66 Comments

A fantastic piece of work, David. My own dilemma is that I was hugely successful in my early 20s, when I felt an utter fraud, and have since, though becoming better and better at everything I do — writing, music, graphic design — known little but failure. The most spectacular failure of my life being my 23-year estrangement from my daughter, whom I adored. And here I'd thought I'd done a better job of being her daddy than of anything else I'd ever done in life.

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Thanks for this John. I got hit by a terrible cold so will return to comments when I fee better.

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John, I don’t think the estrangement of an adult child is necessarily the failure of parenting. Sometimes, (always), people do what they will. Sometimes, with regard to consequences and sometimes not.

Your success lies in your capacity for enduring love and compassion, in the face of rejection.

Whether your daughter weighed the cost of the estrangement is her burden to bear.

Peace to your heart

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Thank you for your very kind comment, Deborah. You offer more credit than I deserve, though. I'm not so sure about enduring love. As one year follows the next, and third parties send me photos of the grandchildren I'm unlikely ever to meet, and whom she's apparently brainwashing relentlessly, my incredulity at my daughter's heartlessness (and, I'm informed, reflexively submissive, pious tradwife arrogance) exceeds my love.

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John, that sounds so tough. Sending you a big hug.

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1dEdited

THIS!!

“I’ve come to realize that a satisfying definition of success needs to have a degree of difficulty to it but it also needs to fit, realistically, within the circumstances of your life––your background, your personality, and your stage of life.”

Thank you!

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Thank you David. I found you and your essay via Laura's Substack and really enjoyed this twin essay structure. I love that you have incorporated your success creating a family into what success means. This is so underrated, especially by men I think. With age and (i hope) wisdom I've noticed how success is shape-shifting and a bit mercurial. But like you, I think it broadly sits in the field of some place we don't start and with something we don't have. I do think the human animal likes to strive and gets a lot from it. That this process is far more enriching than the achievement itself at the end. Perhaps the biggest success of all is simply to be involved with the development of one's own life - to stay attentive and attuned to its twists and turns and to stay a witness to what it needs to stay full. This is no small thing I think.

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Thanks Ruth. I got hit by a terrible cold so will return to comments when I fee better.

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Very well said. Thank you.

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When I teach about the 2008 Financial Crisis, my students generally wonder why the people running the banks, who were already wealthy enough to buy anything they could ever want, kept manipulating the economy to enrich themselves further until the whole thing crashed. I tell them that beyond a certain point it ceases to be about having money and become about having MORE money, which is a psychic need unconnected to actually material reality. For my part, I think you should be prouder of your work here than on Wall Street. After all, here you started at the same level as everyone else and earned every reader through hard work. That’s success by any measure.

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Thanks Librarian. I got hit by a terrible cold so will return to comments when I fee better.

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Get better. I hope to see you back soon.

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I so much enjoyed this essay. True wealth is a definition we must all craft for ourselves; I am happy for you that yours includes a rich family life and a beautiful way with words. xo

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Thanks for this.

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❤️

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I love these essays! I subscribe to both of you so they hit my inbox this morning. I struggle with the concept of success because I was a super girl - got into Yale in spite of growing up poor, then hit the top of my first career at age 28. Yet I didn’t have a “normal” life. No husband or children. At forty I got hit with a bad chronic illness that made it difficult to work full time. I’ve spent a lot of time being poor but I’ve also been able to help a lot of people. I can teach urban school kids who white peoples are afraid of. I’ve talked many people down from suicidal crisis. And now I have the freedom to write what I want, while my “successful” friends are afraid to speak out (mostly in support of Israel and against antisemitism) because of professional consequences. I have freedom. I’d like some more security though !

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Thanks April. I got hit by a terrible cold so will return to comments when I fee better.

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I am curious if after needing to leave the "successful" career due to illness, did the medical aspect of your life improve? Curious if your medical challenges was a rebalancing event to get you to have to be less "successful" in your career to bring you to another place that may be was needed for you in some way?

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Laura and David, I am going to write one comment for both of you now that I have read both and watched the video. (I can't comment on Laura's article so will just write to both of you here.) First, thanks for this wonderful collaboration. I have been reading both of you for some time and enjoy the insights you provide. Second, this idea of success is one that has been rattling around in my mind lately, particularly how subjective it is.

Growing up poor I had this idea that success meant monetary wealth or at the very least, having "things." Nice house, nice clothes, nice job, nice wife, nice kids, etc... Quite naive in retrospect but for a young boy in rural America who was raised to believe in the pursuit of the American Dream, these seemed perfectly normal at that time.

In my career in the Navy over the course of 24 years I thought success meant getting good performance appraisals, getting promoted ahead of my peers, getting selected for premier positions of authority, etc...

