30 Questions & 77,737 Words...
My quest began with more questions than answers. Ultimately 30 questions & 77,737 words from 30 days of focused writing revealed the meaning within my most difficult moments and helped me heal.
In October of 2022 I wrapped up the design, development, and delivery of a yearlong leadership development program. The work had been all consuming for the previous three years and had put my quest for unlocking my earned lessons on hold. With it completed it and me realizing it was time to move on, it was time to resume my quest.
The time away and the need to remain focused to complete the leadership program had served me well. Specifically, it had allowed me to sit with the things I’d discovered from my first five years of serious exploration of my life’s most difficult moments.
With my mind focused on how best to develop the capabilities of leaders, I spent a lot of time reflecting on how our life’s experiences inform and impact our journeys. That was work I needed to do in order to figure out my next steps. Focusing on how to help others provided me with some fresh context and a deeper understanding of the work I was seeking to do.
That said, when I realized it was time to return to my introspective work, I was uncertain about the direction to take. My first five years of searching had shown me the importance of taking time to think through things and not make premature judgements.
Combined with the intense period of work from 2019-2022 in developing something from the ground up, that made me realize I needed a path to quickly dive back into my work.
A writing challenge from a trusted guide delivered the answer…
As has happened somewhat regularly in my quest, the answer I needed came in an email from someone I trusted and respected. I don’t recall the exact timing of the message from AJ Harper, but it was about a writing challenge for the month of November.
There is an annual writing challenge referred to as NaNoWriMo (aka National Novel Writing Month) for fiction writers and AJ was challenging her audience to consider joining a writing challenge around their personal stories. It felt like the perfect transition step for me—a quick path back into the deep work I wanted to return to at a time when I needed to create a new rhythm and reboot my inquiry.
So I responded immediately and agreed to commit to writing every day in the month of November. My attention then turned to the necessary question: How do I proceed?
Since I had more questions than answers, a Q&A approach seemed the most logical. So I began creating a list of questions to be addressed in my month of writing.
I decided the best path for my questions was to frame them using the concept of distanced self-talk (from Ethan Kross’s book Chatter that I use in my journaling). The idea is to ask the question using your name so you respond as you would to someone else. For example, if I wanted to write about why I felt abandoned, I would replace the typically used question: “Why did I feel abandoned?” with this one: “Why did Michael feel abandoned?”
What I had discovered in my journaling with this approach was that it was freeing and led me to insights faster than the approach I had long relied upon. Kross suggests that it works because it shifts our perspective and we become more of an advice giver than a self analyzer (my terms, not his). I figured that to fulfill my objective and make my soon to begin month of writing productive, this was an appropriate way to frame the questions I’d respond to each day.
It is much easier to offer advise someone else…
My list of questions grew quickly, along with my anticipation for the month of focused writing and my return to my investigation of my life’s journey. Each morning I reviewed the list and made some edits—moving things around to create a path that felt logical, reframing and separating the overly complex, and eliminating those that felt like they were beyond the scope of the work at that point.
On November 1st I woke up at 5:30 am and dove into the process. My Google Doc for the day had been created the day before—something I decided to do each day to set the stage for the writing session the next morning. The question was printed atop the document and the empty space was waiting to be filled when I opened it the next day.
I opted for a ‘free writing’ approach, aka writing continuously for a set period without worrying about grammar, spelling, or structure. My plan was to begin by 6 am and write about each question for no more than 90 minutes. To keep track of time and keep me focused, I used a app called “Focus at Will” to provide the ambient sounds of a coffee shop.
As the days progressed the words flowed easily and I often found myself discovering thoughts and ideas flowing onto the page that I didn’t recognize because I had never allowed them in before.
The process was liberating, and at times scary as the heaviness of some moments brought tears to my eyes. It was transformational to watch my thoughts appear on the page without judgement or pretense as they flowed through me as though I was advising someone I deeply care about and trusted. Most importantly, it was calming as the freedom of free writing and the focus on one question at a time provided a level of clarity previously hidden by the noise.
Daily accountability helped a lot…
One of the best things about the writing challenge AJ Harper created was the tracking spreadsheet where each day participants would post the number of words they wrote. Though I did my best to suppress my competitive spirit and try to outdo anyone, my 90-minute time blocks led me to write an average of over 2500 words per day.
To be clear, many of those words would not survive a serious editing process, but the point of the experience was not about serving anyone but me:
A journey to deepening my understanding of my life’s experiences.
An exploration of thoughts and ideas in a safe place at a deeper level to reveal the meaning lost in often rushed and convoluted attempts to discern meaning from too many things at one time.
An acknowledgement of the factual realities and the internal post-mortem perspectives developed in the years since.
Most importantly, it delivered a level of peace within that I’d been seeking for five decades and freed me of the judgements I had been imposing upon myself throughout those years.
Would this process serve you well?
The truth is I’m not sure how well the process I used in November of 2022 would serve anyone else. I’m tempted to suggest it would be powerful based on my experience, especially if you’ve done the work we talked about in the past few weeks posts.
I also know writing is not the first path many use to sort things out. Perhaps other formats such as dictation or even talking it through with someone might work better for you. Or, if you’ve been journaling for years, it might be useful to do a deep dive into your writing using a forensic context and a more detached view.
What I learned from the process I’ve shared here is that when you ready to do the work it is important to give yourself permission to examine your entire journey at a high level. That is the only way to reveal the deeper meaning within the moments that framed your story, and that is where the peace of mind is found.
Today’s Earned Lessons…
#1—Stepping away from the examination of your life’s journey and diving deeply into something else can open the door to deeper understanding when you return to your introspection.
#2—When you are ready and open to it, the answer you need often shows up when you commit to figure something out (it has happened too many times in this work for me not to believe it will do the same for others).
#3—The deeper meaning emerges when you look at the whole from a higher level perspective versus delving deeper into each of the individual moments.
If you found this post helpful, I’d love for you to like and share it with others who might benefit. Thank you for reading and following this journey. I appreciate it and welcome your feedback and ideas on making this work more valuable to you.


Hey Michael, this was an awesome read! I love how you treated that writing challenge and it seemed to have worked out great for you! I also really love that you brought up Ethan Kross’s book! I never thought about using that concept before in my journaling but I’m definitely gonna try it now! ❤️💪