My First Business

Milkiway is my second business. My first venture began almost by accident, around the time of my maternity leave. Borders weren’t fully open yet due to COVID, and many families in Singapore were desperate for transfer helpers.

Before I start the story… I’ve always had this bad habit of monetising my hobbies.

I happened to luck out early on by finding a wonderful helper before my first child was born. She was incredible with kids, baked beautifully, and kept everything spotless. Friends soon started asking me for advice on finding dependable helpers to look after young children or to cook and clean.

What started as casual help quickly became a nightly routine. After dinner, I’d scroll through Facebook groups, cross-reference profiles against the Ministry of Manpower’s database, and spend hours on WhatsApp calls figuring out who was legitimate and who wasn’t. Eventually, I thought: I’m good at building software products—why not build a matching platform for families and helpers?

I sketched out a prototype and hired someone in the Philippines to build it. But the reality was harsh: most helpers struggled with English-based software and preferred to communicate entirely through WhatsApp or Facebook Messenger. In the end, I manually filled out every profile in the database myself. I was constantly scrolling through helpers’ Facebook groups—on the MRT, on the bus, right up until bedtime. It wasn’t healthy, but it was the obsession that kept me going as a first-time founder.

My business partner at the time was a seasoned entrepreneur who knew exactly how much time he could commit. I, on the other hand, threw myself in without boundaries. Pregnancy hormones didn’t help—I was often cranky, and late-night calls left me drained. Still, I learned fast: about MOM policies, domestic worker regulations, and the opaque logistics of bringing helpers into Singapore.

Some of what I discovered was deeply uncomfortable. Helpers sometimes altered their date of birth to remain eligible to work. Renewals involved cash slipped into old passports. Foreign agents would ask for 2–3 months of the helper’s salary as their commission. On top of that, the Indonesian government had a portal to track outbound domestic workers. If your helper wasn’t on the approved list, you couldn’t get them out of Indonesia. It was a system full of grey areas—and I wasn’t comfortable being involved in the parts that weren’t transparent.

Still, I picked up invaluable skills. I learned Google Analytics through a crash course, ran ads, tracked conversions, did competitor analysis, and handled customer complaints (which, in Singapore, will always come no matter what you do). The perfectionist in me wanted everything—every ad, every client interaction—to be flawless. But running a business taught me: good enough is often good enough.

When borders reopened after COVID, demand for remote matching dried up. Ads kept running, costs kept rising, but conversions no longer made sense. I made the painful decision to shut it down.

Looking back, I’m grateful. My business partner gave me the space to explore something outside healthcare and pushed me to make hard decisions on my own. Running a business that’s yours—your idea, your money, your responsibility—sharpens your instincts in a way nothing else does. Every dollar needs to justify itself. That experience shaped how I approached Milkiway when we started, and although we’ve had our share of trials and errors, I’ve been lucky to have a strong team supporting me all the way.

These days, I’m in a much better place. No pointless meetings. No finger-pointing. No rage-writing. Just a life I’m happy to lead, and now, hopefully, the start of a writing habit again—two years post-corporate life.