It was quite the wakeup call to discover that my kids knew next to nothing about my work and would rather I have spent more time at home than off sailing the seas. Even though my version of success provided nicely for our family, that wasn't particularly relevant to my wife and children who would have preferred me to be with them.

One of the reasons I have not gone back to work since retiring from the Navy last year is the desire to force myself to slow down, an attempt to be present for my wife and children in a way I wasn't previously. I realized that it wouldn't matter so much how much money I made or what nice things we have if I didn't have a relationship with those I loved.

Even recently I have struggled to reign myself in here on Substack as it is so easy to compare ourselves to others. I started seeing some growth in subscribers (which is wonderful of course) and is certainly a measure of success in writing. However, at the same time I noticed less personal engagement and a sense I had to "perform" to a certain level to keep the growth going. Suddenly I was distracted again by my perfectionist, workaholic mindset, seeking a false idea of success.

These past few weeks I needed to sit myself down and give myself a stern talking to. So I appreciate the insights that you both provide here. There are many different ways to measure success but some are certainly going to have a much longer lasting impact than others.

Keep up the great writing, both of you. All the best, Matthew

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What a wonderful realization, to look deep within and truly see what you value THEN to take actionable effort to express those values. What triggered that, I wonder? Yes, we all need to work to pay for necessities, whose definition vary person to person. But when the societal pursuits are stripped away, what remains? To find security and stability, joy of expression, joy of play, peace in our hearts and souls and our bodies, healthy relationships and bonds in communities where we feel seen, accepted, understood, and considered. It would be a far far better world if we (writing from the US here) were raised to truly value and support these fulfilling pursuits with integrity instead of false nods while promoting what David speaks to: the pursuit of money, more money and power over others. What does a midlife crisis and wake up call look like for a country?

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Thanks Bonnie. I got hit by a terrible cold so will return to comments when I fee better.

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Thanks Matthew. I got hit by a terrible cold so will return to comments when I fee better.

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Success can feel so elusive. When I retired a few years ago - after working for 32 years in our family’s flight simulation business, I knew I needed to have a plan and have purpose. I started writing a column for our local newspaper and joined some service organizations. I focused on staying healthy and finding ways to give back. I became a grandmother. My husband retired a few months ago and by any standard, we are living a great life in our early retirement. But what does define success? Like you, I get great satisfaction and encouragement when someone reads one of my columns or substacks and sends a thoughtful reply. But there are times I feel like an imposter. There are so many exceptional writers here on Substack and at 61, I hope to continue to grow and learn and become better, but I am also trying to define “success” as doing something you love, that brings fulfillment and maybe even peace - regardless of whether or not others are impressed or even notice. Keep up your writing. You are an inspiration to me - for one!

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Thanks Midlife. I got hit by a terrible cold so will return to comments when I fee better.

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The basketball anecdote brought tears to my eyes. What a beautiful conversation.

I had outward success in my early thirties, when I sold my first company. I felt successful for about two weeks, after which I wondered why all the same insecurities, self-doubts, and panic were still there. I built two more companies, always feeling less than enough, no matter how things looked on paper.

Both my parents died a few years back, which coincided with my turning 50, and being hunkered down with my wife and kids in the pandemic. Like you, I had always prioritized my kids and my marriage over work. The grief broke something open in me, and I left my company, started working on my own, and writing. Now I think of success as loving the people around me as best I can, and exploring the curiosity that's replaced all the things I used to think I knew.

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Rob - nice to find you here. 😊. Such wisdom and perspective in your comment. 🙏

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How hard it is to enjoy our success. I was shocked decades ago when I read that Bill Bradley felt happy for only two hours after winning each NBA championship. We can be extremely good at making the effort to gain success and extremely poor at allowing it to feed us.

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Thanks Kathleen. I got hit by a terrible cold so will return to comments when I fee better.

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Well said!!

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Thanks Rob. I got hit by a terrible cold so will return to comments when I fee better.

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Oh no—hope you feel better soon, David.

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Thank you both!

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"Whereupon she appealed to my father who’d had no idea of our shenanigans. Without consideration of due process, he immediately cancelled all debts and outlawed gambling. My sister was jubilant; I was crushed."

What a funny moment. Without reference to legal precedent, Alexander grabs sword and cuts the knot. Trump issues EO. Indiana Jones shoots the guy with the whip. Man finds banana taped to wall and eats it.

It is inevitable that siblings negotiate elaborate codes of convention governing their interactions. These mostly remain beyond the ken of parents. And just as well, because it would have driven me crazy if my dad had blown up my tiny feudal privileges.

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I got hit by a terrible cold so will return to comments when I fee better.

