Risk Tolerance is Earned

My career journey and the way my parents taught me one of the most important lessons I've learnt to date

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Last month, my 55-year-old Dad quit his job after six months because he was bored.

I’m sure his colleagues thought he was crazy, but he’s been doing this his entire life and taught me a lesson I learnt about three years ago.

My parents left India at 26, landing in a small town outside London with nothing but ambition and each other. I can only imagine how shocking it must’ve been to move from Chennai, where winter meant wearing a cardigan on 30°C days to dealing with snow and black ice, struggling to bike to the next town over, to buy Indian lentils and spices.

They managed to cope with the terrible weather for a few years until I was born, before taking another huge risk to move to the US, where my Dad had a new job opportunity in a bigger market. They lived in Pittsburgh for a couple of years and then moved to Silicon Valley to work for Sun Microsystems through the dot com crash.

Their world tour ended when they moved to Australia with Sun when I was four. While my parents stopped taking big leaps of faith by moving around the world, my Dad continued experimenting with his career, jumping into new roles and pushing himself to explore his curiosity as much as possible.

Through high school and university, I inherited this trait. I unconsciously tested the upper limits of my risk tolerance by following my curiosity. Each year I pursued a new venture that pushed my boundaries from launching Facebook pages in 2012, a tutoring company in 2015, and exploring crypto in 2017.

But when it came to choosing a 'real' career, I took the most risk-averse option possible: a graduate job at a global investment consulting firm managing billions for not-for-profits.

For most of my friends at university, this was the dream: working in a tall tower above the Sydney harbour for a big-name firm. These friends were the smart ones, the ambitious ones, and the ones everyone expected to succeed. Their certainty in going down this path convinced me to think the same.

From twenty floors up, watching the harbour ferries cut white trails through the blue water below, I convinced myself I was set for life.

In the end, my dream only lasted six months. 

Spending every quarter optimising for decimal point level outperformance against a benchmark, creating lengthy PowerPoint decks that would be skimmed in five minutes at best and recommending investments that outperformed their benchmarks by 0.1% drained my ability to dream big and think creatively. I needed to experience the complete opposite - a role where I felt like I could see the tangible results from my work.

My next job was working for a consumer fintech startup as a generalist intern.

On my first day, I was flung into the deep end. By the end of the first week, I’d collaborated with our product designer on UX and our onboarding funnel, started working on formalising a product roadmap and initiated our outbound sales approach. These were all things I'd never done before—and I had six weeks to prove I was worth keeping.

After my first week, I remember catching up with a few uni mates for dinner and telling them about my new job. They looked at me like I’d lost my mind. I had left a job that paid well, to work 80 hours + a week for a startup that had a 0.001% chance of seeing any amount of success. It made no sense to them why I quit. 

To me, taking this job was the only way forward. In the corporate world, I was spending hours of my life adjusting font sizes and aligning textboxes in PowerPoint - a seemingly easy task but something I never quite got the hang of. At the time, taking the risky startup job felt like an easy decision with a potential massive payoff. 

The startup pushed me far outside my comfort zone. 

The highs were intoxicating. Every big marketing push we made resulted in our Slack channel overflowing with new sign-ups. The dopamine rush of seeing the results from my hard work was incredible.

But the lows hit just as hard. I'd hit deep troughs of despair - not great when you have to believe the startup will succeed. I wasn't unhappy in the role, but I had found the upper ceiling to my risk tolerance.

Growing up in a stable environment does something strange to immigrant children. It makes us optimise for more stability. I saw how hard my parents worked and I felt like it was my duty to take the safer path to protect what the family had built.

However going through this experience, my firm belief is that it is my responsibility to aim high and take as much risk as I am comfortable to ensure that I’m working on things that truly matter to me.

In that vein, while I felt jolted by working in a startup, I’m fortunate to work alongside many talented founders as a VC. I’ve had the privilege of working with unicorn founders and experienced mentors. I've made lifelong friends and found work that makes me proud.

Life isn't perfect—some days are slow, and the ecosystem has its frustrations—but I've found my sweet spot between risk and reward. Being recognised in the inaugural Forbes Australia 30Under30 list feels like a quiet validation of the path less travelled (and what prompted this reflection).

None of this would’ve happened if I hadn’t taken a risk. I wasn’t a fit for my graduate job, but I could’ve easily stepped into a similarly stable corporate job.

Risk tolerance is earned through small acts of courage. You don’t need to quit your job tomorrow, but you should push yourself a little bit every day.

It could be as small as taking responsibility for things outside of your comfort zone, talking to people who have made the jumps that you want to make, or joining communities where people are experimenting with new things within your interest areas. From there you can build it up to launching side hustles, or switching jobs and experimenting with your career.

Each small step you take will build your confidence and expand your tolerance. The goal isn’t to take crazy amounts of risk, it’s to push the boundaries of what you’re comfortable with. With that, you'll discover opportunities you never thought possible.

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Abhi