Just four months ago, Ms Joyce Soon, 54, put in 18-hour days, juggling a full-time job with caregiving duties.
Then, in a bolt from the blue, the corporate services executive in a multinational logistics firm was retrenched in June.
A month later, her mother Alice Wong - whom she lived with - lost her decade-long battle with dementia. She died in her sleep on July 2, aged 94.
Since then, Ms Soon has sent out dozens of job applications, visited job fairs and been for interviews. But she has had no luck so far.
"It's been a big, big double blow, with both anchors of my life being knocked off at the same time," says the youngest of five children. From having no time for herself for years, she suddenly has all the time in the world. "I really need to find a job."
The O-level diploma holder represents a small but growing number of mostly single, female caregivers who find it increasingly difficult to return to the job market after their loved one dies.
A recent study on informal caregiving here by the Duke-NUS Graduate Medical School found that one in four caregivers here - or potentially at least 50,000 people - have never been married.
Many have to give up jobs to look after loved ones, jeopardising their financial future. Some like Ms Soon get retrenched. And getting back to the job market is hard.
Ms Soon, who worked in the same firm for 15 years, says the company told her she was retrenched because of restructuring.
But she acknowledges that she would leave on the dot at 5.30pm, eager to be back at home taking care of her mum. "I did not want her staying with the maid all day."
In hindsight, she does not know if that caused her to lose her job. She put in a "good day's work", she says. "But I also know that many employers don't like to see employees leaving on time."
Ms Soon returned from Australia to live with her mother when her father died in 1989. "I did not want her to be lonely."
Her three surviving siblings - including a sister who lives in Melbourne - are all in their late 60s. They help financially and drop in when they can, but are getting on in years themselves.
As she watched her mother's heartbreaking journey into physical and cognitive decline, Ms Soon tried her best to keep her "safe, happy and comfortable".
At 7am every day, she would take Madam Wong, who used a wheelchair in her twilight years, for her daily walk in the East Coast Park or to markets and hawker centres in their Bedok neighbourhood.
Evenings were for mother- daughter bonding. Ms Soon would cook for Madam Wong, feed her and watch her favourite crime TV series CSI with her. Sometimes, she would play her favourite Frank Sinatra and Nat King Cole numbers on YouTube. On weekends, she would gather friends and family for a game of mahjong.
"Mum loved variety in her life. Staring at four walls of the house can make anyone depressed."
These days, Ms Soon is trying to ward off loneliness herself as she spends hours scouring the Internet and newspapers for jobs.
The big hurdles, she feels, are her last drawn pay - at $5,800 per month - and three decades' experience. Her previous job involved multitasking: she was in charge of purchasing, liaised with airlines and telcos, and oversaw office renovations and moves, among others. Many of these can be outsourced.
"Besides, who would hire a 50-something when they can get a 20-something at half the salary."
She stresses that she has told prospective employers that she is willing to take a pay cut. But they feel that she would leave the moment someone offered her higher pay.
"I just don't know how to convince them that's not true," she says. "It's very, very frustrating."