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Nice. I like your writing. When I was a kid I read The Human Zoo or The Naked Ape by Desmond Morris, and in it he asserted something about human creativity being our highest and ultimate calling. I consider myself fortunate because my entire life has been about creativity and invention (engineering, building, invention) and hence I have considered myself to be successful, mostly always. But I totally get your point, and I think many people feel the same way, and maybe only feel like they achieve success when they are able to create (and are successful at it even in little bits). One can have lots of material wealth but if its isn't personally earned or developed (by one's own creation) there exists a lack of meaning. Which is why I think rich kids who inherit wealth so often end up with major life problems, and those who start with nothing but who develop an early calling are far better off. And this plays out with the never-ending saga of Three Generations From Rags To Riches To Rags.

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Thanks Steven. I got hit by a terrible cold so will return to comments when I fee better.

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I finally became successful when I retired from paid employment. I have enjoy success as a father for the past 35 years and have relished it. This is in the fact of the fact that I have never known what to do as a father and have been making it up ever day. The only "plan" I ever had/have as a father & now grandpa is to be an active presence in my daughter's life and grandson's life. Paid employment is a different matter. I did cherish dreams of rising up through an organization, becoming a 2Senior Manager/director/leader/whatever". I come equipped with non-standard mental wiring which means I can understand a supply chain problem and not the people involved in it. I hung in long enough to reach retirement age and have saved enough to be retired without being squeezed. Now I get to live a life on my terms, write science fiction stories that a publisher sees enough value in to publish. Family I love, not flat broke and writing stories other people (very few, still not zero) people will pay to read. I have achieved success beyond my wildest dreams as a young man.

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Thanks Conor. I got hit by a terrible cold so will return to comments when I fee better.

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I love this Conner.

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David, I especially appreciated this: “At my 50th birthday party all my children gave toasts that focused on the time I’d spent with them while they were growing up.”

When we choose to have kids, I would hope that we’d put a big chunk of our intention, as you did whether subconsciously or consciously, on creating the fabric of a “family” and being a role model of virtues such as kindness, compassion, love, and even competitiveness (harkening back to your backgammon games).

For me success would be answered by, “did I prioritize the things that meant the most to me and would be in service to “what I am most ‘at stake’ for.”

From what you wrote and what I know about you through your writing, your intentional effort at raising your children, being a devoted husband, stewarding your inherited wealth, creating your own through a successful career, and contributing to the lives of others through writing, with a humility that comes through your words and expression, feels pretty darn ‘successful’.

I own an investment firm - and work in the financial space. The word “wealth” comes from the old English word ‘weal’ which means well-being. To have wealth in the old days was to have “well-being”. (Boy have we bastardized it!)

Maybe success could be defined as having “well-being” which is distinct for each one of us, and requires us to follow that unique thread inside that is singularly our own.

Thank you for reading this far and for such an excellent essay.

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Thanks James. I got hit by a terrible cold so will return to comments when I fee better.

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I hope you get well soon!

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I'm reading Inner Excellence by Jim Murphy and it is changing my beliefs on the subject of success. If I use the metric that our society here in the USA uses, I'm an abject failure. I don't have money or fame. No one cares what I think about anything except for my wife and grown children. If I made TikTok videos about how to be successful in business I would be laughed off the platform and rightfully so.

But, like you David, my relationship with my wife of 38 years and our sons is where my success lies. Its been there right under my nose this whole time but its been so organic and natural I almost missed it. Missing it would come from a place of self centeredness (Murphy's idea). I could never get past the struggle I was having in an attempt to be "successful". If I could just put my head down, ignore pain and bull through five more horses a week, then I would be successful. Then, if I work on the ranch and shoe horses at the same time, then I would be successful. But, the bills kept piling up and the one year out of 35 I actually made a decent living, taxes took away my "Success." I was doing something wrong, I thought. It must be I am not working hard enough.

Well, as you know David, working more hours, weekends, nights did not make me successful.

Only Love did.

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Thanks John. I got hit by a terrible cold so will return to comments when I fee better.

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Get well soon!

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John. This is beautiful and the last line say it all. Thank you 🙏

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A very interesting and stimulating exercise with Laura Kennedy. I think you are both right that a sense of success has something to do with expectations, but it is also heavily moulded by our childhood experiences. I was brought up to believe that success was something externally granted and related to intellectual or professional achievement. I suffered hugely from having extremely clever siblings who put me in the shade by any measurement. My mother even (kindly?) suggested I might be a very good 'homemaker' (a 1950s word) even thought she had an active professional career. It wasn't until I was in my 30s that I realised that I was really quite clever, too, plus had other strings to my bow that had been overlooked. One of which is self-reflectiveness, which both you and Laura have hugely.

Do do it again. A very good use of Substack.

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Thanks Ann. I got hit by a terrible cold so will return to comments when I fee better.

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GET WELL SOON. Forget Substack for an afternoon or longer!

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