50 Questions to Get to Know Yourself Better

Last week, we talked about the “it” factor that all successful people seem to have in common.

And I say this because that’s the way it is portrayed. It may or may not be true. There could be some successful people that just fake it really well!

But one thing that most successful people have in common is that they are self-aware. And I want you to think about some of your favorite role models that are what you would consider successful.

Do they seem to be self-aware? Do they change their personality based on who walks through the door? Or they unapologetically themselves no matter what?

It’s interesting to think about. And I really do what you to take the time to think about it.

Once you’re done, let’s continue with this blog post. Because today, I want to help you get to know yourself a little bit better. Hopefully helping all of us achieve that “it” factor that is just outside of our reach.

50 Questions to Get to Know Yourself Better | For the longest time I struggled with who I was as a person. Do you know who you are? Do you know what you are supposed to do with your life? What is your purpose? All of these questions won't be answered until you have a level of self-awareness. In this blog post, I want to help you break down the walls and discover who you are. Ask yourself these 50 questions to get to know yourself better.

Who am I really?

Last week, I asked you this question. And I even shared a little snippet of who I am to break the ice.

But to be honest… this has been a question that I’ve struggled with for a long time.

For as long as I can remember, I always changed my beliefs, my likes, and my personality based on who I was hanging out with.

I’m not sure where it started. But I can distinctly remember back to high school when I had my first serious boyfriend. And I mean serious to the point of dating for over 3 years.

Now when you are young and in love, you think that your significant other is your whole world. And he was back then. I didn’t want to go anywhere without him.

We would meet in the hallways after class, hang out after school, on weekends, at football games, sit together on our way to swim meets and every other chance we got.

And back then, that seemed normal. I was either with him or my best friend, Bekah. It was just the way it was.

But then I went to college 2 hours away. Things became more difficult. And I was forced to do things on my own with him. It was like I had to rediscover myself because I no longer had him as a key part of my identity.

And it was weird. Difficult really. But when I had those few months to just be by myself in this strange place where I knew no one, I really came alive! It was like I was a free spirit just running wild ready to conquer the world.

When I went back home for breaks, I didn’t recognize the life I used to live. And I didn’t recognize the person I was when I was with my high school boyfriend. Honestly, that girl was unrecognizable. Because it wasn’t who I truly was. It was who I thought I needed to be for him.

But this wasn’t the only time that I remember falling into the personality of those around them.

And it surely didn’t stop after this. It happened all throughout college. And even a little after.

Because I never took the time to really get to know myself. I just surrounded myself with my swim team and did whatever my teammates did. And then I joined a sorority and I did whatever my sorority sisters did.

I don’t regret it. Any of it really.

I’m glad that I had my high school sweetheart to get me through those years of high school and teach me what real love looks like. I’m glad that I had my swim team to push me to new levels. And I’m glad to have a sorority that filled my life with a whole lot of love, support, and laughter.

But I wish I would have known that high school and college years are critical to discovering who you are. Because by the time I was 22, I really had no idea who I was looking at in the mirror. And it took a lot for me to try and discover who I was, what I believed, what I liked, and what my dreams were for myself.

If I could go back and tell myself anything, I would say:

“It’s okay to make mistakes. It’s okay to not fit in. You are stuck with yourself for the rest of your life. Not the people around you. Take the time to be happy no matter what. And be yourself every chance you get.”

And if you need or needed that little pep talk too, feel free to read those few sentences over and over again until they stick. Because of you, the true you is totally worth it.

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50 questions to ask yourself

A few months ago, I saw this blog post on Pinterest with 5 fast questions to ask yourself.

The goal was to ask yourself these questions so fast that you didn’t have time to think of the answer. You just blurted out the first thing that came to your mind. And I did.

And you know what? My answers brought me to tears.

I uncovered things that I didn’t know were weighing so heavily on my heart. And it brought up some ugly truths about my life.

So I encourage you to not only ask yourself these questions but to answer them with the first thing that comes to your mind. And then once you are done, question why you answered the way you did.

You never know what ugliness is hidden behind the strong wall you’ve built. And once you’ve opened the door to the truth, you can start to break down those beliefs to live your happiest life.

So enough talking, let’s get started with the questions!




