IT worker wants to take a yearlong break from corporate world, asks for advice

Independent Singapore

23-07-2025

SINGAPORE: A local Reddit user who is looking to take a rather lengthy break from work asked for advice on the platform, wondering if anyone could share their experiences if they've taken the same journey.
In a post from earlier this week on r/singaporefi, u/anon_43 wrote he is an IT worker in his 40s and is family's main breadwinner. Their household's total monthly income is S$12,000, and he and his wife have two children, ages 5 and 8.
He went on to say that their household's essential expenses are at S$4,000 a month, and that their HDB flat and car are fully paid. They have S$250,000 to S$300,000 mostly in dividend stocks.
He also described himself as 'a bit jaded from the corporate world' and would like to see if he can do something more fulfilling. At this point, however, as he doesn't know what he is really looking for, he wants to take a yearlong break to 'recharge and reflect.'
Fortunately, his company allows this and he can go back to work with them, but possibly in a different role or team.
Moreover, his family is supportive of his plan.
But since he doesn't want to spend too much of their savings during his break, he's thinking of doing side gigs such as working for Lalamove, and added that he has experience in WordPress site, mobile app dev, creating marketing content such as infographics and doodle animation video.
'Would like to hear from anyone with similar experience who took a break. Can you share your experience? Any regrets? Love to hear any suggestions on how to earn some side income. Thanks, folks!'
A number of commenters on the post, wary of the uncertain job market, were not very encouraging regarding taking such a long break from work.
One asked if the post author can get the guarantee that he'll get his job back after a year in writing, while another suggested he shorten his sabbatical to three months instead of a year.
'Unfortunate reality is that you probably do not have enough to call for FIRE (financial independence, retire early), and 30-40 are your peak earning years. Your skill sets for side hustles are now easily done by AI. Investment is the way to go to be honest, but also to each your own,' one wrote. See also 4 easy steps to bootstrapping your startup brand
Another said he could consider 'upskilling and receive a training allowance up to $3000 per month for selected full-time courses under SkillsFuture.
'I've done the whole sabbatical thing 2x in the past 10 years, always found a corporate job after but found it unfulfilling again, so break again and rinse repeat. I believe there's a term for this now – micro-retirement.'
'I can empathise with OP as the hamster/rat race in Singapore is relentless.
'OP, because you have young kids, try for a sabbatical first. 3-6 months, maybe do some travelling during this time to reframe and reconnect with yourself. If cost is an issue, neighbouring countries are inexpensive,' another wrote.
A Reddit user who urged the post author to plan carefully for his break and the steps after that wrote, 'Pull the trigger with the expectation that there will not be a job after you 'come back' from the sabbatical. That puts your mind to work on considering the question of 'what next'. Your answer will help add clarity to your assessment of your situation.'
However, a commenter in pretty much the same boat encouraged him to go for it.
'Kinda same position as you right now. Sole breadwinner ($14k/month) while my husband is starting up his online business, plus 1 kid. I say forget what people here advise you. As long as your spouse and family members are supportive, then go ahead, as ultimately they will be affected by the situation, not anyone here. If they are not, then rethink it or address their concerns.
'I personally would go down to part-time like 3-day week or half-days, as you'll still earn enough to cover your basic expenses, and spend more time with the kids and be involved in their lives while they are at this age.' /TISG
Read also: 'Is this even legal?': Woman on sabbatical terminated by company after learning she was pregnant