The man with the most careers

Sim says the school-bus potato episode was seminal. “Afterwards, I think I suffered a serious inferiority complex,” Sim recalls. “I felt that the knowledge I had was shaky. I was always questioning it, and that led me to keep learning different things.” Throughout his banking career, Sim acquired new skills, from graphic design and photography to Japanese, interior design, and sailing.

Those skills “were not directly relevant to my work in banking, but now that I’m doing this portfolio career,” he says, “they’ve become useful.”

The idea behind a portfolio career is simple: work several jobs, instead of just one, to create multiple income streams and achieve what Sim calls the “four wants”: money, meaning, health, and happiness. It’s the logical extension of what many would call a career pivot, where an individual transforms his or her career into an unrelated field, typically in search of greater meaning or freedom—as Sim did when he moved from banking into teaching and training. In both cases, developing varied skills over time plays a critical role.

“Think of becoming a combo specialist,” Sim says, likening a person’s skillsets to a fast-food value meal. “You have the burger as your core specialisation, your fries as your secondary specialisation, and the Coke as your interest. And over time as your experience grows, you might upgrade your Coke—your interest—into your fries, or your secondary specialisation into your core. That makes it much easier to pivot.”

While the burger, fries, and Coke on their own might not amount to much, when combined they become a tantalising talent package, creating win-win value for both employees and businesses alike.

“When I was in banking for Citi, I always volunteered to be the photographer for client or company events, even though it had nothing to do with my job,” Sim says. “I was able to send some good photos and footage to clients, or to sales heads, and they’d be really happy, because a lot of the time, even a professional photographer may not know who to take photos of.”

Building up this variety of skills, however, typically takes a shift in thinking that challenges the fast-paced, objective-oriented Singaporean work culture. “Most of us tend to focus on what’s urgent, but not necessarily what’s important,” Sim says. “The things that are important but not urgent, we tend to put to the side”—things like learning a skill that you might pivot your career, or expand into a portfolio, years later.

“Seven years ago, I wrote my first LinkedIn article,” Sim says. “It had nothing to do with my job; it wasn’t going to give me a promotion or pay increment. But if I didn’t write that first article, I wouldn’t write the others, and I wouldn’t have built up the ideas and writing skills for a book.

“If you want to really make a change, focus on the important but not urgent. By the time it’s urgent, it’s too late.”

Sim advocates companies setting days aside for employees to learn skills they desire, to cultivate the diversity of skills and build the mental-health resilience required to adapt to changing market conditions. Shifting to a portfolio career or pivoting to a new line of work can mean absorbing a significant initial reduction in income and job security. But Sim’s journey demonstrates the rewards of persevering.

Singapore’s so-called “Five Cs”—cash, car, condominium, credit card, and country club—have traditionally defined success in the city-state. To those struggling with the sacrifice required to carry multiple careers, Sim offers an overriding sixth C: contentment.

“Rather than trying to make that money and spend it on holidays or massages or therapy, I might as well earn less and spend the time pursuing my interests—like writing a book,” Sim says. “I get to happiness directly, rather than ‘I get money, then use it to buy happiness’.”