Navigating Uncertainties

Date: 16 February 2025

The current education system in most developed cities (like Singapore where I grew up) tends to promotes a specific definition of success: secure a stable job with a good income, find a partner, buy a house, have children—and then "live happily ever after." But I wonder if checking these boxes truly leads to happiness. Having been fortunate enough to pursue medical school in the UK and secure a well-paying medical residency in Hong Kong, I was labeled a "success story" of this education system — that is, until I decided to quit my job (1). While there's nothing inherently wrong with this path, it made me question whether a society where everyone follows this prescribed route can maintain its economic growth, which is ultimately fuelled by innovation. More importantly, this prescribed path promises the notion of certainty while fostering conformity and risk aversion. After two decades in this system, imagining — let alone pursuing — alternative paths becomes obscure. And believe me, the challenge of breaking off intensifies when everyone around you clings to this path of supposed "certainty."

Since pivoting into startups, I've faced numerous uncertainties — from finding a compatible co-founder to deciding on an idea. The whole venture is uncertain. This journey has taken several unexpected turns, evolving from creating a patient-facing medical assistant (www.drchan.io) to developing an AI-powered clinical decision support tool for doctors. Even now, I struggle with the uncertainty between returning to clinical work and continuing down this uncharted path, but here are some useful tips and techniques I have derived from spending some time in this deeply uncertain period in my life.

First, try to surround yourself with people who are also in a similar boat with you. I originally underestimated the power of this. As the famous saying goes it takes a whole village to raise a child. From having a whole bunch doctors that I surrounded myself with everyday to now surrounding myself around builders, this transition will take time and be patient, but consistency and persistence in broadening your network will pay off. As for where to start, one might be surprised to find that the weakest ties often lead to the most fresh and unexpected opportunities.

Secondly, think carefully about one’s current situation - visualise and write down one’s career aspirations, financials, health and personal growth. Ask two questions - am I satisfied with where I am? Is this what I want? When you're young and ambitious, you still have a large threshold for risks and so you should take risks! Drifting along passively and assuming problems will solve themselves doesn’t happen, as per Newton’s third law—you need to take action. As for where to start, try many different things, meet people, read books, ask plenty of questions. Take a step back and look at the bigger picture: if you're likely to live for 75 years or more, how much harm could a few years of risk-taking really do?

And thirdly, trust the process. Drawing learnings from my medical experience actually, where most of the times we have diagnostic and treatment uncertainties, and even in times of high-stress. Taking that mentality across, nothing is actually set in stone until you are in your grave I guess, so take many actions, be action-biased and fail, then fail safely as much as possible.

After spending twenty years (from age six to twenty-six) in a system that prizes conformity and risk avoidance, I can honestly say I'm still deeply uncertain about my life decisions. But one thing I can be certain: merely pondering uncertainty won't reduce it—taking action will.

Notes:
(1) HK has one of the highest paying salary of a doctor in the world, as of 2025, where a resident is paid $8000USD per month, with a low tax rates of 17%. To be earning this in your early-mid twenties remains a dream for people in Asian cities.