Rachael Chew
engineer. eight cities. one question.
Rachael Chew
everything here is something I care about — pick anything up
My Story
my story
about me
buddy AI
the work
Singapore skyline
Mountain drawing
Still life painting
the journey
Mental Health Collective Mental Health Collective community
E-biking in Berlin Buenos Aires eight cities
45
Dear stranger,
I interviewed 150 people in 45 countries about what it means to live well...
a note
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a letter, of sorts —

I've been trying to figure out
how to introduce myself.

The short version is: I'm a software engineer who's lived across eight cities in four years, who cares deeply about building safe AI.
But that doesn't capture it. Not really.
When I was twelve, I watched my mum take her last breath. She was a teacher. At her funeral, everyone wore bright colours because she wanted it to be a celebration. Her former students told me she was the only one who believed in them. That was her gift: not love alone, but the ability to make people feel capable and seen. She fought breast cancer for seven years. She showed me what it means to face any challenge with a bright smile.
Since then, I've carried one question: why did I get to stay? It sounds heavy. But 13 years on, I've transformed this weight into a mission. Since I get this chance to live, I'm going to use my life to make a difference.
Before I knew what I wanted to build, I knew what I wanted to understand. From 16 to 19, I studied philosophy, literature, and geography. Philosophy gave me the question: why do things work this way? Literature gave me the language to sit with answers that aren't clean. Geography gave me the instinct that context shapes everything. How people think. What they value. Who they become. I didn't know it then, but I was building the lens I'd use for everything that came after.
After high school, I took a gap year and tried seven jobs in twelve months. I drafted legal documents at an insolvency firm. I taught literature and English to teenagers. I spent an hour at a special needs school teaching an 18-year-old how to squeeze toothpaste, and I kept thinking: what if the tube was designed for him, not against him? I made a hundred sales calls a day for a startup. At the Ministry of Health, I helped move 40,000 COVID patients through a system held together with spreadsheets and will. Each job was a different answer to the same question: where can I be most useful? And in every single one, I kept hitting the same wall. The information existed. We just couldn't use it.
With four friends, I co-founded Mental Health Collective, Singapore's first nationwide youth mental health initiative. We organised a conference that 3,000 people showed up to. COVID hit halfway through planning. Everyone said cancel. We didn't. But the part I'm proudest of isn't the event. It's the months we spent in rooms with government ministries, working on youth mental health policy. Trying to change the infrastructure, not just the conversation.
That's when it clicked: if I could code, I could multiply the power of human care.
So I learned.
At Minerva, my classroom moved every four months. Buenos Aires, Taipei, San Francisco, Seoul, Hyderabad, Berlin, London. Each city was a lab, and not just for the work. Living in seven cities in four years, four months at a time, gave me something I couldn't have gotten from a textbook: a real-world laboratory for how the brain is shaped by context and culture. I coded in Mandarin with a team in Taipei. I worked alongside cancer researchers in Buenos Aires who showed me that certain Spanish expressions capture things English simply can't, and that the language you think in changes what you're able to think. I shipped features for a hiking app used by 100,000 people. I met a chocolate maker whose biggest dream was a shop in New York. I wrote down how much it would cost. I still have that notebook page. One day I want to fund people with genuine, simple dreams like his.
"The people who'd figured something out weren't chasing credentials. They were obsessed with work that mattered to them, and they would have done it even if no one was watching."
from 150 conversations with changemakers across 45 countries
What I'd actually been circling all along was three questions wearing different clothes. Philosophy asks why. Why do systems fail people. Why do incentives misalign. Why does care not scale. Psychology asks what. What happens in the mind when context shifts, when language changes, when trust is built or broken. Technology asks how. How do you take what you understand and make it work for millions of people whom you will never meet.
I didn't switch from humanities to computer science. I just followed the questions deeper.
And the deepest question I found was this: what happens when the systems we build start shaping how people think? I built an AI evaluation framework to measure where language models tell people what they want to hear instead of what's true. The finding: machines are most sycophantic about the things humans care about most. Values, identity, belief. That finding still keeps me up at night.
This is the work I want to do. Not eventually, but now. Before these systems become something we can't course-correct.
One pattern I've discovered is that I make structure from chaos. I've navigated conversations about Hinduism in Rishikesh, debated the 2023 Argentine election with cancer researchers in Buenos Aires, coordinated calls with engineers and CEOs across six time zones from a coworking space in Berlin. I've created playbooks and triage systems from scratch. I learned Swift and shipped code in a week. I've adapted to new languages, new currencies, new ways coffee is brewed, tuk-tuks in Hyderabad and bikes in London, and I've worked across legal, marketing, operations, engineering. I thrive in chaos. I'll synthesise it.
If you ask me what my superpower is, it's that I can sit across from anyone, physically or through a screen, and understand what they're actually saying. Not the words. The need underneath. And I can use that to move a team toward something none of us could see alone. I don't know what skill category that falls into. But I know it's the thread through everything I build.
The best conversations I've had started with a cold message. This letter is one of those.
— Rachael
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