Life after the 9 to 5: Kenyans who quit corporate for self-employment

Some left because they were burnt out. Others just wanted more control over their time, their creativity, or their happiness. Many say quitting wasn’t easy, it meant giving up a predictable paycheck for something uncertain, but also something that finally felt like theirs.

For Mary Kiraguri, 35, a marketing strategist and founder of Moh’s Kreatives, a digital marketing agency that helps brands grow through storytelling and social media strategy, leaving corporate wasn’t something she had planned. When she transitioned from formal employment to self-employment, the change came with both freedom and financial lessons.

“There was definitely a drop in income,” she recalls. “When I was leaving Dubai, I was earning around Sh170,000, but when I came back to Kenya, most of 2023 averaged about Sh150,000 a month. This year, though, things have been tougher. The new tax laws and the general economic slowdown have really affected small businesses. Because my business depends on other companies being in operation, since I manage their social media and digital marketing, when they struggle, I also feel the impact. I lost about three clients last year who completely shut down because of the increased taxes.”

Still, Mary says entrepreneurship has taught her to think differently about income and stability. “In business, there’s never really a fireproof barrier to protect yourself,” she says. “You can plan all you want, but at best, you save when the money is streaming in and keep some liquid cash for the slow months. Managing cash flow is everything. On a good month, save more; on a bad one, cut expenses so you can sustain yourself and still cover overheads. Even though I work from home, I still have to pay my designer, my software subscriptions, Wi-Fi and rent.”

She’s also learned one powerful lesson that now defines her work ethic. “Always have a skill you can take with you wherever you go,” she says. “That’s what keeps you afloat. I’m able to do my business now because my skills in digital marketing can fit into any industry. I’ve worked in fintech, cybersecurity, hospitality, and even managed schools. What I take from all that is simple—learn a transferable skill because that’s what will sustain you long term.”

Mary had spent years in Dubai’s hospitality and marketing sector, working hard and climbing the ladder. But along the way, she started to notice a pattern: her growth seemed to have a ceiling.

“I’d reached a point where I couldn’t grow any further,” she says. “As a Black woman in the Middle East, the highest I could go was assistant digital marketing manager. I was doing most of the work, but promotions and recognition always went to other people. Even when I tried applying elsewhere, I was told my passport wasn’t strong enough for senior roles.”

That realisation hit hard. She had always been ambitious, the kind of person who gave her best to every role, but suddenly, the dream she had worked towards for years no longer felt possible in that environment.

The decision to quit didn’t happen overnight. It started as a quiet frustration, then became a nagging thought she couldn’t ignore. “I kept telling myself, maybe next year things will be different. But deep down, I knew I had to leave if I wanted more for myself,” she recalls.

When she finally resigned, it was both liberating and terrifying. She didn’t have a perfect plan, but she had a vision, to build something of her own that aligned with her values and creativity.

Coming back home to Kenya, she started Moh’s Kreatives from scratch, handling everything from client calls to content creation. There were no guaranteed salaries, no HR departments, no safety nets. “I remember the first few months were tough,” she says. “You’re suddenly responsible for everything finding clients, managing invoices, keeping the lights on. There’s no one to fall back on.”

Still, the freedom was intoxicating. She could choose the kind of brands she wanted to work with and create campaigns that actually meant something. Slowly, referrals started coming in, and with each small win, her confidence grew. “I’m still learning,” she admits. “But the growth I’ve experienced both personally and professionally is something I’d never have achieved if I’d stayed in that system.”

Looking back, she says quitting corporate wasn’t about rebelling against structure or stability; it was about choosing herself. “People think self-employment is easier or more glamorous, but it’s not. You have to show up every day, even when no one’s watching. But I’d still choose this over being stuck in a place where I wasn’t seen or valued,” she says.

If Mary’s story is one of quiet defiance, walking away from a system that refused to see her worth, then Esther Muthoka’s is about reclaiming creative freedom and mental peace after years of feeling boxed in.

