Shadow work is a journey into the parts of ourselves we would rather not see. Drawing on Carl Jung’s idea of the shadow, it means examining the feelings, impulses, qualities, and contradictions we exclude from our preferred picture of who we are. Journaling can give those parts a place on the page, where we can begin to acknowledge them and consider how they influence our lives.
For me, shadow work has often been uncomfortable, revealing, and ultimately satisfying. But the trek into the self’s shadow deserves respect. An inner wilderness is still a wilderness. We need to pay attention to the terrain, our limits, and the company we keep along the way.
I began learning that lesson more than thirty years ago, in a creative writing course at the University of Montana.
During my sophomore year of college, I studied with Roger Dunsmore through the university’s wilderness studies program. I remember him saying that, when his children were young, he would never allow someone to babysit them who had not confronted their own capacity to do evil: to hurt another human being and wound another human soul.
Over thirty years later, I still remember that.
As I understood him, Roger wanted to know whether a person had faced the possibility of causing harm themselves. Had they recognized that capacity? Had they taken responsibility for it? Could they see beyond their own innocence?
On another occasion, I handed in an essay that was self-congratulatory. Roger handed it back with an “F” and the comment, “Let’s speak about this.”
I sat down with him. The exchange, as I remember it, went something like this:
“Roger, come on. This was well written.”
“I’m not interested in ‘well written.’ I’m interested in seeing you write your guts on a piece of paper. This essay was self-congratulatory and lacked gut. Don’t you ever hand me shit like this again.”
That “F” was one of the finest lessons in writing I ever received.
I had given him prose that made me look good. He wanted writing that allowed me to see myself. There is a considerable difference between the two.
In Jungian thought, the shadow includes aspects of ourselves we do not readily recognize or accept. Some may trouble us: envy, resentment, cruelty, or the desire to control. Others may be valuable qualities we have learned to hide, such as assertiveness or creative ambition.
Looking back, I understand Roger’s demand as an invitation to confront that shadow. I cannot claim to know whether he would have used the term “shadow work.” It is the language I now use to describe what his teaching asked of me.
He wanted his students to come face-to-face with themselves. To recognize what we were capable of. To write beyond the polished account in which we always understood more, cared more, or behaved better than everyone else.
I think he wanted us to become people he could have trusted with his children.
It wasn’t group therapy. It certainly wasn’t individual therapy. It was writing at its finest: writing and journaling about the inner wilderness that exists in each of us.
That spirit remains part of InsightBridge’s approach to personal development: making room for honest inquiry into our patterns, contradictions, and possibilities.
Our studies took us into actual wilderness.
As I remember it, we began the school year with a ten-day trek into northern Montana’s Bob Marshall Wilderness. We ended with a ten-day float along a wild stretch of the Missouri River in Montana.
During the months between those journeys, our courses had us backpacking and floating through the wild stretches of our inner lives.
There were large, looming shadows of every shape and kind.
The landscape outside gave us a language for the landscape within. There were places we wanted to explore, places we avoided, and places where our confidence exceeded our understanding. Writing asked us to pay attention to where we actually were.
I still think about that when someone sits down to journal. The page may look ordinary. The journey it opens can be anything but.
Journaling becomes shadow work when we begin examining what our account leaves out.
We may write about an argument and explain, in convincing detail, why we were right. Then a less comfortable question arises: Did I also want to hurt them?
We may write about someone else’s success and describe our concerns about their character. Then we ask: Is there envy here that I have been dressing up as principle?
Or we may describe ourselves as endlessly accommodating and wonder: What happens to the anger I never allow myself to express?
These are possibilities to examine, not conclusions to impose. Another person may really have behaved badly. A boundary may really have been crossed. Honest inquiry needs room for those facts, too.
A few questions I would bring to the page are:
You do not need to answer every question. One honest answer may give you enough to consider for the day.
For a related exploration, read How to Journal About Pain: Turning Writing Into a Dialogue.
Roger’s response was blunt. In my experience, it became an enduring lesson. But I would not make his bluntness a rule for how everyone should be approached.
The lesson I carry forward is his insistence on honesty.
There is a difference between acknowledging that I acted cruelly in a particular moment and deciding that cruelty defines everything I am. The first gives me something to take responsibility for. The second can leave me trapped in an accusation.
Shadow work needs enough openness to admit what happened and enough care to consider what comes next.
This is also why the distinction explored in When Self-Reflection Turns Into Self-Criticism matters. We can examine our choices without making every discovery a judgment about our worth.
And we can pause. If reflection becomes overwhelming, there is no virtue in forcing ourselves deeper. Significant or persistent distress deserves support from a licensed mental health professional. AI conversations and reflective letters cannot replace that care.
Given those experiences, it is no surprise to me that I eventually created InsightBridge.
I wanted to help others learn about their own inner wilderness: the recurring tensions, avoided questions, and possibilities that begin to appear when we give ourselves time to reflect.
BridgeAI, the proprietary AI reflection system we developed for InsightBridge, supports that exploration through conversational journaling. You put an experience into words, respond to questions, and consider what emerges. Over time, you may find yourself returning to a theme with a different understanding.
Alongside those conversations, an Insight Professional writes you a personal Reflection Letter. In the monthly rhythm I am describing here, the letter draws on what you have shared and offers another person’s thoughtful perspective on the questions and patterns coming into view.
That combination of AI reflection and human witnessing matters to me. An inner journey can benefit from someone who pays attention to it.
I sometimes think of the spirit of the experience as having a professor like Roger Dunsmore take your writing seriously. Someone willing to look beyond the polished surface and ask what else is there.
The comparison is about the quality of attention I hope to encourage. Neither BridgeAI nor an Insight Professional has the final word on who you are. Their responses are perspectives to consider, question, and sometimes disagree with.
InsightBridge is not therapy, coaching, or counseling. It is a platform for personal reflection and development. You can learn more about how it works in our frequently asked questions.
I think the value of shadow work becomes clearest in what we do after an insight.
Perhaps we apologize without explaining away the harm. Perhaps we recognize resentment before it spills into a conversation. Perhaps we finally acknowledge an ambition we have spent years pretending not to have.
These are ordinary moments, but they ask something substantial of us.
My hope is that the journey helps us develop the maturity, depth of thought, and insight to contribute more thoughtfully to the world—to bring more of ourselves to our work, our relationships, and the responsibilities we carry.
I still remember that essay. I still remember the “F.”
More than thirty years later, I am grateful that Roger asked me to put something real on the page.
If you are curious about your own inner wilderness, you can begin with a free InsightBridge session.
You can start with one experience and one question you are willing to ask honestly.