My first decade at work: What went well for me?

It will be my first decade at work in a few months time.

I was lucky to start working when I was 23. I went to the JC route in school. I was also blessed to figure out what I want early on and double down on it to reap compound interest.

If I were to go back to that Jeraldine from a decade ago to show her how life turned out, I think she’d be surprised.

Entering the private sector was not my top choice.

I had very little interest in business despite having an entrepreneur dad.

In JC and University, I studied arts. My world was just humanities, public policy, literature, design, philosophy, history and intellectual discussions about how we can build a better society.

However, I had a really bad break up in university which affected my grades. This meant if I joined the civil service, I would likely be seen as someone of lesser worth.

Journalism was also not for me due to the lack of press freedom in Singapore.

The private sector was my only choice left.

I stepped into this world of capitalism which felt absolutely foreign to me. I was skeptical of corporations. I saw myself as someone who was more suited for the non-profit or government sector.

I did not even know what IPO or Total Addressable Market meant.

I did not know how to use Microsoft Excel and still do not know how to do so.

Money was not a huge motivation for me. 

I recall telling my cousin-in-law who worked in Finance during Chinese New Year about my ideal salary. He looked at me in disbelief.

I never ever dreamt of living in a condo or wanted to own a car.

I felt scared of the stock market and used my Dad’s account to invest for my first few positions.

When I started to fall in love and think about setting down, then I felt money began to be more important to me and started to focus on it.

The transition to working life was not easy.

I missed the intellectual rigour of school. I struggled to adapt to a life where I was doing the same thing every day.

I hated having to report to the office exactly at 9AM and to be flagged out if I arrived at 9:10AM.

I found myself questioning if after 16 years of slogging it out in Singapore’s education system, was I meant to be just an ordinary office worker?

My life is very different today. I am able to invest in private markets. I am doing much better than many people financially. I sell an AI Software that is used for strategy and M&A.

These are a few things I did right:

1.Choosing the right career based on principles, not prestige

Entering the tech sector, not because it was hot or prestigious but because it was aligned to the life I wanted, was one of the best decisions of my life.

Back then, few people cared about tech. There were not as many entry-level roles and opportunities for younger people. The prestigious pathways were consulting, finance, medicine, accounting and law.

I made this decision based on what I wanted in life.

• Innovation: I do not like to work with people who have a traditional mindset. It is really stifling. I had healthy disregard for authority. Non-legacy tech companies have a high concentration of innovative people and a flat hierarchy.
  

• Culture: I wanted to be treated better at work. With lesser supply of workers and a growing demand, this meant companies had an incentive to build better cultures and pay employees better.
  

• Payoff: I realized tech companies required less employees. Due to higher growth and profits, could pay more. In two years from the age of 24 to 26 years old, my salary doubled.

• Stability: I was doing a lot of house visits back then. I felt traumatised to see people retrenched in their 40s with elderly parents and young children to feed. I remember thinking if I were to end up in this state after two decades and how much stress I would be in.
  

• Learning from the best: 99% of my peers were not in tech then. In my NTU cohort, I can only count 2 people who went into the tech industry. One was a really ambitious guy and the other one was me.
  
  I saw my peers who went to USA to study going into this field despite it not being popular back then. Some gave up on their ivy league degrees and scholarship.

2. A lot of self-discovery and quiet contemplation

I dedicated my 20s to a a lot of experimentation: trying new things and learning a broad range of stuff. I spent several years volunteering, doing content creation and attending classes to learn new languages and skills.

I feel like the biggest advantage I have is that I am not a heavy user of technology for entertainment. 

When I was young, my dad was strict about television use. TV was heavily discouraged. I only had a smart phone at university.