That philosophy now sits at the heart of Jetsetting with Janet, her weekly travel podcast and lifestyle platform encouraging South Africans to explore their own backyards while uncovering the people, places and experiences that make the country so special.
As South Africa celebrates Women’s Month, Pillai reflects on finding her voice, redefining success, protecting her wellbeing and the women who helped her along the way.
If you had asked Pillai’s younger self what her future would look like, she probably would not have predicted quite this journey.
Growing up in KwaZulu-Natal, Pillai had dreams and ambitions, but no blueprint for becoming an entrepreneur, leader, mentor, tourism advocate and storyteller.
Her career has unfolded one experience at a time, shaped by leadership roles, challenges, opportunities and the people she met along the way.
“I don’t think my younger self could ever have imagined the journey that lay ahead,” she says.
Looking back, she can see one thing connecting it all: curiosity.
“I have always been curious about people, places and stories.”
That curiosity eventually became Jetsetting with Janet, a weekly podcast exploring travel trends, bucket list experiences and hidden gems, while encouraging South Africans to become backyard explorers.
Because sometimes, you really do not need a passport to have an adventure.
When Pillai was younger, being a woman was largely about proving herself. Proving she was capable, that she belonged and that she could achieve.
Today, her definition is much more expansive.
“Womanhood feels much more expansive to me,” she says. “It is about knowing who I am without needing everyone else to validate it.”
For Pillai, strength does not have to mean hardness, and ambition does not have to mean running yourself into the ground.
“I no longer believe I have to choose between being strong and being soft. I can be both.”
It is a perspective that reflects how her understanding of womanhood has evolved over time, from a focus on proving herself to feeling more comfortable in her own identity.
Pillai has built her career in leadership spaces where women have not always been equally represented. There have been moments when she had to find her voice, challenge expectations and establish her credibility.
But she has learnt that finding your voice does not mean being the loudest person in the room.
“Sometimes it means having the courage to say what needs to be said, to ask the difficult question, or simply to stand firmly in your expertise.”
Those experiences taught her not to shrink herself to make other people comfortable. They also shaped her approach to mentorship.
“Once you have fought to find your own seat at the table, you have a responsibility to make sure the table becomes bigger.”
For Pillai, empowering women means creating the opportunities, connections and encouragement that allow them to grow.
Pillai is refreshingly honest about learning to balance ambition with wellbeing.
“For many years, I believed that being capable meant being able to do everything,” she says.
Eventually, she realised that constantly operating at full capacity is not sustainable. Now, she is more intentional about where she invests her energy.
“Saying no is not failure, resting is not laziness and asking for help is not weakness.”
Wellness is no longer something she squeezes into her schedule when everything else is done.
“Wellbeing is no longer something I fit into my life when I have time. It has to be part of the life I am building.”
That shift has also changed her definition of success. Earlier in her career, it was about positions, recognition and milestones. Today, it is about impact and purpose.
“If I can use my experience to create opportunities for someone else, tell a story that deserves to be heard, mentor another woman, build sustainable businesses or create experiences that bring people together, that feels like success to me.”
For Pillai, success is also simply about having “a life that I actually enjoy living.”
Jetsetting with Janet may sound like international flights and glamorous destinations, but Pillai is just as interested in what is happening closer to home.
The weekly podcast explores travel and tourism while showcasing bucket list experiences, hidden gems and the people behind South Africa’s hospitality and tourism industries.
At its heart is a simple idea: South Africans should not have to cross an international border to feel like travellers.
“I wanted to create a platform that says: let’s look again at the places we think we know.”
The platform has grown into a broader luxury lifestyle and travel space bringing together travel, wellness, culture, entrepreneurship and storytelling.
Pillai is particularly fascinated by the people behind a destination: “The entrepreneur, the chef, the winemaker, the artist, the hotelier, the community and the storyteller.”
For her, those stories can transform somewhere from a place you visit into somewhere you connect with.
One of Pillai’s biggest takeaways from travelling through South Africa is that we often overlook what is right in front of us.
“We sometimes become so focused on international travel that we forget what is right on our doorstep.”
From wine regions and coastlines to townships, heritage sites, food experiences and rural communities, she believes there are stories everywhere.
“Travel doesn’t always require a passport. Sometimes it requires a different perspective.”
And that is exactly the curiosity she hopes to inspire.
“There is so much beauty in South Africa, but more importantly, there are extraordinary people whose stories deserve to be discovered.”
Pillai is quick to acknowledge that her journey has never been a solo one.
Throughout her career, she has encountered women who believed in her, challenged her and opened doors before she even realised she was ready to walk through them.
“Those women taught me something very important: you don’t rise alone.”
That lesson now shapes the way she mentors others. For Pillai, empowerment is not simply telling women to be confident. It is creating the circumstances where they can actually grow through opportunities, knowledge, encouragement and sometimes simply hearing, “I see you, and I believe you can do this.”
For Women’s Month, Pillai has one message for women still figuring it all out: do not rush.
In a world of highlight reels and carefully curated success stories, it is easy to feel as though everyone else is ahead. But your journey is uniquely yours.
“Don’t allow someone else’s definition of success to become the measure of your life,” she says.
Find your voice. Own your story. Invest in yourself. Surround yourself with people who see your potential, and do not be afraid to reinvent yourself.
Most importantly, do not wait until you feel completely ready.
“Sometimes confidence comes after you take the step.”
And for every woman still finding her way, Pillai has one final reminder: “Your story matters, your voice matters and there is still so much of your journey left to write.”
