Goal Setting by Asking Questions

57 Questions You Should Ask Yourself

by sscheper on April 9, 2010

Walking through walls

A focused person is one who walks through walls because they know where they’re going and why. Nothing can prevent them from reaching their destination. They secretly tell themselves, “This is what I’m doing; this is where I’m going. If anyone wants to join me, fine.” Of course, their attitude isn’t one of disrespect; it’s one of determination. It’s of humble ferocity. A person that lives with this fire immediately has an aura when they enter a room–and they don’t have to say a word. You know they’re driven and you know they’ll be going somewhere.

This, of course, begs the question, “How did they get into this state?” The answer is simple; they’ve found their purpose. They’ve found their long-term focus. And they’ve found it through asking themselves questions.

So often we stray away from our purpose. We do the opposite of what we’re naturally good at. We will be exploring how to become a focused person by diving into the following chapters:

  1. Painting a picture of yourself (future chapter)
  2. Finding your path through questions (this chapter)
  3. Setting focused goals (link)
  4. Finishing the goals you embark on (link)
  5. Bringing goals to reality through personal productivity systems (future chapter)

This chapter is about number 2. We’ll explore the questions you must ask yourself in order to help you find your path. These questions will help you gain a glimpse into what focused goal you should set (which is covered in the number 3 above).

Why Asking Yourself Questions Is Important

In a different chapter on the concept of flow, we find that flow is a wonderful indicator of purpose. Flow displays what you’re passionate about. The state of flow occurs when the mind is so entrenched in the task at hand that time stands still. You get lost in your task because it’s natural; it’s exhilarating. It’s your purpose. In order to find what your purpose is, it’s best to think back to when you were in that state of flow. Through the series of questions below, you’ll be auditing your past and your dreams. You’ll be exploring the last time you were in a state of flow. This prepares one to set goals that are actually meaningful; rather than setting goals merely to set goals.

57 Questions to Ask Yourself

  1. What is the first instance of being in the state of flow that you can remember?
  2. Did you have any friends or family there to appreciate what you were working on?
  3. In your opinion, what’s the most amazing idea you’ve ever had?
  4. Why was this amazing?
  5. Looking back, what was the dumbest idea or venture you’ve ever embarked on?
  6. Why was it dumb?
  7. What thought-process led you to this idea in the first place?
  8. Before you pass away, what’s one mark you want to leave on the world?
  9. What are the barriers to achieving this right now?
  10. What is the next step to achieving this?
  11. What do you do every day between 6-10am?
  12. What do you do every day between 10am – 2pm?
  13. What do you do every day between 2pm – 6pm?
  14. What do you do every night between 6pm – 12am?
  15. Describe your first undertaking or achievement that was successful.
  16. Describe another undertaking that was successful.
  17. What was the difference between the two?
  18. How do you feel about money?
  19. Have you ever been given significant responsibility over others? If so, how did you act?
  20. How do you react to compliments?
  21. Do you like to compete? How do you see rivals?
  22. Do you like your day job (if you have one)?
  23. Who do you look up to (past or present people)?
  24. Why do you look up to them?
  25. What do you and your role models share in common?
  26. Where are you different?
  27. Do you believe that some people are naturally geniuses, or naturally just more talented in what you’re passionate about?
  28. How do you respond when you see people that claim to be overnight successes, or simply lucky?
  29. What was the last argument you had, and what was your position?
  30. How do you react when someone is hostile towards you?
  31. How do you react to failure?
  32. What drives you to keep pressing on after failure?
  33. Which do you enjoy more: The feeling of achieving the goal, or the process of trying to reach the goal?
  34. If you never had to work, where would you spend your time, and what would you spend your time on?
  35. What do you fear most?
  36. How would you react if the above happened?
  37. What makes someone an expert in a specific field?
  38. What is your dream?
  39. Describe a complex situation in which you had a lot to learn. How did you go about learning, and did you enjoy this process?
  40. Would people say you’re someone who diligently pursues every single detail, or are you more of a big-picture person?
  41. What difficult decisions have you made recently, and would you make this same decision?
  42. Describe your decision-making approach.
  43. What maxims or beliefs do you live by?
  44. Do you like facing concrete, short-term challenges; or do you enjoy conceptual, abstract long-term challenges?
  45. Are you more of a visionary, or more of a person that makes stuff happen today? Why?
  46. What’s the biggest risk you’ve taken in recent years?
  47. Was the risk worth it? Why or why not.
  48. Describe a situation in which the pressure to compromise your integrity were the strongest you’ve ever felt.
  49. Are you better at starting a lot of projects, or squeezing results out of fewer projects?
  50. Do you believe in asking for forgiveness rather than permission?
  51. What sort of mood swings do you experience? Where and what does this usually stem from?
  52. Describe your sense of humor.
  53. When there’s a difference of opinion, do you confront others indirectly or directly?
  54. When was the last time you put your foot in your mouth, and what was it about?
  55. Are you a natural leader? If so, cite how you are and why.
  56. What drives you everyday? Why do you get out of bed? (besides putting bread on the table)
  57. What pace do you work at? Are you fast, slow or moderate worker?


goal setting

Goal Setting Software

The questions above are long and open-ended. In order to get the most out of this exercise, sign up for the upcoming Goal Setting Application. When it’s ready to be released, I’ll notify you through email. Sign up to get notified below:

Photo Credit: Marco Bellucci

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{ 9 comments… read them below or add one }

Dave Everitt April 24, 2010 at 11:32 pm

57 questions is a lot. Possibly far too many. I found myself thinking “I could be doing something I enjoy instead of reading this” (which is one of your points about TV and other distractions). The essential question is “when you die, what do you want to leave as your legacy?”


Scott April 25, 2010 at 8:14 am

That’s an excellent question, Dave. I’ll be sure to add that. It may be the 58th ;-)

I realize all of those questions are a lot; however, I’ll be releasing a goal-setting app that will make those questions do-able, and hopefully a great experience.


Dave Everitt April 25, 2010 at 12:43 pm

You already kind of have it – number 8 :-)


Scott April 27, 2010 at 7:49 pm

Haha, OK cool. Thanks, Dave.


Bob July 5, 2010 at 6:59 am

I dont know if this is a serious topic but i find it helpful. It’s interesting because for now i cant still find the focus that i should have.



omri July 16, 2010 at 8:54 pm

this is great. i appreciate you working on this and sharing it with the world. i am trying to get focused and get rid of doubt and believe in myself. i hope this will continue to help me. thank you Scott.


Mohamed Sa'ed Ilkacase, September 29, 2010 at 1:06 am

I very delighted these questions and I will as myself soon and ably to my daily life, this make me thinking and thinking is mind breathing, so I can say my brain breathed to day and inhaled a pure life oxygen of personal rightness, let my friends be realistic about their living process by sitting a goals,


Roxanna February 10, 2011 at 2:12 pm

I think these are great! I’m a 24 year old, stay at home mom but kind of got lost and caught up in my fiance and daughter, so much that I didnt really know ME anymore. I pick and choose off of this list and blog out the questions daily to help me get back to me. Thanks!


Jersey William May 2, 2012 at 1:42 am

hi mate,

i am going to read some time-management source and i have to read all of your post but this is the long-waste time to read because i think i can even answer of the above questions. lol


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