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July 5, 2025. I get a call from my colleague, Eve. “Ty, please come to the venue right now”. This was strange as I wasn’t supposed to show up until two hours later. She, however, sounded very worried, and I rushed to the venue. Nairobi traffic has a way of making you sit with your thoughts. It was D-Day for my one-man comedy special dubbed “Millennial in Denial”. A bad feeling gnawed at me the whole time. Something did not feel right. When I got there, everyone was huddled in small groups speaking in hushed tones. Before I even got the chance to ask what the problem was, Eve approached me and, in a defeated voice, said, “There is a problem with the roof. There is a risk of cave-in and it can’t be repaired on time. If it rains like last night, people could get hurt. So they are saying we cancel the show.”
Eve’s words hit like a freight train. I didn’t even have the time to process what she was saying. I was still in denial. I moved around seeking clarification from everyone, yet getting angry at anyone who breathed my way. Finally, a deep, empty admission that this was indeed happening settled on me. Show biz is cruel, man. Especially for creatives. For you, it’s a dream, it’s a part of you that you are sharing with the world. It’s a very raw and emotional journey. Every success is euphoria on steroids, but every setback feels like your parents were right that you should have gone on to practice law.
Months of preparation had gone into this day. I had comedians from Uganda and Tanzania ready to join my Kenyan colleagues to open for me. We were going to compare our different experiences as we threw jabs and friendly roasts at the state of each other’s countries. A lot of writing, research, and practice had gone into the jokes themselves. Countless interviews and social media engagements had gone into promoting the show. People had come from as far as Nanyuki and Mombasa, but in the face of a leaking roof, all that meant nothing. Nature has a sense of humour, but it’s not funny when you are the joke.
It was two hours to show time. And there I was, lost, with everyone waiting for me to make a decision and chart a way forward. Adulting is messy. Who put me in charge of things like this? Some of the audience was already at the gate waiting, and others were on their way. So, tears welling up in my eyes, I took to Instagram and announced the cancellation, apologising to everyone and assuring all who had bought tickets that they were still valid and that a new date would be announced. Then I switched off my phone and waited for the worst.
It took a while to recover from the cancellation. The financial loss was one thing, but the emotional kick in the teeth, that takes everything from you. Having to put on a brave face and joke. Explaining away something that wasn’t even your fault. But there was a strange familiarity about that disappointment. Not that I had experienced a cancelled show before. No. It was the feeling of doing everything in your power, and it still not being enough. Whether it’s a career, friendship, school, the economy. Some days you do everything you can, and life just says, “No.”
You know, every African millennial carries some version of that collapsing roof. A moment when effort met instability, when preparation ran headlong into a structure that could not be trusted to hold. For me, it was a cancelled show. For many, it was a degree that cost your folks loans and sacrifices that led nowhere. For others, it was a job offer that dissolved. Some who went to study in the diaspora, enveloped in the hope of an entire village, made a quiet return home that felt like reversal rather than rest. Different details, same recognition. It feels like life made promises that it decided to break just for fun and moved on.
Africans born between the mid-80s and the ’90s were supposed to be the game changers. The generations that came before us had fought for independence, for democracy. Now it was our turn. The path was set, and the instructions were clear. Go to school, work hard, stay out of trouble, wait your turn. And guess what? We did. With an earnestness that now feels almost naïve. We became the most educated generation our societies had produced, fluent in the language of reform, rights, and opportunity. Reminded every day that patience was virtue and preparation was insurance. The promise was clear. If we stayed ready, the future would eventually call our number, and we would be there waiting with an excited “Hello!!”
But life hates going according to plan. Both for the individual and for humanity in general. At some point, for Africa’s millennials, the roof began to sag. Slowly at first, but with warning signs we were trained to ignore. Most, if not all, institutions seemed to hold their shape even as their strength eroded. Promises remained visible while their ability to carry weight quietly disappeared. At first, you think, I only need to work harder. I mean, like school, life should reward merit, right? What we read as personal delay was often structural strain. What we absorbed as individual failure was, in truth, the sound of a system weakening above us.
I use the promise of education because it’s very relatable. Especially to Kenyans who, in 2002, were promised free education for all by the new government. President Kibaki led a fierce drive where local chiefs were mandated to arrest parents who refused to take their children to school. As a result, classrooms multiplied, and universities rose from dust and optimism. Degrees were framed as proof of discipline, of worthiness, of having done right by one’s parents and one’s country. For many families, especially those crossing into higher education for the first time, education carried the accumulated hope of generations. It was meant to be the bridge between sacrifice and arrival, between obedience and dignity. We were taught to believe that if we carried this promise carefully enough, it would carry us in return.
