Too Smart To Try

May 13, 2024

My dramatic meltdown on the boiling blacktop at the bottom of a barren red rock slot canyon in St. George, Utah was a turning point for me, though I didn’t know it at the time.

(This week is the second in a three-part series – if you want the first part of the story, you can read last week’s newsletter here.)

It was the first time I had really failed at anything. 

That may sound strange or that it’s coming from a place of hubris.

​In fact, it’s quite the opposite. It’s not that I was so good at everything I tried that I could never be beaten. I never failed at anything because I was running a deep subconscious program designed to keep my ego from the pain of losing.

​In other words, I carefully selected when and where to apply myself so that I could completely eliminate the chance of failure.

I only took on challenges where success was virtually guaranteed.

​My dear friend and coaching mentor, Elliot Roe, calls this program Too Smart To Try.

​Here’s how it works:

 “Too Smart to Try is a program designed for ego protection. The subconscious mind has built up an image of who this player is, and their worth is directly correlated with their intelligence. By trying and giving 100 percent of their effort, they risk failing and shattering that ideal version of themselves. If you never try and never give it all you can, you can always look back and say, “I would have been successful if I’d really tried.”

He goes on to explain:

 “This program is developed by a child who has above-average intelligence and is told so, and even praised by those around them… The problem comes when that intelligence is not challenged. Assignments, grades, and test scores come easy, and these individuals are never forced to put in extra work or struggle to find a solution. They learn to view their intelligence as an innate personality trait, not something that they need to work hard to improve or maintain.

When that trait gets closely tied to their self-worth, the subconscious creates a program to avoid any situation that might call their intelligence into question. Failure is no longer viewed as an opportunity for growth, but as a risk to their identity and value as a human.”

– Elliot Roe, A-Game Poker

​I had spent my entire life building an elaborate ego defense mechanism.

​When I was in first grade, my mom was called into my prestigious private elementary school to discuss my standardized testing results. My teacher and the principal were in the room, making her extremely nervous. They told her that they had never had a student at the school with such high scores and that I was reading above a sixth-grade level.

​Even though my mother chose not to tell me about the results at the time, my abilities became apparent nonetheless. School was a breeze for me, and through elementary school, I could achieve perfect scores without studying.

But when I got to junior high and was placed in honors classes with my peers, my edge started to slip. I started to bring home the occasional B, confounding my parents to no end. Why would a kid with such talents not use them to their full potential?

Even at this young age, I was a natural handicapper, someone who possessed an intuitive skill for accurately assessing the cost-benefit analysis of effort versus results. To this day, I have an innate ability to understand and predict the potential returns on various kinds of investments, whether those investments are of time, resources, or emotional energy.

​Applied to schoolwork, this analysis was obvious to me: I needed to be near the top of my class to get into the best colleges, but the monumental extra effort required to be at the actual top would only marginally improve my chances of getting into the Naval Academy, my school of choice. Because their admissions process weighted well-roundedness rather than pure academics, I knew that I would be safe doing just enough to get by.

could have been valedictorian, of course, but I chose not to.

​And so began the story of the rest of my life.

​I did succeed in graduating near the top of my high school class, and received a senatorial appointment to the Naval Academy.

​When I got to the Naval Academy, the program intensified. The academic load was crushing—even the smartest kids would buckle under the pressure. I saw immediately that I had two options: study around the clock, or continue leaning on my natural abilities to merely skate by.

I chose the latter.

This time, the decision came with an unexpected consequence. I found that I was regarded by the rest of the students as a dirtbag, someone who shouldn’t have been admitted and wasn’t living up to the ethos of such a prestigious institution. 

I could’ve chosen to make a change, but instead, I doubled down. I embraced my reputation and became a notorious rule breaker. If I’m honest with myself, I enjoyed the negative attention. It allowed me to try on a new persona, that of the rebel, as opposed to the relatively mild-mannered overachiever from high school.

​All the while, the voice in my head was clear: I could easily succeed if I wanted to, but I was choosing not to because it wasn’t worth the effort.

Again, I graduated, but this time by the skin of my teeth. It was enough of a wake-up call to adjust my aim.

​When I got to flight training in Pensacola, I knew that the stakes were much higher here than with academics. Schoolwork didn’t really matter, but now I was flying high-performance aircraft, and there were life-and-death consequences for missteps.

​I decided to fly P-3 Orions, a big, lumbering reconnaissance aircraft that offered a laid-back, land-based lifestyle—one that suited my new persona quite well.

​But because of the perks, slots for P-3s were coveted amongst my classmates. The Navy allows students to select their career path based on order of merit, meaning that the higher your rank amongst your peers, the better your chances of getting what you want.

​So, I took flight school seriously, and I excelled. However, even then, I was still able to call on my God-given intelligence, and I didn’t have to work that hard. Once I understood how the program worked, I was able to apply the same cost-benefit analysis that I always had and extract maximum performance from my carefully measured efforts.

​I also maintained my rebel persona, carefully out of view of the instructors this time, but fully displayed on the vibrant, testosterone-fueled party scene that is alive and well within our military culture.

​By now, I was in my mid-20s, and my subconscious program was fully developed:

Try when it matters, blow off anything that doesn’t, make sure to succeed, but look good doing it. And by all means, don’t let anyone see you making any effort – it’s got to appear to come naturally. 

Fast-forward a decade, and I had moved back to my hometown of Midland, TX, to pursue my long-time dream of building a business.

If there was ever a place for my rebel, natural handicapper, too-smart-to-try program to flourish, it was the good ol’ boy culture of West Texas.

​I went to work for my uncle and his business partner, a very successful oil man whom I consider to be my first real mentor. He is a man whom I deeply respect and admire to this day. Here, in the fast-paced environment of buying and selling, arbitrage, and deal-making, my natural abilities finally found a perfect fit.

I was young, I was arrogant, and damn if I wasn’t good at it. I felt like I was able to see how the game worked in ways that others couldn’t. I was making money hand over fist, and the best part was that I was barely trying.

​Of course, because I was on commission, the junior partners of the firm were making a lot more. This put us on a crash course, and eventually, tensions started to form. I went to my mentor, bringing solutions rather than complaints, but to my surprise, it backfired.

He told me that he was too comfortable and making too much money to shake things up at his firm but that I was welcome to try it on my own. There were no strings attached; best of luck. 

By this time, I had brought in my best friend from the Navy, and we set up shop in his living room. We even taped a makeshift sign printed on 8.5×11” paper to the wall.

Palmares Energy was open for business. 

We couldn’t have known then, but we were in for one hell of a rocket ship ride…

To the young, arrogant version of myself who was too smart to try,


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