How to be a great mentor in business and life

One of my growing concerns about artificial intelligence is that it increasingly abstracts away the need for mentorship inside organizations. When young people get hired today, it’s becoming easier for managers to spend less time teaching and more time just handing over tools. In the short run, that can look like efficiency. But I do worry about what gets lost over the long run — especially for people just starting their careers.

That’s part of what made this wide-ranging conversation between author and interviewer William Green and Nima Shayegh so enjoyable. I was especially struck by Nima’s reflections on his years of training under Lou Simpson — one of the most respected long-term investors of the past half-century. Like all great mentors, Simpson taught through osmosis: long conversations, careful questions, shared reading, and repetition over many years.

Listening to Nima — now running his own investment firm — talk about that experience was a good reminder that mastery is rarely a solo act. Even with better tools, it still comes from having someone walk alongside you, over time.

Key quote: “There were no Bloomberg terminals. There was no financial TV on. It was like the library of a scholar — a comfortable chair, a couple piles of reading material, and this just very calm presence. He looked at me as he led me inside and he said, ‘Make yourself at home. Let me make you a coffee.’ … And I remember thinking to myself, ‘I should be making you the coffee.’ And when he returned, he didn’t launch into some kind of monologue. He didn’t try to assert how smart he was. He would ask these questions with this very sincere curiosity. And it was this remarkable receptiveness for someone with his experience and with his reputation.”

The all-important context we’re missing

I enjoyed Morgan Housel’s recent essay, “A Few Things I’m Pretty Sure About.” As usual, it’s wide-ranging and reflective.

But what stayed with me most was a simple idea: how much context we’re missing when we judge people — and the world — in real time.

Housel opens with a reflection on chronic pain, then widens the lens. Most harm, he argues, is unintentional. Behavior almost always makes sense once you understand the system surrounding it; the problem is that we rarely have that information while we’re living inside the moment. That perspective carries through his thoughts on housing, AI, and politics.

“When times are good, people get complacent and stop caring about good governance,” he writes. “When times are bad they get fed up and say, ‘Enough of this.’ And I think we’re not far from that today.”

Key quote: “I have a theory about nostalgia: It happens because the best survival strategy in an uncertain world is to overworry. When you look back, you forget about all the things you worried about that never came true. So life appears better in the past because in hindsight there wasn’t as much to worry about as you were actually worrying about at the time.

A few more links I enjoyed:

What the Hell is Water? – Christopher Tsai

Key quote: “‍The idea that much of what we experience in life goes undetected connects deeply to an issue that I’ve been pondering a lot lately: investors’ rigidity — or myopia — in judging companies’ valuations and assessing business durability. In the context of investing, the water in which we swim includes all of the ingrained assumptions, mental shortcuts, and dogmas that many investors accept, often without questioning… This danger is particularly evident when considering the origins of enduring business success, an area where unexamined assumptions tend to blind investors to the subtle forces at play.”

The most successful information technology in history is the one we barely notice – via Big Think

Key quote: “It may seem obvious that books are a technology, yet we rarely think about how they work. They just do. Read most any list of history’s important inventions, and you’re unlikely to find the humble book. The printing press will absolutely be present, possibly taking the top spot. You may even spy paper in the running. While such innovations helped create the modern book — and we’ll discuss them soon — they are also distinct from the book as a technology in and of itself. So, if books were so transformative, why don’t we think about them the same way we do microchips, microwaves, and the steam engine?”