  1. Are you happy? Where you are right now, doing what you’re doing, the life you’re living… are you happy? If not, what do you think you need to be truly happy?
  2. What does a perfect day look like to you?
  3. If you could change just 1 thing about your life, what would you change?
  4. If you only have 6 months left to live, would you change the way you are living your life now? What would you change and what would you do?
  5. What’s holding you back from living the life you would live if you were dying (refer to the question above)?
  6. What are 5 things that can put a smile on your face no matter what?
  7. If you inherited 1 million dollars from an uncle you’ve never heard of before, how would you spend that money? And how would you live your life?
  8. Have you ever felt truly loved by yourself or someone else? If so, can you distinctly remember a moment where you were filled with love?
  9. What does it take for you to feel loved by yourself or someone else?
  10. Is there someone inside of you that is blocking love from your life? Maybe a belief or a past experience.
  11. Do you ever underestimate yourself? If so, name a time where you underestimated yourself and why you did it?
  12. What lies do you continuously tell to those around you?
  13. What is your happiest memory?
  14. Are there any lies you’ve been telling yourself regularly? Such as I’m ugly, why am I so stupid, no one loves me, etc.
  15. What is your biggest self-limiting belief?
  16. If you could have any career, what you it be?
  17. What is 1 problem that you see in the world?
  18. Is there anything you could do to help solve that problem in the previous question?
  19. What are you truly passionate about?
  20. What gifts or talents do you have that you typically hide from yourself or others?
  21. Is there anything in your life that you are ashamed of?
  22. When you have free time, what do you like to do for fun?
  23. What legacy do you hope to leave behind once your time on Earth is over?
  24. Are there aspects of your life that you worry about?
  25. What is your greatest fear?
  26. Do you believe that everything happens in your life for a reason?
  27. What is your proudest accomplishment in life?
  28. In your life, what matters the most to you?
  29. Do you prefer to spend time alone or with other people?
  30. Would you consider yourself to be an introvert or an extrovert? Are you energized by being with others or spending time alone?
  31. Are there any dreams that continue to repeat themselves when you sleep?
  32. If you could be a fly on the wall, what would people say about you behind closed doors?
  33. Do you feel like you know your purpose in life? If so, what is it? If not, is there anything holding you back from discovering your purpose?
  34. What would you consider to be your biggest failure in life?
  35. Do you rely on others to tell you what to do or how to act? If so, how can you remove this expectation and act based on your own beliefs?
  36. Are there areas of your life that you notice you compare yourself to others? Your body, your job, your friend group, etc.
  37. What are your short-term goals? And what are your long-term goals?
  38. If you could go back 5 years, what is 1 decision you made that you would change?
  39. What are your greatest strengths?
  40. How is your relationship with money?
  41. What do you believe is possible for your life?
  42. Who is your greatest role model?
  43. Do you believe in a greater force? Whether that is religiously or simply believing in the power of the Universe?
  44. Are there people in your life that bring you down, hold you back, or fail to bring you joy? If so, is there a way that you could rid them from your life or confront them with your problems?
  45. What do you want people to say about you at your funeral?
  46. How do you feel and react when you fail?
  47. What do you believe if the meaning of your life?
  48. When something bad happens, do you tend to place blame on yourself, those around you, or a greater power?
  49. Do you believe in destiny? If so, what do you believe is yours?
  50. What would it mean to live your happiest life being your truest self every darn day?

There are so many questions that you could ask to get to know yourself better. And I encourage you to continue to ask yourself questions outside of this one sitting.

For the longest time I struggled with who I was as a person. Do you know who you are? Do you know what you are supposed to do with your life? What is your purpose? All of these questions won't be answered until you have a level of self-awareness. In this blog post, I want to help you break down the walls and discover who you are. Ask yourself these 50 questions to get to know yourself better. | Part 3 of the Create Your Success Online series #beyourownboss

Grab a journal or a notebook and ask yourself questions once a week. Mix them up and make them interesting! You don’t want to just ask yourself what’s your favorite color… although that is interesting to know.

You want to dive deep into the beliefs and thoughts that aren’t actually your own but given to you when you were growing up.

Now, this was an intense post for the day. And I’m hoping that it left you feeling a little confused and unsure of where to go from here. That’s actually a good thing!

I promise it will all fall together. And this will all make sense in the long run.

So until next Friday, my friends!

XO, Cath


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About the Author

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Cathrin (Cath) creates content that encourages bloggers & online entrepreneurs to be themselves, chase their passion,  and create their success online. 1 year after started her blog (TheContentBug.com), Cath left her full-time position working in the digital marketing industry to pursue her dreams of being her own boss. In weekly blog posts, sporadic YouTube videos, and constant talking on Instagram stories, Cath hopes to spread her story and be an inspiration to others who desperately want to change their lives.

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