurt chances, opportunities, people, and even yourself. Or it can help you become better – a better family member, friend, lover, coworker, manager, etc.