What my daughter knows that most adults don't
‘You’ve always played to win, not to not lose,’ I reminded my daughter.
For as long as I can remember, that’s how she made decisions.
The decision no one understood
She aced her PSLE and scored enough points to get into the top school in Singapore. But she chose to stay in her affiliated primary school because they offered her a full scholarship into the prestigious IP program — a through-train going direct from secondary school to A levels. Spots reserved for the brightest in the school.
Two years in, she decided she didn’t want an A level diploma. She wanted the IB. Better preparation for the university path she had in mind.
Her friends were skeptical.
‘Are you sure you want to give up your spot and sit for O levels?’
‘Are you confident you’ll score well enough to get into the IB school you want?’
We sat with the principal. Interviewed with several teachers. Got formal approval for her to withdraw from the program.
Afterward, people assumed she’d left because it was too tough. She didn’t correct them. She just went back to class and topped multiple subjects and got on the principal’s list on the O level track.
Choosing by design, not by status
When it came to choosing a school for IB, she bypassed the school everyone assumed she’d pick - the one with the highest status - and chose another for its community and service culture. She applied under Direct School Admission and got in before her O level results were even out.
At her new school, people asked if she’d chosen it because she couldn’t get into the rival school. She decided to play along. Let them think what they wanted. Then walked up on awards day, the student who topped 3 subjects in her level.
She is quietly, completely, herself.
Now we’re approaching her final IB exams and looking at universities. She has her eye on law at a top UK university. Pricey. The school she truly wants doesn’t offer the scholarships. The ones that do aren’t the ones she wants.
I’m telling her to go for what she truly wants anyway. Because based on everything I’ve watched her do, I know she’ll find a way.
What she’s teaching me
I’ve said no to promotions at work. More than once. Roles with more status, more money, more power.
Each time, I said no it wasn’t because I couldn’t do the job. But because I knew exactly what the trade-off would cost. Late nights. After-hours socials. More administration, less of the work I actually love. Less time with my kids. A marriage quietly paying the price.
People don’t always know what to do with that answer. Just like they didn’t know what to do with my daughter opting out of the IP program.
When you say no to something with obvious status, people assume you couldn’t handle it. They rarely consider that you simply wanted something different.
But I still needed the income
Saying no to promotions when you still need to provide for your family isn’t simple. I still needed the money.
That’s exactly why I started building income outside my job. Work I could do in my own hours. A global audience not limited by my time zone or my employer. Full autonomy over what I build and how.
That’s my design. Not the promotion track. Not quitting my job. Something else entirely. Ambition doesn’t have one shape.
A job is part of the strategy. Just not the whole strategy.
What career design actually looks like
It’s not always chasing the next rung. Sometimes it’s knowing which rungs aren’t for you and building something different alongside the ones that are.
My daughter is teaching me that every time she makes a decision most people wouldn’t make.
And it’s exactly what I help women figure out for themselves.
If this resonated
If you’re at a point where the obvious path doesn’t quite fit, but you’re not sure what else is possible, that’s where Career Redesigned comes in. I write every week about what building alongside actually looks like in practice. No hype. No pressure to quit anything. Just a different way to design this. Click the button below to subscribe: