Are Bucket Lists Overrated?

As I contemplate, “Where to from here?” at 86, I realize it’s the day-to-day things that spark happiness.

By David I. Leo

Editor’s note: David Leo is a longtime columnist with Rethinking65. Read more of his articles here.

David Leo
David Leo

In his book “30 Lessons for Living: Tried and True Advice from the Wisest Americans,” author Karl Pillemer suggests that his “experts” — the more than 1,000 individuals ages 70 to 100 whom he interviewed — provide excellent advice for all of us to live by. Among the very good lessons to be learned through the book are how to have a happy marriage, how to have a successful and fulfilling career, and, critically, “aging fearlessly and well.”

Several of the lessons in this 2012 book, which I stumbled upon for the first time several months ago, may impact some of us more than others. For example, there’s the lesson to abandon the fight against aging, live a life without regret, and especially, “live as though life is short – because it is, by making sure to do important things now.”

Pillemar also states, “Happiness is a choice, not a condition.” The single best piece of advice is to take responsibility for your own happiness throughout your life. I often quote Harvard professor Tal Ben-Sharar, who states in his book “Happier”: “The ultimate currency for a human being is happiness.” Full stop!

‘I Don’t Know What 86 Is Supposed to Feel Like’

Pillemer’s book gave me pause, not so much to rehash where I didn’t effectively incorporate “the lessons,” but to think about how I should live my remaining years. Noting that I am now 86, I asked myself if I should have a “bucket list” that needs completion before I stop aging.

While I am cognitively sound and physically capable, I can see the lights at the end of the runway even if I’m fortunate to have another ten or more years.

Many things always come to my mind when I think about my advancing years. I wonder about other people my age and their thoughts. When I look in the mirror, I no longer see that handsome young man of 50 years ago. (Handsome is probably an exaggeration but I do remember 50 years ago.) I don’t feel 86. Then again, I don’t feel any age, and I don’t know what 86 is supposed to feel like.

I do know I have a few more aches and pains than I did years ago. I see more doctors than I did years ago, and take more medications than I did years ago. My knees and hips won’t let me run like I used to. But, other than that, I don’t know how I’m supposed to feel.

Is there supposed to be a pressure to make this part of my life, my last hurrah as it were, something special? Am I supposed to enshrine its value, share my special wisdom with my progeny, take my wife to special places, tell my country where they’re screwing up or where they’re doing well, or contribute that last ounce of value to my coaching clients?

Am I supposed to take some sort of special trip to visit my hallowed birthplace which essentially is somewhere around the fish market in Hunts Point, The Bronx, New York, where there used to be a hospital and where I “saw” my first day? Or at least, they tell me that was where my first day was on April 2, 1938.

Still Seeking and Creating Happiness

So, I thought about it, and thought about how I currently live my life, and if I had any special to-do’s to wrap up my years with the Big Bang, if you will. And I think the answer is “no.”

As I reflect below, and think of the lit runway down the road, I think my path is clear: continue doing what I’m doing, seek happiness everywhere, and create happiness wherever I can. As Ben-Shahar says, this is how I will get it:

  • I’ll continue to enjoy time with my wife while quietly watching TV in the evening after I’ve finally gotten off my “damn PC.” She will continue to yell at me if I speak and interrupt the show’s dialogue. She is the loving and loved person who helps keep me going in the right direction.
  • I’ll continue to speak with and visit my children and grandchildren as they are my loves and my true legacy, among all the things I will leave behind.
  • I’ll continue to help my family when I can and when they want it.
  • I’ll continue to think lovingly, daily pretty much, of my dear departed brother and sister. I’ll remember all the good things they imparted on my life.
  • I’ll continue to cook dinners for my wife, as we both enjoy that part of the day.
  • I’ll continue spending three hours working out at the gym three days a week for as long as I can.
  • I’ll continue sharing my 65 years of business and educational experience with my clients, helping them improve and grow their businesses so their clients and their own families’ benefit.
  • I’ll continue to write my thoughts occasionally, partly in hope that they benefit any readers and partly to get them out of my brain and onto paper so I can make room for other thoughts.
  • I’ll continue to travel to places near and far to enjoy the beauty of this world while it still exists. I am always seeking the next trip to regain the peace and serenity I found in Monopoli, Italy — in its olive groves, by the Adriatic Sea and in the sun. Sitting in a restaurant by the sea in the beauty of “old town” — while watching others pass by, feeling the sun’s warmth, enjoying the food, and relaxing — was the epitome of why we are here on earth. I don’t think there’s anything more.

I am sure those feelings exist in many places where there are good people and good values. To me, it’s in the “old country” as my grandparents would say — not the rat race of America where our way of life and our politics can destroy.

  • I’ll continue to find people to admire for their values, wisdom, caring and ways of life.
  • I’ll continue to read non-fiction to learn things I don’t know, while humbly knowing that what I don’t know is infinite. My mother often asked me, “Are you afraid you’ll miss something?” My answer was always yes.
  • I’ll continue to try and be helpful to others and improve my charity.
  • I’ll continue to be a conservative spender.
  • I’ll probably continue to be upset about my shrinking height, now 4 1/2 inches less than during my high-school years.
  • I will continue to support causes in which I believe in, not only for me but for my progeny and my species who deserve a better use of our planet than we currently provide it.
  • I will continue to voice my opinions to our political leaders even though it doesn’t seem to help.
  • I will continue to occasionally go to the “piazza” around Madison Square Park to sit in the sun, have a coffee, and read a book or just watch people and think about being in Italy in the sun, by the sea.
  • I will continue to wonder why I have so many good things in my life, and hopefully be grateful enough even with all my flaws.
  • I’ll continue to wonder why the world is always at odds for some reason or other when there are so many positive ways to enjoy our brief time on such a beautiful planet.
  • I’ll continue to have a few regrets and try not to let them get me down. My regrets include not having spent enough time with my sons when they were growing up, not having been much more intentional in taking charge of my own life, worrying about everything, not being more aggressive in my education and learning, and not asking my parents more questions.

Basically, I’ll continue to live my life as I have these last couple decades in hopes it will satisfy those I love and myself. I have no major complaints today, and no “bucket list.” I hope I can say that every day for a long time and continue being grateful for all my gifts.

With love and appreciation, David

David Leo is founder of Street Smart Research Group LLC. He is an author, speaker, coach, consultant, and trainer to financial professionals. David has worked with the financial services industry for decades, originally as a consultant with IBM and then with UBS/Paine Webber before starting his own firm. If you would like more information about his services, contact him at [email protected] or visit

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