In a culture obsessed with flash, trendiness and superficiality, the pursuit of essence; of timelessness and vision often gets unappreciated. To live without superficiality, without chasing trends, is not only to point the way forward but to walk it oneself. It is a dual task; one must be both the model and the mentee, the creator and the creation, learning and realising oneself in the process. No one knows this as former Miss Uganda Oliver Nakakande.
Oliver with her limitless optimism and bewitching smile, is a girl who escaped poverty and neglect through hard work and a sharp eye for opportunity. She left Uganda only to return, seeing it anew. She took odd jobs but rose to become an executive, declaring, “Here I am. I want to learn your trade.” She gathered knowledge, confidence, and put them to use. And, as with many things of true value, it happened almost by accident. In the end, only she could provide what she needed.
What she discovered was a world; one that offered more than glamour or fame. For those lost in the wilderness of struggle, she became proof that one could bootstrap their way to a better life.
Halfway between misery and the sun

Oliver does not romanticize hardship. “I hated it,” she admits. “The grueling work, the harsh bosses; it could break anyone’s spirit. I didn’t survive because I was stronger. No, I had something else: A moral compass, a sense of right and wrong, and the example of my mother.” Like Camus, she found herself “halfway between misery and the sun,” understanding that while all may not be well under the sun, “money is not everything.”
Her mother’s legacy was her greatest inheritance; integrity, faith in humanity and a relentless love for independence. With it came responsibility, to speak for the voiceless, not just in their bitterness but in their kindness, their capacity for love.
Years later, while pursuing a marketing degree in Dubai, a friend reached out; “Miss Uganda is auditioning. You would be perfect.” Oliver hesitated. “This isn’t my thing,” she insisted. Deep down, she had once dreamed of modelling, but fear held her back; fear of rejection, of exposure. “I am a private person,” she said. “I don’t want the limelight.”
But her friend was relentless. She picked up the forms at the Sheraton, printed Oliver’s photos from social media, and even forged her signature. “Nobody will know,” she insisted. Oliver laughed. “You really think I am that good?”
When she returned to Uganda for the summer, her friend pushed her to attend the auditions. Reluctantly, Oliver went; only to realize she was uninvited. The room was filled with called-back contestants, each confirmed via phone or message. When the organizer confronted her, “Did we call you?” Oliver admitted the truth. “No. But I came to audition.”
As she gathered her things to leave, a judge emerged, exhausted. “Why the delay?” The organizer gestured to Oliver. “We didn’t call her.”

The judge paused. Then she said, “Let her try.”
And with that, the uninvited girl stepped forward, into a future only she could claim.
When the judge looked me up and down and said, “Can’t you see this is Miss Uganda?” it felt like fate. Suddenly, my confidence surged. Maybe I could be Miss Uganda. They let me audition. I walked in, shaking, and admitted to the judges, “I’m nervous, this is my first time.”
They appreciated my honesty, told me to dance to shake off the nerves, and somehow, I made the final 22. Me. The girl who wasn’t even called back. When I told my friend Ruth, she laughed. “I knew it!”
That moment taught me to show up no matter the odds, you never know what is waiting on the other side. It taught me to ignore the voices that say you don’t belong, because you might be exactly where you’re meant to be. Most of all, it showed me the power of people who push you. Ruth never doubted me. She was like those friends who lowered the paralyzed man through the roof to reach Jesus. We need those people.
The reinvention
The next step was a month-long boot camp. I barely had time, my summer break was short, and I had to return to Dubai for school, but I went anyway. Living with 21 strangers was wild. I would never been to boarding school, and suddenly, I was sharing space with girls from all over Uganda. But I wasn’t there to compete; I treated it like a vacation. I woke everyone at 6 AM for runs. I wasn’t the fittest, but I was loud about it. Then came the surprise; when they asked contestants to vote for the most helpful among us, my name came up the most. Why? “When I was sick, she gave me Panadol.” “She shared her perfume.” I hadn’t even noticed. I was just being myself. And that is how I became Miss Congeniality.

