87 Comments
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Frank Gullo's avatar

From the outside, your craft and focus in building this Substack at least since I've started reading appears ambitious in the best possible way. Even a restless Ulysses casts ambitious shadows.

David Roberts's avatar

Thanks Frank!

Tom Grey's avatar

Seems you’re doing great, 34 more before hitting 100. I’m enjoying retirement, trying to help my kids & grandkids. Using zoom & discord to reconnect with a couple of old-like-me friends from school, all with different but adjacent type problems. My hobby of singing karaoke songs, all the hundreds of songs like, led me to a small karaoke goal of singing all the Beatles songs. Learning all the lyrics is fun, 4-10 per week. Pop music lyrics have taken the place of poetry, most poetry, and good music makes poetic lyrics more accessible. Safe emotion expression is kinda cool.

Losing my Religion, REM, was a song I sang a year or two ago, most songs I only sing once.

Your substack is a fine hobby for you, and I’m grateful you’re keeping it up.

David Roberts's avatar

Thanks Tom. Glad you noticed the song allusion. All the lyrics to all the Beatles songs is impressive. And I believe many pop lyrics are poetry.

Harvey Sawikin's avatar

I made a good catch of a ball sitting in the Mezzanine at a Mets game when I was 14 and got a round of applause. Top two or three moments of my life. Don Hahn hit it. Still with the Mets.

David Roberts's avatar

I'm jealous! Have her had a try at a foul ball. A moment of intense scrutiny by thousands of strangers.

Caroline Smrstik's avatar

"Is it a binary choice between being gifted in the Steve Jobs sense and being decent?"

I never used to think so, but when I glance around this modern world it does seem to be an either/or proposition. How sad.

Good Humor by CK Steefel's avatar

True. Power corrupts. Absolute power corrupts absolutely.

Audrey's avatar

I think also many Steve Jobs types have undiagnosed and untreated neurodivergence that increases their inventiveness and brilliance but can also affect interpersonal relationships.

NubbyShober's avatar

Excellent observation. Narcissism, for example, apparently exists on a spectrum--and can be excessive, or too little.

Malignant Narcissists like Prez Trump, have toxically high levels, and for example will deliberately stiff (financially damage or destroy) contractors if they think it will improve their reputational or financial standing. Lying, cheating, conning, stealing: all become reflexive behaviour.

My hypothesis is that taking a single-minded and ruthless Steve Jobs-like approach to career development, can accelerate the accumulation of power and money.

Henny Hiemenz's avatar

Which is why, unfortunately, so may a-holes wind up in positions of power

April's avatar

Love 💕 this, mostly because there’s a Debbie story. But I do think it’s an important question that you pose. For the first twenty years of my adult life I was a union organizer, mostly for registered nurses. It was all consuming. I worked all the time, climbed quickly to an executive position, all my friends were organizers and I had very little else in life. A long term partnership with someone who was not an organizer brought some balance but also a lot of conflict. I left at 40 to get my masters in public health and never went back. I’ve never stopped missing the thrill of being “all in” though. The ups and downs of very contentious campaigns and strikes, the extreme and definitely unhealthy closeness with my coworkers. It’s hard to be normal. I don’t think I was a jerk but I was difficult to live with. Now I live with someone with four feet 👣 named Loviefluffy and I’m easier to live with. I have a regular schedule and a pretty routine life.

David Roberts's avatar

Thanks April. Someone involved in politics once told me that a political campaign was like a baby crying for attention 24/7. I imagine that union organizing was like that.

April's avatar

Very much so. And no control over your schedule because things happen fast.

Mary Roblyn's avatar

David, thank you for this honest and nuanced post. You’re living proof that you can be both gifted and a mensch. (I hope this is the right word. I’m a Lutheran from the Midwest.) The story about Debbie is a real treat. $14 for bacon? Uff-da.

David Roberts's avatar

Ia free Mary, the bacon price is insane.

Isabel Cowles Murphy's avatar

As a woman married to a similarly ambitious man, I would love to read this arc from Debbie’s POV. I bet she’s both grateful for your passions and relieved by their tempering :)

David Roberts's avatar

Isabel, I will ask Debbie to comment!

