Important Questions To Ask Yourself

Import Questions To Ask Yourself

This is is part of my live-learning series! I will be updating this post as I continue through my journey. I apologize for any grammatical errors or incoherent thoughts. This is a practice to help me share things that are valuable without falling apart from the pressure of perfection. 

I am writing this at the end of quarter 3, 2021 and the beginning of quarter 4. It’s weird to think of years in quarters. It seems to build through the process of being an entrepreneur and doing taxes and reports. 

Quarters somehow coordinate with seasons and create a nice rhythm of optimization and reflection. 

So, today, on a rainy Sunday in Toronto, I am doing some reflection on important questions to ask yourself. 

Yesterday, while journeying, I had this thought of what are the questions that I need to be asking myself? What are the questions I am too scared to ask myself? It was a bit of a breakthrough moment. 

If I am consciously or subconsciously too afraid to ask myself these questions, these are blockers in my life that I will not be able to overcome. 

I am sharing a list of self-generated questions for myself that I hope will be helpful for you as you ask about important questions to ask yourself. 

I will also share some resources I gathered in this journey with valuable questions and prompts that helped me generate my own questions.

As always, thank you for visiting and reading. I appreciate it a lot. If this resonates with you, or if you have a question to add that has been helpful for you, please feel encouraged to send me a message.

Self-Generated Questions 

Why am I anxious constantly?

Why don’t I feel safe?

Why did I choose the path of entrepreneurship? Do I feel it has fulfilled me?

Knowing I cannot change the past, what can I do now to build a better future?

What is something I am doing consistently that I would like to stop doing?

Why am I so alone at almost 30 years old?

How can I be a business owner and still feel disconnected sometimes?

Why do I feel like I’ve missed out on many opportunities in my life?

Why am I generally unhappy? 

Why am I unable to build a team of people who are better than me?

Why did I move to Toronto?

Why did I not feel at home in London, Ontario where I was born?

What is the opportunity cost of the path I am taking? 

What would I regret most if I did not try to accomplish this year? Next year? In my life?

Why am I so angry sometimes?

Why do I get stressed too easily?

How can I accept my body after damaging it so much in my early twenties? 

How can I learn to love myself?

How can I live in the present moment?

How can I detach myself from work and enjoy life more? 

Who is my best friend?

Why am I doing what I am doing?

What am I scared of?

When, where and who with do you feel most at home?

Why haven’t you achieved the financial success you believe you are capable of?

Why am I so unfocused?

Why am I scared of commitment?

Questions From Resources Below

Life Questions

How will your life be different in a year?

What is my definition of success?

How often do I apologize, even when it’s not my fault?

When was the last time I told myself “good job”?

What’s preventing me from being truly happy now?

Do I think I’m doing something of value with my life? Why or why not?

If money wasn’t an issue, would I still be in my current job? If not, what would I like to do instead?

What traits of leadership do I need to work on?

What are my biggest mistakes?

If you have one year left to live, what would you do?

If you have one day left to live, what would you do?

If you have one minute left to live, what would you do?

What advice would you give to your younger self?

Who are the people who have achieved similar goals? What can you learn from them?

When do you feel most inspired?

What would I do if I wasn’t afraid of anything?

What life lesson did you learn the hard way?

What do you wish you spent more time doing five years ago?

What’s a belief that you hold with which many people disagree?

What would you do differently if you knew nobody would judge you?

Which activities make you lose track of time?

If you had to teach something, what would you teach?

Are you holding onto something that you need to let go of?

What is the most defining moment of your life thus far?

Where would you most like to go and why?

When do you feel most like yourself?

If you could live one day of your life over again, what day would you choose?

What can money not buy?

What stands between you and happiness?

On a scale of 1-10, how happy are you with your life right now?

If money was no object, what would you do all day?

Relationship Questions

Am I willing to make compromises in a relationship? If so, what kind of compromises?

What are the “dealbreakers” in a relationship for me?

What impact did my parents’ relationship have on my view of relationships and marriage?

What are the top 3 lessons I learned from my past relationships?

Family Questions

Why do I want (or don’t want) to have children?

What is your most beloved childhood memory?

Friendship Questions

Do I have any unfulfilling friendships that are draining my energy and happiness?

Do I worry too much about what others think of me?

Health Questions

What am I doing to reduce and prevent stress?

What stressed me out most?

Great Resources For Questions To Ask Yourself


Ask Yourself These 20 Questions to Improve Your Self-Awareness | Shine
120 Questions to Ask Yourself to Understand Who You Really Are
10 Life-Changing Questions to Ask Yourself Today | Inc.com
101 Questions To Ask Yourself in Life – Personal Excellence
15 Life-Changing Questions to Ask Yourself Today | Cleverism
87 Self-Reflection Questions for Introspection [+Exercises]
30 Thought-Provoking Questions You Should Ask Yourself Every Day
365 Deep & Thought Provoking Questions to Ask Yourself (& Others)
50 Journaling Questions to Ask Yourself for Ultimate Self-Reflection | Life Goals Mag

I hope even one of these questions inspired you. Now that we know some good questions, it’s time to answer them. Good luck. 

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This is is part of my live-learning series! I will be updating this post as I continue through my journey. I apologize for any grammatical

Import Questions To Ask Yourself
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Important Questions To Ask Yourself

This is is part of my live-learning series! I will be updating this post as I continue through my journey. I apologize for any grammatical

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