Reading this book from the perspective of 2025, I think Robert Caro got Robert Moses wrong.1 Yes, he was obsessed with power. Yes, he ruined neighborhoods and destroyed communities with highways and slum clearance programs. Yes, he failed to treat the black citizens of New York City as having equal significance with its white citizens. He had all of these failings and it is important not to shy away from them.
Yes, Moses hoarded power. He had sharp elbows. He pushed the limits. He was also prepared, on time, organized, and ready to work tirelessly. He didn’t enrich himself or his family, but instead funneled money into getting power, so he could do more building. He built with all the limitations and blindspots of the generation he grew up in but he did build. He could be petty and attention seeking and yet he was also fantastically productive, not for just himself and his ego, but also for the people of New York.
It’s important while reading the book to pay attention to the other characters coming of age alongside Moses, people like Jimmy Walker, who are comically corrupt by today’s standards. When you do, you get the feeling that Caro is comparing Moses not to the other men and women who could’ve been chosen to lead at the time but to a hypothetical perfect public servant that never did exist and never could exist.
I first heard of Robert Moses in a City Planning Survey course that I took as a sophomore at UNC Chapel Hill. The TA who taught the class had an infectious enthusiasm for city planning and so that summer I found myself reading the Jane Jacobs classic Death and Life of Great American Cities.2
So I came into the book with a sense that the problems with American Cities are downstream of the choices that Robert Moses and his disciples made to orient them towards cars and away from walking and public transportation and neighborhoods with a sense of place.
But after reading the book, I think the problem for American cities isn’t that Robert Moses ruined them, but that there have been no Robert Moseses since: civic leaders with the intellect and power to reshape cities with a new, imperfect vision of what the good life is. We know from Amsterdam and Paris that this sort of transformation is possible and yet we’ve chosen to stay stuck in time, living with the same problems year after year.
The Robert Moses of 2025 would probably not favor cars over other forms of public transportation or redline minority neighborhoods. He would be imperfect in new ways that we cannot yet see or understand. But he would build.
It’s a credit to Caro’s immense ability that I can read his work and come to very different conclusions about what it means. ↩
This is a book with a handful of big ideas:
1. There are considerable similarities between the UFO stories of the 1950s and 1960s (then current, the book was published in 1969) and the stories of fairies / angels and demons / other mythical creatures from before the space age
2. Those similarities are interesting even if you don’t believe that UFOs come from extraterrestrial life
3. Even if these phenomena aren’t real the way the Empire State Building is real, they still impact the world in real ways
4. The (then current) UFO stories are folklore in the making, which makes it interesting in its own way
I’ve never gone deep on aliens / UFOs so I’m not up on the lore, but I think most of the points above are now mainstream?
Beyond this, there were a ton of stories about weird things happening, including a series of stories from 1890s America that just seemed bizarre. The one that will stick with me is the Mystery Airship of 1896 and 1897 where (potentially?) an airship floats around the western and midwestern states, occasionally stopping and having conversations with local farmers. You can choose to believe this or not, but either way it’s a fun wikipedia read.
On the whole, this increased my belief in the supernatural marginally.
Set in a noir version of post Spanish Civil War Barcelona where somehow everyone is one degree removed from a brilliant yet fantastically unsuccessful author.
In my mental library, this book is part of a trilogy with Range and Talent about how to do your best work.
The book probably only gets published because it’s about late bloomers, but I can’t think of any part of it that is only applicable to late bloomers.
I thought about survivorship bias basically the entire time I was listening to the book. Some of it is definitely embedded in here, but some wisdom is too.
A common theme in Oliver’s late bloomers is earnestness. Earnestness to the point of being annoying to their contemporaries. I think earnestness is a quality that ages really well.
Many of the lessons I took from this book can be reduced to the sorts of things a youth baseball coach would say to me during practice. This is related to the earnestness.
The need to move through periods of exploration and exploitation at different stages of a career is a lens that will stick with me. If you think your potential is capped in your current situation, it’s probably time to turn the dial towards exploration. This is not one I got in youth sports.
Luck from motion — when you get an opportunity because you’re out in the world doing interesting things
Luck from awareness — when you notice an opportunity is available to you (or you’re open to it)
Luck from uniqueness — opportunities that come to you because of your unique interests, passions, and projects
“The harder you work, the luckier you get!”
Networks are important because of the influence they have on your aspirations. You need to be around people that expand your idea of what’s possible through words and actions.
It’s really important to (appropriately) display your work. People can’t bump into you if they don’t know you exist.
Caring is a source of alpha. Ray Kroc was one of the late bloomers. McDonald’s dominance made more sense when I better understood how much Ray Kroc cared. His passion for french fries isn’t something I share, but it makes sense that he of all people created the dominant fast food company. He cared more than anyone else!
Being a little reckless can be a good thing as you age. He cites a study (I think this one) where people who make a life change by flipping a coin are ultimately happier when it forces them to change rather than stick with the the status quo.
People who keep trying have more successes and more failures than those that don’t. Chaos and failure are not to be avoided but part of taking many chances at success. You do your best work when you do your most work. Quantity precedes quality. “You miss 100% of the shots you don’t take.”
Courage / not counting yourself out is underrated. Believing that you have the ability to be excellent is not sufficient for becoming excellent but it is necessary. This is increasingly important with age. Persistence and determination alone are omnipotent.
Recommended if you, like me, hope your best work is ahead of you.
One of my favorite biographies. Incredibly well paced and readable.
I think Ike has to be in the top 5 most influential Americans. Some of my contenders, in no particular order:
Washington <- not becoming a King or Emperor is arguably the most influential thing about the country to date
Grant <- wins the Civil War, two term president, leader of Reconstruction
FDR <- 4 term president, New Deal, leads the country through World War II
Lincoln <- holds the country together during the Civil War
MLK <- for the Civil Rights Movement and its impacts
Ike obviously belongs in this list. As much as it pains me to say it, I think he's obviously above Lincoln, who is my favorite of the group, but just isn't on the national stage for long enough.
Here's the case for Ike:
Wins the war in Europe
Incredibly popular 2 term president
Repeatedly refuses to use tactical nuclear weapons in early Conflicts, leading to today's norm of not using them
Assorted other stuff I enjoyed from this book:
Eisenhower had a mistress during his time as the Supreme Allied Commander. Kay Summersby started as his driver and became his companion. The book provides good evidence that when the war was over, Eisenhower cabled Marshall to say he was staying in London with her and divorcing his wife and Marshall said he'd run him out of the Army. Ike then leaves her behind while taking the rest of his staff. The War Department removes her from photos (!) and then Truman destroys the cable to protect Ike (!). And you thought he was boring!
The planning for invasion of Europe reminds me of ~every major product launch I've ever done. They Allies agree super early on, like 1942 that they must invade Europe via France, no other routes make sense and then spend 2 years doing everything but this while Eisenhower reminds them why they have to do it.
The book makes a compelling case that Eisenhower prolongs the war and cedes Berlin to the Soviets by ignoring Monty's advice in September of 1944. I'm not enough of a military historian to critique the case, but it was interesting.
Ike has basically zero command experience before becoming Supreme Allied Commander and was mostly put in as a placeholder for Marshall.
His most important skill was his ability to drive consensus and still make his own decisions.