Why Being A Student Entrepreneur Is So Frustrating (And The One Big Insight To Take From It)


I switched into the public school system right after the 3rd grade.

It was a rude awakening: I went from a Montessori School where I was able to design and create my own education plan every single day to a school system that told me that I had to learn about Math at 11:10 and English right after recess.

I hated it. I still resent a lot of it, though I’m now grateful more than anything else.

For the past 13 years, though, I’ve gone through our school system knowing that I didn’t belong in it. There’s always been a deep tension between my schooling and how I think about things.

For the past 13 years, I’ve been trying to articulate why it is that I don’t get along with the traditional classroom. My answer has evolved, but I knew that it was never accurate. It’s started with frustrated ad hominem attacks, grew to half-true generalizations, and further evolved into specific but slightly-inaccurate criticisms.

But, after 13 years, I finally figured it out. I have my finger on the pulse.

But before I tell you I want to clarify one thing before I explain:

It’s never been that I haven’t tried in school. I really love learning new things and I’ve spent excessive amounts of time researching further about what I’m studying in school. I took AP and honors classes in high school and played the game. I jumped through the hoops. I really did try to the extent I can — and I still do.

An Unlikely Book: Nassim Taleb’s Antifragile
I recently started Nassim Taleb’s book on disorder, probability, philosophy (etc) called Antifragile. One of the book’s major points is as follows:

Fragile things are hurt from disorder and change, while robust things are indifferent. It’s been thought for a long time that these things are opposites. But Taleb makes the distraction that this isn’t true: the opposite of something that is is hurt from disorder, is something that gains from disorder. Hence, that thing is antifragile.

Why Entrepreneurs Aren’t Made For The Current System
At my core, I’m an entrepreneur. My whole life I’ll be looking for things that I can change, solve or disrupt in some form or another. I want to build and lead large groups of people to accomplish things together.

We’re also now in an age where information is a commodity. You can find nearly anything you want to learn by connecting with the right person on twitter, watching the right youtube video, or searching for the right collection of webpages. Instructors no longer have the monopoly, and for those that like to take their own route, it’s a fact that is hard to ignore because it devalues the current education system by a lot.

While there’s still value in learning from a teacher or professor, the unique value has decreased immensely.

Though schools and universities are still a unique place to connect with others in an intellectual way and learn from other world views and perceptions, a core offer it sells to undergraduates today is becoming worthless.

As an entrepreneur, my biggest problem with the current education system is that it isn’t training me to become an antifragile thinker, to learn in a world that is rapidly changing. Instead it tries to focus on teaching a robust system and memorize fragile facts — which has been great for previous centuries, but falls trough in dynamic and increasingly complex systems, like the one we live in today.

Milk Gone Bad: The Current Education System
The current education system is nearly always a balance between fragile and robust. Memorization certainly has it’s place, and the deep understanding of a topic is definitely important in some respect. But the reality is that artificial intellgence is going to be able to do both soon, and most things can be easily researched or looked up thanks to the internet.

It’s weird to think, but it’s true.

I would make the argument further that the current form of public education is largely becoming an outdated system for the 21st century, but the point I want to make is that that it is completely outdated for entrepreneurs today. But again, it’s important to note there’s a lot of overlap between these types in reality, and all three types should be taught in some capacity. But when it comes to the overwhelming focus in what the current teaches, it falls short.

So why am I still in school then?

In short, to meet people and take advantage of the great opportunities that a world-class institution like Penn State offers. Plus, my parents really want me to graduate.

Nonetheless, I really believe there is a bigger cross-section between entrepreneurs and universities that would like to be believed in popular culture. I really love both – and that’s why I wish they worked better together. Furthermore, this isn’t to say that understanding and memorization are not valuable with context of an antifragile education – because they definitely are to a good extent. But the problem I’m talking about is that the overwhelming focus is on the wrong side of things – for everyone, especially entrepreneurs.

Better Defining An Antifragile Education
So what does an antifragile education actually look like? It’s tough to say but here’s my best stab at it:

Based on the definition, an education that becomes more valuable as the world changes and evolves, I would make the argument that it includes these two primary components: Perception Management and Critical Thinking Frameworks.

Perception Management
Perception management is a term that comes the US military. I’m using the term in this post as the skill of being able to look at problems from different angles, depths, and breadths with an active effort in increasing one’s self awareness. Here’s the definition that the US Department of Defense uses, via Wikipedia:

Actions to convey and/or deny selected information and indicators to foreign audiences to influence their emotions, motives, and objective reasoning as well as to intelligence systems and leaders at all to influence official estimates, ultimately resulting in foreign behaviors and official actions favorable to the originator’s objectives. In various ways, perception management combines truth projection, operations security, cover and deception, and psychological operations.

What got me thinking about the idea of perception management in the first place, though, was a short allegory that came up in our most recent senior class:

Two fish were swimming in the sea and a third came up to them and said “how’s the water today, guys?”.
They both replied “great”.
When the third fish swam away the first fish turned to the second fish and asked, “what’s water?”

Good perception management means you’re able to continuously expand your awareness while being able to actively challenge and adapt your current view. Another part of it is actively reminding yourself that there’s a ton that you don’t know. It’s also what allows us to be creative and and express ourselves artistically.

As the world changes, your education and ability to manage your perception become increasingly valuable because your worldview becomes more expansive and thoughtful.

Critical Thinking Frameworks
The second part in which I would define as an antifragile education is a focus on developing critical thinking frameworks. Critical Thinking frameworks are often taught in engineering courses because problem solving techniques are needed to adapt to the changing world around them. When it comes to most STEM focused majors, I would argue that this is often taught really well. While there is still a some focus on memorization and content understanding, it’s strongly needed give the type of work and specialization being done.

As an entrepreneur, I find the problem solving frameworks I learn in my thermodynamics class completely different than what I learned in my Calculus classes, which are different than my computer science classes.

Each though, are building a toolkit that becomes more valuable when it’s tested by a changing world. Focusing on memorizing and understanding the content in these courses is conversely vulnerable to any new discoveries or changes made to that content.

The critical thinking frameworks I learn in my non-technical courses have taught me other critical thinking tools, if you were to call these that, like empathy, influence, emotional intellgence, among others.

Again, the point is to derive frameworks that grow and become more useful as you think about problems in the way your trying to solve that given problem.

With my company, I think about the equation of state of a business (thanks thermodynamics), the deep problems of my users (thanks sociology), and navigating the laws that might get in my way (thanks environmental law). Being able to extract the “general equation” rules from different parts of your education is the real lesson here to make your education more valuable in today’s world.

A Fish Out Of Water
It’s taken me 13 years of frustration to be able to articulate and understand why I’ve struggled with the current state of the education as an entrepreneur.

There’s certainly been a place for the some of the things that I’ve had to memorize and understand, a lot of it has always been useless after the exam. With all of this, it would be unfair to think that every student doesn’t have a responsibility to be approaching their education with critical thinking skills and make sure their education is an antrifragile one. But, frankly, the current state of the education system in the US is often lazy, naive, and fragile, and has a responsibility to lead it’s students in doing taking that initiative.

It’s programs like the Penn State’s Presidential Leadership Academy and my extracurricular involvement that have made it worth it. But in the end, I’m grateful for having experienced it all, despite the poor fit. It’s made me realize, well, I might be a fish out of water.