From career break to job offer: How mum-of-two made her gap work in her favour

The silence after hitting “submit” on dozens of job applications can be deafening. For women returning to work after career breaks, that quiet amplifies the doubts: Am I out of date? Will they see the gap before they see what I can actually do?

Natalina Chan, 35, gets it. After three years in the US supporting her husband’s career while raising two young children, the ex-marketer was ready to restart her own. Six months before returning to Singapore, she began what seemed like a smart, proactive job search.

“I sent out maybe 20 to 30 resumes,” she recalls. “I didn’t get any interviews.”

The silence fed the familiar anxieties. The job search felt isolating too – no one around her was navigating the same thing. “I kept asking myself how long I’d have to keep doing this.”

Things shifted in December 2024, five months after she started. After discovering Workforce Singapore’s (WSG) career matching services online, Natalina connected with a career coach through WSG’s partner, AngusKnight Singapore (AKG Singapore).

Resume strategy: Turn a career gap into a strength

Natalina began her first online coaching session that December, determined to stop the three-year break from becoming the headline in every application.

Her coach recommended three short online classes offered by AKG Singapore, covering resume-building, managing recruiters’ expectations and interview techniques.

He also worked with her one-on-one to tighten her back-to-work narrative – steering her away from explaining the gap and towards what employers actually hire for: skills, outcomes and fit.

“The main advice from my coach was about tailoring and reframing the stories to showcase that my skillsets and experience were relevant for the roles I was applying for,” she says. “I eventually developed two to three stories about picking up certain skillsets specific to the job.”

It is a struggle many returning mothers face, says a WSG career coach. “The most common mistake we see is mothers underestimating their professional value after a career break.

“It often shows up in two ways – they present themselves with less confidence, and they overlook how caregiving experience can translate into professional strengths.”

For example, managing a household can demonstrate planning, prioritisation and problem-solving skills that employers value when backed by concrete examples.

Rather than hiding the break, WSG encourages job seekers to acknowledge it simply and move on quickly to what they bring to the table.

In resumes, they could include a short section – such as “Career Break” or “Professional Development” – stating the reason in a line, then highlighting relevant skills strengthened during that period.

WSG also advises returning job seekers to consider targeted certifications or online learning aligned to the roles they want, to show recruiters that they are keeping up and ready to contribute.

“When returning mothers project confidence in their capabilities and show a clear understanding of the role requirements, they position themselves as viable candidates rather than applicants who need special consideration,” says the WSG career coach.

“The goal is to position a career break as a period of skills development rather than professional stagnation.”

Balancing career and motherhood: How to negotiate flexible working arrangements

Natalina’s career coach from AKG Singapore also prompted her to think through what a sustainable return would look like.

“He asked me how I envisioned spending time at home versus at work,” she says.

That conversation mattered because she had been through burnout. Before leaving Singapore, she had juggled work-from-home demands during the pandemic while caring for her young children, with no clear line between her job and her role as a mother.

Work, as a core part of her identity, made the emotional tug-of-war more painful.

“My maternal instinct was asking me to go [to my baby], but I wanted to be at my laptop. It was suffocating,” Natalina recalls. That experience gave her clarity about what she needed this time around. “Sometimes ambition might be bigger than capacity,” she says.

The WSG career coach adds: “We advise mothers to be transparent about their availability early on, and to show they’ve planned their return thoughtfully – including childcare arrangements and backup plans.

“It helps employers see that flexibility requests come with responsibility and foresight.”

Doing it differently today

By the time Natalina returned to Singapore in January 2025, she had a clearer strategy. Within about two months of applying and networking, she secured a role through a referral and started work in February 2025 as a regional marketing manager at digital rewards platform WOGI.

The transition back came with its own learning curve. “[With] AI [and other new] tools – marketing is very different today. I had to relearn everything,” she says.

What helped, she adds, was that the coach’s support didn’t stop once she signed the offer.

“It’s not just getting the job, it’s about how I return to work,” she says. Her coach continued to check in – not only on practical issues she felt awkward raising at work, but also on how she was coping at home as she settled back into working life.

A year into the role, Natalina says she is more deliberate about where she puts her energy.

“No one should be expected to show up for everything,” she says. “I still have my two kids, and I still want to do great work.”

Returning to work after years as a stay-at-home mom? Explore WSG programmes and services through the herCareer initiative that can help you make your career comeback with confidence.