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25 Questions to Ask Yourself

25 Questions to Ask Yourself

Ask better questions, get better answers

Jay Yang
August 31, 2025

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3 Thoughts

You already know what it takes to live a good life. To give more than you take. To love more than you hurt. To do hard things, love your family, and work on meaningful projects. The hard part is not getting distracted with all the chaos going on around you.

II.

You need a North Star. Because how else are you supposed to distinguish between an opportunity and a distraction? How else are you supposed to decide if something takes you closer or further from your goals? How else are you supposed to determine when you’ve found ‘enough’? If you don’t know where you’re going, then any path will take you there.

III.

Success isn’t really success if it looks good to the world but feels bad to you. Who cares if you own a yacht if you’re too busy to use it? Who cares if you have a mansion if you’re miserable inside it? Who cares if you have a lot of money but sacrifice your health to earn it? Who cares if you have success but no one to celebrate it with? There’s too much focus on looking rich and not enough focus on being rich.

2 Quotes

Surround yourself with friends who randomly spend their time thinking about how you could be more successful, and do the same for them.

— Jack Altman

II.

“Creativity is seeing what everyone else has seen, and thinking what no one else has thought.”

— Albert Einstein

1 Game-Changing Idea:

25 Questions to Ask Yourself:

What is my definition of success if money was taken out of the equation?
If I was less afraid of other people’s judgment, what would I say?
Am I really happy? Or am I just really comfortable?
What would it take to snap me out of a bad mood immediately?
What’s the first thing I think of when I wake up most days? Is that what I want to be thinking?
If I could pick one person and get 10% of their future earnings, who would I pick and why? How can I adopt the skills, beliefs, and character traits of the person I picked?
What’s the biggest difference between who I am and who I pretend to be?
When was the last time I had so much fun I lost track of time?
Imagine I had a really great day at work and I’m telling my partner all about my day. What is it that I’m telling them?
What’s something that’s always been different about me?
What do I get most jealous about?
Do I have a skillset that will be useful 5 years from now?
If there was only one goal I could commit myself entirely to, what would it be?
What would I do differently if I increase the timeframe?
How would I like to be spoken about at my funeral?
How can I complete my 2 year goal in the next 3 months?
What’s true about my life today that would make my 18-year-old self disappointed?
Am I being too aggressive or too passive right now?
Is taking things so seriously improving my performance? How can today feel like play?
What’s my favorite way to fail? What am I willing to struggle for?
What am I saying no to by saying yes to this new opportunity?
What does a perfect day look like to me?
What’s something I’m self-conscious about and how does that affect my life?
What do I love about myself that has nothing to do with money or success?
What have I been wrong about lately?

Until next week,
Jay “Ask Better Questions Get Better Answers” Yang

Ps. walkie talkie

Kind words for ‘You Can Just Do Things’

If you don’t ask, the answer will always be no.