A Journal Exercise Using the Steppingstones of Our Lives by Merle R. Saferstein

In Ira Progroff’s book, At a Journal Workshop, he introduces steppingstones, which are landmark events in one’s lifetime. They are milestones or pivotal moments—those events which come to mind when we reflect on the journey our life has taken from birth until the present.

If you were to close your eyes and imagine you were watching a movie of your life, what are those moments that would stand out and flash across the screen? Another way to consider this would be: What are the events/moments when your life was never the same once these particular happenings occurred?

Spend a few minutes and list ten to twelve steppingstones in your life.

When you have completed this list, choose one event and write about it using the following prompt:
• At that point in my life,…

The next prompt to journal about is:
• When I reflect on this steppingstone,…

You might continue on and write more using these prompts:
• As a result of this steppingstone, I learned…
• At this moment in my life,…

You might consider journaling on all of the steppingstones you have listed. Doing so can often be enlightening and can uncover thoughts and feelings that you’ve buried long ago.

Another way you can do use steppingstones to journal is to list the different places you’ve lived, significant people in your life, or the various jobs you’ve had throughout the years. With each of these categories, you can use the same prompts as listed above.

In the legacy classes I teach, I introduce students to writing their ethical wills. An ethical will is a spiritual document people leave for their loved ones. It consists of one’s life lessons, values and beliefs, and hopes and dreams. When beginning to write an ethical will, I often suggest that people start with their steppingstones and write about what they have learned from each one.

Steppingstones can be used as an outline for a timeline, which is helpful if one wants to write an autobiography. In doing a life review, one might begin by using the list of steppingstones as a guide.

Regardless of what one does with these steppingstones, they are always a reflection of our lives. Writing about them opens a window into the significant moments we have experienced.


Guest Author:  In 2012, Merle R. Saferstein developed and now teaches a course entitled Living and Leaving Your Legacy®.  Merle is a member of our IAJW Journal Council.  You can listen to Merle teach about legacy writing and ethical wills by accessing her recent Telechat interview on Reflections of a Lifetime through Journaling in our IAJW member Audio Library (please note, you need to be an IAJW Member to access the audio library).

2019-05-21T14:17:38+00:00 May 21st, 2019|Journal Writing Prompts|


  1. Cheryl Finley May 31, 2019 at 10:33 pm - Reply

    Merle and Lynda,
    Thank you so much for this insightful, motivating article. It feels like a catalyst for expansion in the way seeing and mining the gold of life’s stepping stones. Thank you!

    • Lynda Monk June 6, 2019 at 10:40 am - Reply

      Hi Cheryl, it was a fun exercise to do. I hope you love it!

    • Merle R. Saferstein July 1, 2019 at 8:23 am - Reply

      Thanks so much, Cheryl. I’m delighted that this has been a meaningful exercise for you.

  2. Weavingthreads July 16, 2019 at 8:31 am - Reply

    Dearest Merle, I LOVE moving through life one stepping stone at a time. Engaging in journal writing and an art medium to create the masterpiece of one’s life with an ethical will, a BEAUTIFUL legacy sentiment. Thank you for sharing. 🙏

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