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Career Transition

The Moment I Bet on Myself: How I Stopped Waiting to Feel Ready

March 30, 2026
Damilola Pelumi-Kolade

There is a version of this story I could tell cleanly. The one where I did the research, made a plan, and stepped confidently into a new direction. That version is not the true one.

The true one is that I sat on the decision for weeks. I had heard about the program through a community for Black immigrant professionals transitioning into tech. I had read about people who had done it with backgrounds similar to mine. I had no real reason not to try. And yet—signing up felt enormous.

Not because of the coursework or the commitment, but because it meant saying out loud to myself (more than anyone else) that I believed I could do something I had never done before in a space I had no formal claim to. I was not a tech person. I was a makeup artist with a Master's in Forest Economics who had recently moved to Canada and was working a customer service job to keep things together. Tech felt like someone else's lane.

What eventually moved me was not confidence. It was exhaustion. I was tired of circling the decision. Tired of researching without committing. Tired of waiting for a version of myself that felt ready enough.

So I made a plan. Extra shifts at work. Weekend makeup gigs to save up. Cutting back on anything that was not essential. And I signed up.

The certainty came after the decision, not before it. That is the part nobody tells you. You do not wait until you are sure. You move, and the sureness follows.

If you have been sitting on something, waiting for the right moment or the right feeling, I want you to know that the step is the thing. Everything else builds from there.

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Damilola Pelumi-Kolade is a Career Transition Strategist helping professionals transition into BA careers with confidence and clarity.

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