The Gifts of a Disorienting Dilemma
Finding wisdom in the messy middle
This week, I found myself wondering what wisdom I could possibly offer when I am still very much inside a struggle.
Not triumphantly on the other side.
Not holding some beautiful lesson tied with a bow.
Just here, learning in the messy middle.
Over these past few months, I have been navigating a baffling conundrum — the kind of experience that defies a straightforward solution and challenges assumptions about what is helpful assistance and what becomes unhelpful interference.
I am persistent by nature. I am also a fixer. When someone I care for is suffering, my instinct is to keep searching: for the right resources, the right words, the right person, certain there must be a right solution to their painful problem.
That part of me is loving, creative, and resourceful. It is also obsessive and exhausting, especially when it forgets that I, too, am a human being in need of care.
In transformative learning theory, there is a term I have always found powerful: the disorienting dilemma. It describes an experience that contradicts what we thought we knew, forcing us to question, and perhaps even release, deeply held assumptions in favor of less familiar — and potentially more uncomfortable — ways of seeing.
I have studied this concept for years. But lately, I am not just thinking about transformation. I am living inside it.
And what I am noticing is that transformation does not feel expansive at first. It feels depleting. Confusing. Vulnerable. The default roles we know how to play are no longer the only ones being called forth.
I find that my Fixer, Advocate, and Researcher all continue to show up. But I am auditioning other roles to add to the ensemble:
- The Learner
- The Listener
- The Boundary-Keeper
- The Complexity Holder
To explore these new roles, I attended a support group for those navigating serious challenges with loved ones. I left with the quiet relief of being among people who understood things I did not have to over-explain.
I am also talking to experts, listening, reading, and slowly discovering that there is no single right or straightforward solution. That tending my own life and growth is not a distraction from care. It is part of what makes it sustainable. That holding complexity requires a more flexible and spacious way of being.
Maybe this is one of the hidden invitations of a disorienting dilemma.
- 🌱To make room for new meaning.
- ✨To try on new ways of being.
- 🌊To let life teach us, even before we know exactly what we are learning.
So perhaps the wisdom I have this week is not fully formed but emergent. The kind that comes from the messy middle of things. The kind that points us, slowly and imperfectly, toward what may need to be released and what may be ready to be embraced.
Here’s to the wisdom we don’t have yet, the meaning still forming, and the courage to keep growing in the middle of it all.