David Roberts's avatar

I asked Debbie and she said that she has always kept me "balanced." And it's true that whenever I was spending too much time on any one thing or obsessing, she would intercede.

Carll Tucker's avatar

Hey pal, You've got ambition. This post is proof. Writing well is even harder than making money. Drives me nuts when folks characterize my Good Morning Project as a hobby. Hobby? A post a day plus countless new friends keeps you plenty busy, busier than I ever was running companies (and happier). Please do not permit your new ambition to flag -- we'd miss you. Love, C

David Roberts's avatar

Thanks Carl. It's true that writing takes a lot, especially your publishing schedule!

Wendy McCulloch's avatar

Great question… and I’m not being patronizing here!!

That binary choice of being gifted or being decent … (ie interpretation being that one cant be both )… is a total cop out .. an excuse for being an asshole … a reflection of the lack of accountability in today’s culture! (wow I really sound like an old fogey dont I)?

The comment “but he’s brilliant” .. yes and I consciously say “he” here .. is often used as a retort to “what an asshole”.

Did they say that about Mozart, Van Gogh, Galileo?

What about Keith Richards, Barry Gibb, Tina Turner, Jimmy Carter, Paul McCartney, Obama .. random nice and gifted folks here (sorry about the contemporary music references here but that’s my own personal experience).

Here is an animal analogy .. what about a brilliant herding dog that can direct a herd of sheep into a tiny pen .. but starts attacking and eating the sheep .. the farmer doesn’t say “ thats ok .. “hes gifted”… its not tolerated and the dog gets SHOT! (NZ reference here). I little exaggerated.. I know but makes the point !

And yet we make similar accomodations for humans ???!!!

Thanks for your substack … love your sandwich story … !!

David … thanks for giving me a platform to get that off my chest !!!

David Roberts's avatar

Wendy, I believe you can be gifted and decent in many endeavors. Love your sheepdog analogy! Thanks for your well-considered comment.

mm's avatar

Warren Buffett. Reed Hastings (Netflix). Very gifted and very decent people.

NubbyShober's avatar

It'd be interesting to do a tally of the top 500 US billionaires, and find out how many kept their decency.

A Canadian money Guru named Harv Eker wrote about the Psychology of the Extremely Rich, alleging that They all go through a multi-year phase of Playing. Buying yachts, houses, expensive clothes, etc., etc. But that most of them then grow out of it.

But that they tire of it after a few years, realizing that there's got to be more to life. So they re-engage with newer or modified goals. The psychologically healthy ones, anyway. The unhealthy ones still trying to fill an inner black hole of need with more money and/or power.

Henny Hiemenz's avatar

Exceptions that prove the rule?

Donna McArthur's avatar

As I approach sixty the idea of goals has been on my mind mainly because it’s a way of showing up fully for ourselves, but of course it’s not the only way and we don’t have to become a single-minded asshole about it.

In the essay I’m currently wrangling I talk about my friend choosing to go back swimming to train for the seniors games in our province after not being in the pool much for decades. It was very inspiring to watch her show up like that.

I think it’s about commitment to our own lives and with that commitment comes intentionality. This can be present in every move we make or we can be more single minded about it.

Thanks for a great essay David. I love it when something that’s on my mind pops up elsewhere.

David Roberts's avatar

Donna, I look forward to reading your essay.

Donna McArthur's avatar

Thanks David, it will be out on Sunday.

Audrey's avatar

I love the way you put this, that goals should be considered a commitment to your own life. Pursuing goals for their own sake without a cherished outcome is very life-affirming.

Donna McArthur's avatar

Exactly Audrey, however big or small it is a goal is a commitment to our self. It's a way of earning our own respect. I think one of my goals should be to work on my grammar and punctuation🤣

Mark Bykowsky's avatar

I once found myself sitting in a tiny chair in Siena, Italy watching the Palio with my wife and son. Following the conclusion of the horse race I witnessed among the observers a level of grief that I had never witnessed before. Approximately 9/10ths of the observers cramped into the Piazza del Campo felt extreme pain that their bareback rider had lost....It brought back memories of the pain I experienced when observing, high above in the Blue Section, my Rangers losing to the Boston Bruins in the 1972 Stanley Cup Finals...And you haven't lost ambition...It is just manifested in other ways, and to the benefit of all of us.

