In a panel discussion co-organised by Gen.T and fashion label Boss, three young leaders the meaning of being your own boss
Hear the word “boss” and one of the most familiar images that would appear in people’s minds is that of a well-dressed executive of a successful company. There’s nothing wrong with that depiction of a boss, but it can be limiting.
As society evolves, so has the idea of a boss. In 2023, it has become less tied to an individual’s level of success and wealth, and more to how they choose to live their life.
Read more: Startup founders weigh in on what it takes to be your own boss
For fashion brand Boss, the term is inclusive and reserved for anyone who leads a self-determined life. They are forward-thinking and self-aware, and they define their own rules while inspiring others to realise their own potential.
On May 10, at the chic penthouse ETTA, Gen.T and Boss brought together three young leaders who embody these qualities for an insightful discussion on the topic. Sharing their own fearless yet challenging career stories were Vanessa Paranjothy, who co-founded Freedom Cups, a social enterprise that offers eco-friendly, reusable menstrual products through a buy-one-give-one model; Mediacorp artiste Ayden Sng, who wears multiple hats including actor, model and host; and Vanessa Ho, who leads Project X, one of the few organisations to provide support to sex workers in Singapore.

Above Panellists shared personal stories of burnout, sacrifices and learning on the job
Kicking off the discussion with how they each started in their careers, Parajonthy shared: “[My sisters and I] felt that it was a crime that we’re in the 21st century and 70 percent of the world’s women still have no access to any form of sanitation over their monthly bleeds. So we sat down and thought about why and how we can solve this problem.”
In Sng’s case, consulting was his first job out of school. But in 2019, he made the shift and debuted as an actor. He’s now evolved to become his own personal brand and has a small production house on the side.
For Ho, she was 18 years old when she had her political awakening. She started to read up about culture, law, society and gender, “and that’s when I gained the language I have today to talk about them.” She later sought out a suitable platform to use that language and help others—and found Project X.
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Paranjothy also shared her views on the glamorised image of entrepreneurs today. “Entrepreneurship now is extremely sensationalised and our universities are kind of pushing this idea that it’s extremely sexy to be an entrepreneur. But it’s really a [career that requires] perseverance, grit and resilience. You need a lot of inner resources to keep going. And that, to me, comes from having an external goal, which could be helping women who can’t possibly help themselves.”
For Ho, needing to grow Project X required a “mish-mash” of learning from different people and places. As she candidly shared: “I had to learn how to grow the organisation. And with millennials, we google everything. Every time we ran into a problem, I turned to Google.”
Read more: Super’s Steven Wongsoredjo on why you should dream small before you dream big
She also turned to mentors, but most lessons had to be learnt on the job. And that is because “I do feel, sometimes, that I’m trying to create something slightly different and there aren’t always a lot of models out there.”
There was also a lot of learning on the job for Sng. “Most actors in Singapore don’t go to [acting] school. We kind of get picked off the street and get paid to learn on set,” he shared. “So you’re experiencing many things for the first time. As cliché as it sounds, a lot of it is about faking it till you make it. But you have to be reflective as well; if you’re not doing a good job, what should you be doing to get to that point?”
Paranjothy later also expressed that one of the toughest decisions she’s had to make was deciding to find a job to prop up Freedom Cups during the economic slowdown caused by the pandemic. “For a long time, I thought, oh wow, you must be such a failure that you couldn’t keep this running on your own. But I think being cognizant of the fact that there were external circumstances, you’ve tried your best and you’re not giving up—I essentially have two full-time jobs now… that has been one of the biggest challenges I’ve had to overcome mentally.”
For Ho and Sng, the thinking is that decisions aren’t difficult if they have to be made for the better of their organisation or their own well-being. “As long as you’re always trying to persevere, there aren’t a lot of options. There’s only one option and you just run with it.”
After the discussion, guests continued to mingle and savour cold cuts, sliders and cocktails prepared for the evening until deep into the night.
See more honourees from Singapore on the Gen.T List.
Credits
Photography: Max Chan
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