The first time I felt the fear—or maybe anxiety—of academic failure was in 2001. My parents had recently decided that I wouldn’t be attending public school anymore. Instead, the plan was for me to transfer to a private Catholic school along with my older cousin, assuming I passed the entrance exam.

To my eight-year-old self, it seemed like the world would end if I wasn’t successful. The details of the test day are hazy at this point, but what I do remember is crying. Between my mother and the teacher proctoring the exam, eventually I felt comfortable enough to not completely hate the experience. My nerves settled, I took the test, and the next year, I was enrolled in my new school.

That pattern of anxiety and fear of failure when facing new academic challenges stuck with me for most of the next two decades.

Eventually, those feelings gave way to internalized thoughts that became a constant, harsh self-commentary:

These thoughts fueled a pattern of procrastination because, obviously, it’s easier to push off the thing you’re afraid of failing at until there’s no choice but to tackle it head-on. This habit became reinforced every time I procrastinated and still managed to succeed. Sure, I could cram and get things done last minute—but that’s no way to engage in deep learning. Eventually, the bill came due.

For most of my academic life, I was the kind of student who did just enough. I was smart enough to scrape by, pulling A’s, B’s, and the occasional C (yeah, there were worse grades, but this is my narrative). Looking back, I can’t believe I even raw-dogged the SATs—zero studying, zero prep.

High School highlighted how poor of a student I truly was. Comparing myself to peers should have been a wake up call. Unfortunately, it wasn’t.

Like most people my academic drivers eventually went from “How will my parents react to a bad grade?” to “Oh fuck, what am I going to do with my life?” and “How am I gonna make money?”.

Two pretty strong motivators.

Despite the near constant anxiety that induced, my habits didn’t change all that much. Yeah, I took a greater interest in my classes, but I couldn’t really say I was learning. I was doing what most students in America do: rote memorization of selective facts, just enough to pass a test or complete an assignment.

I was attaining a functional knowledge of what I needed to know, but nothing more. And again, this worked–especially for topics I found interesting. It was always enough to get by but never enough to shake the feeling that maybe I’m just not cut out.

That lasted until I came to a concrete wall of sorts: the real world of my first internship.

In my Sophomore year of college, I took an introductory course to web application development. The professor had a practical method of teaching; the entire course was essentially project building.

At times we built individual projects and at others we paired up in groups. I started off strong in the class, learning the very basics of building a website (HTML, CSS, JS). These distinct and simplified implementations were pretty easy to get a grasp of.

A few weeks into the course was the university career fair, and, being connected to one of the companies that would be there, our professor suggested we go. All I knew at that point was I was in year two out of four and student loan payments had my head lined up in the scope of their .50 cal. So I went to the career fair.

I ended up getting an interview, my professor wrote me a letter of recommendation and a few weeks later, I learned that I’d be doing a six-month co-op program as a software engineer.

However, by then I was starting to get lost in the course. New technologies were getting introduced ever week, giving us almost no time with what we’d just learned, and still, I was spending almost no time attempting to reinforce earlier lessons outside of class.

When the final assignment came—requiring us to use some thing called Git to copy some other code, make some changes, and make some kind of request to get those changes included. Truthfully, when I finally read the instructions two or three hours before the midnight deadline—I had no idea what the fuck was going on.

Turns out, you need more than a couple hours to understand an entire technology stack, fix bugs, implement features, and use version control. Whatever Frankensteins’ monster of an application I submitted must’ve been good enough (or the TA lazy enough) that, once again, I scraped by.

But, instead of feeling accomplished, I finished with a familiar thought:

On day 1 of the co-op, I arrived nervous and intimidated at a corporate campus in New Jersey. The place, I thought at the time, was impressive. Even the cafeteria seemed cool. The specific office space I’d be working in had just been through a remodel, making it the nicest part of the building.

I was introduced to my peers, also completing co-ops. Some had already released apps, most accomplished in other ways, and then there was me — a guy who barely had grasp of fundamentals and definitely hadn’t built and released a product. I didn’t belong. I didn’t belong and I was the dumbest person in the building.

After a tour and explanation of what the team did, my manager tasked me to work on the front-end of the platform and assigned my first ‘ticket’ (whatever that was).

So I’m sitting in a room with a group of people I KNEW were smarter than me, assigned to work on technology I’d never touched before, at a level of complexity I’d never seen before, following a process that was completely new to me.

Then my new manager asked me a simple question, a dumb question, an obvious question, that honestly changed my life:

I told him a textbook would be great and just like that he handed me his copy of an AngularJS (R.I.P) textbook.

I didn’t fully understand much about the codebase or how it all worked and I’m sure looking back a lot of my early questions were incredibly revealing and stupid; but I was committed to one thing probably for the first time in my life: I wouldn’t fail.

In the days and weeks after that first day I came into work, opened my laptop and textbook on the picnic-like table seating area where all the engineers worked next to each other, and I struggled.

I spent hours and hours and hours and hours… failing and failing and failing and sometimes succeeding. For awhile after starting in the role all I felt was the fear and anxiety that I wasn’t good enough, too dumb, not smart enough, and that eventually everyone would know.

That fear didn’t stop me though. Whether I was in the office or at home my laptop and that textbook were open in front of me, and I dove deep. Seeking not just solutions but the what, why and how it all worked.

I learned to ask for help and, most importantly how to ask for help. I learned how to identify the root of problems in code, how to articulate where I was struggling, and how impactful the evidence of effort can be when seeking guidance.

Over time, I was given increasingly complex tasks, new technologies to learn, and tighter deadlines. In those weeks I’d spent learning, I’d cracked the code on a missing piece of my life:

I’d learned how to learn (so dumb, but alas)

It turns out that the how is pretty simple: Go Deep, or rather First Principles Thinking.

I had unknowingly stumbled into, and taught myself a mental model. Gaining a core competency in application development, rather than a simple functional knowledge, required that I break down all the information into smaller fundamental truths that I could pick apart, absorb, challenge, and wrap my mind around.

As I went through this process, it became clear that the full picture often isn’t complex at all; it’s a number of extraordinarily simple building blocks working together to form a mirage of complexity.

So I took that lesson and began applying it elsewhere. I went about deconstructing the entirety of what I believed myself to know into core truths/building blocks, and when I reassembled the pieces I found my most fundamental truism:

Maybe I’m not so dumb after all.

A guru might say enlightenment isn’t a destination but a state achieved through consistent practice. I think the same is true here.