She was a young part-time waitress at a cafe, and had just been "promoted" to manage the popular drinks bar - something usually only the full-time staff would be considered for.
That was because the highlight of the now-defunct cafe, Essential Brew at Holland Village, was its tea-infused beverages.
The new responsibility was huge, but Soi 55 owner Rebecca Chiu, then 18, was excited to take it on.
And she made history on her debut - causing the entire kitchen to short-circuit after mishandling a blender on a busy Saturday night.
"The power only came back after about half an hour. I thought I was going to lose my job," Chiu told AsiaOne at her stall at The Cathay.
Fortunately, her boss was "really nice about it" and she continued working at Essential Brew for a few more years while she read law at the National University of Singapore.
It was not her only job.
The 31-year-old was an avid part-timer after completing her A levels at Hwa Chong Junior College up till her university days, because her parents stopped giving her pocket money.
To support herself, she gave tuition and worked several places at once, most of them F&B establishments such as, apart from Essential Brew, Frolick (remember this hugely popular froyo chain in the 2000s?) and The Wine Company.
Like many Singaporeans, Chiu loves food and sees it as a bonding experience for people.
"I always knew that F&B was something that I wanted to do at some point of time," the petite woman said. "That's why I went around to get more experience and see how things run in the real business."
It seems like all the lessons have paid off for Chiu, who credits her entrepreneurial ambitions to her businessman father.
She started Soi 55, known for its Thai milk teas and snacks, in 2014 after realising she couldn't get anything that tasted close to what she had in Bangkok.
The trendy brand started making a profit in less than six months, and currently has three outlets around Singapore.
Of course, Soi 55's success didn't come without challenges. One of them was shortage of labour, which forced Chiu to change her business model.
"I started to rely less heavily on full-time staff and placed more emphasis on part-time and ad hoc workers," she revealed.
This helped her to find and manage new staff more easily, and labour costs were brought down as well.
Chiu discovered she was not the only one facing the labour shortage problem in the F&B industry.
As a "natural progression" from her own experience, Chiu started a second company last year: MyWork Global, an on-demand jobs platform for ad hoc positions.
"If it worked for my business, I think it would work for everyone else's as well and not just in the F&B industry but across many others," Chiu said.
For her, not being able to find enough workers is a "very sad" reason for businesses to wind up especially when they've got everything else done right, and because she knows the blood, sweat and tears behind the glamorous appearance of being your own boss.
Her advice for other budding entrepreneurs?
"If you are doing it just for the money it will be very challenging, and there are some days along the journey that you will find it extremely difficult to get out of bed and get to work. The only thing that will ultimately drive you to do so is passion for your business."