50 Questions To Ask Yourself To Know Your Deepest Insecurities

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your deepest insecurities

Your deepest insecurities are stealthily influencing your life. 
The reason we struggle with insecurity is that we compare our behind-the-scenes with everyone else’s highlight reel. – Steven Furtick

Every one of us is insecure about one thing or the other. We all function with insecurity every day. Some people perpetually struggle with them, some are trying to get over it, some have bravely embraced them while a few others are unaware of it. If you imagine yourself devoid of insecurities, you reach a state of perfection – a flawless functioning individual. But, here you go, when people try to mend themselves too far to achieve what is unachievable, they lose their individuality and uniqueness.

One of the main reasons for being insecure is that we compare our worst with others’ best and we allow it to influence our lives. We compare our factual flaws with the illusion of utopia. Instead of focusing on what is so unique about us, something that makes us who we are, we always look forward to what others have and we don’t. We will never stop comparing and never be satisfied with what we have.

Hence, our insecurities will never be completely erased. Nevertheless, one must try to understand and embrace one’s flaws and insecurities and make the best out of it. 

Relationships fail because people take their own insecurities

Even the best of us have faced failures, insecurities, and self-doubt. But what separates the winners from the losers is that winners embrace their weaknesses instead of hiding them or avoiding them. When you know your insecurities you can face them well, smile, and be friends with them. 

As Kobe Bryant says, 

I have self-doubt. I have insecurity. I have a fear of failure. I have nights when I show up at the arena and I’m like, ‘My back hurts, my feet hurt, my knees hurt. I don’t have it. I just want to chill.’ We all have self-doubt. You don’t deny it, but you also don’t capitulate to it. You embrace it.

Read 12 Self-Care Tips to Take Better Care of Yourself

When you know your insecurities you can face them well, smile and be friends with them. 

Here Are 50 Questions That Will Bring Out The Core Of Your Insecurities

your deepest insecurities info

And help you be more courageous at handling them effectively:

While asking yourself these questions, it is necessary that your respond to them as honestly and truthfully as possible –

1. What are the things that make you anxious?

2. How often do you seek other people’s approval?

3. What do other people say is the thing in you they find most annoying?

4. What are your value systems?

5. What is important for you, being yourself or being what other people want you to be?

6. What are the qualities you wish you possessed?

7. How often do you feel irrationally jealous of others?

8. Have you ever lowered your standards to get something you wanted?

Read 50 Deep Questions That Can Strengthen Intimacy In Your Relationship

9. Do good qualities in other people, bother you, even to the slightest?

10. Do you feel being imperfect is perfectly natural?

11. Do you often engage in negative self-talk?

12. Does engaging in self-sabotaging activities give you a weird sense of pleasure?

13. What is the craziest thing that you have ever done in order to avoid failure?

14. Are you okay with other people disliking you?

15. Does it bother you when you see other people get what you think you deserve?

16. Are you being true to yourself?

17. At what stage of a relationship are you most likely to withdraw emotionally?

18. What is your biggest flaw that you like to rationalize to keep going in life?

19. How do you handle criticism?

20. How do you react to other people having an opinion different from you?

21. Is it your fear of commitment or your fear of intimacy that makes you shut down more?

22. Do you avoid your true feelings just because they make you feel uncomfortable?

Read 100 Questions To Ask Your Teen Other Than “How Was School?”

23. If need be, will you engage in playing mind games?

24. When was the last time you felt really insecure about the parts of yourself you pretend don’t exist?

25. What is the height that you have reached just to prove yourself?

26. What is the boldest thing you have done just to feel like you are still in control?

27. What is the most toxic thing about yourself you actually kind of secretly like?

28. Are you irrationally scared of losing people in your life?

29. What accusation would you defend yourself most fiercely against, even though you know it’s true?

30. How do you deal with your rage?

31. Do you often feel like others are way better than you?

32. How do you rationalize people leaving you?

33. How do you cope with being betrayed?

34. How do you react when you find out that your efforts are not being genuinely appreciated?

35. How much do you enjoy being in control?

36. What qualities in others do you like the least?

37. How often do you apologize to others for no reasons as such?

38. What’s the worst habit you have that rewards you the most?

39. Have you gone to great heights to please people?

40. What’s your most reliable way to deal with aggression?

41. How do you react when you find mistakes in your work?

42. How do people find out that you hate them?

43. What’s the most taboo fantasy you’ve ever had?

44. Do you keep dragging an unhealthy relationship or you free yourself out of it?

45. How would you feel if you come to know that you have been toxic to someone at some point of time?

Read 8 Deep Questions To Ask Yourself If You Keep Attracting Toxic Partners

46. Would you change yourself just to be loved or approved by others?

47. Have you ever been extremely self-critical to the point of punishing yourself?

48. Would you give up on your dreams just because other people don’t want you to pursue them?

49. How often do you lie to other people for your own advantage?

50. Do you have a problem trusting the intention of other people?

Being unaware of your biggest insecurities only creates a blinding mirage about yourself. So make sure to identify your insecurities and embrace them. So always remember, as Brandon Sanderson said:

The hallmark of insecurity is bravado.

Please share this post with anyone who you may think will find it valuable and helpful.


50 Questions To Ask Yourself To Know Your Deepest Insecurities
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