Navy at Wake Forest football game, Winston-Salem, NC, 11/23/2002. Left to right: An alumnus of USNA ‘68 whose name I’ve forgotten, Admiral Naughton (USNA ‘68), the author (Nowhere class of ‘never), and Robert Owendoff (USNA ‘68).


I recommend you read The Art of Being Human first if you have not already done so. It’s a quick read that provides context for this.

Gold bars

As a junior in high school I decided to apply for admission at the US Naval Academy. I wanted to make a career in the military, and it seemed becoming an officer was the way to go with better pay and more responsibilities. The service academies are all fine institutions and are as selective as Ivy League schools, but the USNA (also known as Annapolis) was my choice for a few reasons. One is I really liked the location the campus. Situated on the Chesapeake Bay in Annapolis, Maryland, a midshipman can enjoy crab cakes while sailing on a dinghy in between classes. The baroque architecture is bright and lively, not like the gloomy gothic revival fortress that is the US Military Academy in West Point, New York–where the cadets read by candlelight and sing Gregorian chants to pass the time.

The only pictures anyone has seen of the US Air Force Academy (USAFA) are of the chapel (google it and see if you can find anything different), and I was turned off of the USAFA partly because of this weird presentation by a recruiter at a service academies event. He was a lieutenant or captain in the Air Force, and he said “Why should you attend the US Air Force Academy? This is why you should want to attend the US Air Force Academy–these gold bars” Holds up pair of single gold bars that a newly commissioned second lieutenant would wear– I figured he’d read too much Robert Kiyosaki or Peter Schiff and was on a mission to tell high schoolers to do what they must to obtain the precious metal–if they can’t buy gold, then they could become officers in the Air Force and have tax payers bank roll their gold bars. There were other weird parts to his presentation, and I remember two or three USAFA cadets had traveled with him and they were in on it too.

In addition to the amenities and vibe of Annapolis, the institution also has a broad range of career opportunities. You can spend your summer flying T-38 supersonic jets, driving ships or nuclear submarines in the ocean, rolling in surf and sand with Navy SEALs, and other exciting things. Upon graduation you can either be commissioned as an ensign in the Navy, or a second lieutenant in the Marine Corps.

Finding my in

I’m in! – Every hacker in a movie

I had a family friend, the late Robert “Bob” Owendoff, who was both an Annapolis graduate (class of ’68) and a former professor. Bob took me to a Navy football game where he introduced me to then superintendent of Annapolis, Admiral Richard Naughton, who was a classmate of his in 1968. That class was a “stars fell on…” sort with other notable alumni like Oliver North and Jim Webb. Bob retired from teaching at Annapolis, and he was a kind, generous person who spent his time looking after his airline captain wife’s two Bichon Frises (Beau & Ollie), volunteering as an usher at our church, and helping guide me through the process of applying to Annapolis and even took me on a week long trip where we toured Annapolis and he introduced me to important staff at the academy including the dean of admissions. Bob was a genius who corrected errors on sundial information he discovered in the Encyclopedia Britannica and created land navigation guides that were used by the Cub Scouts, as well as Marine and Army pilots in Vietnam–it’s an important detail to his story that he was only sixteen years old when he did this. He went on to graduate from the academy and serve as a naval surface warfare officer before teaching subjects like nuclear thermodynamics at the academy. If you visit the academy today, you can see his graduating class’s gift, which is a sundial inspired by his work. I can’t find the photograph I took beside the sundial but if you google it there are a few wonderful images. Here’s one that is for public use and shows detail of the sundial:

Self-Orienting Sundial, Class of 1968 gift to United States Naval Academy

Self-Orienting Sundial, USNA

Losing my in

Admiral Naughton soon resigned from his position at the Academy after just on year on the job. Apparently, yelling at and assaulting a Marine on New Year’s Eve wasn’t good behavior from a vice admiral. He was demoted, decided to resign, and I lost my in.

My next option was a congressional appointment and I learned that the competition was fierce. My congressional liaison told me my district competitors included kids who had all the boxes checked: Varsity letter athletes? Check. Perfect SAT score? Check. Class president? Check. I couldn’t ever compete with these kids who I assumed had always known they wanted to go to a service academy and spent their entire high school tenure campaigning for class president in the morning, practicing sports in the afternoon, and running drills for standardized testing in the evening. These ambitious teenagers were also selfless and they spent their weekends volunteering. I’m sure there are many who’d had more challenges than me, but I think the nature of my challenges didn’t lend itself to bearing fruit that resembled the prototypical Annapolis candidate.