David Roberts's avatar

Mark, there's an awful silence in a hockey arena when your home team has been eliminated. too painful to watch the handshakes. I've read about the Palio but have never seen it. It makes sense that the losing teams would be forlorn. Your comment makes me want to see the race.

Mark Bykowsky's avatar

The Palio Festival is a four day pageantry filled affair highlighted by the race. We obtained our tickets via our hotel in Siena. It is an unforgettable experience, one which, at one particular instance, may bring back memories of your career in private equity.

Librarian of Celaeno's avatar

Have you ever thought about teaching? There are probably a lot of ambitious younger men who could really benefit from the tutelage of someone with long experience in finance.

David Roberts's avatar

I have thought about teaching. I'm connected to an organization that teaches ethics to college kids at undergraduate business schools and then keeps in touch with them as they start their careers. I have not been one of the speakers yet. Thanks for the nudge in a good direction.

Librarian of Celaeno's avatar

My school assigns groups of teenage students for us to mentor aligning with the sex of the teacher. The boys I had in my group asked me one day about investing; they hear things on social media about it. I pulled up my (meager) Robin Hood account and went through the basics, and I’ve never had a group pay more rapt attention. They wanted to tools to be successful and empowered. I have only a basic knowledge of such things, and I can only imagine what they would have gotten out of listening to someone like you. If you can do that in your area, you’ll be providing great service. And if you’re ever in the South, I’d be grateful if you could spare a moment to swing by here.

David Roberts's avatar

Absolutely. Let me know via email where you are so I can keep it in mind! robertsdavidn@gmail.com

Shay Paulson's avatar

Let’s not limit it to young men! If you had a masterclass or a zoom class where we could ask you questions, I’d certainly tune in!

I enjoy your posts, David, and always look forward to reading.

Diana M. Wilson's avatar

What Frank said--and Sandwich Gate! I needed that laugh this morning....

LH Cardwell's avatar

Sandwich gate made me laugh 😂

Jennifer Silva Redmond's avatar

I'm pretty sure that most super- ambitious men are World Class Dicks (WCDs) but I don't think one HAS to be a WCD to achieve great things. I have a husband and two brothers and a best friend who have achieved (relatively) great things in their careers and none are WCDs. I am at peace with knowing that my highest acclaim will probably come from editing other writers' great books, not from my own writing. I always enjoy your honesty. Maybe honesty and vulnerability are the answer to avoiding WC Dickdom.

David Roberts's avatar

Thanks for the comment Jennifer. I definitely believe you can achieve a great deal and lead a terrific life and avoid being a WCD. Perhaps that avoidance is itself a crucial and unifying goal!

Jennifer Silva Redmond's avatar

Can we make that a trending goal? We sure need it!

Good Humor by CK Steefel's avatar

I knew you were funny! You wanted to be president then you turned 6! Haha. And sneaking in the sandwich fiasco. A gem.

I read that the Harvard study about goals was a bunch of BS.

Dark Matter reminds me of the comedy The Family Man. Good movie.

Great essay.

David Roberts's avatar

Carissa, I really liked that movie, too. A great "alternative worlds" movie.

Kathleen Weber's avatar

For good or ill (definitely for both) insatiable ambition is part of the American character. It got us to the front of the world pack in science, industry, military matters, etc. BTW, it's scary to see the same kind of intensity in the national character of China.

Yet insatiable ambition by definition cannot lead to happiness, a state of being happy where you are and not where you plan to be.

For example, you accepted reality when you heard that a Jew had never been elected president. Joe Kennedy knew equally well that no Catholic or Irish American had ever been elected president, but he never accepted that reality. But there's a gigantic downside to that level of ambition — virtually every Kennedy has a very large bat crashing into the walls of his belfry.