Some journeys exhaust you physically, some leave you mentally stranded, and others give lifetime lessons. This one did all three.

I found myself stuck in Nairobi CBD with luggage too bulky for ordinary movement, luggage that immediately turned me into a walking surcharge. I had already paid extra to get into town, knowing too well that once luggage enters the equation, logic leaves the fare structure. Even after paying, the PSV still dropped me halfway, somewhere along Haile Selassie Avenue, defeated by traffic that had not moved for over twenty minutes. From there, progress became a chain of negotiations. A trolley guy demanded KES 300 to get me to Ronald Ngala. From Ronald Ngala, I would still need to pay around KES 400 to continue my journey, a route that normally costs about KES 70 when you are unburdened. By the time I did the math, I was staring at a total of nearly KES 1,000 just to keep moving in fragments.

That is how I found myself choosing an Uber or Bolt ride, not because it was cheap, but because it was predictable. The app quoted KES 860. The first driver arrived before rejecting the ride, saying I had too much discount for the luggage I had. The second one agreed to move me. We packed the luggage and started moving along Moi Avenue. Then, just like that, the rules changed. He told me he could not take me for KES 860. I needed to pay KES 1,100. The car was already in motion. I stood my ground, asking how a price could change after acceptance and departure, but the day had already drained my resistance. Remembering the chaos I had endured since morning, I told him I would pay KES 1,000. At that point, money had lost its emotional sting; it had already been bleeding out of me all day.

That wasn’t the end of it. He insisted I change the destination on the app to a spot a few meters from where we were. He demanded that this be done before we left town, luckily for hm, the traffic was on stand along Moi Avenue, so he had enough time to make me do his will. If the app reflected the full distance, he explained, the platform would charge him KES 350–400, but shortening the trip would cost him only about KES 150. I asked him why he needed to corrupt both the passenger and the very app that feeds him. He shrugged. You can also guess what I imagined at that moment if I were to ask him to drop me off for an alternative cab. I handed him the phone so he could adjust the address as he wished. I no longer had the energy to fight every moral battle I encountered that day. I can’t remember a moment when I was more desperate, to the extent of being walked on as this driver did. I had the option to report this driver after the ride, but I let that go.

We drove in silence for a while, the kind of silence that follows unresolved tension. Then, as often happens with strangers who share confined spaces, the silence cracked. He told me he hadn’t slept the night before. He had driven a client to Machakos and back, spending the entire night working. He stayed in Machakos waiting for the client to complete their errands. The client paid him KES 8,000. To him, it wasn’t enough. He had spent KES 1,200 on fuel, and the fatigue weighed heavier than the money. I listened, convinced this was someone who would never feel compensated enough, yet still depended entirely on what he earned to keep going.

He spoke of his life with a mixture of pride and grievance. He didn’t pay rent. He had been sold a plot in Athi River, land he acquired at a price far below market value, where he built his own apartment. For him, this was a donation. He framed it as a lesson: Never disqualify yourself, never be afraid to say what you have, never assume you are unworthy of a deal. Sometimes, he said, sellers are simply trying to dispose of what they have. His stories spiraled outward, touching on power, confidence, and proximity to opportunity. He spoke of Mike Mbuvi Sonko and his wife, how a man from modest beginnings rose through unexpected love, business, spectacle, and bravado to become one of the most powerful political figures in Nairobi. He made me know that Mike Sonko got married to his then-boss, whom he worked for as a personal driver. The irony with this example was that Mike Sonko was a trustworthy driver who did his job wholeheartedly, leading his then-client to fall in love with his honesty and diligence. Sonko’s life, in all its excess and contradiction, became proof in his mind that honesty and reliability can bend reality, even if it eventually exposes your flaws.

I confirmed his proposition by giving him a story of another driver who regularly chauffeured an Indian client who never used his parked car. The driver’s curiosity finally overcame fear. He driver asked why the car always sat idle, and the answer shocked him. He could buy it. The driver initially disqualified himself, assuming the price would be out of reach. When pressed to say what he had, he offered KES 250,000. The car was worth over a million. The deal was done. The moral, I couldn’t agree with him any less, was simple. Speak. Ask. Dare.

By the time he mentioned plans to take his family out for lunch that Saturday, the next day, so they wouldn’t have to cook at home, I saw the contradiction clearly. Here was a man who complained relentlessly, bent rules casually, and yet still planned moments of care and normalcy. He failed to appreciate what sustained him, even as it sustained him completely. The work he resented was the same work that fed his family, built his home, paid his car loan, and carried him through sleepless nights.

That journey through Nairobi became more than a commute. It became a mirror. It reflected a city where movement is negotiated, honesty is flexible, and survival often overrides principle. It revealed how easily moods shift, how strangers become philosophers, how hardship can breed both wisdom and entitlement. It showed me that boldness, when unchecked, can slide into dishonesty, and gratitude, when neglected, turns sustenance into grievance.

In the end, Nairobi didn’t just take my money that day. It handed me a lesson about who we become when the system strains us, about how we justify our compromises, and about the thin line between confidence and corruption. It reminded me that while making bold moves is necessary, knowing who you are and appreciating what already carries you might be the boldest move of all.