The Irony of Experience

Hitting the two year mark at work is a unique spot in my opinion. You’ve worked for a while now, but you also haven’t… if that makes sense?

People with more established careers can (correctly) tell you two years is a blink compared to the lifetime of work ahead which is depressing to think about btw.

But at the same time you feel like those two years of work experience means everything¹, especially if you consider how much you’ve grown compared to the previous version of you who was still in school.

Funny how 2 years of work experience matters, even though you know it doesn’t.

IYKYK

I feel like a younger me, at best, can only get a surface level understanding of what I’m trying to express. The first hand experience of having gone through it myself, completely alters what gets conveyed. Put in another way, I bet people who’ve gone through similar experiences can discuss what I’m trying to get across. Whereas, people who haven’t can only agree or disagree.

Younger me would just say “yeah makes sense” or “huh” and go back to what I thought was super high priority at the time². I was just too naive and ignorant back then. And it’s funny because it follows that current me would do the exact same thing to other topics or ideas that I can’t relate to yet. I’m just as naive and ignorant now.

I would always get annoyed when people never elaborated on some inside joke and instead say “if you know, you know”. Well, it looks like I would fully agree in that statement now - except the experience of life is the inside joke now.³

Analogy Time

I guess all of that’s to really just say:

It’s possible to know what you don’t know, but impossible to experience what you haven’t yet.

I guess this blog is really about realizing that first part. When you’re young and ignorant, or maybe this was just me, you just never really think about things you don’t know because why would you? You don’t know better.

Maybe view experience as a circle. Anything beyond the circle is unknown to you. As you experience more things, your circle of what you know expands. But at the same time, as this circle grows, the surface area⁴ of unknowns increases.

I’m realizing (just now) that this surface area of unknowns is quite large and that I don’t know shit. Which is ironic since I’m only realizing this now that I have more experience. Actually let me retract that first part where I said my surface area of unknowns is large. You can’t really say one’s circle of experience is small or large. It can only be relatively small or large.

Compared to people further in life, my circle is tiny. Compared to college me, my circle seems huge. The irony of experience is realizing how much you don’t know.

Apparently, it’s a quote from Aristotle. He puts it better than I can.

The more you know, the more you realize you don’t know.
– Aristotle

Knowns, Known Unknowns, and Unknown Unknowns

Expanding on the circle analogy further, we can, we can say the immediate circle is all known. You know everything since you’ve experienced it.

The parts touching the surface area of the circle are known unknowns. You know they exist, but acknowledge you don’t know it yet.

Well, then there’s the rest of the universe that is neither in your circle nor touching your circle. You’re not even aware of them yet. Those are unknown unknowns⁵.

Experience isn’t taught from a Textbook

School teaches you a lot of about the knowns. Everything is about expanding that circle to basic pieces of knowledge everyone should know. If you pursue higher education, you get to learn a more specialized skillset that is unique to your circle. That’s the premise for hiring straight out of college.

What school doesn’t do is teach you how little you know. This makes sense. School’s purpose is to teach you things. In my experience, once you graduate, you’re quickly made aware of how many known unknowns exist.

Most things in school have known answer and solutions. In the workplace, there is no such thing. There’s just no way to even know if you’re doing the right thing. Companies go out of business all of the time.

Classmates often have similarly sized circles of experience when you’re studying together and taking the same classes. The workplace is full of people with decades of working experience that eclipse your circle of experience.

But you can only realize this once you see it for yourself. Someone in school will have a harder time recognizing this until it happens.⁶ And that only teaches you how many known unknowns are out there. It doesn’t even uncover the unknown unknowns.

As for unknown unknowns? Well that’s just impossible by nature. You can realize that unknown unknowns exist. And I guess everyone knows implicitly that they exist, like duh. But their significance only materializes once you’ve consciously identified them and realize that they exist because they don’t yet exist. And to recognize this, as a prerequisite, you have to have experienced a lot to realize you haven’t experienced a lot. Lol. Yes, I’m also reading back to myself what I wrote, and I think it makes sense to me even though it’s totally ironic. IYKYK.

Or maybe, it just took me a while to figure things out while everyone else has already realized this earlier than me. Probably that tbh.

So What?

You’ll never know everything. That’s just the nature of unknown unknowns and life I guess.

I can probably see a few responses to this.

• “You’re talking out of your ass.”
• “Why bother then?”
• “What’s next to learn?”

Luckily, I’d describe myself as an optimist and go with the first last option. Life isn’t easy I guess.

As a funny side note, in response to someone saying the first thing, saying this entire concept is nonsense and made up, someone can just say “if you know, you know” and shrug, leaving you fuming.

A younger me probably didn’t pay attention to what Aristotle once said. “The more you know, the more you realize you don’t know” never made sense to me until one day it did.

Everyone has a different set of perspectives (circles) after all.

Story Time

On another note, considering unknown unknowns can be useful for practical purposes.

I was working on a critical piece of Stripe infrastructure and was enabling a new feature in late 2023. Due to the sensitive nature of changes in this space, a partner team kept asking me about how risky this change was. If messed up, it could cost Stripe a lot of $$$$.

I spent a big chunk of time listing out a list of uncertainties (known unknowns) and calling out strategies we could use to derisk those areas if things turned south. We went over these identified areas and had strategies in place to mitigate against each of these scenarios.

But I think more importantly was considering the unforeseeable factors (unknown unknowns). There were things that no one could forsee coming, and having general actions in place to assuage those hidden circumstances, I argued was most important.

So essentially, I appended “unknown unknowns” to the list of uncertainies and made the partner team aware of it. They wanted a risk-free feature rollout - adding unknown unknowns was me telling them that a 100% risk free rollout doesn’t exist. That probably was super annoying to see. Oops.

I did my due diligence. Had the mitigation plans in place and rolled out my feature. None of the known failure modes occurred. Nice.

Well, on October 6th 2023, I was celebrating my 24th birthday on the 22nd floor of the Seattle Stripe office, Literally just, I’m not even exaggerating, as I was going to take a bite of cake, my pager started going off.

Causing a Stripe API outage on my birthday

Well, it turns out that day, the unknown unknown made itself become known. GG. Maybe a story for another time.

Moments before disaster 10/06/2023. Happy birthday! - Stripe

1. In full disclosure, I personally haven’t hit the two year mark yet. But I think two years of time encapsulates the “short but long” idea well. Maybe it’s the “correct” time relative to my current position and spot in life. ↩

2. Getting good grades, finding internships, hitting master in TFT, etc other things college me thought was important. ↩

3. That said, please don’t say “if you know, you know” to me if you’re using it to avoid having to explain a joke. It’s still annoying. ↩

4. Ok… I know this is technically circumference. I think surface area is better for the analogy than circumference is. Circle > sphere, and surface area > circumference for the sake of this analogy, so I’m going to comingle the two. Also, the math nerd in me is complaining because area grows faster than circumference does as radius increases, which isn’t quite correct in terms of the analogy since I believe that experience grows slower than the rate at which known unknowns grow. But you know what, it’s fine. This is my blog, I can do whatever. ↩

5. I actually formed this mental model myself through my own experiences at work. However, the original usage of knowns, known unknowns, and unknown unknowns come from United States Secretary of Defense Donald Rumsfeld with his “there are unknown unknowns” saying, hence the title of this section. I liked the terminology, so I yoinked it. ↩

6. I would always ignore my parents when they would say “you’re just a kid, don’t worry about it”. Funny how that works out later. ↩