But the world and its markets were not ready. Potential and hope are very deceiving. In the following years, graduates armed with credentials but little leverage entered a labour market that could not absorb them. Short contracts, if you were lucky, delayed pay, titles without security. Slowly, a new word emerged: “Hustle”. I hate that word. On the surface, it seems innocent, even dignifying the strive to work. Scratch the surface, and it reveals an ugly truth. “Hustle” emerged as both ethic and euphemism, a way of dignifying instability without naming its cause. It pedestalled shortcuts and connections as the way you made it. It made genuine effort and those who were ethical look foolish. The structural failure was rarely acknowledged; in fact, it was normalised. And so, many of us learned to live inside the ever-widening gap between qualification and fulfilment.
At first, we comforted themselves by thinking that success and fulfilment were just delayed rather than denied. We learned to speak about ourselves in the language of correction and self-improvement. There were probably skills to upgrade, brands to refine, mindsets to fix. Slowly and reluctantly, failure was individualized, even when it was widely shared. Many of us stopped describing our circumstances and started diagnosing ourselves. First, there was therapy speak, the Internet told us we had ADHD or were anxious avoidant, or something like that. Anything to diagnose the sadness, really. Silence followed, because shame thrives in isolation. It is easier to believe that you alone have fallen short than to confront the possibility that the structure itself was never built to hold you. Because, then, everything is still somehow in your hands.
Do not get me wrong, this is not an activist piece of writing meant to deny personal agency or pretend that effort does not matter. Rather, it is intended to help us see things from a place of scale. A lot of African countries expanded education faster than they expanded capacity. They ended up producing graduates without producing sufficient industry, stability, or pathways. Policy celebrated access while quietly deferring absorption. The result was a generation trained for participation in systems that could not fully receive them. What appears, in hindsight, as individual underachievement was often the predictable outcome of institutional overreach and retreat, a mismatch between promise and provision that no amount of personal discipline could resolve.
Enough with the political talk. Let’s talk technology. African millennials grew up crossing thresholds. Between letters and email, from memorizing phone numbers to having thousands of saved contacts, from waiting three days for a response to instant blue ticks on WhatsApp. Technology did not arrive all at once; it kept arriving. Just as we adjusted, something newer replaced it. Each change was framed as progress, as access, as possibility. But it also required constant recalibration. We were asked to keep up, to stay relevant, to learn new ways of working and living in a world that rarely paused long enough for anything to settle.
The result was a life lived in transition. Just as something began to make sense, it became outdated. Skills expired. Platforms shifted. Industries rebranded themselves out of recognition. There was little sense of arrival, only the pressure to adjust again. For many millennials, stability began to feel like a personal failure of the imagination rather than a reasonable expectation. We learned to stay flexible, but flexibility came at a cost. It is difficult to build confidence, intimacy, or long-term plans in a world that keeps insisting you remain provisional.
Living that way also changed how we looked at ourselves. Phones collapsed distance and time, putting African lives next to Western ones without context or scale. Progress began to look universal, almost mandatory. You could scroll past someone your age buying a house, starting a company, announcing a second child, all before lunch. None of it explained where they were standing or what had been handed to them. Comparison crept in quietly. Not always as jealousy, but as a dull sense of lateness. Like showing up for a race already in motion, unsure when it started or whether you had missed something essential.
It is not lost on me that I am writing this as a professional comedian. Someone whose job, at least on paper, is to make things lighter. Perhaps that is why this feeling is easier to recognise than to resolve. What settled in was not rage, but something flatter. Resentment without heat. A grief that learned to pass as a joke. We became skilled at laughing first, at naming our disappointments before anyone else could. It is easier to call it “the process”, or make a joke about being thirty-five and still explaining your life, than to admit how much of this was meant to be temporary. Humour, for many of us, became less a celebration than a coping strategy. It was a way of keeping the weight from fully landing.
That weight shows up most clearly in our relationships. Marriage, in particular, arrives less as desire than as reminder. Compared to the generations before us, who seemed to move from school to work to family with fewer interruptions, millennials are marrying later, if at all. Many of us spent our twenties stabilizing what was supposed to have already been stable. By the time marriage enters the conversation, it does so alongside rent, uncertainty, and the fear of committing from an unfinished place. Questions come from home, from relatives, from people who mean well and struggle to imagine another timeline. Each visit feels like an audit of progress. For many millennials, intimacy has had to negotiate economics first. Love becomes careful. Commitment feels heavy. It is difficult to promise permanence in a life that has trained you to expect delay.
This carefulness extends beyond our private lives. Millennials are often described as politically aware, and the description is accurate. We know the language of power. We can name the failures of the state, the corruption of institutions, the vocabulary of reform. But awareness has not translated into influence. Many of us learned how to diagnose problems long before we learned how to fix them. Over time, this produced a cynicism that is not rooted in apathy but in familiarity. We have seen enough to distrust easy answers, but too little change to believe our knowledge is enough. What remains is a sharpness without leverage, a constant sense of seeing clearly while standing still.
