Beyond corporate life: Why some Singaporeans choose portfolio careers

[SINGAPORE] When finance professional Jason Lee, 51, left corporate banking in 2023 to focus on his grunge rock band, the number of hours he found himself pouring into the various roles he had taken on in place of a full-time job was not insignificant. 

Juggling his music career with lecturing at a polytechnic and running a consultancy can be hectic, but this mix of roles afforded Lee something that a nine-to-five job could not: the flexibility of a portfolio career.  

“The hours are there, but they’re not set in stone,” said Lee, the lead vocalist and guitarist of There Be Wolves, a rock quartet he co-founded in 2017. 

“I had come to a point where I was relatively content in need, and I didn’t want to presume that I had forever left. I figured I needed to do things fulfilling to myself.” 

While music had always been part of his life, stepping away from the corporate world was a game changer, creating space for his two passions: songwriting and teaching.

His current career path has given him greater control over his schedule and – more importantly – the ability to react spontaneously when musical inspiration strikes. 

“You do need that uncluttered mind to sit down and write (music),” he said. 

Shifting perceptions 

Lee is part of a growing wave of professionals who are eschewing the traditional practice of working for a single employer in favour of portfolio careers, with a mix of multiple roles or jobs.

Such careers are gaining traction here: About one-third of Singapore respondents in a 2025 survey by the Association of Chartered Certified Accountants reportedly engaged in employment beyond their main job.

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Julien Salanave, a professor of management practice in entrepreneurship and innovation at Essec Business School, pointed out that conditions in Singapore support the formation of portfolio careers.

He cited the Republic’s “unusually high density of platform-economy infrastructure” and an ageing workforce that needs to keep earning past the traditional retirement age.

Moreover, the government’s policy stance – with initiatives such as SkillsFuture, mid-career programs and its push for working longer – "effectively subsidises” portfolio career formation.

Jaime Lim, managing director of recruitment firm RevUp Consulting, highlighted a “noticeable” rise in portfolio careers in Singapore.

These careers are increasingly being seen not just as temporary arrangements, but also as a more mainstream approach to career development and risk management, she said.

Workforce Singapore (WSG) principal career coach Chris Lau said that historically, holding multiple jobs was considered something borne from necessity rather than choice.

He noted, however, that such perceptions are changing as technology enables a new generation of portfolio careerists to use this form of employment as a vehicle for creativity and entrepreneurship, rather than just a stopgap. 

For one, accessible digital platforms now allow freelancers and consultants to showcase their work and connect with clients globally.

“Online marketplaces, social media marketing, digital payment systems and remote collaboration tools have eliminated traditional barriers that once made portfolio careers logistically challenging and financially risky,” Lau said.

“The Covid-19 pandemic has also accelerated this trend, with many organisations becoming more open to flexible work arrangements and project-based collaborations.”

Greater control and protection

The flexibility of portfolio careers gives individuals more control over their time, allowing them to focus on priorities such as caregiving or passion projects. 

Freelance writer Edward Yong, 48, said that juggling multiple gigs lets him care for his parents – both in their 90s – something that a full-time role would not allow. 

No two days are alike for Yong, whose roster of assorted projects as a voice actor, copy editor, music instructor and Greek and Latin language teacher allow him to accompany his parents to medical appointments that could take three to four hours.

RevUp’s Lim noted that rising costs of living, economic uncertainty and artificial intelligence disruption also spur individuals to diversify their skills and income streams as a means of “career protection”. 

This is because portfolio careers reduce dependence on a single employer and provide “some protection against layoffs or economic downturns”, she said.  

Prof Salanave concurred that trust in the single-employer career was “already eroding” before the Covid-19 pandemic began.

“The pandemic broke whatever (trust) remained for a lot of mid-career professionals in their 30s and 40s, (who) watched senior people get retrenched and concluded that diversifying their employer bases was not less safe than concentrating it,” he said.

Entrepreneur Tan Shi Liang, 38, noted that diversifying income streams spreads risk and creates a “safety net”. 

The founder of two F&B brands also runs his own entrepreneurship consultancy and manages real estate investments. When one venture underperforms, he can lean on another, he said.

On the flip side, Yong pointed out that flexibility and multiple roles can blur the boundaries between work and rest, resulting in a lack of work-life balance.

Other trade-offs of portfolio careers include the lack of workplace benefits, as well as inconsistent income, as revenue from gig work can fluctuate from month to month. 

Can portfolio work meaningfully shape one’s career? 

For early career workers, portfolio careers may offer avenues for personal growth through which they can gain knowledge and skills, broader networks, and traits like adaptability and resilience.   

WSG’s Lau observed that young professionals who have yet to determine their career direction may pursue portfolio careers to explore different options. They can take on different roles to “test the waters” before committing to a field, he said. 

It was through such dabbling in various ventures that Gen Z entrepreneur Edmund Chong, 29, discovered his calling to marketing. 

A string of gigs – from copywriting to a vending machine business and a finance and side-hustle newsletter – led him to establish marketing and creative agency VentureStudio. 

“These different experiences helped me to find what I am passionate about and wanted to focus on,” he said. 

When it comes to future prospects, Lau said that having had a portfolio career can be a “strong asset” for roles that value agility, broad networks and an entrepreneurial spirit.

However, portfolio careerists may be disadvantaged when applying for traditional corporate roles that prioritise deep specialisation. 

Moreover, Prof Salanave said that whether portfolio careers add value to one’s path may depends on whether the accumulated body of work translates into a “distinctive portfolio”, where “each engagement compounds in a certain direction”.

Navigating HR policy   

As portfolio careers gain traction, firms are reshaping their human resources policies and shedding the “traditional expectation of an exclusive full-time employer relationship”, said Lim.

Employers are growing more accepting of side gigs, provided employees disclose external work and avoid conflicts of interest or performance issues, she noted.  

In tandem, companies are increasingly tapping freelancers, contractors and project-based workers to access specialised skills more flexibly. 

“This reflects a broader shift towards ‘portfolio talent’, particularly in knowledge-based industries where companies value specialised expertise on demand,” said Lim.

A portfolio career is not just a lifestyle preference but a “rational individual response to a labour market that has become more portfolio-shaped at the system level”, said Prof Salanave.

“What we call ‘a job’ is just a temporary bundling of tasks that made economic sense within a particular system of work. AI and digital coordination are unbundling these packages faster than at any point I’ve seen in my career,” he said.

“Workers who notice this unbundling early respond by assembling their own bundles across multiple employers, rather than waiting for one employer to do it for them.”