20 Self Reflection Questions for 2019

It’s such a good feeling to come to the end of the year and feel a sense of achievement, closure and completion. What better way than to look back on the year and reflect on what you have learnt, how far you have come, where you could have stepped up and what you would like to cultivate in the following year.

Self Reflection is one of the most important tools we can practice. It helps with our communication with others, and allows us to become more aware of our thoughts and actions, which allows us to foster self-compassion, self-acceptance and self-responsibility. Self reflection helps to build emotional self-awareness; by taking the time to ask yourself the important questions, you gain a better understanding of your emotions, strengths, weaknesses and driving factors in your life.

I suggest printing out the following questions or journaling them into your diary. Be accountable and read them out to a friend and get her/him to do the same!

All you need is:

  • 30 – 60 minutes of undisturbed quiet time
  • A pen and paper (yes, actually write these down – it’s therapeutic).
  • An open mind to reflect and be REAL with yourself
  • A close friend to share your answers with, or
  • Share this on your Instagram story and tag @rosie.rees.

So get comfy, put some good tunes on, grab a cuppa and dive deep.


  1. What are three things you am most proud of achieving this year? (Let yourself boast!)
  2. What have been your three biggest challenges you’ve faced this year? (i.e. finances, health, a break-up, social life, work etc.)
  3. How did you grow from these challenges?
  4. What old habits or addictions inhibited you this year?
  5. What new habits did you create this year?
  6. What three fear(s) have you overcome and how? (i.e. I went parasailing in Bali this year and this overcame my fear of heights over water).
  7. How have you nourished your body most this year? (Close your eyes and ask your body)
  8. Name an occasion where you nourished your spirit/felt connected to your higher self? (Close your eyes and ask your soul)
  9. What projects have you completed successfully? (business, personal, health, fitness)
  10. What has personally triggered you the most this year? And how can you heal, overcome or work through this in 2020?
  11. What have you procrastinated, deflected or avoided the most?
  12. Where do you feel most stuck, uninspired and stagnant?
  13. What have you frequently complained about most this year? (Hot tip – ask your partner! They will be able to tell you.)
  14. What have you felt most shameful about? (Shame is simply the desire to not be “bad” and to always be “good”. Healthy shame is important for self-reflection, but beyond reflection it may move into self-sabotage.)
  15. What are some selfless, loving or caring things you have done for others this year? (look for proof that you are a good person!)
  16. When were three times you felt most alive?
  17. Who are three people you would love to spend more time with in 2020?
  18. How have you showed up in your relationship with your partner? And how could you show up more fully for your partner in 2020?
  19. How did you manage my finances?
  20. If you could achieve one thing next year (business related or otherwise) what would it be?

I also suggest doing a Vision Board for 2020! Find yourself a cork board or large piece of cardboard and cut out images from magazines or Pinterest to stick on your vision board.

Where attention goes, energy flows.

Sign up for our VISION BOARDING & WINE event on January 3 2020 in Perth: SIGN UP HERE

I hope these have been helpful questions for self enquiry. Self reflection helps to build emotional self-awareness. By taking the time to ask yourself the important questions, you gain a better understanding of your emotions, strengths, weaknesses and driving factors

Please share these questions on your Instagram story to inspire your friends and family to do the same!

Love Rosie x