The hand of an elderly person.

3 Things You’ll Regret When You’re Older, Proven by History

Lessons from prominent figures of history.

They say history doesn’t repeat itself, but it rhymes. Well I hope you like poems. The past is full of them. Situations that show themselves over and over again. Instead of ignoring them, you can learn from them. You can apply them to the verses of your own life. In turn, you can live a more meaningful existence. The following lessons are pulled from well-known figures in time.

As you move through this article, consider how you can learn from their happenings. Observe what they did and whether or not you should follow their example. Or, quite possibly, if you should choose a different route altogether.



My eyebrows furrow. If you were next to me, you would see visible bewilderment on my face. In Shoe Dog by Phil Knight, Knight recounts his founding of Nike. From its earliest inception to going public and beyond. As he tells of his experience, he mentions something that takes me by surprise. He says that at the end of the day, his biggest regret is that he can’t go back and do it all again. This is his biggest regret?

Leading up to this statement, I’m sure his answer will be something like, I wish I didn’t work so hard or I wish I spent more time with my family. Nope. It is I wish I could do it all again. Here’s someone that loved what he did. He got meaning from his work – even through the hard times (of which there were many).

The lesson: Fill your life with meaningful pursuits.

In your life, consider the various aspects of who you are. You as a spouse, parent, athlete, homeowner. Then, consider what fulfillment looks like for you in each of those areas. Write it down. Keep it brief. A single sentence is perfect. For instance, in the case of myself as parent, fulfillment to me looks like: A loving and wonderful relationship with my daughter.


Put some eggs aside

The Power Broker by Robert A. Caro focuses on the life of Robert Moses. A man whose power within New York City is nearly unmatched in the 1900s. He builds bridges, parks, and highways. He writes legislation that gives him evermore control. Near the end of his life though, he gets sloppy. He makes errors on the chessboard. This allows his enemies to worm their way in and eventually remove him from his posts. Moses is left with a massive void. His brain is sharp as ever, but he has nothing to use it on. He’s found pacing, unsettled by the vast stretches of time he has always wanted but has grown to hate.

Ironically, he should have seen this coming. In Moses’ early political days, he befriends someone by the name of Al Smith. Al Smith is to become governor of New York. Once elected, he brings Moses with him and helps him along his climb to power. Smith eventually gets tired of politics though and retires. He waves goodbye to his loving supporters and embraces the peace of retirement. This quickly becomes a prison for him though as he loses his biggest source of fulfillment. Transforming into the stereotypical old grouch, his days are filled with yearning for what once was.

The lesson: Diversify your passions.

Don’t put all your eggs in one career-focused basket. Be multifaceted. That way if something disappears, you still have other areas of purpose in your life. In the previous section, you figured out what fulfillment looks like to you. Now, set goals in that direction. Start building that meaningful, variety-filled existence.


Between a Rockefeller and a hard place

“[Rockefeller] fretted endlessly about his company and, below the surface, was constantly on edge. In one of his few admissions of weakness, he recalled that ‘for years on end I never had a solid night’s sleep, worrying about how it was to come out … I tossed about in bed night after night worrying over the outcome … All the fortune that I have made has not served to compensate for the anxiety of that period.’”

In the biography of John D. Rockefeller, Titan by Ron Chernow, one thing is clear. He is incredibly wealthy, but not all that happy. In fact, it’s not until his later years that he finally starts to let himself have fun. Up to that point, even though he is financially successful, he is consumed with worry and stress.

On the other hand, you have someone like Morrie Schwartz. You may have heard of Morrie before. The book Tuesdays with Morrie by Mitch Albom is named after him. The book explains how Morrie is diagnosed with the fatal disease, ALS. Essentially a death sentence. Yet Morrie makes the most of his remaining time – visiting with loved ones and interesting individuals alike. Through the pain of ALS, Morrie focuses on gratitude. On how he is lucky the way he is going. Because he has the ability to say goodbye when so many others don’t have that chance.

The lesson: Be grateful.

Would gratitude have allowed Rockefeller to enjoy more of his journey? You’d have to ask him. It certainly worked for Morrie though. That said, one of my current goals is to think of things I’m grateful for. I do it for five minutes and I do it five days a week. This exercise reminds me of all the good that surrounds me. It brightens my mood. And on rough days, it brings me back to center. Combine this practice with your other goals and you will find that fulfillment is that much easier to attain.


Moving forward with fewer regrets

Learn from the past. Recognize that situations won’t be exact, but they will rhyme. Notice the patterns and apply them to your own life. Avoid the mistakes of your historical ancestors. Instead, transcend them. To live a life with fewer regrets:

  1. Consider what fulfillment looks like to you.
  2. Set goals in that direction.
  3. Regularly practice gratitude along the way.

I’ll leave you with the following quote from Morrie: “So many people walk around with a meaningless life. They seem half-asleep, even when they’re busy doing things they think are important. This is because they’re chasing the wrong things. The way you get meaning into your life is to devote yourself to loving others, devote yourself to your community around you, and devote yourself to creating something that gives you purpose and meaning.”

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