On the afternoon of 29th January, I rang my boss, told her of my intention to resign, and proceeded to send an email titled “Thanks Everyone!” to all my colleagues.

I have decided to take a risk and pivot into writing full-time about investing.

The decision to take the plunge into self-employment isn’t an easy one, and it is definitely scary. I’m fully aware that this road will be tougher and that I will be “eating grass” for quite some time.

Minimizing Regrets

In my email to my colleagues, I shared about a framework I picked up from Jeff Bezos, CEO of Amazon.

Bezos uses a helpful mental model for approaching tough life decisions—the Regret Minimization Framework.

Bezos imagined that he was 80 and asked himself if he would look back and regret not trying to start an online book store back in 1994—something that didn’t exist at a time when many hadn’t even heard of the internet.

He was a successful investment banker back then and his boss said, “You know what, Jeff, I think this is a good idea, but it would be a better idea for somebody who didn’t already have a good job.”

Bezos made the decision with his heart and not his head and the rest is history.

When I’m 80 and reflecting back, I want to have minimized the number of regrets that I have had in my life. We may think that our regrets stem from errors of commission, but in reality, most of our regrets are acts of omission—the things we didn’t try, the risks we didn’t take, or the paths we didn’t travel. Those are the things that haunt us.

This framework helps me think beyond the moment. It helps me look past all the fears and doubts that may be holding me back and assess things with a different perspective.

When thinking from a longer-term perspective, my fears and doubts appear miniscule in the grand scheme of things. With a 20-year time horizon, we make decisions in a very different way.

A Gift from Our Past

Everything we own is simply a gift—our awards, our academic achievements, and our job titles.

It is a gift that your past self is giving to your present self, and it’s up to you to decide whether to accept that gift.

You owe your past self nothing, other than to consider whether these gifts are helpful today.

It’s easy to focus on the gifts you own today. You’ve spent effort to come this far. Throwing it all away on a mid-career leap just seems too costly an endeavour.

But there’s a cost to everything. When we choose to remain status quo, we sacrifice the opportunity of tomorrow to cling to the gifts of today. We fear the loss of gifts, but the loss of opportunity is just as costly, even if it’s harder to quantify.

Not everything that counts can be counted and not everything that can be counted counts.

My Past

Those who read my previous articles on How Much Allowance I Give My Mum and How I Got By Uni and Poly Without Paying would know that I came from a low-income family, took up a scholarship, and supported my parents with my iron rice bowl.

So when my friends first heard about me leaving my iron rice bowl, some of them gave valid concerns.

“You siao arh? Study so hard to get to where you are and then you leave your iron rice bowl?!”

I am thankful for the concern from loved ones. However, our needs change with time. An iron rice bowl is needed in some circumstances but not in others.

When I was young, my austere circumstances drove my decision to undertake a public sector scholarship. With the tuition fees covered and a monthly allowance, I was able to enjoy the final bit of my education without worries.

However, as I moved through life and acquired more resources, money became less of a concern.

Of course, I was careful to not let my lifestyle inflate with increasing wealth as I did not want to keep shifting my financial goalposts at the expense of pursuing my dreams.

Starting new ventures will invariably be a bumpy process fraught with risk. Nevertheless, having more resources while keeping my expenses reasonably low allowed me to take these risks and foray into the realm of writing and analyzing companies full-time.

The Biggest Risk

Quitting our jobs is frequently viewed as risky and unsurprisingly, we falter when making the jump.

I’ve often heard people asking for advice on quitting their jobs. They lament about how they hate their work but cannot quit, citing their numerous “responsibilities”.

But is it, really?

I have seen many high-income earners who are unable to quit their current jobs and pivot out while they are young because they are prisoners of their lavish lifestyle—cars, condos, branded goods, etc.

Beneath the husk of “responsibilities” lies another layer of truth.

It is often the lifestyle we can’t give up, the desire to impress others, or the fear of failure. Or perhaps, all of it.

The fear of taking a risk paralyzes us and prevents us from reinventing ourselves or pursuing work that is more meaningful to us.

Sometimes, however, not changing or evolving might be the greatest risk.

Making the Jump

It doesn’t have to be a big scary jump. Take a tiny step forward everyday.

You don’t have to quit your job immediately and make a drastic switch. Start something on the side, start small and consistently put in the work.

Small actions might not seem like much at first, but over time, they can have a compounding effect.

“A journey of a thousand miles begins with a single step.” – Chinese Proverb

I started SteadyCompounding.com about a year back and have since published more than 50 articles.

Taking that first step was tough. I second-guessed myself numerous times over feelings of inadequacy and doubt that my work would be worth the time and effort I’d invested. Because I’ve always avoided the limelight, writing on a public platform seemed out of character for me. I wasn’t sure how my friends would react, and I avoided announcing my blog or publicising my work on social media for fear of not being good enough.

For several weeks I published and published without much readership and I just focused on doing good work.

Of course, doing good work alone doesn’t guarantee success. Even the best investment ideas are not guaranteed to succeed. Luck plays a bigger role in our successes than we realise. However, consistently doing good work and delivering value is the best way to create luck.

About two months in, my work was recognised and shared online by several fund managers and this helped put me on the map. More importantly, this validation gave me the confidence to start pushing out my work publicly.

I started contributing content on Seedly (the largest online personal finance community in Singapore) and have repeatedly featured as a top writer for the Seedly Opinions initiative. Requests from other blogs and publications started streaming in and I’m immensely grateful for the opportunities.

Publishing my work online has helped attract many top-notch people into my life. Some are investors, some are creators, and all of them are highly passionate and motivated individuals. Exchanging ideas with them has helped me improve significantly—both as an investor and a writer.

For me, studying companies, writing online, and speaking with high-calibre individuals feels like what Warren Buffett would call ‘tap-dancing to work’.

Now that I’m doing this full time, I often reflect on the question: What actions can I take to produce outsized results?

And the answer is almost always to do good work. Do good work, deliver the most value and everything else will fall in place.

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