Joan Nabwire Osogo: The Tenacious Bootstrapping Kenyan


Joan Nabwire Osogo’s life was turned upside down one month before she was even born. Her father died and all his assets were seized by his male relatives, forcing her mother to abandon the family home and her comfortable life and move with two small children to a one-room dwelling in the Nairobi slum of Huruma. Although as a child she always dreamt of someone coming to save her from the filth and hopelessness, Osogo knew she could only rely on herself to make this happen.

“Once I got fired from a job and went from being able to provide for myself and my mother to barely having anything to eat and almost becoming homeless. That experience changed me. I realized then the importance of being self-sufficient so that external events don’t dictate whether you can put food on the table or not!”

Thanks to the support and influence of an uncle, Osogo had the unusual opportunity to attend a good school and after graduation, went to Alliance Française to improve her French. While there, she learned of an au pair program in France and applied.


“Although I knew it would be a long time before I would see my family again, at 19 years it was a godsend because the family provided food, accommodation, and a salary. It was my ticket out of Kenya, but I worked hard for it. On my weekends off, I took house-cleaning jobs so I could send money home.”

After 14 months, Osogo set her sights on America and, with her French paperwork in order, got a visa. After a brief stint in New Jersey, Osogo moved to California to live with a step sister where life got hard very fast. It took ten years to get her immigration status in order, during which time she couldn’t attend university or get an office job. She worked the night shift at Denny’s for six years and volunteered for the Obama Campaign for almost a year and a half before she was finally able to enroll in a two-year community college. During that time, Osogo got pregnant and, one month before the baby was born, the father walked away from the relationship.

Osogo with her daughter
Osogo with her daughter

Undeterred, the single-minded woman enrolled in the University of Southern California’s Marshall School of Business with her one-and-a-half-year-old daughter in tow. She found a government program that paid for daycare as long as she stayed in school and maintained good grades, and she received other forms of support.

“It was a blessing because, as a single mother in university, there was no way I could work and go to school full time. I commuted four hours a day, and returned just in time from school to collect my daughter from daycare. I honestly don’t know how I managed because I would almost always not be able to attend school events, do homework with my peers, or just socialize and network.”

“In Kenya, the wealthy advance while the poor hardly ever move forward regardless of their abilities. The goal of Jitahidi Group is to democratize the hiring process by, on the one hand, equipping local youth with the skills and resources they need to excel in their careers and, on the other hand, partnering with companies to give these young people a shot either as interns or entry-level employees.”

During her second year at USC, Osogo approached the career placement office about getting a summer business internship in Kenya. To her surprise, she was told there were no such opportunities and instead she should apply for a fellowship and do volunteer work in the non-profit sector. Osogo was amazed that, despite its diversity and size, the entire African continent was still being viewed as a place not where someone could gain great business experience, but rather a destination to vacation, volunteer, or work for an NGO.

The seed of Jitahidi Group – which translates from Swahili to “pulling yourself up by your bootstraps” – was planted.

“I wanted to change perceptions about doing business in Kenya and working with locals but I knew first I had to address a root cause of these beliefs. The opportunity to get an internship – never mind to work – at a company is beyond the grasp of even the most talented Kenyan youth if they are not connected. In Kenya, the wealthy advance while the poor hardly ever move forward regardless of their abilities. The goal of Jitahidi is to democratize the hiring process by, on the one hand, equipping local youth with the skills and resources they need to excel in their careers and, on the other hand, partnering with companies to give these young people a shot either as interns or entry-level employees.”

Osogo pitched the idea to a few businesses competitions and received such great feedback she decided to take a leap of faith and, after graduation, return to Kenya to give it a go.

“When I think back, it was pretty crazy. I’d spent years getting my papers in order and decided to go ‘home’ where I hardly knew anyone and certainly had no network. I naively walked into several banks thinking that they would give me a loan to grow my business and was surprised at their terms. I don’t think any startup, especially a woman-owned one, would be able to comfortably meet their demands. This suffocates many entrepreneurs and prevents them from pursuing their ideas.” Osogo argues, adding. “But at least rent, food and transport in Nairobi is a lot cheaper than California. And certainly, as a student of entrepreneurship, being my own boss has always been a dream, especially if I can create a legacy for my daughter.”

Korogocho youth
Osogo with youth from Korogocho.

If Jitahidi Group’s core business pillars are career development and recruitment services, the company’s free youth training initiative is the foundation. After winning a pitch competition at WECREATE, Osogo received four months of workspace at the women’s entrepreneurial center where she holds some of the trainings.

“We run workshops on everything from career development, resume writing, and recruitment fairs to how to dress for work and properly network. There are also separate workshops with Kibra Youth and young people in Korogocho, who live in conditions worse than what I experienced in Huruma, and I am hoping to start a mentoring program with my former high school, Pangani Girls. But we have a long way to go. The first time I asked the students to prepare resumes, almost all gave me hand-written versions. I was getting upset that they must be serious if they want employers to consider them. But then young woman explained it would cost about a dollar to type out and print the resume, and they did not have that. At the same time, they can’t find a job. It’s a vicious cycle!”

Osogo is confident of Jitahidi’s success. The Kenyan economy is rapidly growing and numerous multinationals are setting up shop and need trained, mentored, and empowered young employees. Besides, Osogo is determined to succeed.

“I read once that everything that you wish for in life is on the other side of your fears. I already faced mine when I returned to Kenya and put everything I had into Jitahidi Group instead of finding a job. Creating a means to place deserving youth in internships and jobs gives me such purpose. I finally have the chance to help young people like I was – hungry to learn and motivated to succeed – access opportunities where they have a chance to prove themselves. Then it’s just down to the individual and not who he or she knows.”

If you are opening a business in Kenya, contact Jitahidi Group for your intern and employee needs. 

Joan Osogo’s tips for starting up:
  • Never give up, no matter how tough the journey. Start each day afresh and set achievable goals. This helps you put things into perspective and not get overwhelmed.
  • No matter what came before or the rejections you have received, always put on a smile and approach the next client with a positive attitude.
  • Do a lot of research before you launch, it will save you future headaches. For example, think about the fees you have to pay for a reliable law firm to register your business, an accountant to help with the tax returns, the numerous trips that must be made in the notorious traffic. Plan for those financial costs and demands on time.
  • Network, network, network! WECREATE Kenya is a great resource for women entrepreneurs to get training, network and meet mentors.
  • Fail forward! Make a lot of mistakes in the beginning so you don’t have to make them when the business is established. More importantly, make these mistakes early and learn from them. That’s the only way you will grow.

6 thoughts on “Joan Nabwire Osogo: The Tenacious Bootstrapping Kenyan

  1. WAY TO GO JOAN-JITAHIDI!!!Proud of Another mother, Pagarian for paying it Forward, Paying Back to community!!! More Power also for Eastlands determined blood!!!

  2. Very inspiring and exactly what the Kenyan youth needs. Big up my sister and I wish you all the best as you seek to transform this country by engaging its youth in meaningful enterprises

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