Mr Joe Herman, in his 40s, embarked on a similar journey after getting laid off from his role in a marketing agency in 2018 and going through a demoralising job search.
After sending out around 50 applications with no outcome, he realised that something was not working.
“I had worked across many industries – hospitality, tech, automotive, even journalism – but employers wanted someone with a clear, linear career path, which was tough for mid-career switchers like me.”
This led him to take his own leap of faith.
“Honestly, I got tired of trying to be someone else just to land a job. I kept thinking – why not build something around who I am and what I’m good at?”
That thought became the foundation for his own business – a training and communications consultancy launched in June 2018.
Things were not immediately rosy when he became his own boss – they were just as brutal with cold pitches, no responses and self-doubt.
Then, things shifted when he changed his approach. Instead of purely pitching to clients, he started listening and engaging with them to learn more about their needs.
A father of two, Mr Herman now juggles his business with parenting, having redefined his idea of career success.
“I could work with people I genuinely liked, focus on projects I cared about and still be there for my kids. It wasn’t easy, but it felt right.”
As for Mr Jarieul Wong, 41, the opportunity to start his own business came unexpectedly after he was retrenched from his role as head of communications at an e-commerce firm in December 2022.
What followed were months of exhausting job hunting. Financial concerns loomed, especially with his late mother’s medical needs at the time, and the pressure from his family to find a “proper job” intensified.
Mr Wong, who is not married, said: “I was drawing quite a high salary in my previous job and that became a problem. In some interviews, the main question was, ‘How much of a pay cut are you willing to take’?”
He recalled that some jobs would have required him to take a cut of as much as 25 per cent to 30 per cent.
“Initially, I was firm about not wanting a pay cut, but after months of searching, my stance started to soften. I suspected some employers were hesitant to hire me because they feared I’d leave the moment a higher-paying opportunity came along.”
His break finally came when a Malaysian public relations agency he had previously worked with proposed opening a Singapore office and asked him to lead it. In September 2023, he took the plunge and launched the Singapore branch of IN.Deed Communications.
It has not been easy because he did not draw a salary for much of last year and now runs the business solo, but the job satisfaction justified his decision.
“I get to work from home, care for my ageing dog and pitch for clients I believe in.”
1. RESKILLING TO STAY RELEVANT
Other jobseekers found renewed purpose in entirely different industries, often after significant periods of uncertainty and reflection.
For Mr Mohamed Yatim Abdul Ghani, 54, the transition from head of information technology (IT) at an international school to adjunct lecturer and digital transformation consultant was not immediate – it took him three to four years, lots of effort and a deliberate push to upskill in emerging fields.
He was retrenched in 2018 after a departmental restructure. Although he had sensed it coming, the emotional and financial impact hit hard, especially when he lost tuition benefits for his four children who attended the same international school.
To make ends meet, he became a private-hire car driver for nearly two years.
As job applications went unanswered and household bills mounted, he began to notice that most roles in the technology industry now required skills in artificial intelligence (AI), data analytics or Internet of Things (IoT) – fields that were emerging buzzwords when he was working in IT.
“My experience looked dated. I realised I had to reskill.”
Mr Yatim enrolled in SIT’s postgraduate certificate in data engineering and smart factory in July 2021, attending classes for eight months alongside younger students.
Then, a chance encounter at a job fair with a consulting firm offering technology consulting services led to a contract opportunity – and later, a fractional role as an associate senior consultant, where he helped to translate complex technical solutions into understandable terms for clients.
