Gen Y Speaks: Success always came easy to me, until a tough job forced me to reckon with failure. Here’s what I learnt

“What do you mean, you don’t know?” 
I stared blankly at my boss, totally lost for words. 
The footnote he was questioning me about stared back at me from the very bottom of a dense document — to some, a small oversight; to me, an indelible hallmark of my latest failure. 
In my defence, it was among hundreds of documents I was typically assigned to read each night — but this was not the first mistake I would make at this particular job, nor would it be the last. 
That particular meeting had been a breaking point of sorts. After it, I sat down at my desk and asked myself, for the very first time in my life: “Am I really that bad at what I do?”
My father is a self-made man who had climbed the corporate ladder to become chief executive of an international company. He’d ingrained in me from a young age that I should aspire to be “a scholar in the classroom, an athlete on the field, and a master in the performance hall”.
I was the typical “model student”, graduating with straight As from secondary school and junior college while holding leadership positions in multiple co-curricular activities — captain of the rugby team; vice-president of debate club; even head prefect. 
At university, I did a double degree in business and law, and took well to both disciplines. I graduated with first-class honours in both my degrees and emerged class valedictorian. 
After a short training period at a local law firm, I was invited to work for the Supreme Court, the highest judicial court in Singapore. Only the top 1 per cent of each law cohort receive such invitations, and as a 25-year-old at the start of his professional journey, I felt extremely honoured. 
I loved everything about the job. My bosses were kind, the work meaningful and fulfilling. I had amazing colleagues, many of whom I remain good friends with today. 
Up until that point, I’d never really had any significant setbacks in my life, aside from a few bumps and hitches. I naively assumed the next phase of my career would be just as smooth-sailing. 
After a few years, I wanted to delve deeper into the world of business. So I left the Supreme Court and joined a Magic Circle firm (the term bestowed on the five most prestigious multi-national law firms headquartered in London).
Going into it, I knew that navigating the jump from public litigation to private corporate work would be difficult — but I saw it as just another challenge which I would successfully tackle. After all, that was what my entire life had set me up to expect, right? 
The reality could not have been further from my imagination. 
Each day in my new job was a struggle in a way I had never experienced before. 
I struggled to pick up a subject in which I’d had almost no prior exposure. While the firm had offered me a title appropriate for my years of practice and assigned me work accordingly, I struggled to keep up with peers and even juniors with more relevant experience.  
I struggled to adjust to a new culture and method of learning. In my previous job, I’d been guided by more experienced seniors; here, I was expected to learn everything by myself on the fly. 
I struggled to relate to my bosses, some of whom had different working styles and priorities than I was used to. 
Nearly two years and a litany of mistakes later, it was clear that I was not doing well in this job. 
Doubt overtook me — so much so that I went on an introspection exercise, calling up five ex-colleagues and close friends, and asking them to tell me what they thought my strengths and weaknesses were. 
Eventually, I had to admit defeat and leave the firm. I was jaded. Tired. Discouraged, and honestly, a little bit lost as to what had happened. 
Two months later, I joined another practice to pursue tech (something I’d always loved). I worked with startups, venture capital funds, and gaming companies.
And, over time, I started to really enjoy what I do again. 
Some things that helped were a genuine interest in the subject matter, a better culture fit, and a more relatable boss — but here’s what really struck me upon starting anew.
It took some time, but it soon dawned on me that I had learnt and grown so much during my years of painful, uncomfortable struggle. The countless nights spent trading sleep for work, the 7.30am meetings (that usually followed a 4am late night), the harsh and sometimes unnecessarily snide remarks. 
Somewhere in the midst of all that struggle, I’d picked up far more than I even realised. Every single mechanism, arrangement, process, and type of agreement — even as I’d been drowning, bit by bit, everything was getting retained in its own way.
Everything I had learnt then helped me to prosper in the next phase of my career. By drowning a bit (or what felt like a lot), I had somehow learnt how to swim. 
Learning something new is always hard. Sometimes, it’s really hard. 
But that first intense period of struggle and discomfort is a necessary first hurdle to getting on track.
Getting in shape? The first 2 km is the worst.
Stamping out bad habits? The first two months are the hardest.
Learning a new language? The first 10 lessons are the most uncomfortable.
But if you keep your head down, and stick to it with perseverance and humility, everything will fall in place. Because failure can really suck — but it can be a great teacher.
I left legal practice in 2022 to start my own tech company in the blockchain and video gaming space. The last two years have felt almost like a repeat of the two years I spent struggling and drowning in that Magic Circle firm. 
The patterns are strikingly similar: Jumping into a new discipline; taking on new tasks and responsibilities for the first time; always feeling like I can’t catch up with everyone else who has more experience. My co-founder and I also made our fair share of mistakes as we built the company from the ground up. 
Don’t get me wrong — I still hate failing. But I now see that failure is an essential part of learning. 
In my new role as a boss, I also find it much easier to empathise with others when mistakes are made. 
As we step into 2024, I find myself armed with a quiet confidence that the hard work, suffering and struggle will prepare me for whatever will come next. 
Our failures don’t have to define us — with the right attitude and perspective, they can become small but valuable footnotes in our stories, enriching the pages with lessons learned and wisdom earned. 
ABOUT THE AUTHOR:
Nathanael Lim, 38, is the co-founder of Avium, a venture-backed gaming creator company with presences in Singapore, Indonesia, Malaysia and Vietnam.