18 Journaling Prompts for Doing Teshuva from Self-Awareness and Love

You may not have realized it, but the world is obsessed with Teshuva.

This is a ludicrous statement, if you translate the Hebrew word “Teshuva” to mean “repentance”.  One look at the state of the world verifies that world population is certainly not repenting on masse. 

But if you translate Teshuva (as is more etymologically correct to do so) as “return”, I think you would agree that the world is obsessed with Teshuva (even if they don’t know this word).

The explosion of self-help resources, motivational books, speakers and quotes, astounding therapies and mind-body healing modalities testifies that everyone wants to come home – to themselves and to their wholeness.  There is no greater incentive for returning to Self – Teshuva – than living out loud as the person you are meant to be (and reaping the blessings that come with that).

During Elul and the High Holy Days, we are given this gift of return – to ourselves, to our loved ones and to G-d. There is no more auspicious time in the Jewish calendar than now to iron out the inevitable creases in our hearts and mend the rifts in our souls that rob us of exuding our natural – spiritual – beauty.

In the following 18 journaling prompts, I invite you to try the effectiveness of journaling as a way to embark on your very own process of returning to your deepest essence and greatest potential.

Find a quiet time and place, a notebook and a pen, perhaps put on some gentle music, and begin to write about as many of these prompts (plus or minus according to what feels right) in your journal.  I hope you will return to this practice many times, especially once every year before Rosh Hashana.

In the first nine questions you will be meeting your true self up close and personal. You will be accessing your deepest dreams and desires for yourself and your year ahead and finding the unique beauty of your soul. I guarantee that no matter what you have been through or where you have been until now, what you will find when you hit your spiritual center is love.  (If you don’t, you haven’t gone deep enough.)  

Once you have touched your core, you will then be able to examine what are the areas that obscure this authentic self and higher knowing.  Self-knowledge is self-power.

Teshuva from love (as opposed to from fear), say the sages, has the power to retroactively and magically transform our past errors into merits.  Pursuing connection and expression of all that is good and true in yourself, Hashem and the world (and discarding all that inhibits this connection) is such a return.

May you be blessed with Divine Assistance in your returning to yourself and a truly good and sweet new year.

Happy journaling!

 Touching your true self

  1. What are some of your greatest gifts that Hashem has given you?
  2. What are some of your greatest resources and assets that He has given you?
  3. What do you want most for the coming year?
  4. What are you grateful for in your life right now/ this past year?
  5. What are some of the significant milestones, events, breakthroughs, accomplishments etc. from this previous year? (year in review)
  6. During what periods/ when in general did you feel most alive/most yourself?
  7. What are some of the biggest struggles you’ve had this past year? (when you felt most alienated from your true self?)
  8. In what areas have you grown the most?
  9. What are some of your greatest insights/ pieces of wisdom that you now have that you didn’t have as strongly last year?

How do I implement this self?

  1. What is your life asking of you most right now? What are some of your top areas of priority that require your attention that you have allowed yourself to become lax or distracted in?
  2. Are you using your G-d given gifts to serve Him? (refer to your answer to question 1) How could you utilize your resources better to bring about greater kiddush Hashem?
  3. What behaviors are blocking you from being your best self? What can you do to reduce and eliminate these behaviors. Run the Teshuva program!*
  4. If there was one midda that you would like to change to be a more balanced person, what would it be? Can you think of a way to bring yourself into better balance in this area now that you have the insight?
  5. If there was one emotion that you could snap your fingers and it would be gone or reduced from your life what would it be? Can you think of something productive to tell yourself what you have this emotion to correct it?
  6. What recurring thoughts do you have that make you feel fearful, anxious, lonely, depressed or alone? What would be more spiritually productive thoughts to have in these moments?
  7. What is one area in the category of between man and G-d that you would like to improve in? What is a practical way to improve this?
  8. List one area in the category of between man and man that you would like to improve in – How can you implement this change in one small way that you can do consistently
  9. What is one area in the category of bein adam l’atzmo, between man and himself, that you would like to improve in? If you changed this way about how you related to yourself, it will enable you to serve Hashem and love others better. How can you begin to work on this/ do this?

*The Teshuva Program: admit/ confess, regret the past, accept a better future.