The Day I Walked Away from Microsoft
On August 15, 2015, I made a decision that changed the course of my life. This is where the story begins.
There’s a moment in every person’s life that becomes their personal watershed, where everything swings in a new direction. For me, that moment came quietly, without fireworks or drama. It was the 15th of August, 2015.
At the time, I was living in Dubai. My life, from the outside, looked like a well-oiled dream. I had a powerful job, the kind of job that was both respected and possibly envied. I was the Head of Public Sector for Microsoft’s small-to-medium segment across the Middle East and Africa. I was responsible for driving a quarter of a billion dollars for the company.
I was flying high, literally and figuratively. At times I would fly to six countries in a week. Business class as standard. First-class on occasion, complete with a shower in the sky and heated floors. I had a black edition Porsche parked in my building’s garage, a permanent residency in one of the world’s most glamourous cities, and an apartment that felt like a postcard.
But beneath the polished surface, something had shifted.
It wasn’t burnout. It wasn’t frustration. It wasn’t even a lack of gratitude—I loved what I was doing. I loved the people, the challenge, the impact. Public Sector at Microsoft wasn’t just about revenue—it was about making a difference. I had met prime ministers, led development initiatives, and helped modernise cities. It was purposeful work.
But still… I felt the quiet pull of something else. Something more raw, more uncertain, but also more mine.
And so, on August 15, 2015, I made a decision that most people in my position wouldn’t dare consider. I decided to leave a perfect job.
Two weeks later, I handed in my resignation. And one month after that, I was gone.
I didn’t just leave a job. I left a life. I gave up my Dubai residency—the kind that’s tied to your work visa. I sold my car. I packed up my apartment. I shipped my furniture back to South Africa. I boarded a plane with no plan B and no golden parachute. Just an itch to build something of my own—and the uncomfortable thrill of not knowing how.
This wasn’t a side-hustle leap. This was full-scale free fall.
What followed was a reinvention. One with far less gloss and a lot more grit. I went from boardrooms and heated floors on Emirates, to the rocky terrain of Cape Town entrepreneurship. I traded predictability for the chaos of building a business from scratch. No more guaranteed income. No more global brand behind my name. Just me, an idea, and a relentless refusal to go back.
It’s now July 8th, 2025. In just a few months, on October 1st, I’ll mark 10 years since I left corporate life. A full decade since I traded comfort for calling. And as that milestone approaches, I find myself reflecting—not with nostalgia, but with curiosity.
Did I make the right call?
Am I better off?
Was it worth it?
These are the questions I want to explore with you over the next few weeks. Not in a glossy, LinkedIn-influencer kind of way. But honestly. With all the lessons, bruises, breakthroughs, and contradictions intact.
I want to tell the real story of what it means to walk away from everything you know - to choose freedom over familiarity, mission over money, and self-authorship over status.
This post is the prologue.
And now, I turn to you—whether you’re a dreamer in a day job, a burnt-out entrepreneur trying to remember why you started, or just someone who’s curious about what happens when a life is radically reimagined.
What would you want to know?
What questions have you asked yourself about leaving, leaping, building?
What fears or fantasies do you associate with this kind of decision?
Let’s co-create this story. I’ll be showing up here weekly sharing the full extent of my story, unfiltered, unguarded, and (I hope) useful. I’d love for you to be part of the dialogue.
So drop a comment, reply with your thoughts, or just reflect silently for now. But know this: the real story starts now. And it’s one worth telling.
Make it rain, KG