How to make the mid-career switch you’ve been dreaming about

There are many reasons someone may want to leave not just their job, but their entire industry. “One of the top reasons people want to change their careers is because they’re concerned about the future now that artificial intelligence and automation are starting to play bigger roles in our lives,” says Jonathan O’Brien, Regional Admissions Director for APAC at General Assembly, which offers courses and mentoring specialising in digital marketing and tech.

Some on the other hand, may want to pursue lifelong passions, such as former lawyer-in-training Woo Wai Leong, who won the inaugural season of MasterChef Asia in 2015 and is currently chef-owner of Restaurant Ibid. Regardless of the reasons you’re contemplating a career switch, know you’re not alone.

A 2018 study by online employment solutions provider revealed that 80% of Singaporeans planned to switch their careers. Meanwhile, according to Ministry of Manpower, placements by professional conversion programmes, which re-train mid-career professionals with the skills they need to pivot their careers, have seen a significant rise, increasing six-fold from 810 placements in 2012 to 4,973 in 2018.

But what is a career change like and how do you prepare for one? Woo, along with other career changers, share their experience making the switch, while O’Brien and General Assembly career coach Stefanie Padilla talk about ways to do so successfully.


Lay the groundwork

O’Brien points out that one of the biggest challenges of a job change, especially if it’s mid-career, is the pay cut that accompanies it. Woo, along with three other career changers we spoke to all share in this experience, citing that their new salaries post-switch were at least 30% lower.

O’Brien advises those looking to change their career to plan ahead and ensure that they have the time and resources to do so. This includes being realistic about your financial responsibilities so that you can still maintain financial stability despite the switch.

School teacher Lisa Tay did just this. Prior to leaving a 15-year career in real estate consulting during her late 30s to pursue teaching, she downsized to a smaller apartment. Tay credits the move as part of what helped her continue meeting her financial commitments in spite of the pay cut.

Leverage your existing skills

To ease your transition, Padilla advises identifying the skills that you currently possess and researching roles in your desired industry to see which of those are transferable. “Don’t ever forget your professional experience – the skills you’ve picked up are something you can bank on,” she says.

Engineer-turned-writer Andy Sim took a similar approach by landing a role as a technology writer with HardwareZone, a consumer electronics portal, when he first switched to writing in his 30s. For Sim, being able to tap on knowledge from his previous career helped make his early days in writing less daunting.

Another advantage of leveraging your existing skills is that it can help you avoid starting over at a junior level, says O’Brien, adding that a career coach can be helpful in auditing your skills to uncover the skillsets that are complementary.


Indra Katono, CEO of the Jigger & Pony Group (left) shifted from a career in private equity while chef and restaurateur Woo Wai Leong (right) was a lawyer in training before changing his focus.

Get a taste first

Before making the switch, both career coaches and changers agree that one of the most important things to do is to test the waters of your new industry. Indra Kantono, co-founder and Chief Executive Officer of the Jigger & Pony Group, helped out part-time at Jigger & Pony bar for a year before deciding to leave his career in private equity to join the venture full-time.

Meanwhile, Woo took a similar approach, spending two years prior to establishing Restaurant Ibid working dining gigs to gather experience and learn the dynamics of the industry. However, he caveats that the food and beverage industry’s low barriers to entry were key in letting him dip his toes before diving all in. If you’re unable to work part-time in the field you wish to switch to, he suggests seeking out peers and mentors from the industry to speak with.

Career trial programmes are also designed to help. O’Brien highlights that General Assembly’s free workshops let attendees test out different subjects before making a bigger commitment. He adds that individuals can also make use of online learning resources, such as Coursera and Udemy, which also provide exposure to different fields.

Making the leap

If you’re genuinely considering a career switch, there are a number of programmes available to help you do so, from the Professional Conversion Programme offered by Workforce Singapore to General Assembly’s full- and part-time courses. Certain industries also advertise for mid-career switchers – answering one such advertisement by the Ministry of Education was what set Tay off on her new career in teaching.

Financial support can also be found through the SkillsFuture Mid-Career Enhanced Subsidy programme, which provides assistance for courses for Singaporeans above age 40 looking to re-skill or upskill themselves. On top of this, the recent announcement of an additional $500 top-up of SkillsFuture credit for Singaporeans between 40 to 60 (on top of the broad-based top-up of $500) aims to provide greater support for those looking to change jobs mid-career.

Before you make the leap, understand that switching careers may be one of the hardest things you might do. Sim adjusted to his new profession as a writer within months, while it took Kantono a few years before he was fully comfortable with the breadth of responsibilities he had as CEO.

Woo, therefore, advises fellow career switchers to be kind to themselves. Whether you’re taking on the herculean task of going from employee to employer, or trying to shift industries, challenges are inevitable. Padilla, who works closely with career switchers to support their transition, also points out that the pivoting process comes with its own hurdles, such as rejections and slow progress with your job search.

But O’Brien, who has helped thousands upskill and reskill into the tech industry through his work at General Assembly encourages that a mid-career change is very much possible. “I’ve seen many make the shift with zero prior experience, so don’t discount that there is a pathway.”