Writing and Maintaining Your Stepping-Stones Journal Entry

One of ongoing lists that I maintain in my journal is called Stepping Stones, developed by Dr. Ira Progoff, author of the classic, Journal Workshop: Writing to Access the Power of the Unconscious and Evoke Creative Ability.

I first read about the Stepping Stones exercise in Tristine Rainer’s book, The New Diary:How to Do the Journal for Self-Guidance and Expanded Creativity

What Is the Stepping Stones Exercise?

The stepping-stones exercise involves writing a list of important events and turning points in your life, similar to this generic example:

I was born in 1976.
Attended James McKee Elementary School.
Drew dinosaurs on large pieces of construction paper
Won 2nd place in the science fair contest.
Got lost while trying to walk home.
First kissed a girl when I was 13.
Didn’t make the basketball team in 7th grade.
Won 3rd place for an art sculpture piece.
My first girlfriend was Andrea.
Took a poetry class in 11th grade.
Graduated from Grover Washington High School.
Drove to California with my arm in a cast to attend college.
Majored in art in college.
Slept in my car for two days.
Married my high school sweetheart, Andrea.
Got divorced two years later.
Purchased my first house in the country

Your list might start from your birth , or you might focus on the formative years of your life and include more details of events, experiences, and turning points that brought you into adulthood.

So far I have 31 stepping stones in my list, and I have set up a schedule to review and add to my list every three months. Some months there’s nothing I feel that needs to be added, but that’s because my list focuses on really important points, achievements and turning points in my life.


I recommend brainstorming experiences in single sentences so you don’t get bogged trying to remember details you as develop your list. As you make the list, you will begin to see and reflect on those events that helped shape your life.

It’s great to make your list chronological, but don’t let that hold you back from drafting a list of important steps and turning points in your life and then later adding dates rearranging the list chronologically.


Some of your stepping stones could be springboards for longer detailed journal entries. Individual experiences could be used for the basis of a memoir,  fictional stories, personal essays, or blog posts.

Note: if you use a digital journal like Day One, you can tag and/or bookmark your Stepping Stones entry and mark on your calendar to revisit it on a regular basis. 

You might also keep a Stepping Stones list for your children or a relative. Shorter Stepping Stones lists might be for a long range goals you achieved, a challenge you experienced, a list of career changes, the path you took to graduate from school, or the significant turning points of a relationship or marriage. The point of the exercise is to reflect on your development, and to remember just how valuable your life is and has been.

Also note that as you write your Stepping Stones, some examples may feel troublesome and uncomfortable to think about while writing. At such points, try closing your journal entry and revisiting it the next day or so when you’re ready to complete it.


As we grow older, we often look back and wonder what we have accomplished in our life, and what experiences led us to become what we are today.

Sometimes we undervalue our accomplishments and experiences because they are not “large” enough. We compare ourselves to others, or we beat up on ourselves for not doing more.

But each of our lives has value, no matter how small or great our experiences seem to others.

The Stepping Stones activity helps use value our life, and it can motivate us to build goals and get more out of our lives. We don’t have to compare ourselves with the lives of others, we simply need to know what we want and what is important in our life.

I hope you find the Stepping Stones exercise useful. Let me and my readers know what you think of the exercise and how you use it in your journal writing.


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Bakari Chavanu

is the creator of NaJoWriMo, and is the author of the interactive iBook, Starting From Day One: Using the Day One Journaling App to Record and Enrich Your Life
  • I really love this idea but unfortunately before HS graduation I don’t really have many stepping-stone memories. In 5th grade or so, I did come in second place in a trivia contest and won some credits at the school’s scholastic book fair, however!

  • I think this is a great idea, I know I really do undervalue and just forget my previous accomplishments. What I think would be a wonderful gift would be to do it for my children. Thanks for doing this great post. I look forward to tomorrows journal session where I can start on my own stepping stone.

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