Unconventional moves

It seems to be a law of nature, inflexible and inexorable, that those who will not risk cannot win. – John Paul Jones, “Father of the US Navy”

My family moved around a lot when I was growing up. The benefit of this is that even as an adult I still seek novelty and adventure, and I’m not afraid to try something new even if it seems I’m unqualified. It’s not that I don’t get scared, but I’ve learned to muster the courage to press through tough or ambiguous situations. Nonetheless, my upbringing didn’t lend itself to shaping me to be competitive for an ivy-league admission track.

My mom graduated from a Mississippi high school in a class of three students, then completed half of nursing school before dropping out to marry my dad and travel. My dad grew up poor in a small Canadian fishing village and dropped out of school in eighth grade, and he started traveling in the US when he was nineteen and performing organ in tent revivals. They always supported the idea that their kids would go to college, but didn’t know a level of commitment beyond asking us to make As or As & Bs.

They let me sign up for baseball in third grade, but they took me out before the season started because we were going to be traveling and missing games and practices. A year later they put me in Tae Kwon Do, where I did quite well (and even skipped a belt ranking after less than a year of practicing), but we moved to Texas and that was the end of my martial arts career. From kindergarten to high school I went to nine different schools (including one home-school stint) spread out across six moves between five states.


Alabama→ California→ Georgia→ Alabama→ Texas→ Alabama→ North Carolina

We moved from Texas back to Alabama and I transitioned to a private school there in eighth grade. The school had me and my sister do placement testing before starting classes. My studious older sister completed her placement test in a day. I completed mine after a day and a half. My mom cried when the principal delivered the test results. He informed her that I had tested at least one year or up to a year-and-a-half behind in all subjects. He added that that most students finish in a day or even half a day, but he’d never seen anyone take as long to complete the placement test as I had. I received no prize or further recognition for that.

Mom didn’t think anything was wrong with me, but the principal’s declaration of my anomalous performance gave her doubts. Even still, she advocated for me telling him how my report cards from teachers would include notes like, “Kyle is a bright student, but he often daydreams in class.” She told him pulling me back would not challenge me but actually bore me and I would probably be less successful, but he wouldn’t relent. They struck a deal that would allow me to more than twice the work in the school year until I caught up to my appropriate grade level. As a carrot, my parents promised to buy me a new bass guitar I’d been wanting if I did all the work and made straight As. I can remember looking at the magazine ads featuring that bass guitar, even the musicians posing with the instrument and the layout of the ads. I remember going to the manufacturer’s website and reading the hardware, wood, and finish specs. I completed all the work, made straight As, and parents made good on their promise. I still have that bass guitar today.

Ibanez BTB bass guitar ad, magazine circa 1999 featuring System Of A Down member.

One of the original ads of my prized bass guitar from 1999.

Trying to rise above the crowd

Competition is for losers. – Peter Thiel

When I was fifteen, I decided I wanted to attend Annapolis and then make a career in the military. At this time my family moved to North Carolina, and once again I was enrolling into a new private school for the start of my junior year. I went out for football where I discovered that football is a great sport for breaking fingers (I missed half the season because I had pins surgically put into my finger) and I’ve got such a bad case of tendonitis in my ankles that I have vowed to never step foot into a pair of cleats again.

I had trouble making friends at my new high school. The school assigned me a buddy who was the class vice president, but he never followed up with me after our initial meeting. I made friends with some students who were seniors, and I was a mascot of sorts earning the nickname “adopted senior” since I was a junior. In hindsight, that wasn’t the best move since they’d be graduating and I’d have to start from scratch making new friends for my senior year.

Beginning my senior year, I campaigned for class vice president. I knew it would be difficult to successfully run against the incumbent class president, so instead I made myself her running mate and vice-presidential candidate. I ran an inexpensive campaign which included doodling “Vote for Kyle–VP” notes and circulating them in classes. I was the only student campaigning for Vice President but I still lost to the incumbent vice president. He was a popular guy, but I bet no one remembers who our vice president actually was but me. Not that I’m bitter or jealous–on the contrary, I think it’s fascinating how things are only as important as you make them.

The high school was privately run by a Southern Baptist church which was once one of the largest churches in Charlotte, NC. It was an adjustment for me, because they didn’t assign homework on Wednesdays, just the other nights. The idea was to free students up to attend Wednesday evening Bible study at the church. However, my church had Bible study not on Wednesday but on Tuesday and I volunteered at my church and played bass guitar in the worship band–a time consuming commitment where I would need to practice songs during the week and arrive early before a worship service for rehearsal and soundcheck. It was a challenge that my study habits had not grown to match.

