Richard is aged 48, single and holds a master's degree in financial management.
Four years ago, the former senior banker lost his $14,000-a -month job. Life has been a long struggle since.
He found work in two small information technology companies. But when the businesses hit a rough patch, he was retrenched.
In between his search for full- time work, he did odd jobs such as washing dishes in a restaurant and distributing flyers.
Flitting from one temporary job to another is typical of many in the growing pool of out-of-work professionals, managers, executives and technicians (PMETs), who are taking longer to find permanent jobs.
Manpower Ministry figures released this week show that, on average, only 47.9 per cent of residents last year got a job within six months of being laid off - the first time in at least seven years that the proportion fell below 50 per cent.
The situation is worse for PMETs and degree holders, whose re-entry rates are 43.9 per cent and 42.5 per cent, respectively.
In addition, 1 per cent of degree holders in the resident labour force were jobless for at least 25 weeks, compared with the overall average of 0.8 per cent.
One of Richard's biggest obstacles is convincing employers that he is willing to work for as little as $3,000 a month, or to take a chance with him despite his lack of experience.
At one job fair, he applied for a caregiver role but was told it required related experience.
"I am willing to adapt, but I feel employers are not willing to adapt. They keep wanting people with the right experience," he said.
Experts say one of the biggest dilemmas facing jobless PMETs is whether to take the first job that comes along even if it is less than ideal, or to wait for a better one.
"Once they fall off a career track, it may be hard to get back on because, if the industry picks up again, employers may see jobs like driving Uber or selling property as irrelevant experience," said Singapore University of Social Sciences labour economist Walter Theseira.
NeXT Career Consulting Group managing director Paul Heng said PMETs need to be alert to technological changes and upgrade their skills in time.
Citing the insurance industry, he noted that technology has made it easier to buy products online instead of through agents.
National Trades Union Congress U PME Centre consultant Loh Peizhen advised people who are unemployed for long periods to keep their skills relevant and to spend time networking.
"Consider doing short-term project work and reconnect with old networks and form new networks," she said.