20 Transformational Questions to Ask Yourself for the New Year

By Tiffiny J. Fambro | Confidence

Jan 05

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Happy New Year! I cannot believe how fast 2021 went. I learned so much from my experiences and am ready to take on a new year with new intentions, goals, habits, and transformations.

As I was preparing for this new year, I thought about all of the coaching clients I have had an opportunity to work with. The women who have come to me to support them on their journey towards getting clear on the next steps of their lives, rebuilding their confidence (especially after divorce), and gaining the courage to take action and move forward.

As part of my coaching sessions, I constantly ask my clients questions to help them explore a deeper understanding of themselves. Claude Levi Strauss, a French anthropologist, said, “The wise man doesn’t give the right answers, he poses the right questions.” Questions allow us to think critically on a deep and meaningful level. It opens up to understanding various solutions, possibilities, and perspectives.

When we question ourselves (who we are, what we want, why we do the things we do, etc.) we build a deep self-awareness. This helps us live more authentically and build confidence in our talents, skills, beliefs, and self-acceptance.

Below are 20 transformational questions that I challenge you to ask yourself for the new year. These questions will help you dig deeper into the next steps of your life, what you want, and what’s holding you back from getting there.

Transformational Questions to Ask Yourself

1. Using one word, how do you feel? (Explain with an emotion word such as happy, content, sad, angry, indifferent, apathetic, rage, blissful, etc.) Why?

Understanding how you feel right now is important in learning your current emotional state. It gives you clarity on whether you want to stay in this feeling state or change how you feel.

2. How do you want to feel? Why?

This question asks you to go deeper in reflecting on how you want to feel. It helps you explore the reason why you would want to feel that way. So much comes up for my clients when I ask them “why”. Think through your why’s and write down all the reasons without judgment.

3. What part of you or your life needs healing?

When I say “healing”, that can be physical, mental, and emotional. Asking yourself this question doesn’t mean that you have suffered some terrible trauma, but it could mean that you have neglected a part of your spirit and that needs healing. Or, maybe you have suffered deep trauma and you do need to find peace. Either way, be honest with yourself when you ask yourself this question, and don’t be afraid to go deep.

If this question sparks major emotions and you need help, take a look at Onlinetherapy.com. This company offers online connections to licensed therapists/counselors all over the world as well as various activities to promote mental health and quality emotional health.

4. What do you need to forgive yourself for?

Society tends to push this notion of forgiving people that have done something bad or harmful to you. However, I say, instead of focusing on forgiving others, try focusing on forgiving yourself.

Perhaps you need to forgive yourself for the pain that you caused yourself, or for the pain that you may have caused others, or for not going after the goal you wanted to achieve, etc. The point is to ask yourself this question and allow your mind to wander where it needs to find the answer.

5. In what areas of your life do you want to see improvement? (finances, family, friends, career, health) Why?

This question speaks for itself. You may be happy or content with your life but still, ask yourself this question. You can also ask this question for every area of your life and see what comes up for you. This will give you clarity on what systems you may need to put in place to start working on those specific areas.

6. What are the core values that you have for your life? (make a list)

Core values are the personal beliefs that dictate how you live your life. Here is an example of some of my core values:

  • Authenticity
  • Kindness
  • Openness
  • Personal freedom
  • Expression
  • Self-love
  • Independence
  • Commitment
  • Loyalty
  • Respect
  • Honesty
  • Physical and mental health
  • Joy
  • Financial stability
  • Abundance

So, be mindful to think of yourself, your beliefs, how you live your life, and write out as many core values as you choose.

7. What are you tolerating or dealing with right now? Why?

This question is asking you to think through your personal life and the people, experiences, and situations that you allow. There may be people and experiences that you like but there may be some that you are just dealing with to be “nice”. I want to you take off your “nice” hat and be honest with yourself. Who or what are you tolerating?

8. What do you want more and less of in your life? (Make a list for each)

For your “more of and less of” lists, you can add tangible objects or experiences like money or sex. Or, you can add emotions like love or anger. The idea is to get real with yourself and don’t hold back. Be honest with how you feel.

9. What do you really enjoy or love? Why?

For this question, be willing to reflect. You may want to make a list and ask why for each. For example, “I want more love and this is why…” or “I want more peace and this is why…” List out as many as you choose and feel free to take a break and add more as you think about it throughout the week.

10. What do you really dislike or hate? Why?

Write out what you dislike and the reason why next to it. Make a list for yourself and don’t hold back on allowing your thoughts to flow freely.

