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.

This post may contain affiliate links. If you make a purchase through my links, I earn a commission that helps to keep this blog running—at no extra cost to you. You can read my full disclosure here.

---

You Might Also Enjoy

350+ Good Icebreaker Questions for the Best First Conversations
30 Tips for How to Get and Stay Motivated
425+ Best Never Have I Ever Questions for a Juicy Game
365 Motivational & Positive Thoughts for the Day
425 Good Truth or Dare Questions for the Best Game Ever
175 Good Questions to Ask Your Crush
100 Good Questions to Ask Friends (Just for Fun!)
125+ Would You Rather Questions for Couples (including dirty ones!)
75+ Road Trip Quotes to Inspire Your Next Long Drive
Being Grateful: 100 Things to Be Thankful For Today
8 Life-Changing Books About Fear and How to Overcome it
50 Fun Questions to Ask Your Partner To Get to Know Them Deeper
365 Deep & Thought Provoking Questions to Ask Yourself (& Others)
Long Term Goals List: 40 Examples & An Easy Technique to Achieve Them