Navigating the Unexpected: A Story of Career Transition

Michelle Rhee
Sep 2
5 min read

A person in a blue shirt and black cap stands on a hilltop, overlooking a forest and distant mountains under a cloudy sky.

The Climb and the Aspiration

I never saw it coming. After years of climbing the corporate ladder in digital media tech, I had established myself as a senior leader in program management office (PMO). My days were filled with strategic planning and scaling initiatives that shaped how our tech organization operated. I had learned the delicate art of leadership, when to push, when to pause, how to find balance, and how to navigate the politics required to drive real change.

My role was never just about managing projects. It was about building the foundation of how a modern tech organization worked. Still, I aspired to earn a full seat at the strategy table, where decisions affecting hundreds of employees and billions in revenue were made. I could see the summit, but I had not yet reached it. The challenges were immense, but so was my drive to see the vision materialize.

I sensed change long before it arrived.

The Turning Point, the unexpected?

When the announcement came, I was not caught off guard. The signs had been there: shifting priorities, tightening budgets, reorganizations that did not quite add up. I stayed composed when I heard my name on the list, because part of me had already begun preparing for the possibility.

This first career break after years of dedication carried a weight I had not anticipated. My safety net of performance, relationships, and impact had been disrupted by forces beyond my control. Still, I found myself more curious than devastated. What might this space allow me to consider that I had been too busy to see before?

The Pause

The pause stretched longer than I expected. What began as a break became an unplanned sabbatical, a rare chance to step back and see the forest instead of the trees.

At first, the silence was overwhelming. No early meetings. No urgent emails. No teams waiting for direction. Without the constant motion of my professional life, I found myself asking: Who am I when I am not leading transformation or writing the next roadmap and KPIs?

Gradually, I filled the space with intention. I traded conference rooms and virtual meetings for mountain trails, replacing strategy sessions with sunrise hikes. There is something profoundly clarifying about the rhythm of putting one foot in front of the other. The noise fades, and only what matters remains.

The mountains became my office for reflection. From the ridge lines, I could see how small details, tactical choices, and sweeping vistas all connected, just as in leadership.

I reconnected with parts of myself I had neglected. I read for curiosity, not just for work. I had long, meandering conversations over coffee. But it was the wilderness that reset me the most, where the constant hum of professional life finally quieted enough for true insight to emerge.

The AI Awakening

This pause also gave me the space to explore AI and emerging technologies that are reshaping our world. What began as simple curiosity about ChatGPT turned into a strategic deep dive. I realized that years of orchestrating complex programs had prepared me to see both the opportunities and the risks of AI. The essential questions were not only “Can we build this?” but “Should we build this, how do we scale it, and what does it mean for the organization?”

I saw patterns everywhere AI was not just another tool, it was rewriting how we think about alignment, execution, and accountability. The frameworks I had once used to scale global operations now mapped naturally to AI governance. My experience with cross-functional leadership applied directly to conversations about ethics and trust.

Most importantly, I realized that my skills were never confined to a title. The ability to see systems holistically, to identify points of leverage, and to guide people through transformation is a leadership currency that transcends industries.

The Recalibration, the Transition

As months passed, I poured energy into learning, networking, and reimagining what my career could be. I refined my professional brand more times than I can count, half-joking that I now hold a PhD in personal branding.

Yet beneath the activity was a deeper shift. For the first time, I was advocating for myself, not just for my teams or organizations. This transition was not about finding the next job. It was about defining the next chapter on my terms.

The Realization That Changed Everything

During this time, I named something I had been doing instinctively for years: translating between worlds. Helping executives understand technical and resource constraints. Helping engineers see business impact, the larger picture. Helping teams navigate the messy middle of change as servant leaders.

I saw that my career was not just about program management or operations. Those were containers. My true value was bridging strategy and execution, seeing both the forest and the trees, and now helping organizations step into an AI-augmented future with clarity and purpose.

The New Horizon

Today I stand at a different kind of threshold. What once felt like rejection now feels like redirection. A Story of Career Transition that is still unfolding and navigating the unexpected is still a challenge. However, I'm now drawn to opportunities I might never have considered before: potential speaking engagements that share lessons on resilience and reinvention, consulting roles that leads to applying a strategic lens across contexts, and leadership roles that demand foresight in a world reshaped by AI.

The path forward is not about returning to what was, but expanding into what is possible. Titles matter less than impact. Organizations matter less than purpose. And the real question is no longer “What’s next?” but “How can I help organizations succeed in a world that is reinventing itself?”

What once felt like a break has become a breakthrough. And while I cannot predict every step ahead, I know I will walk it with clarity, resilience, and the ability to create meaningful impact where it matters most.

Sometimes the best views come after the most unexpected detours.