Six Things I Didn’t Learn in School - Part One: Experimentation

I am the well-formed product of an assembly line education and professional system.  I have the right certificates on my wall. I live a very comfortable and safe life. Sure, I've taken action against the more absurd manifestations of bureaucracy, but in the end, I’ve always returned back to the warm embrace of steady, risk-mitigated, quantifiable “accomplishment.” 

I’m a product of system that incentivizes behaviors rooted in early 20th century homogeneity – and I readily comply. 

None of these things are necessarily bad, and they minimize volatility and uncertainty. However, it’s all a bit unsatisfying.

I’ve observed that there’s a different part of our society that embraces a different ethos And they too succeed. While having a lot more fun – and changing the world. 

There are six observations I’ll explore in this series. All are insights I wasn’t taught in school, but that I’ve observed as elements to success in the 21st century. 

1)     The power of Experimentation and Iteration

2)     Mentorship, Sponsorship, and the impact of relational networks

3)     Always Be Selling – Why persuasion matters more than data

4)     Time, not Money, is the greatest source of wealth

5)     It’s Never Too Late to Start

6)     Non-consensus and Right is how you win bigly

Let’s begin.

Part One: Experimentation and iteration create more value than simply following the rules

When I was an F/A-18 Hornet instructor pilot, the most complex phase for my students was Basic Fighter Maneuvers. Civilians know this as " aerial dogfighting." The goal is to maneuver aircraft flying at over 500 miles per hour and pulling in excess of 7 g’s into a position to get a weapons shot on a maneuvering adversary. 

As with training to any complex and dangerous task, risk mitigation is critical. We had extensive briefing guides and training rules that usually took just shy of 60 minutes to explain. As instructors, we conducted “murder boards” to ensure we used the correct phraseology in the proper order. 

By the time brief was over, the student was usually overwhelmed – and they hadn’t even walked to the jet! So, near the end of my tenure (it took trial and error to get to this point), I’d leave them with one thought – “no matter what happens up there, if you don’t know what to do, just try something. If it fails, we’ll debrief it and use it as a learning experience.” This was a bit shocking after the lengthy script.

I’d given them permission to fail. And fail they did. But the beautiful thing was that in subsequent flights, they didn’t fail in the same way anymore. They learned and got better. And they started having a lot more fun.

How did I learn this? When I was a young pilot, there was one training flight where I found myself in a very defensive position. I was out of airspeed, near the hard deck (the altitude we use to simulate the ground), and the senior pilot was dialed in behind me. I put in a hard left rudder…and got schwacked. 

It failed miserably. But I never did that maneuver again. Soon, after many iterations of experimentation, I started to develop intuitive pattern recognition. Without thinking, I could successfully respond to the maneuvers of my adversary.  A few years in and I’d become a halfway decent fighter pilot.

I’ve seen this in business too. Overnight success really does take years of hard work. 

In my current role looking at search fund investments, I’m awed at the number of small business owners who’ve built small, but cash-flowing companies in completely "boring" industries. Many of these founders are in their 60s or 70s. They spent decades to reach revenue in excess of $10mm a year. They started small, adding one thing at a time with little experiments year over year. The best ones discarded those experiements that don’t work, and reinforced those that did. These are normal folks without fancy degrees who had the audacity to try something small and used iteration to achieve success.

Schools incentivize and reward “correct” answers. They teach us how to get from point A to point B, whether it be a math problem or analysis or a historical event. I remember being coached on how to do well on History AP exams – “five paragraph structure, with a clear introduction…three supporting paragraphs with evidence…and a succinct conclusion.” Voila – a 5 out of 5! But schools don’t reward iterative, exploratory behaviors. They rarely allow experimentation, failure, and redemption. Adult society reflect the methods we teach our young.

Simply taking a stab at something can have a powerful downstream impact. When I was a speechwriter, my drafts were torn apart and sometimes completely discarded. Yet, in every speech, the core idea of what I was attempting to communicate was retained. The anchor a junior speechwriter throws down drove the subsequent narrative – even for a four star admiral.  First drafts matter.

Our world is complex, and the more I experience, the more I realize that reality isn’t black or white. Uncertainty defines our existence. The only way to truly thrive amidst uncertainty is to embrace humility by dive right in by trying something. In the end, after twists and turns, we discover more remarkable and enduring truths than if we'd waited until perfection struck. 

What are you afraid to try?