After graduating university with a teaching degree, Kevin Otieno landed a coveted job teaching high school math in Nairobi that paid Ksh48,000 per month.
On paper, it seemed like the ideal path after getting his qualifications. But within 2 years of teaching, Kevin felt deeply unfulfilled.
The rigid bureaucracy drained his creativity. He yearned to have more autonomy over his time and career.
That’s when Kevin decided to take a leap of faith into the world of freelance design.
Today, just 3 years after quitting teaching, Kevin earns over Ksh200,000 per month working just 15-20 flexible hours weekly as a freelance designer. He gets to travel frequently and enjoy true work-life balance.
Here is an inside look at Kevin’s journey from teaching to building a successful freelance design business that granted him the freedom and income he craved.
Table of Contents
Why He Decided to Leave Teaching
After the first few months as a high school math teacher, the initial excitement of having his own classroom began to fade for Kevin.
The rigid requirements enforced by school administrators quickly drained him. The curriculum was strictly prescribed, leaving little room for creativity.
Kevin felt bored reteaching the same concepts year after year with no ability to innovate. The bureaucracy and school politics also became frustrating over time.
But what truly pushed Kevin over the edge was the awful work-life balance. He worked 12+ hour days between teaching, grading, lesson planning and other administrative duties.
He had little energy left to enjoy life outside school.
Kevin knew he couldn’t sustain this long-term. He yearned for more freedom and flexibility to work and travel.
That’s when he started exploring ways to leverage skills outside the classroom into a location-independent income.
Discovering His Passion for Design
In his free time outside of teaching, Kevin had developed a growing passion for graphic design. He loved spending hours on his laptop learning design programs like Adobe Illustrator and playing around with graphics.
Kevin has always been naturally artistic and creative. He taught himself how to use design software by watching online tutorials and following digital artists on Instagram.
He started taking on occasional side projects for friends and family, designing logos, social media graphics, posters and more.
The delight people took in his designs gave Kevin a rush of fulfillment.
Kevin realized that if he could attract freelance design clients, he might be able to turn his passion into a viable new career path.
This discovery gave him the confidence to take the leap out of teaching.
Building His Portfolio
In order to successfully land clients, Kevin knew he first needed a solid portfolio showcasing his graphic design abilities, even though he was still a beginner.
In the 6 months prior to quitting his teaching job, Kevin treated portfolio building like a part-time job. He designed mock brands, posters, restaurant menus, and apparel graphics.
The key was curating a diverse range of visually stunning design samples targeted to the types of clients he wanted to attract. This included small businesses, nonprofits, social media influencers and more.
Kevin also created profiles on freelance websites like Upwork and Fiverr, using his portfolio to display his abilities.
This gave him a way to apply for gigs prior to going fully independent.
Quitting With No Safety Net
At age 25, Kevin handed in his resignation at the school.
His family thought he was crazy walking away from a stable government salary.
Kevin had no other job lined up and only about 6 months worth of living expenses saved up.
But he was determined to give his side design hustle everything he had.
“It was terrifying giving up the comfort of a paycheck every month. But my desire for freedom and fulfilling work overpowered the fear,” he recalls.
Kevin moved back home with his parents temporarily to minimize expenses. He converted the family living room into a design studio, ready to fully immerse himself in building his freelance business.
Early Client Wins
At first, Kevin struggled to secure clients outside of friends willing to pay for designs. He applied relentlessly for gigs on Upwork but was edged out by designers with fuller portfolios.
To build momentum, Kevin resorted to drastically underpricing his work, charging just $5 for a logo design. This helped him win some initial happy clients and get critical reviews to boost his profile.
He also started directly cold emailing local small business owners, offering very discounted graphic design services. Slowly he started getting bites.
Within 3 months of dedicating himself full-time, Kevin had a handful of regular freelance clients.
This gave him confidence he could rely on design income to sustain himself.
Scaling His Business and Income
As he got better at communicating his value and demonstrating the ROI of good design, Kevin was able to increase his rates over time.
Within 9 months of going freelance, he had grown his monthly income from under $1000 to over $4000 working about 25 hours a week.
Here are the key strategies Kevin credits for growing his business:
- Niching down – He transitioned from general design to specializing in branding, logos, and social media content. This helped him stand out.
- Referrals – Satisfied clients were eager to recommend Kevin to other businesses. Many new clients came from word-of-mouth.
- Raising rates – As he got more advanced skills and reviews, he increased his prices.
- Automating workflows – Using Trello and Asana to schedule projects and streamline design tasks enabled Kevin to take on more clients.
- Subcontracting – He started outsourcing basic tasks like image editing to freelancers so he could focus on more strategic design.
- Recurring revenue streams – Monthly retainers with brands needing frequent content gave Kevin income stability.
Achieving His Dream Lifestyle
Today, 3 years since taking that terrifying leap away from teaching, Kevin is earning over Ksh200,000 per month working just 15-20 hours per week as a freelance designer.
He has been able to achieve his ideal lifestyle goals:
- He sets his own schedule and vacations when he wants.
- He gets to work from coffee shops or co-working spaces, avoiding a daily commute.
- He earns significantly more than his teaching salary.
- He feels deeply fulfilled doing creative work he loves.
- He gets to travel frequently, living as a “digital nomad.”
Kevin has absolutely no regrets. He shares this key advice to others considering a similar leap:
“Build up savings for at least 6 months of expenses. Expect the transition to take 1-2 years to gain momentum. But trust that if you deliver insane value, you can make freelancing work.”
At just 28 years old, Kevin’s story shows that with calculated risk-taking, passion, and perseverance, you can turn design skills into an income and adventurous lifestyle far exceeding traditional professions.
The only limit is how far you’re willing to push outside your comfort zone to achieve work and life on your own terms.