Mr Aik Beng Chia, 50, started his working life 27 years ago as a display artist for the Esprit store at the exact location where Apple Orchard Road now stands.
Now, he will be back, but teaching others about iPhone photography as one of Apple's Red Dot Heroes.
Although a graphic designer by trade, he is famed in the local photography fraternity for his candid street photography work using his iPhone camera. But his photography journey was not "a bed of roses".
His previous passion was illustration. He suffered from depression in 2008 due to "personal reasons". And, overnight, he just gave up his illustration work.
"I had to find an alternative to treat my depression because I was not seeking any medication," he said. So he chose photography as a means to divert his attention whenever he felt "emo".
"I wanted to buy a proper camera system, but it was too expensive back then," said Mr Chia.
Then, a friend reminded him that his iPhone (the first model, which he imported from the US) had a camera. So why not use it instead? And thus began Mr Chia's journey into iPhone street photography.
Mr Chia has used every iteration of the iPhone from the original to his current iPhone 7 Plus.
He feels he has a head start. Back then in 2008, no one would notice when you held a smartphone up to take pictures.
Now, he has to deal with people being defensive whenever he holds up his iPhone.
"The biggest takeaway for the participants will be the tricks that I have learnt all these years," he said. He will not only be touching on how to take photos on the street, but also on the apps to use to edit photos.
"People always say our little red dot is boring. But you need to look closer and observe, and you will see things differently," he said