• Anita Chastain, MBA

25 Best Questions to Find Your Authentic Self [Updated]

Updated: May 28

Do you ever feel the real you is hidden somewhere underneath the person you're supposed to be? This article presents the 25 best questions to help you find your authentic self again.

Have you reached a point where you're going through the motions of life, but you feel like the life you're living doesn't really represent the real, authentic you? Maybe you feel like your life lacks authenticity. What others see on the outside doesn't really reflect how you feel on the inside.


So what could have happened that you found yourself living a life that just doesn't feel right?


In my case, I became so focused on what I believed other people wanted me to be, that I ignored what I wanted. Eventually, I realized that I was living a life that no longer felt true to me.


My life lacked authenticity. I concluded that I was missing an important part of what made me, me.


That realization prompted me to make changes in my life. A lot of those changes centered around prioritizing my personal values and the ways in which I spent my time.


Take the free Simple Life Quiz to learn more about where you are right now in your journey to authenticity and a simpler, more meaningful life.


Our Authenticity Gets Lost in Day-to-Day Life

Life is hard. I think many of us find ourselves in an ongoing struggle to manage everyday life:


Caring for our kids, spouse, and parents.


Meeting our work obligations.


Paying bills.


Cooking meals.


Doing all the things that keep our homes and life functioning.


Juggling the demands of day-to-day life is hard, really hard. Because it is hard, I think we sometimes let our own needs slide. We take less care of ourselves in order to spend more time caring for those around us.


It's important that we take care of ourselves too. If we don’t, we may wake up one day feeling empty, discouraged, and unfulfilled.


Maybe you’re there right now. I’ve been too, and it’s an unhappy place to be.


Rediscover Your Authentic Self


If you're feeling like you're living an inauthentic life, maybe it's time to rediscover the person you want to be. Once you rediscover the person you want to be, you can figure out what you need to change to be that person.

Right now, you're probably wondering:


How exactly do I do that?


Today, I'm going to give you 25 questions to help you rediscover your authentic self. This is really the first step in your journey toward living an authentic life.


But first, let's look at how we figure out what we want and what we want to change.


Change Starts on the Inside and Works Its Way Out


I reconnected with my authentic self by looking inward, then using what I learned there to shape my outside actions. I thought about the values, interests, and dreams I had lost after years of plodding along in life.


Rediscovering those things helped me become a happier person and find a healthy balance in my life.


I believe we can all live an authentic life.


The first step is figuring out where we are right now. We need to sort through what's working and not working in our lives. Then, we need to figure out how to change our life to align our actions with the person we want to be.

Writing Brings Clarity into Your Life


One of the most powerful ways I’ve found to bring clarity into my life is through writing, including journaling. Set aside time for you to spend alone with your thoughts, and start writing.


Writing out your innermost thoughts is a powerful and transformative experience. It certainly was for me.


As you write, use the privacy and freedom of the experience to be totally open and honest with yourself. There's no reason to be anything less.


Are you ready to get started? Grab some paper and a pen (or an electronic screen) and get ready to write.


Woman walking with her back to the camera

25 Questions to Help You Find Your Authentic Self


When you’re ready to start on the journey to rediscover your authentic self, these questions will help you uncover your priorities, values, and dreams:


Self-Assessment Questions


These six questions provide a starting point for self-reflection:


1. Which three people have had the greatest positive impact on your life? How did they inspire you?


2. What three things bring the most happiness into your life?


3. What three things do you like most about yourself?


4. What three things would you most like to change about yourself?


5. What three accomplishments are you the proudest of?


6. What three outcomes do you regret the most and what would you do differently now?


Authenticity Questions


This next set of questions help you uncover the values that matter to you and how those values are being lived out in your life:


7. What parts of your life don’t feel authentic to you?


8. What five core values guide you in day-to-day life?


9. In what ways are you living - or not living - your core values?


10. How would you benefit from living a more authentic life?


11. What fears or other constraints keep you from living a more authentic life?


12. What would you need to change to live a more authentic life?


Creating Change Questions


These seven questions address issues related to change - what changes you want to make in your life and how to make them successfully:


13. What does your ideal day look like? How is it different from the life you’re living now?


14. What steps would you take to make every day look more like your ideal day?


15. Which of your thoughts and actions are driven mostly by the fear of negative consequences?


16. Which of your thoughts and actions are driven mostly by the desire for happiness?


17. What steps can you take to reduce fear and increase happiness?


18. What are you the most excited about in your life right now?


19. What three small changes could you make that would allow you to feel happier and more at peace?


20. What three things can you do today to make tomorrow less stressful?


Imagining the Future Questions


These three questions help you visualize a more authentic life and the steps you need to take to make permanent changes in your life:


21. Over the next six months, what obstacles might get in the way of leading a happy and fulfilling life?


22. How do you see your life being different 12 months from now?


23. What steps do you need to take to make changes “stick” in your life?


Growing Through the Process Questions


The last two questions ask you to reflect on what you've learned so far and to apply what you've learned in order to succeed in your quest for authenticity:


24. What are the three most surprising things you've discovered about yourself after answering these questions?


25. What are the three most important things you need to remember as you begin this journey?

Thinking through the deep questions of who you are, where you are, and what you want in the future is critical to personal growth.

Thinking through the deep questions of who you are, where you are, and what you want in the future is critical to personal growth.


But here's the thing:


Change requires honesty. We won’t experience serious growth or change if we aren’t honest with ourselves. We need to be honest about the good and not so good aspects of our life.


Woman smiling

Self-Assessment: Be Honest with Yourself But Not Harsh


As you answer these questions, be honest with yourself, but not harsh.


Don't blame or attack yourself for mistakes you’ve made in the past:


Blaming and attacking yourself are counterproductive. All it does is make you feel bad. It does nothing to change what happened. So let it go.

We all make mistakes. Accept them, then move on.

We all make mistakes. Accept them as part of your life experience, then move on.



Conclusion


Change often resembles a slow walk down a winding path more than a giant leap over an obstacle. This is why persistence is an important part of change.


Don’t stop before you reach your destination. Adjust your direction, the number of steps you take, their size, or how quickly you take them, but don't stop till you reach your goal.


Making changes so you can live your life more authentically takes time. Stay focused, stay committed, and stay the course.


You can do this.


Which of these questions had the most impact on you? Email me at anita (@) simplelife365.com and let me know. I would love to hear from you.

NEXT: You might enjoy reading 5 Things that Happened When I Quit Trying to be Perfect.