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.
Think a problem through
Each page below takes a hard question people carry, about decisions, work, partnerships or what comes next, and shows the question underneath it. Reading one is a way to think things through, and to get an outside perspective on a problem from something that asks instead of advising.
If you are working out how to think through a decision you keep putting off, or just how to think clearly about one thing for twenty minutes, pick the page nearest your situation and bring your own version to the chair at the end. It is a free decision making tool from a nonprofit, with no account and no card, and it leaves the deciding to you.
- How to make a hard decision when clarity and impatience feel the sameI think I need to let a loyal long-timer go; how do I know whether this is clarity or impatience?
- How to challenge assumptions, starting with the one you never statedPeople 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?
- Talk through a problem until you hear yourself say itThey 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?
- How to know when to stop a project you builtDoes 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? How to find your blind spots without 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?
- Scale or replicate? The difference nobody makes you stateAm I trying to scale an organization or replicate an idea, and do I know the difference?
- Helping or enabling: the help that keeps people needing youWhom does my system leave dependent, and what would it take for them to become owners?
- When work feels meaningless: depleted, or done?What work would I keep doing if no one ever thanked me for it?
- Who am I after stepping down? The question the role was answeringI’m stepping down after twenty years; who am I when I’m no longer the one responsible?
- Should I end my business partnership, or keep building with the same person?Should I keep building this with my current partner, and if so, in what structure?