claude knows more about me than they do

i'm going to alaska anyway

Yesterday, late at night, I was working through something I hadn't said out loud to anyone. The full thing: the context, the history, what I was actually afraid of. I gave it all to Claude. What came back was careful and exactly right.

Later this week I'm going to Alaska with seven other guys I've known since my Shanghai years. We're each somewhere between forty and sixty, business founders scattered now across Bali and Palo Alto and New Hampshire and Lisbon and Washington. Once a year we agree to be in the same place at the same time. I wrote about it last year. The annual gathering is part business strategy retreat, part personal cobweb-clearing, and a healthy dose of male camaraderie, good meals, and time outdoors. At this stage of life, that takes more coordination than most M&A deals. We do it anyway.

This year, I've been wondering why.

What AI now knows about me has started to feel like a lot. It holds what I give it, and it doesn't need to protect its own version of events. It's available at two in the morning without hesitation. The conversations with AI are cleaner, more direct, without the friction that shapes what people say to each other after years of shared history. The integrations deepen every day: it reads my emails, my business bank account, my CRM, and everything else that makes up a working life. It knows more about me right now than any advisor or peer, and I haven’t had to curate a word of it.

So what are our annual gatherings actually for?

If this week turns out to be mostly a chance to be somewhere remote and beautiful with people I like, that is enough.

From our 2025 ‘retreat’

AI sharpens my thinking and sends me off feeling clear. It won't know, months from now, whether I followed through on any of it. These men will. They are keeping, without saying so, a quiet tally: the gap between what I said I was going to do and what I actually did. That kind of reckoning only exists between people who see each other regularly and who care whether you followed through.

These men are in the same passage I'm in. Each of us is in some state of motion or transition, myself included. We are playing block and tackle with the present while also thinking about the next chapter. The Man From Shanghai is wondering whether years spent building businesses that bridge China and the West were worth it. The Man From Park City is gearing up to scale his medtech venture to unicorn level. The Man From New Hampshire is on his third act entirely: after commanding troops in combat theatres, and then rescuing businesses from indoor air pollution across China, he is now setting up new ventures while acquiring expertise in maple tapping and hog husbandry.

AI can map all this with precision. But it is not in it. Something happens when you are all inside the same uncertainty at the same time. It isn't analysis. It's recognition.

AI is intelligent without being experienced or vulnerable. These men are all three.

I can fire up agentic workflows when I want them. No one summoned these men to Alaska. They chose this week, the same as I chose it. Each of them is spending one of a finite number of weeks on earth, and one of them is this.

So we're going to Alaska. We booked our flights months ago. Sixteen years of that choice will be in the room when we land.

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Adil Husain is a competitive strategist who advises CEOs on how to compete and grow in contested markets. He is the Founder and Editor-in-Chief of business media company The Intelligence Council, and Managing Director of the global advisory firm Emerging Strategy. He has spent 25 years advising C-level executives at global companies on competitive strategy, market entry, and international growth, with on-the-ground experience across China, Southeast Asia, and major emerging markets.

You can reach him here for a conversation: ahusain@emerging-strategy.com

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