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5 More Lessons from West Point

On my first day at West Point, I reflected on what it took to get there. The Academy is highly selective and the application process is unlike anything else I experienced in high school. To earn my place in line, I had to pass an athletic test, be a varsity athlete, endure a rigorous medical exam, and get the blessing of a Congresswoman. I had done a lot to be there.

Little did I know that this was NOTHING relative to what the next four years held in store for me.

I previously wrote a post about some of the most important life lessons West Point inculcated (nod and wink). I’ll link to that at the end of this post. There are many more lessons and I’m contantly reminded of this knowledge at seemingly random points in my path. These important lessons from West Point have served me well through life. Read on to gain this important knowledge and power-up your mental toolkit!

1. Lead From the Front

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Lead from the front. It’s intuitive, right? You can’t, by definition, lead from behind can you?

You will never be an effective or respected leader if you don’t lead from the front. It shows the people who are part of your team that you’re competent and that you’re courageous. You’re not above getting your hands dirty or getting soaked in the rain, just like them.

A fresh platoon leader will not gain the respect of his soldiers if he never goes to the front of the formation and puts himself at risk. This is the most immediate and obvious angle to this lesson. However, there’s nuance.

Leading from the front shows YOU that you deserve to be there. You immediately know if you blanche and fail to step up to the task at hand. Your subordinates may not immediately pick up on this but you know you’re failing to live up to the responsibilites of your role. Over time, you’ll develop a justly-earned reputation: coward.

This is a feeling that creeps into your psyche and eventually makes you an unconfident and ineffective leader who is full of self-doubt. This seeps into your soul and guarantees that you’ll continue to fail and shuck your duty.

Nip this feeling in the bud and give it no place to take root. LEAD FROM THE FRONT.

2. Do Not Lie, Cheat, Steal, or Tolerate Those Who Do

This is the Cadet Honor Code. From our first day at the United States Military Academy until the day we graduated, the Honor code followed us like an omnipresent mantra.

Without your honor and your word, you are nothing. In the Army, we regularly put our lives in each others’ hands. This requires intense and immediate trust.

I always, by default, trust another officer. My trust is theirs to keep or lose. This dynamic is essential to a functioning military. If you lie, cheat, or steal, your integrity is immediately tarnished and trust in you is irrevocably altered. A moment of weakness undoes a lifetime of good.

We were trained to constantly be vigilant about doing or saying anything that would cause others to lose their trust in us. We were shown that you have to be ruthless against any breaches of trust that you may be thinking of allowing yourself. What starts out seemingly small and insignificantly inevitably tangles into a Gordian Knot that will ensnare you.

The first part of the Honor Code governs our behavior. The second part, “or tolerate those who do”, holds others up to the same high standards. Don’t associate with or tolerate a liar, a cheater, or a thief. Their stink will rub off on you and affect your judgment. 

Look, we’re not perfect. A breach of the Honor Code at West Point usually meant you were immediately kicked out of the Academy. But sometimes you blurt out a response or answer that you didn’t mean or you immediately realize isn’t correct. If this happens, immediately own up to it and correct the mistake. Catching a potential issue like this, even mid sentance, makes me trust you even more.

3. The People Around You Matter

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There were more tough and challenging moments at West Point than I can even remember. In the most extreme and prolonged moments of suffering, however, I realized something: your team is the most important factor to any mission.

I lived in the woods for two months without the benefit of a hot meal, bed, shower, or toilet. At one point during this experience, we didn’t eat for three days. We constantly had to watch out for ticks, chiggers, “no-see-ems”, snakes, and other unpleasant animals. But you know what? I have never enjoyed myself as much as I did with those Special Forces soldiers that summer nor have I ever felt that cameraderie and team bond so strongly.

You can be in horrific and unthinkable circumstances, but if you’ve got a tight-knit team around you, you will persevere.

Conversely, you can be in relatively comfortable circumstances and be miserable if you’ve got the wrong team. When I was an investment banker, the air conditioned high-rise tower in Manhattan was a far cry from the boonies I had previously been in. Aside from the 100+ hour weeks, the circumstances were comfortable. Excessive even. Too well fed. Highly compensated

However, my small team at the bank was highly toxic. One associate had a sexual misconduct charge lobbed against him by the only female member on the team. Even after that, he still didn’t stop saying things like “Katy is a giant slut” loudly and within hearing distance of her.

