Questions to ask yourself

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 Future Self

What do you think I am like when things are going well for me?

Most self examination focuses on the bad weeks. A description of you at your best gives you something to recognize and recreate, rather than only faults to avoid.

From: Questions to Ask Your Siblings About Yourself

When did I come through for you?

Worth asking straight after the previous question so the conversation does not end on the debt. His answer often reveals a moment you thought was minor at the time.

From: Questions to Ask Your Brother About Yourself

Is there a version of me you miss?

The answer may be a period you remember as unimpressive, which is worth knowing. If she misses who you were before a job or a relationship, ask what she saw change and what it cost.

From: Questions to Ask Your Sister About 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?

Explicitly releasing an unresolved worry separates what still needs your attention from what is only replaying. Writing down the earliest hour you could actually do something about it is often enough to stop the loop.

From: Daily Questions to Ask Yourself