Esther, now a content and website strategist, social media manager and public speaker, had done what many young Kenyans dream of: she got into the system early, landed a decent job, and began climbing the corporate ladder. Her path led her into government spaces, where the work was structured, the salaries steady, and the benefits secure. But behind that structure was a silent frustration that grew louder with time.

“I wanted more,” she says simply. “I wanted the flexibility to do more than just give everything to one company. In most corporate spaces, especially in government, you’re limited creatively, you can’t explore new ideas because you have to stick to brand guidelines, management approval, and all those layers of restriction.”

Her voice softens when she describes the environment she left behind. “It was also a bit toxic,” she admits. “You find yourself in spaces where most people are older, and being young and fast at your work makes you a threat. You’re seen as someone who’s trying to shake the system. Even when your intentions are good, it doesn’t always sit well with people who’ve been in that space for years.”

She tells of meetings where her ideas were brushed off or treated as too ambitious, and of the quiet isolation that comes when you’re young, vocal, and good at what you do in a system that values seniority over innovation. “You can’t be good and vocal at the same time,” she says, half-smiling. “If you are, you become a target.”

Instead of quitting abruptly, Esther decided to wait her contract out. It was a strategic choice, she wanted to leave on her own terms, and she wanted to be ready. “During that period, I started working on myself,” she says. “I took a few courses, public speaking, social media management, digital marketing, even LinkedIn branding. I knew what I wanted to do, but I needed to sharpen my skills before stepping out.”

Her exit plan wasn’t met with full support. Her parents, like many Kenyan families, were skeptical. “Of course, they were worried,” she says. “In their eyes, stability means having a job. When you tell them you’re leaving a government job to freelance, they panic. But for me, the fulfillment I was getting on this side, the freedom, the creativity, I can’t trade that for anything.”

Esther calls what she does now freelancing, stroke consulting. She offers website and content strategy services, helping brands not just build websites but also maintain and monetise them. “I realised most people think websites are just static, you design, launch, and forget. But your website is an asset; it can earn you money, attract clients, and build credibility. That’s where I come in.”

The transition from nine-to-five to full independence wasn’t smooth. “In the beginning, I missed the structure,” she says. “In corporate, there’s a system already in place. Out here, you are the structure. You decide what time to wake up, when to work, when to rest. It takes a lot of discipline, and sometimes you fumble. You have to learn by doing.”

There were fears, too; familiar ones to anyone who’s taken the leap. The imposter syndrome that whispers you’re not good enough, the uncertainty of not always knowing when the next client will come, and the haunting question of whether she’d made a mistake. “Sometimes it gets hard,” she admits. “You have good months and bad ones. You start doubting yourself. But then you remember why you left in the first place.”

Her first few steps into self-employment were small but deliberate. Before officially quitting, she began branding herself online, talking about her skills, posting her work, and building visibility. “I used the little savings I had to get pro versions of the tools I needed, like Canva and CapCut. You don’t need a huge investment when you’re a service provider, just the right skills and tools to complement what you do,” she says.

Now, she handles full-scale marketing for clients, running websites, managing social media pages, crafting content strategies, and even speaking publicly about her journey. “Because I’m vocal, I get invited to speak at events and panels,” she says. “I use those spaces to talk about creativity, work-life balance, and why it’s important to design a career that works for you, not just one that looks good on paper.”

The freedom, she says, is both her biggest blessing and her greatest test. “You’re no longer clocking in at eight or leaving at five. You work around the clock sometimes, 2 am, midnight, whenever you’re most productive. But it’s different because it’s yours. You own your time.”

Financially, she says, the growth has been gradual but rewarding. “At first, you don’t make as much, because you’re building a portfolio and learning how to negotiate,” she says. “But once you find your rhythm, it’s better than what I earned before, not just in money, but in satisfaction. I get to work with different clients across industries. I’m constantly learning.”

Still, she admits there are things she misses about corporate life, the daily banter with colleagues, the sense of belonging, the structure that kept everything predictable. “I miss the people, especially those who mentored me,” she says. “And sometimes I miss dressing up for work. These days, I dress comfortably because I mostly work from home. But every now and then, I miss that formal side of things.”

