New release - PASSION STRUCK

Intellectual Humility: The Most Important Skill An Entrepreneur Can Develop
What A Princeton grad taught me about the dangers of ego

Regardless of what your identity is, we as a whole have a picture of ourselves that is different in how the world sees us. In all actuality, our impression of ourselves is of an individual who is somewhat more brilliant, more certain, and somewhat preferred all-around over who we really are. It is great to have confidence. But, the problem with an inflated self-identity is that it can lead to a giant ego, which in turn can become a massive liability. That is why our intellectual humility is so vital to our success.

Let me illustrate this point through a personal story.

A few years ago, a young professional landed a new job with one of the electric scooter start-ups. The young man’s father asked me if I would use my personal connections to help his son, who was in charge of new market development, land Tampa Bay, the country’s 11th largest metro.

I honestly do not typically honor this type of request, especially for someone I have never met. However, the father had helped out my kids and I owed him a favor in return. Additionally, this young man had an incredible resume: Princeton undergraduate, top-five law school graduate, and had just left serving in the current President’s administration. And, this start-up was all over the news and a darling of investors. Its employees had the reputation of being young, brilliant, and sincere in their belief that their electric scooters were going to change the world.

So, I took the gamble, agreed to help him, created a plan, and acted.

I contacted influential friends, contacts who knew the mayors and city council of Tampa Bay and St. Petersburg, the region’s two largest cities, and other colleagues who are leaders throughout the community. I used up a lot of favors and personal chips.

However, in a matter of a few days, I managed to arrange private meetings with both mayors, their respective city council members, and the heads of both city’s transportation departments. Everything was lined up to allow for success, or in the least, setting a great first impression.

As we neared the first meeting date, I began to text the Princeton graduate, who is a Millennial in his early thirties and asked him about the meeting and how he wanted us to present ourselves. I also asked about the meeting strategy and offered to provide my input based on knowing many of the leaders we were meeting. I suggested we either wear a suit or a sport coat, knowing the protocol of both mayors.

After a few days, I didn’t hear any reply, so I decided to text him another time since the meeting was coming the next morning, and he was traveling from New York to attend. I told him I wanted to make sure I represented the start-up brand correctly, and we were on the same page for the important meetings I was asked to attend with him.

I then received a text back that I will never forget.

“I got both your messages. I ignored the first because I thought it was demeaning. You do realize I am a Princeton graduate, an attorney, and just left working for the white house where I routinely briefed the President. You must either be inept or a very inexperienced leader if you do not think I know exactly what to say and wear to a meeting, especially with a Mayor in a third rate city like Tampa or St. Petersburg.”

I Should Have Known That You Can’t Judge a Book by Its Cover

I looked at my phone in absolute shock. Never in my career had I ever been spoken to like that before. Let alone, by someone who didn’t know me. Not only was I going out of my way to help, but I had also put my personal reputation on the line with two Mayors, their respective city council members, and staff.

I immediately started to write a VERY direct response but then decided to take a different and more shrewd action course. Instead, I went to the young man’s father and relayed to him what happened.

What shocked me was that although he apologized for his son’s actions, the father didn’t seem surprised. He assured me he would talk to his son and pleaded with me to continue helping him and asked me to attend the meetings.

I reluctantly said yes.

Picture of a Cat Painting his own image and showing intellectual humility
Photo Source: Reddit

Princeton has a long rolodex of exceptional graduates, like Michelle Obama, Jeff Bezos, Cornel West, Ralph Nadar, Meg Whitman, and President John F. Kennedy to name a few. It is one of the premier higher learning institutions globally, and I hold it in the highest regard.

I realize this story is an isolated case, but this is not the first time I’ve met someone who graduated from Princeton or who had a larger version of self-identity and their “eliteness” than they likely should.

It made me openly wonder if Princeton has an intellectual humility crisis on its hands. From the multitude of articles I read on the topic while researching this article, I may be onto something. What really caught my attention is that many of these articles are written by Princeton Alumni.

