The teenage years are a special place to be. Your heart is like a raw diamond, glistening with fresh dreams and aspirations, full of expectancy and possibility.

But it’s also a time of youthful vulnerability, where you have a great many questions. How to move forward? What’s the best way to get where I want to be? Do I even have what it takes to pursue what I desire?

Many of us out in the working world would’ve loved to be matched with someone older from the field we aspired towards in our younger days. Someone a little further down the road turning back to tell us our passions don’t have to remain pipe dreams. An older girl who could press a bit of courage and inspiration into our palms and uncover their footsteps for us to walk in, should we choose to.

In light of International Women’s Day, we asked some girls between the ages of 13-19 to describe their “future me” – where each teen hoped to be in 10 to 15 years’ time – and linked them up with girls in their 20s who are doing just that.

The catch? In order to gain access to someone who’s been there, done that and didn’t just survive but have thrived, each girl would have to personally interview her living “career match”.

Meet Annabelle, Jolene, Petrine and Tiffany.


is a bubbly 19 year old with a heart for young children, childhood education and the arts. She described her future self as someone involved in the creative arts and helping kids find their strengths and passions through them. We arranged for her to meet Vanessa, 27, who teaches ballet to kids as young as 4 years old.


at just 15 years old, is the youngest of the four girls. She expressed a love for art and illustration but didn’t think she could ever pursue it because entering the art and design industry was not considered a “great” aspiration by her family and friends. We took her to meet Faith, 27, an illustrator and graphic designer who’s been in the business for 7 years.


19, loves fashion and aspires to start her own label one day. Having studied fashion design, she is hoping to further her studies in fashion marketing in hopes of entering the industry. We got her an interview with Rachel, 29, co-founder of Love, Bonito, a fashion brand that’s made waves in Singapore for more than a decade.


19, a young lady with a heart for the elderly, is studying Gerontology so that she can do social work with seniors in the future. She even has dreams of creating a space where seniors can volunteer to help other seniors. We dropped by Khoo Teck Puat Hospital to meet Dorea, 26, a Medical Social Worker from the Geriatric department.


Nervous energy fills in the air as the girls gathered one-by-one to be briefed for their task. “I’ve never interviewed anyone before!” Jolene, the soft-spoken one, is slightly hesitant when we tell her she’s going to be on camera. But she’s still game.

Petrine can barely contain her excitement at getting to meet Rachel. “Do you think I could ask her if I can work at Love, Bonito one day?” We laugh and say we all wish we could work at Love, Bonito one day too. Rachel was even younger than her when she started Love, Bonito in 2006 with a few friends.

Dorea (right) shares her insights on being a Medical Social Worker.

Most of the interviews take place at the workplaces of the older girls. Our first stop is Khoo Teck Puat Hospital, where Dorea has been based for the past 3 years. She hits it off with Tiffany right away, carefully explaining the hospital system and the various facets of elderly social work even before the formal interview starts.

Annabelle (right) chats with Vanessa about life as a ballet teacher.

By the time we have them miked up to get them ready for the camera, the various pairs have already made their introductions and the nerves have settled. Annabelle and Vanessa are seated comfortably on her sofa and chatting like old friends.

Petrine (right) gets advice on the fashion business from Rachel.

Rachel, showing no signs of jet lag despite flying in from a business trip earlier that morning, pops in between her meetings and immediately defuses the tension mounting on Petrine’s side of the interview couch with a smile. “I hope to be like you in the future,” says Petrine. “Or even better,” Rachel interjects.

Faith (left) and Jolene bond over stories of the design industry.

When the cameras start rolling, it’s hard to believe that none of the younger girls have conducted interviews before. Even Jolene is confident and engaging with Faith, having eased into conversation earlier with the equally mild-mannered graphic designer.

The interviews are lighthearted and honest, the older ones sharing their hearts and minds on their journeys so far.

The young interviewers took full liberty in preparing their questions, asking everything they’d always wanted to know about the job. This ranged from “How do I get started in this industry?” to “Did you ever regret doing this?”, ending with words of advice from senior to junior.

Watching two initial strangers in this sisterly exchange is heartwarming, even from the sidelines.

Despite having to take time off their busy schedules to offer us a glimpse behind the scenes, the older ones are more than happy to let us into their offices, headquarters and studios so that the younger girls can see where they work.

“I remember when I was her age and had so many questions but no one to answer them,” Dorea shared with us. “It’s nice to be able to help someone younger find out more about what they are thinking of doing.”

Dorea (right) bringing Tiffany around Khoo Teck Puat Hospital.


We’ve been there. We’ve been 15, 19, young and full of questions. Maybe we are 25 now, or 29 – and maybe still with those same questions and more. But while it’s easy to complain that girls are not empowered enough by society, government or media, perhaps it makes the most sense that we take the initiative and reach back to support those who come after us.

“I didn’t realise that there was so much blood, sweat and tears that went behind building her business,” Petrine reflected. “I have a lot of respect for her.”

Annabelle, who just received her ‘A’ Level results, was hopeful. “It gives me courage to know someone who didn’t have a straight path through life and is still making things work.”

Our youngest interviewer Jolene summed up their experience, saying: “I know now that it’s definitely not going to be easy but at least there are happy things to look forward to.”

Faith (left) showing Jolene some of the projects she is working on.

We don’t need to have all the answers to help fellow women along life’s journey. All we need are our hearts, lessons and stories to share.