She also misses the security that comes with a steady job; the insurance, the routine, the simplicity of not having to be your own accountant, marketer, and strategist all at once. “But even with all that, I wouldn’t go back,” she says. “I cannot trade my freedom for anything right now. My mental space is so much better. I’m working from passion, not pressure. And that has made all the difference.”

For Allan Owaga, 30, a former senior Apple consultant at an authorised Apple dealership, the transition to self-employment came with its own set of adjustments.

“Yes, there was definitely a drop in income at the start,” he says. “I’d say roughly around 40 to 50 per cent compared to what I was earning while employed. Back then, my income was stable and predictable, but now it’s more project-based, some months are great, others are lean. I used to earn between Sh150,000 and Sh200,000 monthly.”

When business slows down, Allan leans on discipline and planning. “I usually fall back on savings, reduce non-essential spending, and focus on prospecting or retaining existing clients. I’ve also learned to diversify my income streams within the IT space to cushion the dips,” he explains. “The biggest lesson so far? Patience and adaptability. Self-employment teaches you that consistency doesn’t come from a salary, it comes from discipline, relationships, and the ability to keep showing up even when it’s tough.”

For years, Allan worked as a senior Apple consultant at an authorised Apple dealership; a job that, by his own admission, he loved. His work revolved around handling Apple products, managing client support and overseeing system integrations. “I really, really loved what I used to do,” he says. “I also loved the structure. Everything was organised, predictable, and functional.”

Yet beneath that comfort was a quiet restlessness. “Deep down, I always knew I wanted to build something of my own,” he says. “Something that would give me control, flexibility and purpose.” The decision to quit didn’t come from one dramatic moment. It was, as he puts it, “a build-up of small things, occasional occurrences that, over time, made me realise I was growing comfortable, not necessarily growing forward.”

He pauses, then adds, “The salary was good. My clients were good. The organisation had a great structure. But there was nothing more I wanted from there. I was too comfortable. And that scared me.”

Allan’s job consumed most of his time; six days a week with one off day, never on weekends. The schedule left him little room to explore other ideas that were tugging at him. “I had opportunities outside the corporate system that I couldn’t explore while working full-time,” he says. “It became very, very difficult for me to balance both.”

Eventually, he made the call. “It wasn’t because everything was lined up perfectly,” he says. “It was because staying felt like a bigger risk than leaving.”

When he finally quit, there was no elaborate business plan, no guaranteed income, no safety net. “Honestly, I was clueless about what I was going to do,” he admits. “It came from frustration, anger, and the realisation that I was stuck in my comfort zone.” The days that followed were uneasy. “At first, I regretted it,” he says. “I wondered if I’d been reckless. But I had to remind myself that comfort can be a trap. Sometimes, the only way to grow is to leave.”

His family’s response helped him stay grounded. “They took it surprisingly well,” he says. “They were very supportive, which helped a lot. Some friends, not so much. I lost a few along the way and that still hurts, but I also gained new friends and mentors who’ve challenged me to think bigger.”

The transition from a corporate job to self-employment wasn’t smooth. “I was used to structure,” Allan says. “I used to report to work by eight, set up my desk, have clear deliverables and a rhythm, a routine. Suddenly, every day was unpredictable. There was no one to report to, no targets except my own. It was disorienting.”

The hardest part was building a new structure from scratch. “You have to become your own boss, your own HR, your own accountant,” he says. “When you’re employed, clients come to you. When you’re self-employed, you have to hunt, convince, deliver, and retain the client, all at once.”

Financial uncertainty was his biggest fear. “In employment, you know your payday,” he says. “Outside, there’s no guaranteed income. You start wondering how you’ll maintain your lifestyle or pay your bills.” To stay afloat, Allan turned to his savings. “I’ve always been big on saving,” he says. “So I used what I had put aside.”

