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  • Writer's pictureDr. CK Bray

Things I Wish I Had Done or Learned Earlier in My Life

Ryan Holiday (one of my favorite authors) wrote an article on 24 things he wished he had done sooner in his life. I loved the article and decided I wanted to do the same thing. With excerpts from his article, I have written things I wished I had done or learned earlier in my life. I hope they help you and encourage you to examine your life and make some minor changes that have been with you for years.

Of all the things in life we don’t control, the past is the clearest. It already happened. It’s done. It’s set in stone, and we can look back at it with a clear view of what we should have done differently.

For this reason, the Stoics were not big on regret; I will say that neither am I. There’s no reason to whip yourself or be paralyzed by the “What Ifs” of life. Still, we can learn and grow and do better the next time. In fact, we must, and hopefully we do.

Ryan Holiday interviewed Dr. Edith Eger, a Holocaust survivor and author of The Choice. He asked her about something he regretted, a relationship he had messed up. She looked at him and said she could give him a gift that would solve that guilt right now. “I'll give you a sentence,” she said, “One sentence—if I knew then what I know now, I would have done things differently.” That’s the end of that, she said. “Guilt is in the past, and the one thing you cannot change is the past.”

So below are some things that, while I try not to regret, I wish I had done differently or sooner or better. I think you might benefit from doing them sooner too… So, please take a listen and think about what I have discussed. This would be a great dinner conversation with your family or friends.The small moments with my kids. In our home, bath time and bedtime were a fantastic ritual (It was incredible because the kids were going to bed and it was such a fun habit). We would put them in the warm bathtub, scrub their hair, and have warm towels ready for them as they got out, and then we would read a story and sing a few songs. (All the songs they can sing by memory to this day, twenty-something years later.). I wish I had enjoyed it more and thought less about what I had to do after the kids were in bed. I loved those moments; they passed by so quickly that I realized I should have cherished and enjoyed them more. The daily bath time ritual is one way my children felt safe and loved. It didn’t matter where we were or who was visiting; we had our bedtime ritual.

  1. I should have stood up for myself more and in a stronger manner. In a corporate meeting with close to forty people in the room, my manager put a picture up of my family’s Christmas card up on the screen and mocked it. I was furious and remember grabbing the chair so hard to keep my mouth shut. Looking back, I was going to deal with it later; I should have said something right then and there and called her out. It was a malevolent evil act, and while I would never stand for such behavior now, I did then. I was at the company for less than two years, and that was the beginning of the end. I wish I stood up for myself more vocally in my younger years. Several friends were in the room at the time, individuals I had been friends with for over six years at another company. When they were later asked about what happened, they lied to save their jobs. People always say, “I would hide a Jewish individual from Hitler’s armies. I learned that day that if you can’t even stand up for a friend, you would never have the courage to do something more courageous like hide an individual in your home that, if you got caught, would mean your family would be punished or killed.

  2. I look back at stuff I was so worked up about, things I fretted about, fought about, took personally, held onto, and now think, WHAT? If I had to return and give a younger version of myself, one word of advice would be: “Relax.”

  3. When I wrote my first book Best Job Ever, I wrote it with the intent to be a New York Times bestseller, and the second reason was to help people who needed a job change or to figure out in life what to do. I did those two things in the wrong order, and it caused me much unhappiness. I have changed that ratio now when I’m writing. I am writing to help people and not for the result. It has made my writing experience so much better.

  4. Regarding saving and investing money, there are so many automatic transfers I should have set up earlier. Accounts such as my retirement, my kid’s college, a rainy-day fund, etc.–I am constantly surprised by how large the balances have been. Set it and forget it…the sooner you do it, the more you’ll have. You won’t regret compound interest. I remind every young person starting their first job to set up those accounts right now.

  5. I learned the lesson of the power of habits earlier than most but later than I wished I would have. In my twenties, I should have been setting up microtry’s (small actions to create habits). Great things can happen when you focus 20 to 30 minutes daily on something specific. I could have ruled the world if I would have started that in my teenage years.

  6. Life is too short to put up with anything bad. Bad writing, bad books, bad friends, bad movies, etc. If the food sucks, don’t finish it. If the speaker is boring, get up and leave. If the party or dinner with friends is no fun, go home. Stop powering through the crap.

  7. I should have listened to my wife more and earlier. I have made terrible mistakes in my career as a businessperson and a business owner. Whenever my wife said don’t do it, and I did it, she was always right.

  8. Regarding my parents, I should have had some important conversations with them earlier in my adulthood. Big mistake! My silence sent a message that I agreed with certain behaviors, which cost me peace of mind for far too long. I should have drawn better boundaries with my parents sooner.

  9. It’s clear to me in retrospect that my desire for approval, for being seen, for being a part of something important or newsworthy or exciting, blinded me to numerous things, including the character of certain people I worked for, the motives of friends and also losing the path I should have been on. It’s not your fault that things happen to you; it is your fault if you don’t learn how to adjust accordingly.

  10. Deep down, you know that accomplishing things won’t make you happy, but I always fantasized that it would at least feel good. I was so wrong. Writing my first book and selling over 10,000 copies in the first week…….A total letdown; I was mad I didn’t make the NY Times list. Getting the big Fortune 10 company deal that would take away money worries. Nothing…... A trick of evolution drives us, and no one is immune from making this mistake. The feeling you are seeking comes from the journey, rarely the destination. The destination can often be a letdown.

  11. I put up with bad people for far too long. Individuals I treated so well, and they never even came close to reciprocating in the relationship, even when I desperately needed it. If I had cleared out those relationships earlier, I would have saved some serious brain trauma, rumination, and cortisol overload.

  12. With 36 years of data now, I can confidently say that I have never once lost my temper and afterward said, “I’m so glad I did that.” Well, except once when a person attacked me verbally in my home in front of my children. You don’t do that.

  13. With the exception of the kind of people for whom no contact is a necessary strategy, I have never regretted the impulse to send someone a check-in text or call. How glad I am when I called someone who needed a friend or told someone how much they meant to me, only for them to pass away a few months later. I should have practiced this earlier in my life.

  14. Don’t kick cans down the road. Take care of things right there and right now. It saves you the mental energy of thinking about it all day, all week, or all month. I have tried to be better at this. I also noticed that the project or job never takes as long as I thought.

  15. Most of all, I wish that I had enjoyed my work sooner. I should have enjoyed my first big consulting deal more. I was so worried and fearful. I’ve since made a conscious effort to appreciate that I get to do the work I do and not let it turn into a grind. Why not make each day the win, the joy, the experience as opposed to the end result?

As Marcus Aurelius said, it’s insane to tie your well-being to things outside your control. Marcus writes that success, mastery, and sanity come from tying your well-being “to your actions.” If you did your best, gave it your all, and acted with your best judgment—you’ve won.






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