The Weirdest Job Interview I’ve Ever Had (And Why I Still Had It)

This community fits perfectly because the story combines personal experience, career decisions, and reflection—all in a real-life, first-person tone.

I’ve had my share of job interviews—some boring, some stressful, some surprisingly smooth. But none of them come close to this.

It started with a job posting that didn’t say much.

“Small creative startup looking for flexible, self-driven person. Must like coffee and chaos. No suits allowed.”

It sounded quirky… but also kind of fake. Still, I was between jobs, curious, and honestly just needed something. So I sent out my resume. No cover letter. Just vibes.

The next day, I got an email:

“Interview tomorrow at 2:00 PM, come as you are, no expectations.”

Okay. Weird.

I showed up in jeans and a hoodie, expecting to walk into a half-empty office. Instead, I was greeted by a barefoot guy named Nolan with wild hair and a big smile.

“You should be Caesar! Want a banana before we start?”

I blinked. “Um... no, thanks?”

He led me to a room with beanbags instead of chairs. There were doodles on the walls and a whiteboard that said “Meetings are lies.” I started to wonder if I’d stumbled into an improv group instead of a company.

Then the “interview” began.

There was no talk of a resume. Not “Tell me about your biggest weakness.”

Instead, Nolan asked me:

“If your creativity had a color, what would it be?”

I laughed nervously. “Oh… forest green?”

He nodded seriously, as if I had just said something profound.

Next:

“When was the last time you broke a rule and were glad you did?”

Okay. Now I was sweating a little.

He didn’t ask about my experience. He didn’t ask where I saw myself in five years. He didn’t even look at my resume. Instead, we talked about failure. About chaos. About books. About the weirdest things I’ve ever done for a job (spoiler: I once wore a chicken suit to a product launch).

It felt less like an interview and more like a personality test being written on the fly by some slightly caffeinated philosopher.

I walked out thinking, what happened?

I thought it was a lost cause. But a few hours later, I got a one-line email:

"You're weird, we're weird, do you want to try being weird together?"

And despite every HR-trained instinct screaming "Go for it!"...

I said yes.

This job turned out to be one of the most creatively fulfilling roles I've ever had. Sure, the first few weeks were messy. There were no job titles, no real hierarchy, and the onboarding process was literally just: "Here's a laptop. Build something."

But I learned more in six months there than I ever did in structured, polished, PowerPoint-filled jobs.

Here’s why I took the job — and why I’m so glad I did:

1. It was refreshingly honest.

In traditional interviews, both sides put on a show. You polish your answers; they pretend their workplace is perfect. But this was raw. Nolan wanted to know who I was, not what I remembered from LinkedIn. And that honesty allowed me to be myself.

2. It challenged my comfort zone.

I’d spent years in buttoned-up roles with dress codes and endless approvals. This place was the opposite. It forced me to think quickly, speak up, and take ownership of my ideas without asking for permission. It was scary — and exactly what I needed.

3. It taught me to trust my gut

Logic told me not to take the job. It paid less. It had no clear career ladder. It had no teeth. But something about that interview — the energy, the openness, the banana — stuck with me. My gut whispered, “This is different. In a good way.”

And it was right.

4. Work became fun again.

I started waking up excited again. Ideas came easier. I laughed more. I felt. I was allowed to be my full, unfiltered self, and that made all the difference.

5. Weird isn’t unprofessional — it’s honest.

This weird interview taught me that sometimes, “weird” is the most authentic. The people and places that dig the script often have the most soul.

I eventually moved on from that job (weird companies sometimes burn bright and fast), but I take the lessons with me everywhere I go. I’ve learned to see past the polish and find the fit. To ask, “Can I thrive here?” instead of “Will this impress anyone?”

And now, when I interview others, I ask questions like:

• What’s something you’re terrible at but love to do anyway?
• If your workday had a soundtrack, what would be the first song?
• What’s your favorite kind of chaos?

Because sometimes, the best people aren’t the ones with the perfect answers.

They’re willing to show the real you — even when it gets weird.