• How old would you be if you didn’t know how old you are?
• Which is worse, failing or never trying?
• If life is so short, why do we do so many things we don’t like and like so many things we don’t do?
• When it’s all said and done, will you have said more than you’ve done?
• What is the one thing you’d most like to change about the world?
• If happiness was the national currency, what kind of work would make you rich?
• Are you doing what you believe in, or are you settling for what you are doing?
• If the average human life span was 40 years, how would you live your life differently?
• To what degree have you actually controlled the course your life has taken?
• Are you more worried about doing things right, or doing the right things?
• You’re having lunch with three people you respect and admire. They all start criticizing a close friend of yours, not knowing she is your friend. The criticism is distasteful and unjustified. What do you do?
• If you could offer a newborn child only one piece of advice, what would it be?
• Would you break the law to save a loved one?
• Have you ever seen insanity where you later saw creativity?
• What’s something you know you do differently than most people?
• How come the things that make you happy don’t make everyone happy?
• What one thing have you not done that you really want to do? What’s holding you back?
• Are you holding onto something you need to let go of?
• If you had to move to a state or country besides the one you currently live in, where would you move and why?
• Do you push the elevator button more than once? Do you really believe it makes the elevator faster?
• Would you rather be a worried genius or a joyful simpleton?
• Why are you, you?
• Have you been the kind of friend you want as a friend?
• Which is worse, when a good friend moves away, or losing touch with a good friend who lives right near you?
• What are you most grateful for?
• Would you rather lose all of your old memories, or never be able to make new ones?
• Is is possible to know the truth without challenging it first?
• Has your greatest fear ever come true?
• Do you remember that time 5 years ago when you were extremely upset? Does it really matter now?
• What is your happiest childhood memory? What makes it so special?
• At what time in your recent past have you felt most passionate and alive?
• If not now, then when?
• If you haven’t achieved it yet, what do you have to lose?
• Have you ever been with someone, said nothing, and walked away feeling like you just had the best conversation ever?
• Why do religions that support love cause so many wars?
• Is it possible to know, without a doubt, what is good and what is evil?
• If you just won a million dollars, would you quit your job?
• Would you rather have less work to do, or more work you actually enjoy doing?
• Do you feel like you’ve lived this day a hundred times before?
• When was the last time you marched into the dark with only the soft glow of an idea you strongly believed in?
• If you knew that everyone you know was going to die tomorrow, who would you visit today?
• Would you be willing to reduce your life expectancy by 10 years to become extremely attractive or famous?
• What is the difference between being alive and truly living?
• When is it time to stop calculating risk and rewards, and just go ahead and do what you know is right?
• If we learn from our mistakes, why are we always so afraid to make a mistake?
• What would you do differently if you knew nobody would judge you?
• When was the last time you noticed the sound of your own breathing?
• What do you love? Have any of your recent actions openly expressed this love?
• In 5 years from now, will you remember what you did yesterday? What about the day before that? Or the day before that?
• Decisions are being made right now. The question is: Are you making them for yourself, or are you letting others make them for you?

Credit: http://www.marcandangel.com/2009/07/13/50-questions-that-will-free-your-mind/