What can I do today that I'll be happy I did tomorrow?

Quotes carry someone else's conclusions; they lean on context — the person, the moment, where you happen to be in life. Questions are more malleable. They ask for a re-posturing, where they may teach something new each time they're visited. This is a collection of questions that I've found worthy of revolving around with the same vigor as good quotes.

How to exercise: Keep an active set of 5–7 questions each season and rotate the others during future seasons. When one hits hard, write down the date and your answer — over time the collection becomes a deeper pool of reflection as you grow.

Seeing Clearly

• What is something I know to be true that I am not acting on?
• What am I pretending not to know?
• What assumptions am I making that I should test?
• What story am I telling myself about this — and is it actually true?
• What would I tell a friend in exactly my situation?
• How would I know if I were wrong?
• What do I believe that most people I respect disagree with?
• What's working well right now — and what isn't?

Direction & Time

• What am I optimizing for in life right now?
• If my last day were tomorrow / in 30 days / in a year — what would I do differently, starting now?
• If nothing changes, where will I be in 5 years? Do I want to be there?
• Ten years from now, what will I wish I had started today?
• What would I do, have, or be if I had $10 million?
• What would my ideal life actually cost per month?
• What does "enough" look like for me?
• What season of life am I in — and am I living as if it's a different one?
• What do I keep saying I'll do "someday"?
• What would I work on even if no one paid me to do it?

Leverage & Simplicity

• What would this look like if it were easy?
• What if I could only subtract (remove time/attention or concern) to solve problems?
• What's the one thing that, if done, would make everything else easier or unnecessary?
• If I had only 2 hours a week for this (work, health, a relationship), what would I protect?
• Am I chasing big, meaningful wins — or staying busy with many small, easy ones?
• Where am I the bottleneck?
• What am I tolerating?
• What's the smallest next step?
• What do I need more of? Less of?
• Could it be that everything is fine and complete as is?

Experiments & Creativity

• What if I did the opposite for 48 hours?
• What do I spend a silly amount of money on? How might I scratch my own itch?
• What's the least crowded channel?
• What if I couldn't pitch my product directly?
• If I spent the cost of a degree on real-world experiments instead, what would I try?
• What might I put in place to go off the grid for 4–8 weeks — no phone, no email?
• How can I throw money at this problem? How might I "waste" money to improve the quality of my life?

Fear & Comfort

• What's the one thing I'm avoiding out of fear?
• What are the worst things that could happen? Could I get back to where I am now?
• Am I seeking discomfort, or staying in my comfort zone?
• Do I need to recover what I lost (money, time, trust) the same way I lost it?

Attention & Energy

• What activities give me energy, and which drain me?
• Am I creating more than I am consuming?
• Does how I spent my attention this week match what I say I value?
• When did I last feel fully alive — and what was I doing?
• Am I still curious? What am I learning right now?

People & Character

• Who are the 5 people I spend the most time with, and how do they influence me?
• Whose lives am I impacting, and how?
• Who do I admire, and what qualities do they embody?
• What am I avoiding communicating — and why?
• Where can I express more gratitude?
• Is this mine to carry?
• Who do I need to forgive — including myself?
• Am I being kind, or just nice?
• What would the person I'm trying to become do here?
• What would generosity look like in this situation?

Hard Moments

• In this moment, I see an opportunity to practice what virtue?
• Will this matter in a year?
• What would my 80-year-old self want me to do?