The Question Index

Every page here is a chair left open, with a door on it. The questions are ours to publish and yours to answer, and the answer stays yours: nothing you write in the chair is ever republished here.

• How do you tell clarity from impatience?I think I need to let a loyal long-timer go; how do I know whether this is clarity or impatience?
• The assumption you never stated is the one running thingsPeople close to me say I’ve changed since I began working on myself, and not entirely for the better; what would they have to be right about for me to listen?
• The Socratic method, used on your own situationWhy does it have to be this way, and why can’t it be something different?
• You do not need advice. You need to hear yourself say it.They say most people don’t know what they want and how to ask for it; how would I learn to know, and then to ask?
• The question people who build things avoid askingDoes this project still serve everyone involved in a way that improves the whole ecosystem, and if not, can I set it aside?
• How to stop overthinking, when more thinking is the problemDo we sell the house to fund the venture, or is that conviction talking when it should be fear?
• Analysis paralysis is not a shortage of informationWhen the death-by-a-thousand-cuts sets in: do I need five percent more budget, or a different model?
• What am I missing, and why you cannot find it by looking harderWhat capacity around me is lying unused, and what unmet need could it be matched to?
• What should I do with my life is the wrong size of questionWhat would I tell my younger self that he didn’t know then and I know now?
• Should I quit my job, or is that the answer to a different questionI’ve been offered a role that pays more and means less; what is the cost of saying yes, and to whom?
• Questions to ask yourself, and why the lists do not workWhere in my week am I performing rather than being, and what would I do today if no one needed me to be who they expect?
• How to admit you were wrong, when it costs somethingHow do I correct myself when I discover I have been wrong?
• Scaling, replicating, and the difference nobody makes you stateAm I trying to scale an organization or replicate an idea, and do I know the difference?
• Help that transfers something, and help that keeps people needing youWhom does my system leave dependent, and what would it take for them to become owners?
• When the work stopped meaning anythingWhat work would I keep doing if no one ever thanked me for it?
• Who you are when you are no longer the one responsibleI’m stepping down after twenty years; who am I when I’m no longer the one responsible?
• Should you keep building it with the same personShould I keep building this with my current partner, and if so, in what structure?