Oyindamola Can’t Stop Starting Over

“Starting over” is one of those phrases nobody wants attached to their life because it often feels like another word for failure. It’s as though you tried something, it didn’t work out, and now you’re back at square one, forced to begin again. But your 20s have a way of challenging that idea.

These are your first real years of adulthood. Yet, you’re expected to have it figured out like you have been here before. But starting over doesn’t necessarily equate to failure; sometimes it is attentiveness. You are paying attention to who you are becoming. Few people embody this acute awareness of self better than Oyindamola Odunayo.

Over the years, she has gone from cook to stylist, then interior designer and now brand strategist. At 24, she has become something of a master at the legwork of starting over. If there were a final boss for reinvention, Oyindamola would probably be it.

Looking at her journey, though, it becomes clear that these pivots aren’t driven by indecision but by a stubborn refusal to stay where her heart and creativity no longer belong. And it is not easy because every switch demands courage to be a beginner again. It demands resilience to learn from scratch again. 

For the first edition of Club 20, the 24-year-old reflects on the winding path from dreaming of becoming a nurse as a child to finding her footing as a brand strategist after trying several different careers and why beginning again has become one of her greatest strengths.

When you were younger, what did you genuinely think you’d become? Was there ever a dream job that had nothing to do with where you are today?

I actually thought I was going to be a nurse growing up. It felt like a “safe”, respectable path, the kind of thing everyone around me could picture. But over time, especially once I got closer to the reality of it, I realised I genuinely don’t do well with blood or anything clinical. It wasn’t a slow fade either; it was more of an “oh, absolutely not” moment. Beyond that, though, I never really had one fixed dream job. 

What I always knew, even as a kid, was that I wanted to make money and be able to take care of myself; the specific title or industry mattered less to me than the outcome. That mindset has honestly followed me into adulthood; I’ve never been precious about sticking to one lane if it doesn’t serve me.

Looking back, your career has moved through food, styling, customer service, operations, interior design, and now brand strategy. Were those pivots intentional or were you simply following whatever life put in front of you at the time?

Honestly, I can’t stand being idle or out of work for too long; it does something to me mentally. I genuinely start spiralling if I don’t have something to build or work toward. So looking back, none of these pivots were random, even if they weren’t “planned” in the traditional sense either. They’re all rooted in things I was already doing, like hobbies and skills people around me noticed before I did. 

I cook really well, and growing up, people would actually pay me to cook for events or just for themselves, so at some point I realised, why not turn this into income? Styling happened the same way; my family and friends always came to me to help pick outfits and put looks together, eventually I found an opportunity in that space and took it. So if you map it out, almost every “career” I’ve had started as something informal that people around me validated first, and I just followed that signal.

When you’ve changed careers as many times as you have, did you ever question yourself and wonder if you just couldn’t stick to one thing? How did you navigate that feeling while everyone else appeared to have their lives mapped out?

Yes, honestly, it’s something I think about; there’s a real exhaustion that comes with switching hats that often. You’re constantly relearning systems, proving yourself in new rooms, starting from a slightly lower rung of credibility each time. But there’s also a part of it that’s genuinely fun, because I do excel in each field I step into – I don’t do things halfway. What helps me navigate the self-doubt is being honest with myself about why this is my reality. 

I live in Nigeria, and the truth is, doing just one thing here often doesn’t pay enough to live comfortably, let alone build anything long-term. So multiple income streams and skill sets aren’t a personality quirk for me; they’re survival. I tell myself that once I’m in a country with more economic stability, I’ll have the luxury of choosing one lane, going deep instead of wide, and building seniority in it over time. Until then, I try to see the range as an asset rather than a lack of focus.

Have you ever quit something and then immediately thought, “Wait… what have I just done?” Tell me that story.

I don’t have a moment where I quit and immediately regretted it, but I do have one where

almost took something I knew wasn’t right for me and caught myself just in time. I’d gotten an offer in marketing and gone through the interview process. Right after the interview ended, it hit me that I’m not even much of a talker, and convincing people to buy into a product just isn’t my strength. 

Taking that job would’ve meant forcing myself into a mould that doesn’t fit who I am, and I could already picture how quickly I’d burn out or underperform in a role like that. So instead of a “what have I done?” moment after the fact, it was more of a “let me not do this to myself” moment beforehand which, in hindsight, I think is actually a more useful instinct to have developed over time.

How do you know when it’s time to leave something? Is there a feeling you get, or do you usually wait until life makes the decision for you?

There’s usually a feeling, a kind of fatigue that’s different from normal work stress, more like the environment itself is working against you. But sometimes it’s also circumstantial, not just internal. A good example is interior design. I used to work on projects from the ground up with full creative control, which I loved. But the level of misogyny I dealt with from artisans on site made everything unnecessarily slow and draining; having to fight with senseless men to be taken seriously just to get basic work done wears you down eventually. That’s when I knew it was time to step back. 

It wasn’t that I fell out of love with the work itself; the environment made it unsustainable. And that’s actually part of why I don’t see my exits as final; if a good offer came up in that space again, under better conditions, I’d consider going back.

Now that you’re in brand strategy, does this finally feel like “the one”? What makes this season different from the others?

In a lot of ways, yes, this feels different. I’ve always had an eye for beautiful, intentional things, and what I’ve noticed is that a lot of people and businesses today don’t put real effort into their branding; some don’t even have anything clearly defined; they’re just running on vibes and hoping it sticks. What excites me about brand strategy is being the person who brings that intentionality in by helping someone go from “I have something” to “I have a brand.” I  love when you can look at a business and immediately recognise their identity across everything they touch, their visuals, their tone, their packaging and their online presence. That consistency is what I’m drawn to building for people, and it’s the first career where the work itself feels like an extension of how my brain already works, not something I had to learn to enjoy.

Welcome to Club 20. If everyone in their twenties were gathered in one room and you could play one song that perfectly sums up your 20s so far, what song would it be and why?

Alive by Sia