This behavior was not encouraged, but it was certainly tolerated. This same team tried to haze me and eventually turned on me when I showed that the abuse didn’t phase me or that I wasn’t intimidated. A 155 pound trustafarian is not intimidating to a 220 pound veteran and that bugs them.

The team also frequently tried to get me black-out drunk. I have (or once had) an obscene tolerance to alcohol even though I barely ever drink. My bosses and peers found out about this and put this tolerance to the test. I stopped going out to this bar with them because I quickly realized that they were trying to destroy ability to function at work.

One of my fondest memories is suffering through intense training with a team of future Green Berets. My worst professional memory is in the cushy environs on an investment bank. The people around you matter.

Related: A Summer with the Army Special Forces

4. Tear Down to Build Up

When we first arrived at West Point for R-Day, those first 24 hours were dedicated to the industrial-sounding but accurate “inprocessing.” They shaved our heads. They put us all in the same uniforms. We were yelled at, put under stress, and were expected to perform. Any semblence of individuality went out of the door. I was no longer Moose, I was “New Cadet.”

The cadre were tearing down our previous identities. High school quarterback, president of the debate team, cheerleader…it didn’t matter. None of those identities jump out of perfectly functioning airplanes to engage enemy combatants. But a soldier does.

Once we were mentally beaten down and at the point of breaking, we were slowly built back up. Our newfound abilities restored our confidence and we emerged from training even more aware of our capabilities and limits. We became more confident. I was Moose again, but with some new tricks.

Drastic change or improvement demands drastic methods. You’re not going to lose 20 pounds by skipping the French Fries, you’re going to have to bust your butt in the gym and eat healthily all around.

Muscles have to be pushed to their limit and essentially destroyed (torn down) and then rested and well-fed in order to grow (built up). You’re not going to get a PhD in a STEM field with low effort. Retiring early at 30, 40, or even 50 is highly atypical and requires a different operating system than the one we’re given by default. Greatness takes sacrifice.

If you want to achieve something extraordinary, set your previous habits on fite and build a new set of habits! Break down the previous version of yourself that hasn’t achieved that goal yet and build up the version of yourself that will excel, by default. 

5. Humility is Not Weakness




There’s a fine line between being confident and being cocky.

To me, the difference is humility. Humility is understanding that you’re never the best at any one thing and that you can always improve in some way. If you do happen to be the best, it’s recognizing that this is a temporary status and you’ve got the world nipping at your heels to take that accolade away from you.

You’re not perfect and you never will be. Thankfully. Can you imagine having nothing to strive for, no new skills to learn or goals to reach? Hell no. Overcoming the struggle is the real achievement and the goal is just an azimuth to guide you.

I was a cocky teenager but over time I became confident instead. What made the difference? I wasn’t the perfect human being I thought (wished) I was and I got my ass handed to me on more than one occasion.

I realized I was good but that there was always someone better than me at something. I thought I was hot shit for running two miles in under 13 minutes, especially for a 200+ pound weightlifter. Then I saw a guy run two miles in well under nine minutes and barely break a sweat. This Scandinavian-looking dude had the stride of a gazelle and easily passed me. He made it look effortless.

Confidence told me that though he has me beat on the run, I can still smoke him on pushups and situps. There’s a significant difference between being humble and beating yourself up. Humility told me “so what, your run could be better and you can learn from this man.” I wasn’t competing against him, I was competing against my prior best.

Harness humility to never let yourself become complacent. Use humility to recognize others who are greater than you. Tell them to their face, “you’re awesome at XYZ, show me how you do it.” You are an ever-evolving creature who will forever be flawed. Rejoice in that and turns as many of those flaws into strengths as possible. Your work will never be done and that’s the beauty of it.

Related: 5 Life Lessons from West Point: Knowledge Taught by a Boot Up the Ass

Which life lessons resonate with you the most? How did you achieve or overcome when life was in your way? What did you learn from that? Leave a comment below and share your story!


  1. Sebastian August 27, 2019
    • Moose August 27, 2019