On the occasion of reading Nassim Taleb’s latest book, an anecdote about how he influenced a career decision of mine.


If you’re familiar with Taleb’s thinking, you can scroll past this. In a nutshell (and I won’t do it justice), his books center around the idea that we don’t understand risk.

In particular, “obvious” bell-curve style risks are overrated, and hide latent and tail risks.

A latent risk is one that quietly accumulates, but which we don’t see on an everyday time scale. It’s objectively true that any one cigarette is not risky, but a lifetime of smoking certainly is. Today’s decision is fine, and we justify each day.

A tail risk is one which is (objectively!) unlikely in a bell-curve sense, but which leads to ruin. A single gambler playing 100 games will go broke and not recover, despite the game’s being a mild-sounding 51-49.

(Latent and tail risks are two sides of the same coin, but I make the distinction for my anecdote below.)

My anecdote

In the early oughts, I built tools for Landor, a design firm. We used a technology we now call “classic ASP”, Microsoft’s pre-.Net platform for web applications.

It was good stuff; I built bespoke CRMs and digital asset management systems, and helped the company a lot.

After around 5 years, the low-hanging fruit was built, and the Microsoft world was moving to .Net. For the business’s purposes, though, there was little reason to adopt the new technology – it’d be effort without user benefit. I didn’t disagree!

So I kept building on the old technology, and was productive, and there was little to worry about.

But the time I got to year 8 (having read The Black Swan), I started seeing the real risks. In Taleb’s framework:

  • Bell-curve risk (which friends and family saw): why would you quit? The job is comfortable, the work is appreciated and well-compensated. Every day is fine.

  • Latent risk (which I saw): The world has moved on to the new technology, and I am not learning it. If I stay at this job for another five years, I will be older and with legacy skills.

  • Tail risk (which no one could see): I stay for five years, my skills atrophy, and then company has a bad year and my job goes away.

Long story short, I summoned the courage to quit and start a dating site (using the new technology). It didn’t make any money. But that experience qualified me to work at Stack Overflow, which leveled-up my career in countless ways.

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