100 Questions to Ask Yourself
A curated set of reflective prompts to clarify values, focus energy, and design a life you actually want—start anywhere and follow the curiosity.
1What does a good day look like—and how can I make more of them?
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What does a good day look like—and how can I make more of them?
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Why this works
Translates ideals into repeatable patterns and habits.
2Which three values show up most in my choices?
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Which three values show up most in my choices?
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Why this works
Connects daily decisions to identity and purpose.
3Where am I overcommitted—and what can I gracefully stop?
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Where am I overcommitted—and what can I gracefully stop?
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Why this works
Creates space by pruning low-return obligations.
4What energizes me so much it doesn’t feel like effort?
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What energizes me so much it doesn’t feel like effort?
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Why this works
Points to strengths and potential leverage.
5What am I avoiding that would meaningfully improve my life?
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What am I avoiding that would meaningfully improve my life?
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Why this works
Targets high-leverage discomfort worth facing.
6What story about myself is ready to be rewritten?
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What story about myself is ready to be rewritten?
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Why this works
Invites identity updates that unlock options.
7Who are my five people—and how can I invest in them?
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Who are my five people—and how can I invest in them?
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Why this works
Focuses on relationships that compound well-being.
8What would ‘enough’ look like this year?
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What would ‘enough’ look like this year?
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Why this works
Counteracts endless striving with sufficiency.
9Where do I feel most like myself?
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Where do I feel most like myself?
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Why this works
Identifies environments that support authenticity.
10What promise to myself will I keep this month?
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What promise to myself will I keep this month?
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Why this works
Builds trust with yourself via kept commitments.
11What am I proud of that no one else sees?
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What am I proud of that no one else sees?
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Why this works
Centers intrinsic wins over external validation.
12What’s one boundary that would reduce 80% of stress?
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What’s one boundary that would reduce 80% of stress?
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Why this works
Applies Pareto thinking to emotional load.
13What’s a tiny habit that would help future me daily?
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What’s a tiny habit that would help future me daily?
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Why this works
Designs micro-actions that compound over time.
14Where have my preferences changed lately?
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Where have my preferences changed lately?
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Why this works
Updates routines to match the current you.
15What would this look like if it were easy?
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What would this look like if it were easy?
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Why this works
Encourages simplification and constraint design.
16What am I willing to be bad at while I learn?
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What am I willing to be bad at while I learn?
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Why this works
Normalizes skill acquisition and beginner’s mind.
17If I had a free afternoon weekly, how would I use it?
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If I had a free afternoon weekly, how would I use it?
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Why this works
Exposes genuine interests to prioritize.
18What am I grateful for that I didn’t notice before?
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What am I grateful for that I didn’t notice before?
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Why this works
Trains attention toward overlooked good.
19What would I do if I knew it would work out?
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What would I do if I knew it would work out?
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Why this works
Reveals desire beneath protective pessimism.
20What’s one experiment I’ll run for two weeks?
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What’s one experiment I’ll run for two weeks?
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Why this works
Turns reflection into small, testable action.
Self-Reflection That Leads to Action
Expert tips and techniques for getting the most out of these questions.
Keep It Gentle and Specific
Timebox It
Set 10–15 minute sessions to reflect without overthinking.
Pick One Next Step
End each session with a single experiment.
Review Monthly
Look back for patterns; adjust without judgment.
Weekly Ritual
Simple Flow
Common Pitfalls
Perfection Trap
Reflection doesn’t require perfect answers—just honest ones.
Action Hoarding
Don’t collect insights without trying one small change.