Despite a schedule that didn’t facilitate optimal study and homework completion, I made good grades in most subjects except for subjects that didn’t interest me at the time (like chemistry). I had an SAT score of 1230 or 1260–I’m not certain which it was, but I know it was higher than the minimum required score at the time and it was higher than then POTUS George W. Bush, himself an Ivy League alum and earner of a 1206 SAT score (although it’s not fair to compare, since we took our tests decades apart and scoring likely changed, high school was a long time ago, and he and I have both had life experiences and lots of growth since then. He’s now a painter and artist, and I now work in technology. We both live in the great state of Texas at the time of this writing).

I admire great competitors and people who are on ivy-league tracks and hyper-competitive professional tracks, but for those like me with unconventional paths we can usually can’t compete in their domains at a high level because they’ve honed their skills on conventional paths. Conventional paths constantly provide objective feedback and clear trajectories for growth, and are more economical and efficient. Unconventional paths can equip one with a diverse–albeit, superfluous–skillset and out-of-the-box approaches to domain-specific problems, but the cost comes at a wildly inefficient education. The unconventional path does take up a lot of time, but much of that time is spent on introspection and exploration. Every now and then an unconventional person gets a shot at an established domain and sweeps the competition, but the shots must be calculated and not haphazard. Stay away from competition if you can, but if your unique skillset lends itself to a competitive advantage–take the shot! (see: Elle Woods’ character in “Legally Blonde”)

My parents didn’t set or guide me on a competitive track, but they supported me the best they knew how, loved me unconditionally, and allowed me to consider military service, music, and philosophy as careers. My soul is enriched as I’ve cultivated depth through exploring duty in service, beauty in art and music, and truth in philosophy.

Peter Thiel says that the paradox of competition is you can get quite good at your domain but the competition gets tougher as you climb the ladder until the price of defeating competition might very well be selling your soul, and no reward is worth selling one’s soul.

No plan B

I don’t remember when I received a rejection from Annapolis, but I didn’t have a plan B. I remember telling someone my top 3 choices were “#1 Annapolis, #2 Annapolis, and #3 Annapolis”. I hurried to get my transcript sent to University of North Carolina–Charlotte, and was admitted for the fall semester just in time. My plan was to be an engineering major since all plebes (first year midshipmen at Annapolis) must take the same classes as an engineering major. I could do well in these classes and that would bolster my chances of admission into Annapolis if I reapplied the next year. Turned out I hated the classes, well, I don’t know if I hated it or if I hated seeing my dream slip away. My classmates at University of North Carolina–Charlotte wanted to pursue careers in motorsports and NASCAR, and that didn’t interest me. In the spring and fall semesters I was enrolled in calculus, chemistry, physics, statistics, English, western civilization, and two other courses that were not in the engineering track for my degree: American military history, and jazz improvisation.

The American military history professor was Dr. James K. Hogue who earned his PhD from Princeton University, and formerly taught at the US Military Academy at West Point. It was a class that occurred on Tuesday and Thursday nights, and it didn’t make sense at all with my schedule being mostly morning classes–but I wanted to be around this caliber of professor to receive an education or at least absorb something by osmosis.

I signed up for early morning classes so I would be more productive, but I ended up filling my afternoons and evenings working instead of studying–and I liked working because I received gratitude from satisfied customers, praise from management, and pay checks. This instant gratification made it seem like the goal posts for the Annapolis dream were moving further and further away. After my first year of college I received a warning that I was in danger of being placed on academic probation if my grades dipped any lower. If my transcript showed these terrible grades, I’d have a snowball’s chance at getting into a better school. That was the nail in the coffin of my Annapolis dream, but more than that it was my childhood dream.

Defeat and entering a personal post-war

I’d dreamed of a career in military service, and what could I do now? My eyesight had worsened in my late teens, and I knew they wouldn’t let me do anything fun in the military unless I had perfect vision–but the service academies were paying for PRK to correct vision for their students, and that was another thing I missed out on. In my defeat, I’d also changed interests and hobbies. I was no longer reading military and history books for hours on end. Now, I was reading music books and philosophy.

My life was taking a turn, and it seemed an old identity had died. It’s true the things I had attached to and focused my attention were no longer in the foreground. The kind of people I wanted to serve with everyday and be measured against and ultimately shaped by, they had already influenced me and now I was going down a new path. At that point in my life I was still far away from programming computers, but the foundations were being laid–first with the desire and mental preparation of military service, and now with the study of music (composing patterns of sounds to express emotions), philosophy (logic), and sociology (user experience and social networks).

When one’s imagined future is no longer attainable they might feel like their life is over, because what is a life without a future? My life was not over–it was taking shape.