In 2017, I made a career move that didn’t make sense on paper.

I went from teaching design at a university to joining DBS as an Employee Journey Design Coach—a role that sounded impressive but was also vague. It involved cultural transformation, change management, and employee experience.

But I wasn’t an HR expert. I wasn’t a change management consultant.

So why did they hire me?

A few months into the role, I asked my hiring manager that exact question. His answer changed the way I saw my career:

“Because your background shows you can handle ambiguity.”

That’s when it clicked.

My career had been all over the place—industrial design, entrepreneurship, teaching, retail design. I had failed, restarted, pivoted. And while I saw that as a messy, non-linear path, he saw something different.

He saw someone who could adapt, translate skills across domains, and navigate uncertainty—exactly what DBS needed for a transformation role.

The surprising truth?

Most hiring managers aren’t looking for a perfect resume. They’re looking for someone who can figure things out.

That’s why I tell my coaching clients: Your unconventional background isn’t a weakness. It’s an advantage—if you position it right.

Here’s how I turned my “random” experiences into a compelling story:

1️⃣ Reframed my career shifts as strengths – Instead of saying, “I jumped between industries,” I positioned it as, “I have a track record of adapting to new challenges and bringing fresh perspectives.”

2️⃣ Connected the dots for the hiring manager – I didn’t assume they’d see how my teaching experience applied to corporate leadership. I spelled it out: “I’ve coached students; I can coach stakeholders.”

3️⃣ Owned my narrative with confidence – Instead of downplaying my unconventional journey, I leaned into it. “I thrive in ambiguity. I’ve built new programs, led change, and taught complex ideas to different audiences.”

The result? A role I wasn’t “qualified” for—on paper.

So if you’ve ever thought, I don’t check all the boxes, flip that mindset.

Hiring managers aren’t just looking for skills. They’re looking for problem solvers. Bridge-builders. People who can navigate the unknown.

That’s you.

If you want help turning your experience into a powerful career story, reply with “narrative” and let’s talk.