But what really gave him a push was an unexpected turn, his love for cars. “I’ve always loved building and restoring Mercedes-Benzes,” he says. “One day I posted my car on X, it was fully restored, clean. That post blew up. People started DMing me, asking where to get parts or body kits. That’s when I realised I could actually make something out of it; source parts, give advice, help guys build their cars.”

That small venture became his first source of income outside formal employment. With the little money and encouragement from his family, Allan began building something new, a company called Bell and Cross Investment, an IT firm specialising in system integration, Apple products, security solutions, and tech consultation. “The inspiration came from my background with Apple,” he says. “But also from seeing how many businesses lack proper tech support and systems. I wanted to fix that gap.”

The first months were brutal. “I used to go from office to office, trying to get clients,” he recalls. “It wasn’t easy, especially as a young company. You learn quickly that your title means nothing if no one knows your brand.”

Discipline, he says, became his lifeline. “I had to learn to create structure where none existed,” he says. “To plan my days, manage time, and stay accountable. You have to push yourself, because no one else will.”

Looking back, Allan says entrepreneurship has changed his life, not just professionally but mentally. “It’s given me more freedom,” he says. “But it has also forced me to be more responsible. I have more control over my time and decisions, but I also carry the weight of every outcome. Mentally, it has pushed me to grow sharper, more strategic, and more patient.”

Still, there are things he misses. “Definitely the structure,” he says. “And the consistency, that certainty of a paycheck at the end of the month. I also miss some of my colleagues.”

But what he doesn’t miss are the limits. “In corporate, I couldn’t do other things. My job wouldn’t allow me. Now, I can do whatever I want, whenever I want.”

Before ending the conversation, Allan offers advice for anyone thinking about taking the same leap. “Don’t go blindly like I did,” he says. “Passion isn’t enough. You need a plan, you need savings, and you need a solid support system.” He says. “Before you quit, know your why. Ask yourself: why am I leaving? What will I do next? How will I pay my bills? Am I ready to be stressed out, to be my own accountant, CEO, and secretary all at once?”

He adds, “Entrepreneurship looks exciting from the outside, but it demands resilience, patience, and constant reinvention. So before you leave, sit with it. Talk to your mentors, your family, your friends. Don’t just chase freedom, prepare for it.”

The decision to walk away from a steady job rarely happens overnight. It builds up slowly; through exhaustion, self-doubt, and the quiet desire for something more fulfilling. That mix of emotions, says Anthony Wachira, an award-winning transitions coach and founder of The Influential, is what drives many Kenyans to trade security for self-employment.

He’s seen it countless times, professionals who look “successful” on paper but feel stuck in cycles of stagnation. “The push factors are usually driven by dissatisfaction,” Wachira explains. “You’ll find people who’ve hit a glass ceiling in big corporates where promotions are slow and salary increments don’t match the cost of living.”

Then there are the toxic workplaces, environments clouded by office politics, micromanagement, and a general lack of appreciation. “Some people feel overworked, underpaid, and expected to be on call 24/7. That constant pressure leads to burnout,” he says. “For others, it’s creativity that suffers. They’re bursting with ideas but confined within rigid systems that leave little room for innovation.”

At the same time, there’s a pull, the allure of freedom, flexibility, and meaning. “People want control of their time,” Wachira says. “They want to spend more time with family, avoid the daily commute, and build something that’s truly theirs. For some, it’s legacy, the desire to create something tangible that outlives them, rather than building wealth for faceless corporations.”

But quitting, he cautions, isn’t just a career decision; it’s an emotional one. “At the beginning, there’s euphoria, a feeling of liberation, of taking back control,” he says. “But that quickly gives way to fear and doubt, especially when the paycheck stops coming. The reality of losing stable income, benefits, or even the identity that comes with a job title can hit hard.”

He’s seen clients grapple with loneliness after leaving office life. “You go from a busy, collaborative space to working alone from home or a small co-working area. Suddenly, you miss the tea-break chats and everyday interactions,” he says. “And with that comes imposter syndrome; questioning your abilities, wondering if you were ever as good as you thought.”

