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Inspiring Stories

How A Mid-Careerist Started His Career In Tech

Published by: SkillsFuture Singapore

Making a mid-career switch to tech

Learning a completely new discipline is no walk in the park, especially if it involves a mid-career switch. Previously running the business of a fabric design house, former business manager Timothy Tan, who is in his 40s, made the switch to tech by signing up for the SGUnited Mid-Career Pathways Program In Cloud Support And DevOps in 2021.

The nine-month programme comprises a three-month boot camp and a six-month apprenticeship that combines technical training with hands-on projects and activities. Today, he is a full-time Cloud Engineer at AsiaPac Technology, a service solutions provider that offers cloud computing and systems monitoring solutions.

Taking the plunge

Timothy shared that before signing up for the course, every work day felt monotonous. “It was all about fire fighting in the name of getting more money,” he laughed.

Having studied engineering, he always wanted to get back into tech but never felt like there was a right time for it. “As a business person, you’re always looking out for new opportunities and analysing the various options you have at hand,” he said.

During the COVID-19 pandemic, he chanced upon an advertisement on the tech re-skilling programme and was intrigued to find out more. “The pandemic was a definite wake up call for me to take the plunge and chase my dreams in the tech scene.” Timothy eventually decided on the mid-career pathways program with Microsoft as an apprenticeship was included in it.

Back to school after 20 years

Going back to a classroom setting was in Timothy words: “The best feeling ever.” However, he also said that the boot camp - which introduced core technical IT skills like Microsoft Azure and Linux and DevOps essentials was intensive.

“Imagine stepping into a coding class after 20 years!” he said. “The bootcamp was simply state-of-the-art. The latest and greatest in tech was being taught. And it equipped us with everything we needed. In fact, the manager from my apprenticeship was impressed with what we had learnt, and how we were able to execute in just three months!”

It also helped that plenty of his classmates were mid-careerists looking to embark on a new challenge. “Everyone was so accepting, caring and encouraging. We had people from all walks of life learning together: handicapped, young, or old. Despite our differences, we all held hands and progressed together. Even till today, we keep in touch with monthly kopi-chats,” recounts Timothy. 

Picking up industry-relevant experience in an apprenticeship

After his boot camp, Timothy went on a six-month apprenticeship at Standard Chartered where he honed his tech skills with real-world application opportunities.

“The bank was very supportive — they even gave us an extra month of boot camp to equip us with more skills from data science and full-stack. Together, we did a team project within a month and produced a client on-boarding credit card website,” he said.

“When I returned to the team that I was attached to, my boss was very empowering. He didn’t doubt our knowledge and even gave us opportunities to support the team. I could see my Jira ticket (issue and project tracking) increase day by day as I resolved issues — it was very encouraging!”

Searching for a job after graduation

“Job searching is always daunting,” Timothy laughed. “Of course, there were failures and disappointments, but I truly believe that there is a perfect fit for everyone out there.”

After applying to numerous job roles, submitting at least 10 applications every other day, and receiving replies from 15-20 companies, he secured a job as a cloud engineer.

“The director who hired me knew I had only 3 months of tech experience, but he was a supporter of mid-career change,” Timothy said. “He looked past my little tech knowledge and valued the experience and persistence I had that led to this reskilling journey and eventually this role. I was truly lucky that he saw value in me.

“After so many job applications, interviews, and sleepless nights, I am finally in the cloud(s)!”

Enabling a growth mindset

Putting himself in unfamiliar territory was intimidating and Timothy insists that having a growth mindset was important in his journey.

He shared how the bootcamp curriculum played a big part in cultivating not only his hard skills, but also his perspective. “The persistence to fight on even during tough times and being positive can truly make a difference.”

For more stories of individuals who took on the challenge of a mid-career switch, check out this story of how a former journalist decided to become a data analyst at 34 and also a trainee’s reflection of his learning experience with the SGUnited Skills Programme

About the programme


#GetReadySG is a national skills initiative co-created by Microsoft and Generation Singapore, in partnership with Digital Industry Singapore (DISG), Infocomm Media Development Authority (IMDA) and SkillsFuture Singapore (SSG).

SG United Mid-Career Pathways Program – Company Training (SGUP-CT) is a programme targeted at young professionals and mid-career job seekers impacted by the economic consequences of COVID-19, looking to gain in-demand digital skills and chart their careers in technology.

The SG United Mid-Career Pathways Program In Cloud Support And DevOps is a 9-month program that consists of a three-month job-role specific boot camp, delivered in partnership with Temasek Polytechnic, and a six-month paid apprenticeship with an employed partner.

This programme also provides learners with learning pathways that can lead to industry certification by Microsoft. Prior education or work experience in technology is not a requirement to apply for this program.

At the end of the programme, Microsoft and Generation will assist eligible candidates to facilitate job placement opportunities with Microsoft’s partner companies.

About Generation


Generation is a global nonprofit that transforms education to employment systems to prepare, place, and support people into life-changing careers that would otherwise be inaccessible.

The organisation serves a wide range of under-served job seekers in Singapore and is focused on achieving employment outcomes for learners. To date, more than 38,000 people have graduated from Generation programs, which prepare them for meaningful careers in 14 countries. Generation SG is a registered charity in Singapore. 

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Last updated on 31 Mar 2022