Boot camp was not just about beauty, it was reinvention. They taught us to sit, speak, and carry ourselves like queens. (I was a tomboy; this was new.) We learnt makeup, hair, and public speaking. For the talent competition, I anchored a fake news segment. No, I didn’t win, but I tried. Some dismiss pageants as outdated, but Miss Uganda is more than beauty. It unlocked skills I didn’t know I had, public speaking, advocacy, leadership. It’s about opportunity, representation, and mentorship. The right team shapes you into more than a pretty face.
On finals night, I was overwhelmed. My family, friends, even people from my village packed Sheraton’s hall. When I won, it wasn’t just my victory; it was theirs. Winning was just the beginning. For a year, I worked, traveling, speaking, advocating.
From Uganda to the world
Then came Miss World, where Uganda’s current representative, Natasha, is shining. Not just because she is beautiful, but because she is brilliant. And that is the truth; intelligence makes beauty glow brighter.
When I was crowned Miss Uganda, I didn’t realize it was just the start of a greater mission. The crown wasn’t a finish line, it was a call to serve. My reign stretched to two years due to Covid-19 (earning me the nickname “COVID Queen”), but I embraced every moment. Volunteering has always been my passion, I can’t go a month without giving back to my community.
My advocacy wasn’t random. After returning from studying abroad, I discovered that many of my childhood friends from the village were either teenage mothers, struggling with HIV, or forced to drop out of school. “Where’s so-and-so?” I would ask, only to hear, “She got pregnant,” or “She has AIDS.” Their stories broke my heart and fueled my purpose.
As Miss Uganda, I fought for comprehensive sex education, not just to keep girls in school, but to teach them the lifelong impact of their choices. Visiting shelters for teenage mothers, I met 12-year-olds already raising babies. The reality was worse than I had imagined. This became my Beauty with a Purpose project at Miss World, where I urged Uganda and the world, to recognize that sex isn’t a game. The consequences can alter lives forever.
The Miss Uganda Boot Camp was a month of intense transformation; physically, mentally, and emotionally. Twenty-two young women, including myself, endured rigorous training in poise, public speaking and leadership. Unlike other pageants, we had to supply our own wardrobe, adding another layer of challenge. The experience was designed to strip away self-doubt and rebuild you into a queen; whether or not you ever wore the crown. You entered as a “nobody” and left with the confidence of a woman who could conquer the world.

In contrast, Miss World was a dazzling spectacle of global beauty and grace. One hundred twenty queens, each representing their nation’s pride, gathered under one roof. My roommate was Miss Tanzania, and the bond we formed remains unbroken to this day. While the competition carried prestige, the real work had been done long before; countless hours of preparation, self-discipline, and perseverance. I performed well, but my most unforgettable moment came when the organization chose me as the cover girl for that year’s magazine. It was an honor I never expected, one that humbled and affirmed me in ways I couldn’t have imagined. That single opportunity catapulted my career onto the global stage, with top modeling agencies offering me jobs I had only fantasized about.
Walking New York Fashion Week, mingling with world leaders, attending high-profile events; there were moments I had to pause and ask myself, “How did a girl from Kawempe get here?” I never chased fame, but I always believed in my potential. To me, success isn’t measured in wealth or accolades; it’s waking up each day knowing you’ve made a meaningful impact.
To Dreamers in Forgotten Places
If you are reading this from a village, a slum, or any place the world has overlooked—dream louder. The doors are open; you just have to summon the courage to walk through them. If I Oliver, the girl from Kawempe who fought tooth and nail just to get auditions; could rise to this stage, so can you.
But let me be clear; fame is not just photoshoots, designer clothes, and goodwill trips. The spotlight comes with its own battles, pride, opportunists, and endless distractions. It is easy to lose yourself in the hype, to mistake flattery for genuine connection. Not everyone who smiles at you has good intentions. Staying grounded, focused, and true to your purpose is everything.
So dream big, but walk wisely. The world needs queens; not just in crowns, but in character. And that is a title no one can ever take from you.
Embracing the journey
Right now, as I see my path align with my purpose, doing what I believe God placed me here to do I feel successful. But this didn’t happen overnight. My ambition was born early, forged in hardship and honed through relentless determination.
At 18, my world shattered when I lost my mother on Christmas Day. Standing at a crossroads with my sister, we asked ourselves, “What now?” People laughed when I declared I’d find work immediately, and they were right. No one wanted to hire an inexperienced teenager. So, I became my own employer. Borrowing Shs100,000 from my father, I bought toys in downtown Kampala and sold them at school events. That small profit wasn’t just money; it was fuel. Fuel to get a driver’s license. A passport. A ticket to a future I could not yet see. I did not know where I was going, but I was going.

