She chose fulfilment over the corporate ladder – and ended up more employable for it

A portfolio of meaningful work can look impressive, but how do you turn it into something employers can place, trust and pay for?

It’s a question Joanna Hioe, 35, is sitting with right now. Over the past few years, Joanna has chosen meaning over the corporate ladder – leaving stable roles in research and communications for a fully funded PhD scholarship at the National University of Singapore in disaster management.

Alongside her doctorate, the disaster response researcher has built side projects that began as personal commitments and grew into real work: learning piano for church, then teaching students online across the world; writing, then self-publishing two books; and securing a grant to bring her research into the Filipino fishing community she studies.

Now, as she nears the final stretch of her PhD – with her dissertation defence this month, and a job search soon after – she finds herself grappling with a dilemma familiar to many with portfolio careers: when your work has always been guided by meaning, how do you make it financially sustainable?

“I have the skills: writing, music, research, communication,” she says. “But combining them into a dream role where I can use them seems like a stretch.”

Transitioning from a portfolio career

What many people in Joanna’s situation don’t immediately see is that their diverse experiences aren’t separate, disconnected chapters, says a Workforce Singapore (WSG) career coach.

“Rather than presenting multiple income streams as separate activities, we guide them to identify the common threads and transferable skills that connect their work,” says the career coach.

“Piano teaching, community management, book publishing and grant-funded research may appear unrelated – but together, they demonstrate strong capabilities in communication, self-direction and stakeholder engagement.”

Mapped this way, Joanna’s piano teaching can be presented as curriculum development and adult learning facilitation.

Her books represent product development and project management. Her grant work in the community demonstrates skills in proposal writing, cross-cultural collaboration and stakeholder management.

Instead of “I do many different things”, Joanna’s story becomes simpler and stronger: She has built a track record in communication and community-centred work across different settings.

“We help job seekers like Joanna address the mindset shift required,” the WSG coach says. “Portfolio careers demonstrate valued qualities including time management, independence and ability to create impact across multiple domains – skills highly sought after by employers today.”

The same reframe applies to her doctorate. There’s a common perception that PhD holders are “overqualified” or too specialised, says the career coach, but that is untrue. While being subject matter experts, they are skilled in deep thinking, complex problem analysis and navigating uncertainty.

“We encourage PhD graduates to recognise how their research expertise, writing abilities, teaching experience and creative interests can integrate meaningfully,” says the career coach.

“This holistic approach opens doors to roles in research communications, policy development, programme design, learning and development and purpose-driven community work – many of which provide opportunities for creative expression within professional contexts.”

From exploration to action: Identifying transferable skills

Knowing you have transferable skills is different from understanding what to do with them. This is where many portfolio career builders get stuck in what career coaches call the “exploration phase” – building, testing, developing, but not yet moving toward a defined direction.

WSG’s Polaris programme is designed specifically for individuals in this in-between space.

“Through structured one-to-one coaching, individuals are guided to identify their strengths, values and personality traits through self-assessment tools and practical exercises,” explains the career coach.

“Rather than continuing to explore indefinitely, individuals work through a systematic process that moves them from self-discovery to concrete decision-making.”

For Joanna, Polaris could help answer questions like: Which of her skills are most energising versus draining? What are her non-negotiables around flexibility and creative freedom? What roles exist that she hasn’t considered?

The programme doesn’t force a choice between purpose and financial security. Instead, it helps find roles where these elements reinforce each other.

“We believe that when individuals work in alignment with their core values, they demonstrate greater engagement and performance, which ultimately supports financial stability,” the coach points out.

Marketing yourself professionally

There’s another challenge Joanna is navigating: talking about her work professionally.

“I remember when I had to market my books, it was scary. I already wrote it – I added value. Now I have to tell people and sell it,” recalls Joanna.

For women like Joanna, who have strong skills but feel uncomfortable promoting themselves, it helps to refocus on the value they bring.

“Self-promotion is not about showing off, it’s about helping others understand what you can offer and how you can make a difference,” the coach explains.

“Through our coaching sessions, we guide individuals to uncover the story behind their work: why they created it, who it serves and what problem it solves.”

This also helps to lessen the anxiety.

“Confidence in self-promotion develops gradually through consistent small actions,” the coach adds.

“Whether it’s speaking about your work at networking events, updating your professional profile or sharing a project with your community – having professional guidance alongside can make the whole process feel a lot less daunting.”

Choosing her direction

After defending her dissertation, Joanna will return to Singapore and begin her job search in earnest.

“It can be hard to explain what I do to people,” she says. “Owning my ‘career identity’ – even with the label ‘portfolio career’ – helps me feel like I frame it better.”

She is also thinking more deliberately about what kind of role and work setup would allow her to do her best.

Beyond the job scope itself, that includes the kind of lifestyle she aspires that fits her strengths and personality – including the ability to work across time zones and geographies, which she says energises her.

“In life, you can have a GPS or you can have a compass,” Joanna says. “The GPS tells you exactly where to go. The compass is your general direction. For me, what matters more is the compass.”

For women building portfolio careers, that may be the real shift: not having every step mapped out, but learning how to name the value they already bring – and using that clarity to make the next move with intention.

“There is no single ‘right’ career path anymore,” says the WSG career coach.

“More Singaporeans are shaping careers that grow and change with the seasons of life. With the right guidance and support, it is possible to build a career that is meaningful, flexible and sustainable without having to give up the parts of yourself that matter most.”

In need of career guidance? Explore WSG programmes and services through the herCareer initiative that can help you land a job that suits you.