Still, Wachira insists that with persistence, things shift. “If you keep going, you start feeling better again, you start accepting the changes, and eventually, you settle into your new season.”

According to him, most people don’t just wake up and quit, they plan their exits. “I’d say about 70 percent of people plan their transitions,” he notes. “But the plan is often triggered by frustration, a denied promotion, a toxic manager, or burnout. Those moments act as tipping points.”

That preparation can take many forms; saving consistently, building a side hustle, or acquiring new skills. “There are those who leave on impulse, of course — they just quit and figure it out as they go,” he adds. “It’s riskier, but sometimes it still works.”

For anyone thinking about leaving, Wachira emphasises timing; and preparation. “You need a financial runway,” he says firmly. “At least six to twelve months of savings to cover rent, school fees, food, everything. Starting a business is hard. You don’t know when it’ll break even, so having that buffer gives you peace of mind.”

He also advises testing your side hustle before taking the plunge. “If it’s already generating 30 to 50 percent of your salary consistently, that’s a good sign,” he says. “And if work stress is manifesting physically, insomnia, hypertension, constant fatigue, that’s your body telling you something.”

But even the most carefully planned transitions come with shocks. “The biggest mistake I see,” Wachira says, “is underestimating the shift from being a specialist to a generalist.”

In corporate life, tasks are defined; in business, you wear every hat. “You’re the accountant, the marketer, the admin, the salesperson, all at once,” he says. “Some people who were used to being in senior positions find that adjustment hard.”

Another common pitfall, he adds, is neglecting networks. “You might have an amazing job but a terrible LinkedIn profile,” he laughs. “Then when you leave, you realise you don’t have a professional network to fall back on.”

And perhaps most importantly: “Don’t burn bridges,” Wachira warns. “Even if you’re leaving in frustration, be professional. Kenya’s corporate world is small. The person you upset today could influence your next opportunity.”

Financial preparedness, he stresses, is the backbone of a smooth transition. “If you’re not financially sound, you’ll panic, take bad clients, or make desperate decisions,” he says. “The economy is tough. Have savings, start small, and reduce your startup costs where you can.”

The psychological shift that follows can be equally demanding. “You lose the structure of office life; the routine, the validation, even the small social moments,” he says. “Successful people create new structures. Treat your new venture like another job. Set working hours, dress for work, designate a workspace, and build new networks. Join business groups, masterminds, co-working spaces. Rebuild your tribe.”

When asked what separates those who thrive from those who falter, Wachira doesn’t hesitate. “Mindset,” he says. “Resilience is everything. You’ll hear many no’s, and you have to keep going. Self-discipline is key — working without supervision. You must be proactive, a solution provider, someone who keeps learning.”

He adds that learning to sell, your product, your service, yourself is non-negotiable. “If you don’t know sales, take a course. You’re the face of your business now.”

To anyone sitting on the fence, uncertain whether to stay or go, Wachira’s advice is simple: “Build a bridge, don’t jump. Start your hustle while still employed. Test it. Get your first clients. See how it feels,” he says. “Ask yourself what’s the worst that could happen if you fail, and what regret you might live with if you never try.”

The post-pandemic years, he observes, have made such decisions more common, especially among younger workers. “The pandemic proved remote work is real,” he says. “People began asking themselves if the daily grind was worth it, the traffic, the stress, the long hours. Many realised life’s too short.”

He believes Gen Zs, in particular, are redefining what work means. “They value purpose over paycheck,” he says. “They’re not as impressed by titles or hierarchies. They want flexibility, mental wellness, and alignment with their values. Some see TikTok, YouTube, and other digital platforms as valid career paths, and they’re making real money.”

That shift, Wachira says, is reshaping Kenya’s work culture. “The idea of leaving a corporate job to start your own thing is becoming more accepted. It’s no longer seen as reckless. It’s a real, valid choice.”

He pauses before adding quietly, “And maybe that’s what this new generation is teaching us, that there’s no single script for success anymore.”

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