About
I'm Christopher Leonard. This publication is where I think out loud about change, continuity, and meaning.
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For a long time I treated those as separate careers. Looking back, they were different expressions of the same capability: observe a messy system, find its invisible structure, reframe the problem, and build something coherent from it. The medium was often healthcare technology. The underlying work was sensemaking.
My own path has not been linear. It has included deliberate pauses, fractional roles, entrepreneurship, caregiving, and the ordinary pressures that come with choosing an unconventional route. I treat that experience as primary-source material, not as proof of anything universal. The essays test it against history, psychology, technology, and other people's stories.
I write from a Christian foundation: identity can be anchored even while orientation keeps adapting. You don't have to share that foundation to find the essays useful. I just won't pretend it isn't there.
Private conversations
One
A few lines about what's changing. No forms and no intake questionnaire. If it isn't a fit, I'll say so plainly.
Two
A small number of substantive conversations covering your history, your constraints, and what has stayed true across your roles.
Three
A written Sensemaking Brief: what changed, what's structural, what's noise, which options deserve a look, and what can wait.
Always
Nothing is recorded, published, or shared, and no one is added to a list. You remain the author of what happens next.
This is a thinking partnership. It is not therapy, medical or psychological care, legal advice, coaching, or job placement.
Write to me privatelyFor organizations
Leaders sometimes see something important shifting, such as AI, regulation, or a business model losing its footing, before anyone can name the problem cleanly. I write Organizational Sensemaking Briefs for that moment: research, interviews, and synthesis that produce a coherent account of what is happening, so the decisions that follow are better ones.
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