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I first read Ron Chernow’s biography of Alexander Hamilton in 2014, having previously studied the lives of his contemporaries, specifically, George Washington, John Adams, and Thomas Jefferson. I had a glimpse into his life and how many historians remembered him, but Chernow\’s account totally opened my eyes.

This man was far more than the first treasury secretary of the United States. His accomplishments include:

• Supporting Washington as his chief staff aide during the American Revolution and commanding three battalions during the decisive battle of Yorktown
• Architecting the Federalist Papers which played a pivotal role in defending and ratifying the U.S. Constitution (he wrote 51 of the 85 essays)
• Founding a national bank and building the financial system that established the country’s credit
• Creating the U.S. Coast Guard and the New York Post

Born in Nevis, a small island in the Caribbean, Hamilton’s father left him when he was a boy. Not long after, his mother died of yellow fever and his cousin, who was entrusted to watch over him, committed suicide. Without a doubt, of all the founding fathers, Hamilton’s rise to power is by far the most improbable.

Over the years my admiration for him only grew as I watched Lin Manuel Miranda’s musical and studied more of his life. A few months back, I decided to tackle his biography once more. The biggest lesson from reading this book, at least as it came to a close, is that of discretion.

Hamilton was a genius. Full stop. Yet, despite being a genius, or maybe because of it, he didn’t know when to keep silent. He spoke his mind at all times and this came back to hurt him on countless occasions.

In a letter to his son, sent days before his fatal duel with Aaron Burr, Hamilton wrote that he had “prepared for you a thesis on discretion. You may need it.” Here’s a portion of the letter.

“A prudent silence will frequently be taken for wisdom and a sentence or two cautiously thrown in will sometimes gain the palm of knowledge, while a man well informed but indescreet and unreserved will not uncommonly talk himself out of all consideration and weight.”

To quote Chernow, “This…sounds like the confessions of a man who had never learned to be discreet himself.” It’s been said that all advice is autobiographical, and Hamilton must have been talking to himself in a way, reflecting on times where his indiscretion had harmed him.

The dictionary provides two definitions of discretion:

• The quality of behaving or speaking in such a way as to avoid causing offense or revealing private information
• The freedom to decide what should be done in a particular situation

One can argue that had Hamilton shown more discretion throughout his life, had he behaved or spoken in a way that avoided causing offense to others, he wouldn’t have left behind such a long list of impressive accomplishments. Possibly, but a few moments of discretion could have spared him the hatred of many, and likely would have saved his life.

And what of Aaron Burr, the man who shot and killed Hamilton in their infamous duel? Burr was the antithesis of Hamilton. He rarely revealed how he felt on a given topic. He had the well-earned reputation of doing whatever was politically expedient. Burr was hard to read and many struggled to know where he stood.

Yet, as odd as it sounds, Burr ultimately paid a price for having too much discretion. Years of concealing how he felt and striving to be all things to all people took a toll. He finally reached the point where he couldn’t hide his true feelings towards Hamilton anymore and he lashed out. He had let his anger and hatred for Hamilton fester until he reached a boiling point and couldn’t hold back any longer.

Despite being the Vice President of the United States, Burr unleashed his rage and challenged Hamilton to a duel. He felt that Hamilton had defamed his character and had sought to destroy his political career. While he had plenty to lose from going after Hamilton, there was no turning back. Burr’s rage had consumed him

Ironically, it was Hamilton’s death, rather than Hamilton’s verbal assaults, that led to Burr’s political undoing. After the fatal duel, Burr’s career was never the same. Facing potential murder charges, he fled to the South. He later faced treason charges for conspiring to plan the secession of several western states. So, he moved to Europe and didn’t return to New York until after his acquittal. His professional and personal life remained in tatters until his death in 1836.

It’s easy to point out the foibles of leaders who lived 200+ years ago. It’s harder to take those learnings and apply them to our lives to further our own development.

I invite you to consider the role discretion plays in your life. Are you like Hamilton, committed to speaking your mind at all times regardless of the occasion? Or are you more like Burr, constantly concealing your feelings, unwilling to share what you genuinely think until you reach a breaking point?

Much later in his life, reflecting on the duel, Burr remarked, “I should have known the world was wide enough for Hamilton and me.” Had he been willing to confront Hamilton earlier, had he been a little more indiscreet, they likely could have settled their differences peacefully and without violence. Conversely, had Hamilton been a little more discreet, had he effectively discerned when to maintain silence, his life likely wouldn’t have been taken at age 47.

The world certainly was wide enough for Hamilton and Burr.

As we move forward in our careers, I hope the lesson of these two men stay fresh. Discretion truly is an art.