11. How can you add more of what you enjoy or love to your life?

Think about your life and the small yet meaningful ways to add more of what you enjoy. If you love to travel, maybe you can’t take a trip to Greece, but you can drive to the beach, or mountains, or the local park. If you love shopping, maybe you are not able to spend a ton of money, but perhaps you can write down items that you would like to buy when you have the money. Be creative in thinking of ways to add more of what you love into your life.

12. In the past week/month/year, what were your three most positive and enjoyable moments?

These moments can be personal achievements, work achievements, or just your day-to-day happy experiences. Write what comes up for you.

13. What do you want?

Ask yourself this question and don’t hold back. Be limitless in the possibilities when it comes to asking yourself this question. Allow your mind to explore whatever reality you choose.

14. What is holding you back from getting what you want?

When you think about what you want, be willing to ask yourself what is holding you back. If you say you don’t know, then keep asking the question until you get an answer- be honest.

15. Right now, who or what do you need to release from your life? Why?

Is there a person, place, or situation that you feel you need to eliminate from your life? Perhaps it is a toxic friendship, a dysfunctional romantic partner, an environment that makes you feel depressed, or a stressful job. Write out why you feel that you need to release this from your life. Allow yourself to be honest without shame or guilt.

16. Where do you see yourself in 1 year? 2 years? 5 years?

For this question, think through your goals and what you desire. Where do you see yourself physically, mentally, and emotionally? Think through the various areas of your life such as your finances, relationships, career, and other aspects.

17. If there were no restrictions or perceived limitations, where would you be and what would you be doing?

When you think about this question, remove all the mental fear, guilt, shame, or any emotion that would cause you to limit your capacity to dream big. Take off any perceived beliefs that you think would hold you back from writing out what’s deep in your heart and mind. Take your time with this question and come back to it to add more if you need.

18. What’s one change you could make to your lifestyle now that would give you more peace?

This change could be big or small. For example, you may say that every morning after you brush your teeth, you will close your eyes and think of 1 thing that you are thankful for. You could say that you will drink 1 glass of water as soon as you wake up, or move your desk near the window so you get more sunshine in your day.

The idea is to think of 1 change that is simple to start and incorporate into your life. Don’t make the change too difficult, just make it simple and easy. Do this new behavior until it becomes a habit, then add one more until that becomes a habit, then keep going.

19. What is stopping you from living your happiest, most fulfilling, greatest life?

Reflect deep on this question, because most of us know what the answer is- we just are not ready to face the truth. If you say, “I am stopping me from living my best life”, be willing to write out why.

Many times I ask this question to my clients and they say “well, Tiffiny, I know it’s me”. That’s when I say “okay, and why is it you?” So keep going deeper into your reasons behind the initial answer.

20. Are you willing to change?

This is by far the most important question. When you think about this question, I want you to think about a scale. With 1 being a “no, I’ll do nothing” and 10 being an “I’m starting today”. Answering these questions will help bring out your clarity around what you want in life and how you can transform. But, if you are not willing to change, nothing in your life will happen. Taking action is when the internal transformation manifests into the physical world.


These last 2 years have been challenging for a lot of people. Many have lost jobs, loved ones, and have had to rethink life. However, after any storm, there is always a rainbow, and many times new growth. Let 2022 be the beginning of your rainbow and new growth. Allow yourself to feel your feelings, cry, get angry, and then dig deep into the greatest enigma you will ever face- yourself.

Transformation means asking yourself the right questions and being open to whatever answers come to the surface. It means being able to be vulnerable with yourself and have compassion. It means doing the deep inner work to heal, evaluate, gain clarity, build your courage and self-esteem, and start taking action.


Ready to start the process of gaining more clarity, confidence, and courage? I have created 3 simple steps to help you on your journey.

  • First – Download my Free 5-Day Mindset Detox Workbook – Click Here
  • Second – Join my Free private Facebook women’s community to get coaching and support – Click Here
  • Third– Get started on your CCC journey with my online self-paced entry course The 5 Keys to Magnetizing Confidence for $49.99CLICK HERE to review and purchase the course. 

Don’t let more time pass by, reclaim your life today!

About the Author

Tiffiny has a B.A. in Psychology, and master’s degree in Public Health Education. She worked in consulting for over 16 years, as well as previously owning a fitness and health business. In her personal life, she used personal development, mindset and health strategies to go from being overworked in a demanding corporate career, emotionally drained in a toxic marriage, physically unhealthy, and depressed to becoming an award-winning figure level bodybuilding athlete and entrepreneur. As a women’s empowerment coach, she works to help women get clear on their goals, build confidence, increase self-esteem, take action on their deep desires and create a life they love

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