Thinking About What’s Next · Post 6 of 10
The art of finding out without fully committing.
Here is one of the most common patterns we see in people thinking about a career pivot:
They spend months — sometimes years — researching, weighing options, and thinking about making a move. They read articles. They watch YouTube videos. They have long conversations with trusted friends. They make pro-con lists.
And they don’t move.
Not because they’re lazy or fearful, but because they’re trying to solve a problem that cannot be solved from the armchair. They’re trying to think their way to certainty before they act. And certainty, in this context, doesn’t come from thinking. It comes from doing.
The design thinking approach
Bill Burnett and Dave Evans, who teach life design at Stanford, make a distinction that’s worth internalising: there are gravity problems (things you cannot change and must work around) and design problems (things that can be prototyped, tested, and iterated).
Most people treat their career questions as gravity problems — as if the only two options are “stay exactly where I am” or “make a dramatic leap.” The design thinking approach says something different: you don’t have to choose between those two things. You can run a small experiment first.
A prototype is not a plan. It’s a question made physical. It’s a small, bounded action that gives you real data — about the work itself, about your own response to it, about whether you actually want more of it — that no amount of armchair thinking can give you.
What we heard
Across the conversations we had with Singaporeans who successfully navigated pivots, almost none of them described a single decisive leap. What they described, again and again, were small experiments — some deliberate, some almost accidental — that gave them just enough signal to take the next step.
“Something about it inspired me. I said — just give it a try lah. So I went, I signed on for the course.”
— YC, made the switch from IT to pre-school education at 50
She didn’t know it would work out. She tried a small, bounded experiment. It pointed her in a direction aligned to what she desires.
“I applied for a master’s programme at NTU — just because I was so bored at work and wanted to do something. Then by the time the intake started, I’d already landed a new job. The course and the job ended up happening in parallel.”
— N, eventually moved into AI and healthcare policy at 35
Not a plan. A series of curiosity-driven experiments that, in retrospect, formed a coherent trajectory.
How I prototyped my way into coaching
I’ll share my own version of this, because I think it illustrates the sequence well.
Two years before I resigned from my corporate job, I started quietly exploring what a Second Act might look like. One thread that kept coming up: coaching. I’d been managing a team of ten direct reports across four continents, mentoring agency partners, and genuinely enjoying the people side of my work far more than I’d let myself admit.
But I didn’t sign up for a certification. Not yet. I started by searching my company’s Learning Management System for online coaching modules — free, low-commitment, something I could do on a Tuesday evening to see if this was even worth pursuing. It was.
So I signed up for a three-day in-person course. That confirmed something important: I liked what I was learning, but I could also see how much I didn’t know yet. There was a real gap between being a natural at people development and being a skilled coach. That clarity — that honest assessment of the gap — was itself useful data.
I invested in an intermediate programme next. Three rounds of three-day trainings. Not cheap, but proportionate to what I’d already learned about my interest level.
A year before I resigned, I committed to a full certification programme — 100 hours of coaching practice, formal assessment, the real thing. By the time I handed in my notice, my colleagues and network already saw me as a coach. I wasn’t starting from zero. I was continuing something that had already begun.
The whole sequence took two years. It cost real money by the end. But each step was justified by what the previous step had taught me — and none of it required me to leave my job before I was ready.
What a prototype looks like
A prototype can be very small:
An informational interview — one coffee with someone doing the thing you’re curious about. Not a commitment. Just information.
A short course — a weekend, an online module, a community class. Before you enrol in the full programme, test the subject at minimal cost.
A side project — a small version of the thing you want to build. A blog. A pro bono project. A pitch to one client.
A volunteer role — many of the skills and instincts you want to test can be explored in a low-stakes, non-commercial environment first.
The question for each prototype is simple: What did I learn, and does that make me want to go further or pivot?
The irreversibility trap
One of the reasons people avoid starting is the feeling that any action is a commitment — that trying something means you’re on a path you can’t leave. This is almost never true.
A three-day course is reversible. An informational interview is reversible. Even a new job, taken with a clear time horizon in mind, is reversible.
You are more agile than you think. Start there.
A question to sit with
What’s one thing you’ve been thinking about for more than six months — that you haven’t yet tried in any form, however small?
Not: what would it take to fully commit to it?
Just: what would the smallest possible version of trying it look like?
Post 6 of 10 · Thinking About What’s Next
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