Omobolaji Ajibare on Building a Career in Social Media Into a Business

There was a time when Omobolaji Ajibare was looking for a place to learn how to build a career in social media and could not find one that felt made for her.

She was already working in the industry. She had been since she was 19, managing brands, building online communities and helping businesses understand how to communicate with people on the internet. But the resources she encountered did not always answer the questions she actually had. They told people how to enter the industry without necessarily explaining how to navigate it once you were inside.

How do you build a portfolio? How do you find clients? What should you charge? How do you turn a skill into a career that can actually sustain you?

For a young Nigerian woman trying to understand her place in a growing industry, those were not abstract questions. They were the practical questions that determined whether the career she was building could become a real one.

So she began creating the space she could not find.

That decision would eventually become TheSocialMediaOga. But the company came much later. At the beginning, Omobolaji was not thinking about becoming a founder. She was trying to solve a problem she knew personally.

That distinction is important to understanding what she built.

Before there was a company, there was a pattern.

Omobolaji had spent years helping other people make sense of their work. She began working in social media at 19, and alongside her professional career, spent more than a decade volunteering within her church community, first in social media and later in public relations leadership. She learned to work with limited resources, communicate with different audiences, lead people and remain consistent when there was no applause attached to the work.

She did not know then that she was acquiring some of the skills entrepreneurship would eventually demand.

She imagined a more conventional future for herself. A stable career. Progress through the ranks. Perhaps, one day, a leadership role in communications or marketing.

But there were already signs that she was inclined towards building. She was constantly creating systems, teaching what she knew and helping other people find clarity.

The founder did not appear out of nowhere. The company gave structure to something that had already been present in her for years.

The idea became more urgent during a difficult period in her professional life. Omobolaji was working in what she describes as an extremely toxic environment, and although she knew she wanted something different, she did not yet know what that future looked like.

What she did know was that she had been searching for a community that did not exist. Eventually, she stopped waiting for someone else to create it.

She opened a social media page and began sharing what she knew. At first, she did not reveal who she was. She planned to introduce herself when the page reached 1,000 followers.

It reached 2,000 before she revealed her identity.

There is something quietly significant about that moment. People had already decided that what she was saying was useful before they knew who was saying it. The page did not have her reputation to lean on. There was no personal brand carrying it. There was simply the usefulness of the information and the sense of community forming around it.

Reaching 2,000 followers changed what the experiment meant to her.

It told her that the problem was bigger than her.

And then people began asking questions.

How do I become a social media manager? How do I build my portfolio? How do I find clients? How do I price myself? How do I make this a sustainable career?

The messages became evidence that there were many other people trying to navigate the same uncertainty.

At that point, what had begun as personal problem-solving started to feel like responsibility.

She had the experience. People trusted her. She understood the gap because she had stood inside it herself.

The community could become something more.

But building something around expertise creates its own kind of uncertainty. Knowing how to do the work is not the same as knowing how to build a business around the work.

Omobolaji had to learn how to price her knowledge, package her services, decide what belonged in the free community and what should become a paid offering. She had to learn how to communicate her value while becoming increasingly visible herself.

And she was doing much of that while still questioning whether she knew enough.

The early company was not built from a perfect strategy. She created the content, answered questions, developed resources, managed the community and tried to maintain consistency while carrying the other responsibilities of her life.

She was teaching people what she knew while still discovering what she did not know. That could easily have become a reason to wait. Instead, it became part of the education.

Building forced Omobolaji to understand that expertise and certainty are not the same thing.

She could know enough to help someone else while still having more to learn herself. She could become an authority without pretending to have mastered everything. She could build while becoming.

That understanding became even more important when the predictable career she had imagined began falling apart.

In 2019, Omobolaji was fired.

Then COVID came, opportunities became more limited, and finding another job became difficult. At the same time, the community she had built was growing. People were already trusting her knowledge, asking for help and finding opportunities through the space she had created.

The question was no longer whether the community was useful. It was whether she was willing to treat it as something real.

Moving to the United Kingdom added another layer to that decision. Despite her experience, she repeatedly encountered roles where she was told she was overqualified. There is a particular kind of exhaustion that comes from repeatedly asking an institution to recognise what you already know you can do.

Eventually, Omobolaji stopped waiting.

Going all in was not one dramatic act of courage. It was the result of several experiences pointing in the same direction. If organisations were not going to provide the validation or opportunity she had expected from a conventional career, she could no longer make their recognition the condition for her own progress. She began putting her experience, energy and knowledge into the company more deliberately.

But that decision did not make the uncertainty disappear. If anything, it gave the uncertainty somewhere to live.

She was building publicly while privately carrying questions about where she would eventually call home. As an immigrant, professional growth existed alongside uncertainty about her immigration status and future. There were also moments when the digital infrastructure on which her work depended felt frighteningly fragile. Her Gmail was hacked. Her Instagram account went down.

When your audience, work and livelihood exist largely online, losing access to the platforms that hold them can make years of effort feel suddenly vulnerable.

From the outside, people could see consistency. They could see the opportunities and the growing visibility.

They could not see all the questions underneath.

