21 Hard Questions to Ask Yourself (& to Answer Honestly)

It’s always beneficial to check in with yourself from time to time to evaluate your life, and to help limit life’s biggest regrets. It helps to determine where we currently in our lives and if we are heading in the right direction of our goals. A great way to do this is to ask yourself the hard questions—ones that will be tough to answer.

Hard Questions to Ask Yourself, and Even Harder Questions to Answer

1. Do you feel like you’ve lived this same day many times before?

Take a hard look to see if you are spending each day like the day before. Is your life filled with monotony?  For most of us, monotony means a boring and uninspired life. But to some this is not necessarily a bad thing, especially if you answer “yes” to question number 2.

2. Are you living the life of your dreams?

If you had a choice today of how to live your life, what would you do? Is that what you are doing now?

3. What would you do if fear was not a factor and you could not fail?

Many hard questions to ask yourself are surround by fear. Fear is difficult because it holds us back from attempting so many of our dreams! what one thing would you do if there was no fear involved?

If fear is controlling your life, my article about overcoming anxiety to live your dream has the 8 tips that I used to face my fears. It may help you!

4. What were you doing when you felt most passionate and alive?

Think back to a time in your life when you felt the most passion. What was it that made you feel this alive and how can you recapture that feeling.

5. What are you most grateful for?

Take a moment to consider all the of things in your life that you are thankful for (there is always something!). They could be big or small as long as they have meaning to you.

Need help with coming up with things to be grateful for? Read the article Being Grateful: 100 Things to Be Thankful For Today.

6. What causes you stress in your life?

When are you the most stressed out and what is the cause? Is it the result of a difficult job, a tough family relationship or an unhappy marriage? Identify the cause and ask yourself the even harder question of how to fix it.

7. Am I truly proud of the person that I am?

8. Are there any toxic relationships in my life that need to be dealt with?

9. Am I too hard on myself or not hard enough?

10. What worries me the most about my future?

11. What dreams have I given up on?

12. What do I need to change about myself?

13. What do I want to be remembered for at the end of my life?

14. Am I in control of my life?

15. What makes me happy?

16. Am I a good friend?

17. Who would I trust with my life?

18. What am I most afraid of?

19. Am I contributing to the world?

20. Am I a good communicator?

21. Who am I most jealous of and why?

If you want to learn more about hard questions to ask yourself, and in life in general, then definitely get the book Tiny Buddha: Simple Wisdom for Life’s Hard Questions.

What are some other hard questions to ask yourself? Leave them in the comments.

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13 thoughts on “21 Hard Questions to Ask Yourself (& to Answer Honestly)”

  1. I actually am more sane when I have a routine and follow it every day.  I'm a little OCD and don't like it when something interrupts my schedule or things don't go according to plan.  That's why I HAVE to do the list or otherwise I would never do ANYTHING interesting!  Of course, related to that is my fear of loss of security.  I'd admire people that don't really have a home base, that float from spot to spot on the globe.  I could never be that free. :(

  2. I love taking time before you start out each day listing what you're thankful for. That's probably much more productive than the stream of expletives that goes through my mind first thing. :)

  3. Hello, and I found your blog. I’d love to say I am living my dreams, but not just yet.  I am working on a "poem" book, which I love.  I am passionate about getting it published.  I am so grateful each day for it is Gods gift to me or you.  My motto is " if I am Above Ground, It's a great day, or If I am not listed in today's obituaries, I am happy."  Great blog and so much fun 

    • Wow! Your comment just inspired me. I loved reading the answers to 5 hard questions and your motto is so perfect that I am going to steal it to put in my status on my fan page ;)
      Thanks for reading and I look forward to seeing where your adventures lead you!

  4. Wow! Your comment just inspired me. I loved reading the answers to 5 hard questions and your motto is so perfect that I am going to steal it to put in my status on my fan page 😉
    Thanks for reading and I look forward to seeing where your adventures lead you!

  5. For number 1 my answer is no.
    For number 2 my answer is no.
    For number 3 my answer is I would like to zip line travel with covid – 19 and do every crazy thing imangable!
    For number 4 my answer is traveling before covid – 19.
    For number 5 my answer is god.
    For number 6 my answer is i have no stress.
    For number 7 is as far as I am in life right now I am truley proud of myself.

    Alright thats all the questions ima answer so see ya peepes

  6. Who are you? What do you believe in? What do you stand for? What would you die for? What is my purpose in life? What are my strengths? What are my weaknesses?

  7. Right tips. solving toughest question is meant that you are trying, the information that you have described is really very informative. Subscribed your blog.


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Hey Bucket Listers!
I'm Annette.

I’m a goal obsessed mid-lifer, traveler, experience collector, fear crusher, digital marketer and author with big bucket list dreams. Let's Connect!

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