High heels & helidecks: confessions of a helicopter boss lady Part 1

Let me set the scene: It’s 0600 and I’m walking toward a helicopter, headset in one hand, checklist in the other, full flight uniform on. A rig worker squints at me and says, “Wait, you the pilot?”

I smile. “Nope. I just dress like this to hand out snacks. The actual pilot’s inside my makeup case.” 

Welcome to offshore oil and gas aviation - where the platforms are swaying, the winds are howling, and the assumptions about women are stuck somewhere in 1953.

From Couch Flights to Cockpit Rights

Like many women in aviation, I started young - leaping off furniture with a bedsheet parachute and turning my mother’s living room into a personal wind tunnel. (She’s fine now. Mostly.)

Instead, I took to the skies and landed squarely in one of the most intense and male-dominated sectors of aviation: offshore oil and gas. It’s one of the toughest, most male-saturated corners of the aviation world, where the landings are hard, the cargo is grumpy, and everyone assumes the woman on the manifest is a typo.

If you’ve never landed a helicopter on a swaying metal dot in the middle of a restless ocean,surrounded by drilling rigs and very surprised men, let me tell you—it builds character. And calves.

“That Time of the Month” and the First Slap in the Face

I wish I could say my journey into aviation started with open doors and warm welcomes. But truth be told, it started with a slap in the face.

I was 19 years old, bright-eyed, freshly trained, and showing up to my first interview with a flight bag full of dreams. I was nervous, yes, but proud. I had worked hard. I was ready.

The interviewer, a seasoned male captain, smiled at me across the desk and said, “You know, you won’t be able to fly during that time of the month.”

That. Time. Of. The. Month.

Cue record scratch.

I blink. Smile politely. Fight every Caribbean instinct not to leap across the desk.

Because apparently, menstrual cycles now feature in flight risk assessments?

I froze. My brain scrambled to process whether I had accidentally walked into a 1950s sitcom. He said it like it was a biological fact, like I might spontaneously ditch the aircraft and spiral into a chocolate-fuelled emotional breakdown at 3,000 feet.

It was insulting. It was ignorant. It was so far from acceptable, I didn’t even know how to respond.

I left that room in shock. Angry. Embarrassed. And crystal clear on one thing: I was entering a boys’ club with the door barely cracked - and I’d need to kick it open in heels.

So I walked forward.

Three years later, I landed my first job – Trinidad and Tobago’s first female helicopter pilot. Not because anyone handed it to me. But because I kept showing up, training harder, and proving, without apology, that I deserved to fly.

Passed Over, Then Levelled Up

Years into my career, after building seniority and logging thousands of flight hours, I was again passed over - this time for a leadership position at my first helicopter company even with years of seniority. Years of proven performance.

Let me repeat that, for those nodding knowingly in the back: passed over. Despite experience. Despite qualifications. Despite having logged more hours than some of the guys making the decisions.

No explanation. No feedback. Just…overlooked.

So I did what any self-respecting woman with altitude and attitude would do: I left.

And I didn’t just leave -I levelled up. I walked away from the company that wouldn’t promote me—and walked straight into another page of history, becoming the first female Chief Pilot of an aviation organisation in Trinidad and Tobago.

I became the Chief Pilot of Trinidad and Tobago’s national Search and Rescue (SAR) unit, where I wasn’t just flying into storms, I was leading from the front, directing operations, building teams, and ensuring no one ever asked a young woman about her menstrual cycle in an interview on my watch.

You don’t just survive in this space - you lead it. And occasionally do it in lip gloss and steel-toe boots.

Leading Like a Woman (aka: Calm, Capable, and Occasionally Sarcastic)

Leadership, it turns out, doesn’t require a loud voice or a five o’clock shadow. It requires presence. Clarity. Courage. And a flight bag full of emotional intelligence.

I led flight operations with compassion, conviction, and just enough dry wit to keep morale high in hurricane season. I didn’t pretend to be one of the guys. I showed up fully as myself: precise, firm,empathetic, and always prepared.

I also brought a soft skillset into a hard environment and it worked. Turns out, compassion and competence make an unbeatable flight plan.

Eventually, I moved into my current role as a Flight Operations Inspector for the Government of Trinidad and Tobago. That means I’ve swapped the helmet for a blazer (most days) and now oversee aviation safety, regulations, and operational standards at the national level. But then again I didn’t just walk away from the cockpit - I left two trained, confident, flying female helicopter pilots behind me.

That’s not just career success. That’s changing the skyline.

Culture Shift: The Real Altitude Adjustment

Let’s not sugar-coat it: if aviation culture doesn’t change, talented women will keep walking out.

Here’s the truth no one writes in the POH (Pilot Operating Handbook): If we want women to stay, grow, and thrive in aviation, we don’t just need better opportunities - we need better cultures.

Because women don’t burn out from flying - we burn out from being ignored, overlooked, overworked, and under-promoted. Organisations must do more than post about diversity. They need to live it.

That means:

Zero tolerance for casual bias (or biology-based nonsense).

Career paths that don’t dead-end at “you’re not the right look.”

Actual leadership development programs that include women…and advance them.

When you stop seeing women as “exceptions,” you start seeing the future of flight.

To be continued... Or read part 2 right now