For instance, Princeton 2015 graduate Thomas Horton writes, “the Virtue of Humility seems to lay forgotten under the amoral detritus of our (Princeton) culture which glorifies individualism and the promotion of self-identity.”

He goes even further, “the danger is this: that in being taught to be highly sensitive to others’ identities, we are also implicitly being told to cling to and take pride in our own identity. This is where the danger creeps in. Pride is a vice.”

This is a substantial growing issue in America and one to be fair in which Princeton isn’t the only culprit.

As I get further into my career, I see a greater preponderance of silos, self-interest, and bureaucracy in corporate America. These overtures are ultimately perpetuated by individual behavior.

I believe this individual behavior starts in our higher education schools, which need to be teaching more intellectual humility.

Now in the Iconic Words of Paul Harvey, “The Rest of the Story.”

After not hearing back from the young man after speaking with his father, I thought about not attending the meeting the next day. But, since I had set them up, I could not really back out unless I canceled all of them.

Additionally, I thought his father surely would deliver a stern message to him, and I was optimistic that it would turn out well.

The next morning, I was scheduled to meet the Princeton graduate at our designated meeting place outside the city hall. I got there early and waited for him to arrive along with my friend from one of the significant public relations (PR) firms, who helped set up the meeting, a local lobbyist, and a city council member spearheading the scooter initiative. We all were dressed in professional attire with sport coats or suits.

My friend’s son approached us, riding his scooter up the street and wearing a white t-shirt, blue jeans, a back-pack (which doubles as his suitcase), and converse sneakers. As he approached, the other gentlemen just looked at me in bewilderment. I shrugged my shoulders to them as I had no idea what to say. It was too late to make any changes, so we headed into the meeting.
We all gathered around the executive conference room as the Mayor entered the room.

If you do not know Bob Buckhorn, he is a lifelong Democrat known for restoring Tampa to relevance during his two terms in office through his enthusiasm and brash confidence. His platform focused on creating a city where young professionals would want to live and work — like my friend’s son.

Attract millennials, and you build talent, he often said in meetings.

Photo of Bob Buckhorn showing intellectual humility
Photo of Mayor Buckhorn. Credit: Tampa Bay Times

Therefore, the Mayor is no stranger to meeting with millennial leaders or having them in his office. However, he expects proper protocols and mutual respect. And, he always dresses professionally, typically wearing a tailored suit.

After greeting all of us and thanking me for a recent interview I had conducted with him, he turned to the young t-shirt wearing man and said, “Son, I am nearing the end of my time as Mayor. I have held thousands of meetings in this conference room literally, and you are the first person who has ever entered it with a t-shirt, sneakers, and jeans. Your presentation had better be more inspiring than your preparation and choice of attire.”

So, with that, we all sat down and started the meeting. Since I arranged the session, I started it with introductions and some background. I then turned it over to the young professional who led the discussion by talking about his recent time in the Trump Administration.

You can guess how the meeting went after that.

Following this meeting, the young man attended meetings with several other city council members, the city’s general counsel, the city transportation director, and staff. He told me he “did not need me” in these meetings and so I went back to work for the day.

I had not driven ten minutes when my phone began to ring from my PR friend who arranged the meeting, obviously not happy with what had just occurred. The Mayor had already called and given him an earful about wasting his time. It wasn’t too long before other colleagues had called me reporting their dissatisfaction in what transpired.

The next day, I met the Princeton graduate in St. Petersburg, this time to meet with Mayor Rick Kriseman, another life-long Democrat. I’ve known the Mayor for many years, and we are good friends. Our oldest kids went to the same school together. Like the Tampa Mayor, he wears a suit every day except Friday’s when they have a jeans policy.

We met privately with the Mayor with another friend from the same public relations firm for this Wednesday meeting. Again, my friend and I both wore professional attire. Thinking surely he would learn his lesson from the day before, I anxiously waited for the young man to arrive. And he did, again riding his scooter wearing the same outfit with a different t-shirt. I directly asked him about it, and he told me that this was all he had brought with him in his back-pack.