Was the business going to work? Would she be able to stay? Was she capable of carrying everything she had started? What happened if something she had built disappeared

OmoBolaji is unusually honest about the fact that she did not always feel strong.

There were periods when she was scared and overwhelmed. There were moments when she questioned why she had left the more predictable path of computer science for marketing and entrepreneurship. There were seasons when opportunities slowed, platforms changed, content did not perform and the responsibility of building became exhausting.

Sometimes, she thought a conventional career might simply have been easier.

But she also noticed something about doubt that she had not understood before.

Questioning the path did not necessarily mean the path was wrong.

Sometimes it meant the season was difficult.

That distinction allowed her to keep going without needing to manufacture certainty. The work was also forcing her to confront a different kind of gap.

Omobolaji had assumed that being good at the work would make her good at managing people. It did not.

Building a personal brand and serving a community had required one set of abilities. Building a company required another. Roles were not always clear. Expectations sometimes existed in her head instead of being communicated. Delegation could become micromanagement, or she would delegate and then take the work back herself. Caring deeply about the company could not substitute for the systems a growing team needed.

The uncomfortable part was that the problem could not simply be placed on the people around her.

She had to examine her own leadership.

That meant learning to communicate expectations more clearly, give better feedback, recognise when someone was not the right fit and create processes that allowed other people to work without constantly depending on her.

It also meant confronting one of the easiest traps for a founder who has built something from personal expertise: becoming indispensable to everything.

At first, doing everything yourself can feel like commitment. You know the vision. You know the standard. You know how the work should be done.

Eventually, however, the same instinct can become a ceiling. Omobolaji now understands that being needed for everything is not the same as leading well.

The company needs to be able to function beyond her individual capacity. Structure cannot be something that arrives after growth; it is part of making growth possible.

She is still building that structure. She does not describe this as a lesson she has mastered, and that honesty matters.

Founders are often expected to tell stories from the other side of the problem, once the lesson has been neatly absorbed and turned into wisdom.

Omobolaji’s story is more interesting because some of the lessons are still being lived.

She is still becoming more comfortable with leadership. Still learning how to ask for help. Still learning how to separate her identity from the company’s needs. Still learning how to trust her judgment when there is no guarantee that the decision will work.

That last part has changed her understanding of confidence most profoundly. She used to think confidence meant having the answers and being certain of yourself. Now, she sees it differently.

Confidence is being willing to make a decision, take responsibility for it and continue moving even when certainty is unavailable.

That is a very different kind of confidence. It is also the kind that her journey required.

The woman who began the company was accustomed to helping other people communicate their value. Building required her to do the same for herself. She had to learn to price her expertise, negotiate, become visible, take her ideas seriously and stop waiting for somebody else to decide that she was ready.

This matters particularly to the way she thinks about women building businesses.

She has seen how easily women can mistake preparation for readiness. Another qualification. Another course. Another period of learning before finally putting the work forward.

Meanwhile, people with less experience are often willing to ask for the opportunity before they feel completely prepared for it.

Omobolaji does not believe women need to know everything before they begin.

She believes they need to understand the value of what they already know.

That includes knowing when knowledge should be given freely and when it should be paid for. In an industry where women’s ideas, education and emotional labour can easily become expected as free resources, she has learned that generosity without boundaries can become another form of undervaluing yourself.

Her own journey has made her more deliberate about that distinction.

She has spent years giving.

Now she is learning to build something that also recognises the value of the person doing the giving.

And yet, for all the growth, the part of her story she seems most interested in preserving is not what she has accumulated.

It is who she was able to become for someone else. When Omobolaji talks about legacy, she does not begin with recognition. She goes back to the original absence: the woman entering social media who needed guidance, community and practical answers and could not find enough of them.

She remembers what that uncertainty felt like.

Now, someone else can enter the industry and find a starting point she once had to create for herself.

That is why her definition of success reaches beyond the company.

She wants people to be able to look back and know that she genuinely cared. That she used what she had, even when it did not feel like enough. That she kept showing up through doubt, rejection and uncertainty. That her faith remained part of the way she understood the work and the purpose behind it.

And perhaps that is why the sentence she gives to describe what building has taught her carries so much of the story inside it:

“You can become the person you once needed and build the space you once searched for.”

She has done both. But neither is finished. The space continues to evolve. So does the woman responsible for building it.

The person who once thought confidence meant knowing what to do now understands that sometimes it means taking the next step without knowing where it leads. The woman who once expected her career to be shaped by institutions has learned that she can create the structures she once needed. The social media professional who spent years helping other people communicate their value is learning, in public, to recognise and communicate her own.

People may see the consistency now and assume it comes from certainty.

Omobolaji knows better.

Some of the work was done while afraid. Some of it while questioning whether she had chosen correctly. Some of it while not knowing where she would live, whether the company would work or whether she was ready for the next responsibility.

She kept going anyway.

Not because fear disappeared.

Because she learned that courage does not require its disappearance.

It can be as simple as taking the next step.

Then another. And becoming, slowly and sometimes painfully, the woman capable of carrying what you once only hoped someone would build.