31 Questions To Find Your Why


Why are you failing to reach your goals?

Have you tried losing weight, only to pack on more lbs after eating healthy for a week?

Have you tried to start a business only to get frustrated and confused with what to do next?

Frustrated with how boring your job is?

Why do you suck at reaching your goals?

To be fair you don’t suck. Life is hard and achieving everything you want in life is unrealistic.

Despite what highly successful people will tell you, not everyone can acheive the same level of success.

And that’s okay.

What is good to me, might be great to you.

But more importantly, being happy comes from enjoying what you do, who you do it with, and WHY you do it.

But finding your why is damn hard

Here are 31 tough questions to help you find your why.

The best way to answer these is without thinking. Write down, or say out loud the first thing that comes to your mind.

You already know these answers, you just need to be self aware of them.

These questions are likely questions that you have never been asked. The goal is to understand a little more about yourself and understand your motives.

  1. If you had to choose another name, what would it be and why?
  2. What is your favorite childhood memory involving travel?
  3. What are you currently saving for?
  4. If you had to spend $1,000 in 10 minutes what would you buy first?
  5. If you were fired today, where would you stop before going home?
  6. Where is your favorite place to eat?
  7. Do you have a junk drawer? What is the most meaningful possession you keep in there?
  8. Describe your significant other in one word…
  9. What is your favorite scent?
  10. You are on a plane, the pilot asks where you want to go, what do you tell him?
  11. Would you rather run a marathon or volunteer for one?
  12. Would you rather take a math test or a writing test.
  13. If you had to write 5 thank you cards and put them in the mail right now, who would they go to?
  14. If you could live in any era, and have the same knowledge you have now, which era would you live in?
  15. Would you rather eat an expensive meal downtown, or have a picnic in the country?
  16. Would you rather receive a $5000 raise, or not work on Fridays?
  17. Describe the scariest moment of your life.
  18. What is the biggest accomplishment in your life to date?
  19. What is a goal you have never told anyone?
  20. If you could know the date of your death, would you want to know?
  21. When was the last time you had a great day?
  22. Work is cancelled today due to a company wide illness, you feel great, where do you go?
  23. Who did you look up to when you were younger?
  24. Who is the most successful person that you know?
  25. Would you rather start a business and have 3 employees or 30 employees?
  26. You just sold your shares of a company, how much did you make?
  27. Have you ever given a stranger a ride?
  28. Why don’t you talk to your childhood friend anymore?
  29. What was your favorite pet? Why were they your favorite?
  30. Who gave you the last compliment you remember?
  31. What are you the most grateful for?

How did it go?

Were you surprised with any of your answers? Were some questions harder than others? Did some questions inspire a lack of interest?

Reflect on all of those thoughts and emotions and you continue to strive for finding your passion.

I talk more about finding your passion here.

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