As we entered through security screening, the police officer at the entrance asked the young gentleman who he was there to see. He signed the ledger and told them Mayor Kriseman. He then pointed to his scooter, which he had to take through the metal detector.

The guard then responded, “you do realize this isn’t Friday?”

We went up the elevator to the Mayor’s waiting room. Once we entered the office, we were greeted with a warm reception and sat down to talk. We used the same approach as the day before with me laying out the groundwork for the meeting and introducing the young professional and his company.

This time I thought we were on the right track as the meeting started out by talking about scooter transportation. However, before long, the young man found a way to push his ego to the forefront and again brag about his position in the Trump administration and his transportation work. This to a Mayor who banned President Trump from coming to his city.

Then the Mayor, who had done his homework, started to ask some very direct pointed questions about the negative consequences of scooters in other cities and his concerns. The young man did his best to answer him. Eventually, he told the Mayor that he didn’t need his permission because they were already entering many other markets using a “land and expand” strategy, bringing their scooters into new cities without permits.

It was a cordial meeting; however, I again already knew the result. While Tampa and St. Petersburg may not be New York or Chicago, there is decorum and a political savviness behind how decisions occur. And, we had broken all the cardinal rules.

Following the meeting, I drove my car, and he rode his scooter down the street to breakfast with a prominent city council member and the director of transportation for St. Petersburg.

They also were all professionally dressed.

The End Result of the Lack of Intellectual Humility

Picture showing demise of bird scooters
Photo Credit: Alex Castro

The electronic scooter company landed neither a contract in Tampa nor St. Petersburg. Both cities awarded them to their competitors, much smaller than this prominent company. This same scooter company was once the fastest-growing unicorn. A year later, it started to experience a fantastic demise brought on by erratic decision-making, nepotism, egos, poor leadership, and untruthful and ever-changing success metrics.

As for me, I was never again granted a meeting with Mayor Buckhorn. I believe it greatly impacted my credibility and essential relationships with both Mayors, the PR firm, and irate Tampa friends and colleagues. They had put their reputations on the line to help me arrange the meetings in such short order. I’ve spent 18 months rebuilding them.

The kicker is that the young man never formally thanked me for my efforts in helping him out.

Placing Self Above the Ship

I may not be a Princeton graduate, nor a top-five law firm graduate. I happen to be a US Naval Academy graduate and former naval officer. While the Naval Academy is not, like Princeton, the top undergraduate academic program according to US Newsor focused on self-identity.It may be the top university for training future leaders and instilling a sense of duty, honor, and mission.

I also may not have worked in the White House, but I have met four Presidents and had the privilege of escorting President Clinton on a personal tour of the Academy while I was there. A few short years later, I also gave him an intelligence briefing at a Joint Staff assignment.

During my time at the Academy, I was first introduced to the concept of “ship, shipmate, self” in a leadership training course taught by Admiral Stockdale, the former Vice President candidate and medal of honor winner. It is the opposite philosophy to what is being taught by Princeton and other premier colleges.

This aphorism is an old nautical jargon that taught us that the Navy’s mission came first and foremost in prioritizing effort. It also expresses the importance of teaching that the most influential leaders are servant leaders who are not focused on self but others.

As a junior officer, I quickly learned the importance of respecting and listening to my senior enlisted and officers’ guidance. I heeded their advice as they taught me vital career and life lessons.

I have further learned that you can never go wrong by looking for ways to advance the mission or help the teammate or peer who is on your left of right.

When we lose focus on those two elements, we end up focusing inward. Pride ends up taking over, and you’ll lead not as a servant or selfless leader, but rather from the point of ego.

This is especially important in the brave new all-digital-world that is becoming our future. It is a world perpetuating a siloed mentality of placing self above the ship, just like the young Princeton graduate I tried to help. This type of self-branding is a sure-fired path to disaster.

When an organization’s collective mentality, like the scooter company, is self and self-preservation first, it’s a sure sign of pending doom.

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