High-Conviction Low-Validation Thinking

Insights For The Real World

Hey friends,

It’s graduation season… My friends at Berkeley have officially graduated this week, are entering the “real world”, and I’m super excited for each one of them. Here are a few basic pictures:

My freshman-year roommate, Ali:

Ali and I in freshman year:

And here’s another friend (Lola) who also graduated:

Basically, super proud of these folks and many others. So, back to reality.

As I vicariously-and-virtually lived the whole walking-to-take-the-degree-then-throwing-the-hat-in-the-air-then-getting-bazillion-pictures-clicked experience, I had a few basic questions:

  1. How do you know what to do, and
  2. How can you be super sure about 1?

When I spoke to my friend about these questions, our casual chat got 10x interesting. More philosophically, my questions were about finding order among chaos, imposing certainty on uncertainty, and predicting the future. So, this week, I want to recap my chat with my friend and share a few insights on navigating uncharted territory, as my friends begin a new chapter in the “real world.”


In hindsight, those who made it — “the misfits, the rebels” — always had a high-degree of conviction in a few things. They bet. They took risks. They sacrificed. Many failed and only a minority succeeded. Yet, the common factor among those who made it was a high-conviction in specific ideals, worldviews, and future-states of the world. This is not to say that you should necessarily have a high-conviction; after all, having conviction in specific things is a question of risk-appetite. But this is to say that conviction and the ability to go long on some things is critical to success.

Build conviction; don’t borrow it. You may be right, or you may be wrong. Either way, though, your end-state will have mattered. If you “win”, that’s great. If you don’t, that’s a lesson. But if you don’t build conviction and take risks, that, above all, is the biggest risk.

The number one thing I learned from my chat with my buddy was the skill of building conviction.

Don’t Reverse Engineer

Steve Jobs didn’t “set out” to build the world’s most valuable company. Neither did Gates. Nor did Musk. They all were in some positions, they recognized some problems, they bet on a few things. At the end, their work mattered. Sure, for every Jobs or Gates or Musk, there are a thousand failures. Yet, the point still remains: Forward engineer. Solve specific problems. Focus on things at hand. The results will follow. Don’t reverse engineer.

Let’s say you focus on “building a company” or focus on just being an entrepreneur because it’s cool. Chances are (a) you’ll fail, and (b) you’ll fail miserably. Which is also okay, but learning the lesson in advance helps save time.

If you chase the outcome (ie building a company), you’re more likely to fail as compared to if you chase the process.

Time and again, I find myself referring to this Reddit post on mimetic theory of desire, and realize that, it’s best to find your own raison d'être instead of copying someone else’s. Sure, Jobs is inspiring, especially when you watch his Stanford commencement speech, but exploring the depths of his lessons is equally important as well, because what worked for him may not work for you. Ergo, copying his methods and tactics may not be ideal for you. Which is why focusing on the process, forward-engineering, and thinking for yourself before following the norm becomes incredibly important.

Think For Yourself

We like to think that we think for ourselves, but chances are we don’t. As I grow up, I’m beginning to realize the depths of even the simplest, most-clichéd axioms of life: “Know yourself.”

Knowing yourself is not easy. It requires an intense amount of thought and the ability to work in absence of external validation. (Do read this post by Taleb for a deeper insight into this.) This is hard.

Let’s say you introspect for a day, write down your “values-stack” for another, and come to realize that your career interests are wildly different from what you majored in school.

If you’re like most people and are risk-averse, chances are you’ll disregard your introspection and continue with the path that “makes sense” for you.

If you’re a risk-taker, chances are you’ll change tracks sooner rather than later.

But here’s the catch: Both paths are okay.

Nobody can make a normative claim and suggest that path A is better than path B. But knowing which path is meant for you is far more important, which is where a normative claim can be made. If you know what path you would like to take, great; if not, that’s not bad. But — and here’s the important part — if you don’t know which path to take and you don’t actively try to find out, that is bad.

What matters, above all, is the ability to think for yourself.

Until next time,


PS: I’ve been reading The Story of Us series and have been reflecting on The Thinking Ladder. A few thoughts are inspirations from the series.