The Long Way Round to the Right Work
There's a particular moment in a long career when the pattern becomes visible. Not the career plan—I'm skeptical anyone's plan survives thirty years intact—but the underlying thread that connects choices you didn't fully understand when you made them.
For me, that thread is the space where technical systems meet human ones. Where the elegant architecture fails not because of engineering but because no one accounted for who would actually have to change. I've spent three decades learning that lesson from different angles, and the work I do now exists because of what those angles eventually revealed.
The Corporate Chapter
I spent over twenty years at Pitney Bowes Software, a trajectory that took me from software engineer to Managing Director of Professional Services for the Americas. Along the way, I managed geographically dispersed teams across the US, Canada, Brazil, and India. I led complex enterprise implementations for organizations like CVS and GE. I learned how global organizations actually work—not the org chart version, but the lived reality of P&L management, cross-cultural teams, and the gap between strategic intent and operational execution.
It was, by most measures, a successful career. But success inside a large organization requires a particular accommodation. Over nearly three decades, I had shut down too many parts of myself to meet corporate objectives. That's not bitterness—it's an honest observation about what institutional life asks of people, and what it costs when you comply for long enough.
The fracture point came not from a single event but from the collision of lived experience with new understanding. Between 2014 and 2017, while completing an MBA at WPI focused on innovation and entrepreneurship, I found myself reading authors like Bob Kegan and Jennifer Garvey Berger—scholars of adult development and leadership complexity—and recognizing the patterns they described in the organizations I had lived inside for decades.
One pattern in particular cut deep. I had watched a business strategy designed and executed with no regard for the deeply embedded culture of the business unit. The organizational carnage that followed wasn't a surprise to anyone on the ground—only to those who had drawn it up on a whiteboard without understanding what they were asking people to change. That experience, held up against the academic frameworks, crystallized something: the gap between technical capability and organizational reality is where most transformations fail, and it's a gap that no technology can bridge alone.
Crossing to the Other Side
I had spent my career on what I think of as the data-gathering side of the table—aggregation, insights, analytics. I understood the machinery of how organizations collect and use information. But I could also see how fundamental shifts in privacy and individual freedom were occurring, often invisibly, as that machinery scaled.
When I started my own journey through The Dingle Group, I deliberately crossed to the other side of that table. I had been watching the decentralized and blockchain sector before leaving Pitney Bowes, and once independent, I dug into decentralized identifiers and Verifiable Credentials with the freedom that corporate life hadn't permitted.
What surprised me was where the real opportunity lay. The traditional digital identity conversation—person-centric, focused on authentication and access management—was important but narrow. The larger question was how these technologies would reshape organizations and things: supply chains, trade, regulatory compliance, the fundamental architecture of trust between institutions. That's where my attention went, and it's where it remains.
Vienna and the Catalyst
The chapter I'm living now began, as consequential chapters sometimes do, with someone else's decision. My wife found a career opportunity in Vienna, Austria. That move—a personal one, not a strategic one—became the catalyst for everything that followed.
Vienna gave me distance from the assumptions I had been operating under. It placed me in a European context where questions about data sovereignty, regulatory philosophy, and the relationship between citizens and institutions are framed differently than in North America. It also gave me proximity to the policy conversations that would eventually become central to my work.
The Aeolian Discourse grew from that context. It began in 2018 as the Vienna Digital Identity Event—intimate fireside chats exploring the business, technical, legal, and societal dimensions of digital identity. Nearly fifty conversations later, I renamed it. The word "Identity" in the title had become a limitation, too strongly associated with IAM and person-centric frameworks, creating barriers when the real conversation had moved toward digital excellence across entire organizations. The Aeolian Discourse now hosts conversations at the intersection of technology, governance, and the human dimensions of digital change.
Why a Portfolio Career
The portfolio model—Digital Excellence, non-executive governance, and coaching—wasn't designed on a whiteboard either. It emerged from the recognition that these three domains are inseparable in practice, even when organizations treat them as separate functions.
My standards work reflects this integration. Chairing the UN/CEFACT UNTP Adoption Working Group and having chaired IEEE/UL 2933-2024 taught me that standards are governance made operational—they require technical depth, organizational understanding, and the ability to build consensus among people who see the world very differently. That's governance work. It's also coaching work. And it demands the technical fluency to know when a compromise is elegant and when it's dangerous.
The Growth Edge coaching certification I completed through Cultivating Leadership in 2018 wasn't a career pivot—it was an acknowledgment. The MBA experience, the Kegan and Garvey Berger readings, the lived experience of watching organizations misunderstand their own cultures—all of it pointed to the same conclusion: technical expertise alone is insufficient. The leaders navigating digital transformation need the capacity to see their own assumptions, hold complexity without collapsing it into false simplicity, and lead through uncertainty rather than around it. I'm pursuing full coaching certification this year because this conviction has only deepened.
What I'm Learning Now
My current work with the fashion and textile sector on Digital Product Passport readiness is confirming what three decades have taught me: the barriers organizations face in transformation are as much cultural as technical. The regulatory requirements are clear enough. The technology exists. What doesn't yet exist, in many organizations, is the cultural willingness to change how they think about transparency, data, and what they owe the systems they operate within.
I don't yet have the longitudinal data to prove this quantitatively—that's an honest admission. What I have is thirty years of experiential evidence that ignoring the cultural dimension of change will guarantee that transformational ambitions fall short of expectations. And sometimes go horribly wrong.
The work continues. The questions keep getting more interesting. And I've stopped shutting down the parts of myself that make the work worth doing.
Michael Shea operates a portfolio career from Vienna, Austria, working at the intersection of Digital Excellence, governance, and leadership development. He can be reached through The Aeolian.