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Leadership is Lonely, Can You Carry the Load?

Ian Berg • August 19, 2023

The Lonely Island was a hilarious band, but it's also a tough place to be. Leadership gets you there, your guts keep you there.

It doesn’t matter what your title is. When you find yourself in a leadership role, you have hit the hardest point of your personal and professional path.


It is easy to seek growth because of a paycheck. Everyone wants more things, more chances and more amazing dinners at their favorite chop house or sushi spot. The question is do you have the guts to make it and then take yourself out of the equation.


We all want excellence, but when you land in leadership you become the answer to every problem. No wiggle room here. Every failure is yours alone.


Conversely, you also never have full control or credit of the wins—you didn’t hit the numbers or goals alone. Can you be that selfless?


It is a tough road to walk, it’s the one Green Day was singing about.


I am a huge fan of history, mainly American history and specifically military history. It started as a kid watching Tales of the Gun and World War Two in Color with my dad on Saturday’s when the History Channel was brand new.


One of my favorite paintings is above: George Washington in “Washington Crossing the Delaware” painted by Emanuel Leutze in 1851. Washington is referred to as the Father of our Country amongst other things, and is famous for being revered in his time, a legend among men when he was still upright.


What isn’t often discussed is how far confidence had fallen in 1776 leading up to this daring charge across the Delaware to Trenton Christmas night, 1776. Prior to this epic crossing, Washington had even lost the confidence of his closest confidant, friend and right-hand man, Joseph Reed.


In “1776” by David McCullough the true state of the Continental Army at the time is explored. After the amazing battle at Bunker Hill in 1775 that led to 1,000 casualties of the King’s finest men, the cause for liberty was in full swing and George Washington was the selected leader of the newly formed United States Armed Forces.


Despite him setting expectations that he was “underqualified” for the role, he took the country and its army of ragtag farmers, doctors, lawyers, blacksmiths and beyond on his shoulders and led us to ultimate freedom in 1783.


1776, however, was a very tough year for Washington. Loss after loss piled up on the battlefield, and the pounding in Brooklyn by the British and Hessians during the New York Campaign in August of 1776 was devastating.


McCullough quotes a letter from Joseph Reed to General Charles Lee where Reed states in speaking of the New Jersey campaign and losses, “How often have I lamented it this campaign. All circumstances considered, we are in a very awful and alarming situation—one that requires the utmost wisdom and firmness of mind. As soon as the season will admit, I think yourself and some others should go to Congress and form the plan of the new army.” Lee was second in command of the Army at the time.


The war that had just begun for independence seemed lost by the man that ate, slept, fought and served directly alongside Washington in the war. He was Washington’s personal choice for secretary. At one point Reed had departed in 1775 and early 1776 for home to visit his wife and work on the farms and in his law practice. Washington sent letters begging for his return, it was of “utmost importance” to the success of the war.


Like many, Reed was worried that Washington was out over his ski’s and had reached a point where he was no longer fit to command such a daunting task as a war for independence. The Army was dropping volunteers like flies, and the Congress had not promised contracts beyond the end of the year to soldiers.


No one knows for sure what Washington’s thoughts were completely at the time leading into the Battle for Trenton and the daring river crossing that fateful Christmas night. Very little was written by Washington on his feelings outside of a handful of correspondence with his cousin, Lund Washington.


One thing is known, on November 30th, as Washington awaited the arrival of General Lee and his men to help reinforce the lines outside of New York he received a letter addressed to his aid-de-camp, Joseph Reed. Assuming it to be war correspondence of importance, he opened the letter as Reed was back home on leave.


It was a letter from Lee to Reed answering Reed’s call for Lee to take over the Army. A response to a letter written by Washington’s right hand and friend claiming his inability to lead. Washington had to be emotionally crushed—no doubts here. However, his response was that of a true leader.


He closed the letter and then addressed his own to Reed before sending it off to him. Washington is quoted by McCullough as saying “Having no idea of its being a private letter… I opened it … This, as it is the truth, must be my excuse for seeing the contents of a letter which neither inclination or intention would have prompted me to.”


My guy just said to his friend, his confidant, I wish I didn’t know you wrote this about me bro. But it’s totally cool, my bad for seeing it. WHAT A LEADER.


Washington goes on to organize the crossing of the Delaware and following battle for Trenton with Nathanael Greene and Henry Knox—both amazing generals during the Revolutionary War.


The crossing was extremely bold and borderline nuts. It came during a terrible winter storm and a period of the year that most often armies would rest—not fight. They literally were pushing boats through blocks of ice.


Despite only one of three total parties landing on the attacking side of the river successfully, the Americans went on to route the Hessians holding the city at the time under the first on-field fight with Washington leading the charge. The rest as they say is history, and this battle—while small in scale—was the turning

point of the war.


It gave morale back to the Army, and it showed the gumption and balls of the American Army. In “1776” McCullough quotes Nathanael Greene who served until the end of the war with Washington as saying, “He will be the deliverer of his own country.”


The tides can turn quickly from mortal end to skyrocketing success for you and your teams. Understand that you can and will be the face of failures. But just like Washington, you can be bold and keep pushing. Keep leading your teams and drive yourself forward.


In leadership you will always be the focus. Washington understood this and stood tall, showing little to no emotion throughout the war—even when he surely felt isolated and betrayed by a friend.


Cross the frozen river, help mark your own history. You have it in you to win, you have to face and understand the cost and recognize the selflessness it takes to lead. Never lose sight of the fact that as quickly as you gain you can lose and vice versa.


Be like Washington—when you see the criticism, digest it. Analyze it and the path, adjust as needed, but don’t fucking quit. Be bold and load the boats on Christmas.


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