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Nation building, circumnavigation, and comedy: my favorite biographies

7 February 2019

Over a decade ago, one of my mentors1 recommended I begin reading biographies as a way to understand the life paths, challenges, and tensions that informed the achievements of people I admire. This has set me down a path that I am grateful for. In-depth biographies help me get to know interesting historical figures, and they are empowering, as they teach us how fallible, flawed, and contradictory some of the great people of history really were. Below are the biographies that I consider to be the most meaningful in informing my own life, along with the lessons they have taught me.

Ben Franklin. Walter Isaacson’s “Benjamin Franklin: An American Life” shows a favorable impression of Ben Franklin, though also discusses his less salubrious aspects. The reason it stands out to me, more than anything, however, is Franklin’s use of playbooks. Ben Franklin was a fan of creating playbooks and instruction manuals – whether it was for the fire service he was starting, for the militia he was trying to organize, or the juntos (community organizations) he liked to start. He had lots of ideas, but his focus on documenting them into scalable processes is similar to Jeff Bezos’ style of writing memos and documentation at Amazon, and I believe is a key aspect of success in launching big, scalable projects or organizations.

Ferdinand Magellan. In a similar vein to Ben Franklin’s ability to organize, Magellan’s team was able to circumnavigate the globe due to a focus on research (which convinced him there was a way to cross the Americas by boat) and impeccable ability to organize funds, materials, and people to launch the expedition. Stefan Zweig’s “Magellan” is my favorite biography here, because it focuses on this team building and organizational aspect of Magellan’s work.

At the same time, the story shows some difficult leadership lessons and foibles, two of which are particularly memorable. The first is Magellan’s extemporaneous decision to kill a mutineer on his ship while stuck off the coast of South America due to the winter weather. The swift and decisive decision helped emphasize Magellan’s role as a leader and showed everyone on the voyage that he believed they would find a solution to the problem. I can’t help but ask myself if I would do something so decisive, or in general, how I would respond to a mutineer.

The second story is about Magellan’s death. Buoyed with the success of his voyage and confident in his own leadership achievements up to that point, he entered into a battle without preparation or enough resources and was killed. It serves as an important reminder that regardless of our past successes or accomplishments, we are not impervious to defeat.

Leonardo da Vinci. There are numerous reasons to appreciate da Vinci’s life and work, but the two that stand out to me are (a) his focus on observation, and (b) his insecurity. Both are discussed in detail in Walter Isaacson’s “Leonardo da Vinci”.

Da Vinci’s ability to observe and question phenomena is what led him to much of his success – whether it’s adding minute detail to his paintings or innovating and inventing anatomical research processes to map muscles or veins in the brain. A concrete example of da Vinci’s focus here is his work with cadavers: long before preservation methods were invented, he would sit through the stench of rotting corpses while injecting wax into veins, so he could map the bodies and understand how they worked. This level of detail and love-of-craft is inspiring and worth following.

Next is his insecurity. His notebooks are filled with self-criticisms about lying in bed, not being productive, or even falling for lustful emotions. This is an important reminder that da Vinci was human, suffered through the same challenges we all do, but was able to power through them.

As a side note, it is absolutely incredible that while Leonardo da Vinci was passing away, Magellan was setting off on his expedition, approximately 1,000 miles away.

Robin Williams. Shuffle ahead about 400 years and Robin Williams’ life story (specifically the one by David Itzkoff) also serves as both an inspiration and a reminder of our humanity.

The first lesson is common across all the biographies above but is most relatable here due to its recency: the importance of being prolific and productive to achieve success. Robin Williams made a lot of movies and TV shows; some were critically acclaimed, many were not, and this was something Robin Williams struggled with personally. It’s important to note that success walks hand-in-hand with failure, and as we try to lead and accomplish big things, we will likely fail at many of them. And that’s OK.

Secondly, David Itzkoff describes the challenges many comedians face with substance abuse, anxiety, and the pressures of pleasing a crowd. At the height of their careers, Da Vinci berated himself for lack of productivity, and Robin Williams was afraid of not pleasing his audience. Yet another reminder that extraordinary achievement often comes at the price of tension between success/failure, or insecurity/productivity.

One book that dives into this theme is David Brooks’ “Road to Character”, which explores how extremely difficult life experiences enable us to deal with the tension above and enable extraordinary achievement. It includes a mix of stories, including those of Dorothy Day and George Eliot (Mary Ann Evans). My issues with reading shorter biographies, however, is that one often loses the details about a person’s life and the individual becomes less relatable.

Furthermore, most of the biographies I’ve read focus on people like myself – white, North America/European men. My goal in the coming months is to expand my reading into groups and demographics that are less relatable to my own life experience, so I can relate more to theirs.


  1. The “thanks” goes out to Dr. Don Markwell, who at the time was the head of the Rhodes Scholarships at Oxford, and is now the Head of College at St. Paul’s College in Australia.