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01 · Personal & Relational · Topic

Questions for self-reflection and big decisions

The hardest person to get a straight answer from is often yourself. These sets are for a notebook, a daily check in or a decision you keep circling: a marriage, a breakup, a job, a big purchase. Others are addressed to your younger self, your future self and the child you were.

46 sets · 2,094 questions · each with a note on whyDeal me one at random

A few to start with

  • What was the largest amount of money that passed through my hands, and where did it go?

    Not what you earned, what passed through. It catches the years where a lot arrived and nothing accumulated, which is a pattern people usually only spot in hindsight.

    From: Questions to Ask Your Future Self

  • Who do I measure myself against most, and what do I decide I'm missing?

    Name the person and the exact thing: her confidence, his grades, their easy family. Then check what you're setting side by side, because it is usually their best day against your whole unedited week.

    From: Self-Love Questions to Ask Yourself

  • What did I learn about love as a child?

    You absorbed the model before you could examine it: whether affection was reliable, conditional, or loud. This is frequently the answer sitting underneath every question you have about your relationships.

    From: Questions to Ask Yourself to Get to Know Yourself

  • What am I proud of that nobody else knows about?

    Private pride is the sturdiest kind because it does not depend on an audience. It often points to a standard you hold that is worth keeping.

    From: 100 Questions to Ask Yourself

  • What is one thing I can set down before I sleep?

    Very little gets solved at eleven at night. Write the thing down next to the earliest hour you could actually do something about it, such as nine tomorrow when the office opens, and let the note hold it until then.

    From: Daily Questions to Ask Yourself

  • What was playing in the background at home: a television, a radio, someone practicing something?

    Background noise is a good measure of the atmosphere of a house. Constant television, constant news, an instrument, or silence each produce a different childhood, and this is the sort of detail nobody thinks to record.

    From: Questions to Ask About Your Childhood

Every set on this topic