At 47, Ms Anna Tan has gone through at least five career shifts and worked in sectors as diverse as charity and IT.
Her family and friends have had doubts about her decisions, but that has not stopped her from taking the plunge each time. Neither has she been concerned about being labelled a job hopper.
Instead, she says it is because she dabbled in so many fields and gained so much experience that she is able to run a coaching business, which involves helping people to reach their personal or professional goals.
The Malaysia-born Ms Tan spent most of her working life in London, where she grew up. The Singapore permanent resident, whose late father was Singaporean, moved here five years ago when work opportunities started drying up in Britain. There, she had worked on government and community projects.
She felt she needed a change and took a job here on a four-month contract, to help a local company put its retail arm online.
She found jobs here in project management and change management, fields she had experience in. She has a diploma in leisure and recreation studies and the course included sports coaching.
Last year, the accredited coach co-founded Coaching Go Where, which matches coaches in areas such as life or career coaching with people seeking such services. She also set up Barrage Vision, a change management consultancy.
"I love doing different things every few years. I don't have to play office politics," she says.
Her family members and friends have questioned her, asking, for instance: "Are you sure? You've never done this before."
She feels they were projecting their fears and insecurities onto her.
But when she was mulling over setting up her first company in Britain about 12 years ago, she had support from fellow entrepreneur friends who told her to go for it.
She feels the risks have paid off. "It's because I've changed so much that I had the breadth of experience to set up Coaching Go Where."
She adds that people sometimes underestimate "the power of transferable skills" in changing jobs or even careers.
Mr Douglas Foo, co-chairman of the Tripartite Alliance for Fair and Progressive Employment Practices, says that while not everyone is as comfortable embracing changes in his working life, making career moves in one's 40s is no longer uncommon.
"As the workforce shrinks, employers need to adopt more progressive approaches and mindsets to ensure they attract a diverse pool of talent to maintain a competitive advantage," says Mr Foo, who is also chairman of Sakae Holdings, which owns the Sakae Sushi restaurant chain.
He says employers can enable a smoother transition for staff making a mid-career switch by exploring options such as redesigning their jobs to suit their strengths and tapping programmes and grants available at agencies such as Spring Singapore and the Singapore Workforce Development Agency (WDA).
A WDA spokesman says that since 2007, more than 7,000 professionals, managers, executives and technicians have participated in Professional Conversion Programmes, which help them get skills for new jobs.
These are targeted at a range of industries, such as early childhood care and education, retail, intellectual property and food services.
Older workers considering a career change should prepare well before taking the plunge, say experts.
Ms Woon Peng Ziady, who runs coaching business Chai Coaching, says: "Understand how long you can survive on savings and passive income.
"If you don't have enough, build up your savings first. Be willing to accept a pay cut."
She advises mid-career switchers to consider taking small steps initially, such as joining a course in cooking if one wants to go into the food and beverage industry, or co- investing in a business first.
Ms Jovian Koh, co-founder of ConnectionQ, a coaching and training consultancy, says the preparation is also mental. Middle-aged and older people should do an ego check first, she adds.
"In their own industry, they may have been at a middle or senior level. Now they have to re-establish themselves. It can be hard to establish networks. You have to eat humble pie at times," she says.
"Some people have the mindset that they just want an easier work life. If this is the attitude, they cannot go far - there will always be people more hungry than them."
Ms Peng Ziady says once they have embarked on a new career, they should be mindful to give themselves time to succeed and not have overly high expectations in terms of money and accolades.
Once they overcome the challenges, she adds, the leaps they take can be rewarding.
Some of her clients have found greater meaning in their lives.
She says: "Many people start their career without a direction. When they are in their mid-40s and older, making a switch is like getting a second chance."
As a child, Ms Suguna Tambusamy dreamt of being a nurse, but it was an ambition she fulfilled only last year, when she was 44.
She was drawn to the white uniform, which suggested to her a "pure and noble" profession. She joined the Red Cross as a co-curricular activity in primary school and enjoyed learning first aid.
In secondary school, her housewife mother objected to her career choice because she viewed nursing as "a dirty job" that involved washing people's bodies, says Ms Suguna.
It was when his wife was undergoing treatment for breast cancer that Mr Alan Wong, who had worked 25 years in the retail industry, thought about a career switch.
His wife Jennifer Long, 66, was diagnosed in 2001.
The couple, who have three adult children, went to the National Cancer Centre Singapore frequently for her chemotherapy, radiation, hormone therapy and other forms of treatment, before the disease was declared to be in remission about 10 years later.
A version of this article appeared in the print edition of The Sunday Times on August 28, 2016, with the headline Making a career move in your 40s. Subscribe