Sessions The Society of AI Explorers

Feelings that may be familiar:

• Mental burnout from juggling 5 parallel AI sessions
• The sense of urgency to keep doing more and more, like a book where you keep saying, “Just one more chapter before bed”
• Wariness that AI is leading you astray by giving you false confidence and poor advice
• Fear that you're about to do something stupid because AI isn't flagging what you didn't think to ask
• Skepticism that AI has all the information that it needs to make smart judgments
• FOMO about what everyone else seems to be doing with AI
• Uncertainty about whether the thinking is yours, or where your value is, now
• Self-doubt: Is AI failing because it's stupid or because I am?
• Am I alone in this experience? No one in my life “gets it.”

Feelings like these are real, common, and disruptive. Let's get together to find the wise ways to address them, and develop a partnership with AI that lifts us up without dragging us down.

With Claude Code pointed at a folder of documents, plus connectors set up to give it access other systems, you've built yourself a thinking partner that learns about you and can do work for you. For folks who have a 'Second Brain', 'Chief of Staff', or whatever you might call it, we have so many ideas and tactics to share. What instructions have you put in CLAUDE.md? What Skills have you made? What files do you have and how do you rely on Claude's Memory feature? What kinds of conversations are you having with it? And on and on. This is a roundtable for folks looking to push the frontier of what their system is capable of, by discovering what other folks are doing with theirs.

AI can be hilarious (often accidentally), be a tireless play buddy, spark our creativity, and let us create things we never dreamed that we'd be able to. Let's inspire each other with how we're using AI to just mess around and see what happens. Play predictably leads to discovery and learning that we never could have predicted, and it's such a shame to play alone.

You built a thing. It works (mostly, it could be better, but maybe later). Now what? Hosting, domains, keeping it running, considering feedback, determining who should be using it, promoting it... the list goes on and on. Building the app turns out to have opened more questions than it answered. This is a group for people who have one of these out in the world, or are just about to, and are working out all the rest of it as they go.

Working solo means there's nobody down the hall to ask "wait, am I doing this right?" In AI advisory work, where the ground is always moving, that's a major disadvantage. How are you pricing this? What do you do when a client wants a thing that AI can't actually do? What are you building for yourself versus for them? Which tools have you committed to, and which have you abandoned? Let's compare notes with the colleagues we don't otherwise have.

One way to start is just with any call transcript: “What do you notice about how I showed up on this call versus how the others did, or how someone else might've?” There are a thousand ways into yourself with AI, which is both a blessing and paralyzing. This group is for people who are on that time-honored journey into understanding their own mind, whether they've been using AI or are curious to add AI to their toolbox. Let's find our own individual ways, together.

AI can be aggravatingly mediocre at thinking for you or suggesting movies/books/podcasts/research/ideas that would actually set your mind afire (in a good way). Instead, you can use it to rile up your own thinking and inquisitiveness (two things your mind is inherently built for). You end up with results that feel like they're entirely yours and like you could never have produced them on your own. You produce thinking of the highest quality that sparkles with inspiration. This session is a place to practice this live, learn what works well, and even start to develop a playbook for it.

How many people do you have in your life who you never have to explain yourself to, because they know you so well that they just understand, no questions asked?

How many of them would spend all the time in the world unpacking and working on whatever's on your mind, bringing none of their own baggage or priorities into the conversation? They'll also flag when you're falling victim to your habit of overthinking, or underselling yourself, or never asking for help, or whatever's your pitfall of choice.

Plus, you've given them logins to your email, your calendar, and wherever else you do work and store information. Which means they catch the things you'd have wanted to know but would have missed: one call transcript, and they see the four things that you would want to happen. You can even give them logins to software where you've never worked but wish that you had, and thankfully they are a total expert in every feature and best practice, and they can just take care of everything for you. And if just the right system doesn't exist, they will build one for you from scratch.

This is life with a 'Second Brain' set up in Claude Code or in ChatGPT Codex. There's no code involved, fear not. It starts with a folder. You put things in it (call transcripts, project notes, a description of what your boss cares about), and you start having conversations with it about yourself. That's what we do together in this interactive, collaborative hour. We'll plant a seed, and I'll show you how to foster its growth.