A month later, the show happened. I mention this partly because it feels important to return to where we started, and partly because I do not want you thinking I forgot about it. It was not a victory lap. It was more like fulfilling an obligation. A different venue, adjusted expectations, a roof that appeared willing to cooperate. The audience showed up. The material landed. There was relief, yes, but it was practical rather than celebratory. The kind of relief that says this did not fail, not the kind that says something has begun.
What stayed with me that night was not the performance itself but the material it kept circling. I found myself talking about cat mums and plant dads. Adults nurturing houseplants and pets with the seriousness once reserved for children. Entire emotional investments placed in soil and sunlight. The laughter that followed was not mocking. It was recognition. A roomful of people who understood the appeal of caring deeply for something that would not ask when you were getting married or why your career still sounded provisional.
Marriage came up often, usually as pressure rather than aspiration. Calls from home. Relatives checking in with concern that felt like surveillance. Casual questions that landed like reminders. The laughter here carried tension. Not resistance, exactly, but negotiation. Many people in that room knew what was expected of them. They were simply unsure how to meet those expectations while still paying rent and keeping their lives from falling apart.
Careers surfaced the same way. Not as ambition, but as explanation. Jokes about having to describe what you do without sounding unemployed or dishonest. Shared laughter about how we tell interviewers that we always wanted to sell insurance since we were six years old. About titles that change often and security that does not arrive. About success that feels temporary and failure that feels permanent. These moments landed softly, then lingered. Not because they were exaggerated, but because they were accurate.
What became clear was that millennials do not lack self-awareness. We know our patterns. We joke about gym routines, about therapy language, about activism fatigue, about faith abandoned and rediscovered in cycles. We laugh first because laughter offers control. It allows confession without exposure. On that stage, humour was not deflection. It was a way of saying this is shared without having to ask for solutions.
By the end of the night, the show felt less like entertainment and more like a census. A roomful of people recognizing themselves in small, ordinary admissions. The jokes worked not because they were clever. They worked because they named what many had been quietly carrying. Beneath the cynicism often attributed to millennials is not apathy but exhaustion. Not disengagement, but lives lived in permanent adjustment. The show did not resolve any of this. It simply confirmed it.
Some of us turn inward. We take the chaos outside and try to compress it into something manageable. The body becomes a project. Gyms fill up. Runs get longer. Meals get cleaner. The language of therapy slips into everyday conversation. We learn to say “boundaries” and “self-care” with confidence, even when we are not sure what we are protecting. There is comfort in improvement that responds to effort. If the world refuses to cooperate, at least a body can be trained. At least progress can be measured in mirrors and miles.
Others turn outward. Into politics. Into activism. Into permanent alertness. There is a kind of energy that comes from naming injustice, from feeling awake while others seem distracted. Anger offers structure. It gives shape to frustration and the sense of doing something. For many millennials, outrage became a substitute for power. We posted. We marched. We argued. We became fluent in the language of resistance, even as the systems we were resisting remained largely unmoved. It was not pointless. It was necessary. It was also exhausting.
And some turn upward. Toward faith, or spirituality, or the search for meaning that does not depend on markets or states behaving themselves. Old beliefs return. New ones are tried. Churches fill with people who were once certain they had outgrown them. Prayer becomes less about certainty and more about shelter. This turn is often misunderstood as regression. More often, it is a reaching. When life refuses to make sense, belief offers a place to put the questions. Sometimes that is enough to get through another week.
When it comes to what we passed down, the record is uneven. Millennials were generous with language. We handed over the words. Rights. Trauma. Boundaries. Systems. Accountability. The next generation learned early how to name what felt wrong. What we were less able to give them were pathways. We taught critique before construction. Awareness before inheritance. It is a strange thing to be fluent in diagnosis yet not know where the tools are kept.
There is an irony in this that we do not talk about enough. We wanted to spare those who came after us the confusion we lived with. Instead, we gave them our cynicism dressed as wisdom. We warned them early. We told them not to trust too easily. Not to expect much. Not to wait for institutions to save them. Some of that was necessary. Some of it was fatigue speaking. It is hard to hand over hope when you are still trying to recover your own.
This is usually the point at which a solution is expected. A prescription. A call to action. I do not have one that would not feel dishonest. Millennials are often told to reclaim optimism, to rebrand failure as resilience, to hustle differently. None of that addresses the underlying truth, which is that many of us are tired in specific ways that slogans cannot reach. Naming where we are feels more urgent than pretending to know where we should be going next.
Perhaps the mistake was in believing that every generation must arrive somewhere definitive. That history moves in clean arcs and rewards patience predictably. It may be that our role was never to inherit stability, but to live through its erosion and learn how to remain human while it happens. That is not a romantic task. It does not photograph well. It does, however, demand honesty.
I think often about that roof. About the warning that arrived just in time and the disappointment that followed. It did not collapse, but it did not inspire confidence either. Much like the world many millennials stand under now. We remain rehearsed. We remain ready. We are still waiting, not for rescue, but for structures that can carry the weight of the lives we have already built.
