AI & T-shaped individuals

TTL 28

👋 Good Morfternight friends.

Know the saying “jack of all trades, master of none”?

I don’t really resonate with it, but I do with the longer version: “jack of all trades, master of none, though often better than master of one.”

But I’ve recently come up with an even better version:

“Jack of all trades, master of none — until you learn to prompt, then you master them all.”

I know it doesn’t rhyme perfectly, but that’s not the point. The point is that AI — if used properly — can make you a master of nearly any trade.

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From T-Shaped to Square-Shaped

In recent years, the idea of the T-shaped individual has become a popular metaphor for high-value employees — people who combine deep expertise in one area (the vertical bar) with a broad ability to collaborate across domains (the horizontal bar).

The opposite, if you’re not familiar with the concept, is the highly specialized professional figure, which we call the I-shaped individual.

In a recent conversation with a colleague, I found myself sketching a different shape: the square-shaped individual.

Why? Because with AI, we’re no longer limited to a single vertical of deep expertise.

AI extends our reach. It allows generalists — those with wide but shallow knowledge — to dig deeper into multiple fields. It turns basic familiarity into operational capability.

Take me as an example.

I’m not a developer anymore. I haven’t coded professionally since the late ’90s. But today, with AI, I can spin up working code in modern frameworks, write and validate unit tests, and even run full integration environments — all because I know just enough to judge the AI’s output, spot errors, and iterate quickly.

The same applies to translation, design, marketing, and more.

For centuries, progress meant narrow specialization. The more we knew, the more we had to isolate ourselves into silos to go deeper.

But silos don’t talk, and the cost of isolation is growing.

The advent of AI shines an entirely new light on this famous Heinlein’s quote:

“A human being should be able to change a diaper, plan an invasion, butcher a hog, conn a ship, design a building, write a sonnet, balance accounts, build a wall, set a bone, comfort the dying, take orders, give orders, cooperate, act alone, solve equations, analyze a new problem, pitch manure, program a computer, cook a tasty meal, fight efficiently, die gallantly. Specialization is for insects.”

Now, AI gives us a chance to expand that logic: we can be broader and deeper, we can go horizontal and vertical.

The most powerful professionals of the near future won’t be those with the deepest single skill. They’ll be those who can confidently collaborate with AI — across domains — and go deep wherever and whenever needed.

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That’s it for today.

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Here on TTL, we dig into toolkits, practical tips, and effective strategies, with a focus on leadership and distributed teams (that’s what I do every day, add me on LinkedIn).

Whether you’re steering a tech startup or leading a remote team, these insights are designed to help you navigate the complexities of modern leadership.

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I also publish on paolo.blog and monochrome.blog

Cheers,