Later, I worked at my uncle’s studio, snapping passport photos and editing images. An unexpected opportunity led me to a journalism course, but my hunger for more pulled me beyond borders.
I did not leap from zero to 100. In Dubai, I started as a maid; a fact I have rarely shared. For two years, I swallowed my pride, endured long hours, and saved every dirham. Some would see it as a step back, but I saw it as a necessary step forward. When I returned to Uganda, reality hit hard: friends were now single mothers, struggling to survive. But with no means to help, I made the tough decision to return to Dubai, this time on a tourist visa, determined to carve out a better opportunity.
I researched fiercely, looking for work I could control. Real estate became my turning point. The money I earned built the foundation of my future. By the time I became Miss Uganda, the cameras and glamour didn’t fool me. I knew the crown wasn’t the end goal. Instead, I used the platform to connect, to serve, to build the social capital that would sustain me long after the pageant lights dimmed.
Every stage of my journey; selling toys, working as a maid, breaking into real estate, wearing the Miss Uganda crown, taught me the same lesson: Always look for more, but never lose sight of why you are striving. Now, as I walk this path, I see how each struggle was divine preparation.
Success is not about skipping steps, it is about learning from each one. It is about understanding that the maid, the market seller, the determined girl with a passport and a dream, they were all necessary. They were all part of the story.
And if you are in the middle of your own struggle, remember: This, too, is preparation. Keep going.
The dark side of Dubai
When my visa expired, I found myself in a desperate situation; sleeping in crowded bed spaces with strangers, unsure of my next move. Renewing my visa felt like a miracle, and landing that real estate job seemed like divine intervention. But the truth is, I didn’t get there through conventional means. After countless rejections from employers who said I wasn’t qualified, I took drastic advice from friends already in the industry. They told me to fake it till I made it. So I created a CV that stretched the truth, watched countless YouTube tutorials, and somehow bluffed my way through interviews. The moment of truth came when they asked me about ROI; a term I didn’t even understand. Yet against all odds, I got the job.
Suddenly, I was earning five million shillings a month as a broker. The company invested in me, providing training, securing my license, and even handling my visa. For the first time, I had financial stability. But something didn’t feel right. Deep down, I knew real estate wasn’t my passion. I had always dreamed of studying business, and with the support of my husband, I made the bold decision to leave my lucrative job and go back to school. Just as I began my degree, Miss Uganda came calling; a twist of fate that would change my life all over again.
My time in Dubai taught me brutal lessons about survival. Many Ugandan girls go there seeking opportunity, only to find themselves trapped in exploitative situations. I saw it firsthand; women working as maids in unbearable conditions, or worse, lured into debt bondage where their passports were confiscated. The racism was blatant, unless you were seen as an object of desire. But even then, one wrong move, like an unexpected pregnancy, could destroy your life. The system is designed to keep you vulnerable, and once you are caught in it, escape is nearly impossible.
The sad truth is that desperation and impatience drive many young women into these situations. My generation wants success fast; we don’t want to start small and build gradually like our parents did. Society has failed us by not providing enough opportunities, but we have also failed ourselves by chasing illusions of quick money. If it weren’t for my mother’s lessons in resilience, I might have taken those dangerous shortcuts too.
The real lesson
Dubai can be a place of transformation or destruction; it all depends on the choices you make. If you go, go with a clear plan and unwavering self-worth. Because once you compromise your dignity, it is hard to get it back. My journey taught me that true success is not about skipping steps; it is about persevering through each challenge while staying true to your purpose. And that is a lesson no one can fake.
Face to face with dark force

The real story behind the glamour you see online is not what you think. For two years, I ran with this wealthy crowd in Dubai; the kind of people who would drop Shs100m in a night without blinking. We are talking Lamborghinis, private jets, shopping sprees at Gucci. I was living that “social media dream” people kill themselves trying to achieve. But here is what no one tells you; when money comes that easy, there is always a catch.
These “friends” I met at an international pageant, they were 30-something “retirees.” I kept asking: “How?” How do you have all this without visible work? They would just smile and say, “We are blessed.” The lifestyle was intoxicating. The more I questioned, the more desperate I became to know their secret.
Then came the night they decided to show me.
They served me tea in a modern Dubai penthouse; nothing seemed out of place. But that tea… it transported me somewhere else entirely. Suddenly I was seeing visions; luxury cars, mansions, fame, what my “future” would look like if I said yes. The price? My soul.
For four hours, I was trapped in a spiritual battle. They showed me everything I had ever wanted; the private jets, the designer life, the VIP treatment. All I had to do was agree. But something in me fought back. I started praying like never before.
God told me: “Get up and walk out.” I didn’t believe I could, I had been paralyzed for hours. But when I finally mustered the strength to stand, the illusions shattered. I stumbled out of that penthouse a changed woman.
Here is what I learned the hard way:
The most dangerous lies are the ones wrapped in pretty packages. That influencer you admire? The one always flying first class? Ask yourself: What is really funding that lifestyle? The enemy does not come with horns; he comes with champagne and designer tags.
Real wealth is not about what you flash online. After my experience, I walked away from all of it; the clout, the designer bags, the fake friendships. Because when you have stared real darkness in the face, you learn what truly matters.
To anyone chasing that “social media dream”, slow down. The quickest routes often lead to dead ends… or worse. True success takes work, patience and most importantly, a clean soul.
That glamorous life you are envying? It might just be someone else’s prison. Choose your path wisely. Because some doors, once opened, can never be closed again.