From Businessman to Cloud Engineer


This story is published in collaboration with Generation.

Timothy Tan had been a businessman for so long, he felt like he needed a change. After going through an intensive IT bootcamp, he finally mustered the courage to make a career change.

“I have been stuck with running businesses for over 10 years. Every day felt like a dog chasing its tail, running around in circles and ‘fire fighting’ all in the name of getting more money."

Having studied engineering, he always wanted to get back into the tech scene, but never felt like it was the right time.

“During the pandemic, I saw a Facebook ad of Generation Singapore’s partnership with Microsoft and the government to offer tech reskilling through a 6-month bootcamp and apprenticeship. I took that as a sign that it was finally time.”

He researched for opportunities for a career switch and decided to go for Generation’s program because it also offered an apprenticeship.

Although he found the application somehow intimidating at first, he was thankful that he made it through. “I focused all my energy on getting into the program, and it paid off. I resigned, jumped in, and never looked back,” he said. “The pandemic was definitely a wake-up call for me to take the plunge and chase my dreams.”

School is in

Stepping back into studying was the best feeling ever. "The bootcamp was intensive, but in the best way possible. It was simply state-of-the-art. The latest and greatest in tech was taught to us and it equipped us with everything we needed. In fact, my manager from the apprenticeship was really impressed with what we had learned, and was able to execute projects in just 3 months.”

Timothy also found the bootcamp enjoyable because of the supportive community of his cohort mates. “Everyone was so accepting, caring, and encouraging. We had people from all walks of life learning together—handicapped, young, or old. We held hands and progressed together. Even till today, we keep in touch with monthly kopi-chats.”

The instructor paced the class according to the participants' abilities, and even stayed back to help if there were questions. "The Generation team was incredible too, checking up on us frequently and giving us the encouragement that helped us pull through.”

From client to intern

“I used to be a client of Standard Chartered Bank, and now, I became their apprentice. It never occurred to me that this could happen—it was very cool and eye-opening."

Timothy shared that Standard Chartered was very supportive, even giving them an extra month of bootcamp to equip them with more skills from data science and full-stack. “Together, we did a team project within a month and produced a client onboarding credit card website,” he said.

“My boss was very empowering. He didn’t doubt our knowledge and even gave us opportunities to support the team. With the perspective and growth mindset built-in by Generation, I could see my IT ticket system increase day by day as I resolved issues. It was very encouraging.”

Timothy's mentor, Mathur Sunil, gave him tailored and relevant advice at every stage of his journey. “He is very experienced. As we progressed to the apprenticeship stage, his mentorship method changed too, and encouraged us to learn the role instead.”

Daunting job search

“Job searching is always daunting and interviews can be scary. Nevertheless, I applied that fighting spirit taught to us. Of course, there were failures and disappointments, but I truly believe that there is a perfect fit for everyone.”

After applying for hundreds of roles, Timothy managed to score a cloud engineer role 3 months after his apprenticeship.

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

“After so many job applications, interviews, and sleepless nights, I am finally in the cloud(s). I now have a job opportunity and it’s the best-case scenario that I could ever have anticipated.”

Having a growth mindset is very essential as well as having the persistence to fight on even during tough times, Timothy said of his experience. "Choosing your attitude even in difficulties, and staying positive, can truly make a difference.”

This article was first published by Generation.