← Lab Notes · Ikigai Collective

What Is the Question We Should Be Asking?

Week 5 · May 21, 2026

What Is the Question We Should Be Asking? — Lab Notes cover

Three people showed up. We kept the hour anyway, and it turned into the deepest conversation so far: religion, philosophy, and how to think with machines. Low attendance, we learned, is a feature when you treat it as depth instead of failure.

The thread that mattered: how to use AI so it sharpens rather than flatters you. One member described how a shared set of custom instructions transformed his daily AI work: allowed to contradict, required to ask questions, forbidden to praise by default. He had already passed it to a dozen people outside the group; the Collective’s ideas were propagating on their own. The counter-evidence to the “AI makes you delusional” discourse was simple: it does not happen if you actively ask the machine to prove you wrong.

David traced his motto, “What is the question that I should be asking?”, to its lineage: Socrates, who gave no answers and taught the seeking of knowledge; and Daniel Dennett, who argued that we think better than the ancients because we have better tools for thinking. AI is the newest tool for thinking. Most people still use it as a tool for answers.

Sustainability of sharing came up too: it is impossible for anyone to keep up with everything, and that is precisely the value of a group where each member scouts a different frontier and reports back.

One venture update, one time-zone accommodation for a member’s family evening, and two new invitations to people on two more continents. Small night, long half-life.