The Moment I Knew I Had to Leave
Part 2 of 5: A look into the decision that ended my corporate career and began my entrepreneurial life.
Last week, I told you about the day I walked away from Microsoft.
It was the kind of story that people often associate with a crisis, a burnout, or a spectacular fallout. But none of that was true for me. Things were going well—really well, in fact. I was living in Dubai, flying around the Middle East and Africa, leading a $250 million business for Microsoft, and doing work that mattered. There was no obvious reason to walk away.
But I did.
And the response to that story was overwhelming. So many of you wrote to me, commented, and reached out privately with your own questions, thoughts, and reflections. It became clear that we struck a nerve; not only because everyone wants to leave corporate, but because many are asking deeper questions about their lives and work.
So, as promised, this is the next chapter.
Over the coming weeks, I’ll unpack the full journey—five parts, five windows into the truth of what it really means to walk away from the known and step into the uncertain. Not the highlight reel. The real reel.
Today, I want to go back to the very beginning—not just the day I left, but the moment the decision truly formed.
I Wasn’t Even in Dubai
When I made the decision to leave, I wasn’t at my desk in Dubai. I was actually in the United States on a short work trip. Being away from the daily momentum of my life gave me a rare moment of stillness.
It’s funny how physical distance can offer emotional clarity.
I remember sitting quietly in my hotel room, laptop closed. And in that quiet, the thought came, not as a dramatic epiphany, but as a clear knowing.
I was going to leave. Not someday. Not eventually.
Now.
It was an unnervingly quiet moment. No music. No emotional fanfare. Just a firm internal decision: This chapter is done.
Let’s Talk About the Money
Before I go any further, I want to be careful here. I don’t want to sound like one of those “money doesn’t matter” people, wearing beads and speaking in riddles.
Money does matter. Try living without it and you’ll find out just how much. It’s a vital tool. A vehicle for freedom. A force that lets you build, protect, and sustain the things you care about.
But I started seeing something different during that period of my life: once you reach a point where your basic needs are met, and maybe even exceeded, you begin to see money for what it really is.
It’s a mechanical problem. A solvable equation.
And once that equation is figured out, something else creeps in and demands your attention: Why am I really here?
What am I building? And for whom?
That’s the part many people don’t anticipate. When you’re just trying to survive, your purpose becomes making enough money to keep the wheels turning, for yourself, your family, your obligations. But once that part gets handled, something deeper rises to the surface.
And that’s what happened to me.
A Crisis of Integrity
At the time, I was often invited to speak publicly—at conferences, panels, and other events. And I had a message I believed in deeply: that business, done ethically, is one of the greatest forces for good in the world.
That it can unlock human potential, move societies forward, and allow people to showcase their value through their work.
I hate to admit this but while I was delivering that message, I wasn’t fully living it. I was still on a payroll. Still safe. Still slightly removed from the leap I was encouraging others to make.
And that started to bother me. Not in an obvious way, but in a personal, possibly even spiritual way. I felt a tension between my beliefs and my own choices. I knew I couldn’t keep telling others to pursue their purpose if I wasn’t willing to do the same.
It was beginning to feel dishonest. And for someone like me, that was a signal I could no longer ignore.
Why I Didn’t Ask for Advice
When you make a decision like this, the instinct is often to phone a friend. Call mentors. Ask for guidance. Gather input. But I didn’t.
I knew that inviting too many voices into the conversation would muddy the clarity I had found. Well-meaning people would project their own fears, doubts, and limitations onto the decision.
They hadn’t felt the internal shift. They hadn’t heard the quiet certainty that I had heard. So I chose to hold my own counsel. It remains one of the most private, personal decisions I’ve ever made.
The Shift from Thought to Action
Once the decision was made, I didn’t stew in it. I shifted gears.
I opened a spreadsheet. I mapped out my finances—income, expenses, obligations—and calculated my runway. I asked the hard question: How long can I go without earning, and still meet my responsibilities?
The answer wasn’t comfortable. But it was manageable. I wasn’t planning to build a side hustle. I was going all in.
Once I had clarity on the numbers, I made a second list. This one was more a tactical action plan. I was living in Dubai, where my visa was tied to my job. Leaving meant dismantling my entire life structure.
Here’s what I wrote down:
Resign from job.
Give notice on apartment lease.
Sell car.
Ship furniture.
Exit Dubai.
This wasn’t just a career change. It was a geographic, emotional, and professional migration. And I approached it like an operator. No sentiment. Just execution.
The Resignation
Telling my boss, Chris Bartlett, a man I deeply respect, was one of the hardest moments. Not because I had doubts. But because I loved my team. I loved the work. I loved the company.
Chris was kind and generous in that moment. He offered to help. He even tried to find ways for me to stay. But I had already crossed that internal threshold.
I kept the reasons simple. I said there were some personal matters I needed to attend to, including caring for my mom. That was true, but not the whole truth.
The full story was more complicated, more internal. And I knew it wouldn’t make sense to everyone. It didn’t need to.
What Comes Next
This was just the beginning. The moment the chapter closed, but before the new one began. In next week’s post, I’ll share what happened next. I move beyond the decision into the more practical bits. If you’ve ever wondered what it’s like to actually do it, to leave, to start, to bet on yourself, next week is for you.
Make it rAIn,
KG