When your job no longer fits: A realistic guide to switching careers

After spending 12 years working in the technology field, riding the highs as head of product was not enough for Tay Jia Ling to continue pursuing a corporate career.

“I was on an unknowing journey of understanding what joy meant to me,” she says. “Like many Singaporeans, climbing the corporate ladder was the thing to do, but when I started to introspect, what I thought was happiness for me was actually not it.

“There are two pillars that bring me joy: opportunity for growth and camaraderie with like-minded people,” the 36-year-old explains.

“I wasn’t growing [in my previous job] anymore, and I wanted to challenge myself in a different way.”

At the end of 2023, Jia Ling gave up her six-figure per annum salary to travel the world, before starting home-based business Curry Kong with her brother, Jia Han, in May last year. While they had never planned to start a business together, the idea was sparked by their parents’ cai png (economy rice) stall in Tampines, which ran for 20 years before closing in 2014.

Citing a gap in the market for old-school flavours, the siblings convinced their parents to join their new curry rice venture. The family whittled 30 dishes from their beloved cai png store down to seven signature ones for curry rice, which includes chicken, mutton, chicken cutlet and pork meatballs.

Jia Ling pauses for a moment, deep in thought, when asked if her new-found business aligns with her pursuit of joy. “Curry Kong does encompass the two pillars that bring me joy,” she muses. “On top of that, I feel like we are losing a lot of these local food flavours. If the next generation can still taste things like that, I will feel like there’s purpose here as well.”

When women think about leaving their jobs

Sabrina Ho, founder and CEO of career platform Half The Sky, believes career switches don’t follow a linear path. While most women think of leaving their long-term jobs in their 30s, they are triggered by specific inflection points, such as leadership changes, stalled progression or shifts in personal priorities.

According to Sabrina, the trigger points for leaving a long-term career typically fall into three key areas: mismatch of values and work stagnation, caregiving responsibilities and, lastly, burnout and toxic environments.

Kamini Manivannan, 33, an English teacher at Trehaus School, remembers experiencing burnout when she was working in a public relations firm nine years ago.

“It was around the two-year mark of the job. I was very stressed out and used to go home late at night. Sometimes, I didn’t go home at all,” she says. “I would shower in the office, change my clothes, and then keep working.

“I asked myself, ‘Is this my life?’ It was vibrant and fun, but it truly hit me when I was home and my mum had to check with me whether I had time to talk. The fact that my mum asked if she was disturbing me turned into a reality check for me.”

Kamini knew that transitioning out of PR and navigating the waters of early childhood education – a sector that her heart led her to – would not be a walk in the park. However, she felt that there was no better time to start from ground zero – and she has not looked back since.

Her love for early childhood education is palpable. “When you work with adults, you never get the same innocence and happiness. It refreshes you, even though you might be having a tiring day,” Kamini shares with a smile. “I would love to eventually be in a position where I can inspire a younger generation of teachers, or whoever wants to be in this industry.”

Financial safety nets to set in place

Finances are often the biggest concern when women leave a stable career to pursue a passion – especially when it comes with a significant pay cut. The decision carries additional weight if they are balancing long-term financial responsibilities, such as supporting family members, contributing to household income, or planning for life milestones such as home ownership.

Serene Chua, private investor and founder of @moneycoachserene, advises single women to have at least six months to a year’s worth of income as a buffer when planning to leave a full-time job. With kids and dependents, she says 12 to 18 months of income is best.

For additional financial security, Serene recommends having different income streams to help with the transition. “Calculate your income and expenses to ensure that there is a positive buffer for peace of mind. Before quitting your job to follow your passion, there should be side income from properties you own, a sound investment portfolio that gives you recurring dividends, perhaps a lucrative side business with shareholder distribution, or freelance work that pays,” she suggests.

The reality of starting over in your career

“When it came to money, I asked myself, ‘How much is enough? What’s the runway I require?’” Jia Ling shares. “Why am I planning for legacy insurance when I don’t have plans to have kids anytime soon?”

After doing some financial projections, Jia Ling realised she had a “comfortable runway”, especially since she has no children to provide for. Still, she erred on the side of caution before she started Curry Kong by ensuring that she was debt-free. Living with her parents was a viable option, so she sold her house and paid off her car loan, knowing she would not draw an income from Curry Kong for the first two years. Any profit made would go straight back to the business.

Her personal goal was also not to touch her savings, which begs the question of how she manages her day-to-day expenses. “It’s not glamorous at all,” Jia Ling reveals. “Jia Han and I wake up early every single day to be Grab drivers in the mornings, in order to buy us time with this venture. I think it would be scary if I saw my savings deplete monthly while on this entrepreneurial journey.”

Kamini took a pay cut of more than 50 per cent when she left PR. She recalls the juggle while studying for her conversion diploma in Early Childhood Care & Education – Teaching, a prerequisite for entering the early childhood industry back then. She would work as an assistant teacher in a preschool in the mornings, while giving English tuition and teaching creative writing classes to earn an income on the side.

Is passion enough to overcome all?

Chasing a passion is not always a bed of roses.

“A common reality check is that external factors do not disappear,” Sabrina states. “Passion paths still come with uncertainty, difficult stakeholders and performance pressure.”

For Dawn Bey, 36, who ran fashion label Minor Miracles from 2019 to 2023, opportunity cost and a change in family circumstances impacted her decision to leave her business in search of stability and flexible working hours.

Minor Miracles was an independent fashion and textile brand known for its bright, hand-designed prints and playful womenswear. “I was so happy doing it,” she reflects. “But when your passion becomes your job and it never stops, it affects all other areas of your life.”

Dawn realised her priorities had shifted when her son, Luke, was born in 2023. “I would try to be present and play with him, but my mind was on the social media calendar for Minor Miracles, for example. My schedule was all over the place, and I knew something had to give, because it was just not working out.”

She started to think about finances differently and the opportunity cost that came with running her own fashion label. “I was making this amount of money, but at the same time, putting in so much work and taking time away from the family. I asked myself: ‘Was it worth it?’” Dawn says.

While she had no regrets with Minor Miracles, she knew it was time to call it quits with her first baby around. Today, Dawn is a senior product designer at European retail company Lidl & Kaufland, where she designs the womenswear collection. It offers her the best of both worlds, as she still finds ways to be creative, yet enjoys the benefits of being a full-time employee. She shares: “Work-life balance is good at my current job, and I get things like health insurance for my family– these little things count!”

Rethinking your next career move

Switching careers or chasing a dream job doesn’t remove the realities of work – most of the time, it just reshapes them. Before walking away, it may be worth asking whether the next opportunity lies not in starting over, but in making the most of where you already are.

“The job market is changing quickly, especially with AI reshaping roles. Even strong candidates are taking longer to land the right opportunity. The more senior you are, the longer the transition tends to take,” Sabrina explains. “Also, test your passion before you commit fully. Today, you can build, validate and even monetise ideas while staying employed. Use evenings or weekends. Use AI tools to accelerate execution. This reduces risk and gives you real data on whether your passion is viable.”

She adds that many professionals underestimate how long it takes to rebuild credibility and networks in a new field. Before calling it quits, she suggests maximising where you are first. This includes tapping into training opportunities, exploring cross-functional projects, and building transferable skills – particularly in AI and digital capabilities – while strengthening networks and your personal brand.

Ultimately, the grass isn’t always greener on the other side. The decision to stay or leave often comes down to personal circumstances – and what works best in each season of life. “Career contentment is about being in an environment that enables you to grow, contribute meaningfully, and operate at your full potential,” Sabrina sums up.