The Field Guide To Overcoming Risk Aversion

Life can only be understood backwards, but it must be lived forward - Søren Kierkegaard

Hot take: I think most of the annual reviews you read online are performative.

Here is the usual script:

1. Showcase how 2024 was a killer year by featuring your greatest hits (sprinkle in a few ‘failures’ because no one can truly have a 10/10 year)
2. Tell you how they plan for their year ahead and the powerful frameworks they use to build a successful, rich and happy life.
3. Offer you their ‘annual planning template’ as a lead magnet or a paid digital product.
4. Not talk about anything concerning the annual review until the end of 2025 (where they will need to tell you about the new framework and template they are using)

To be clear, I am not anti-annual reviews.

I just think that if you want to extract the most value from those reviews, it’s better to do it in private.

When you conduct your year in public review, you have every incentive to project the best version of yourself.

I mean who really wants to admit that you have been short-tempered, greedy and impatient this year?

Chances are you are not auditing your life, but curating it.

As Epictetus puts it,

Some things are in our control and others not. Things in our control are opinion, pursuit, desire, aversion, and, in a word, whatever are our own actions. Things not in our control are body, property, reputation, command, and, in one word, whatever are not our actions

You learn much more from reflecting on your actions than celebrating your milestones.

I think the more productive thing to do in public is to share a year-defining lesson that others could learn from.

I only share one because it forces me to dig for the gems of insights that have reprogrammed my mind in a fundamental way.

Taking A Huge Risk

As I entered 2024, I knew this would be a pivotal year.

My scholarship bond with Enterprise Singapore would end in August. This meant that I could either voluntarily stay on as a civil servant or try my hand at something new.

I had the privilege of choice for the first time in my professional career.

I chose to take my biggest professional risk so far by leaving Enterprise Singapore to work on The Front Row Podcast full-time.

Keith Yap

Hi, I am Keith, the host of Front Row Podcast. I host conversations with thinkers, practitioners and leaders to help you understand the ideas shaping the Asian Century.

YouTube

The whole process of just jumping into the deep end taught me how to better work with risk.

The Risk of The Status Quo

One of Daniel Kahneman and Amos Tversky’s earliest insights was that we feel the pain of loss more intensely than the pleasure of gain. We place more value on not losing $100 than on gaining $100.

This explains why many people generally avoid analyzing the status quo. We don't want to lose what we have in the pursuit of something better.

Why fix what is not broken?

However, one thing people forget is that the status quo has its own set of opportunity costs.

And, I wanted to figure out the downsides of my staying.

I spoke to people ahead of me - older scholars, middle and senior management.

I decided to leave for two reasons.

First, I am not cut out for civil service.

To excel in the Singaporean civil service, you need a certain disposition and skillset. You must be comfortable navigating red tape, do a lot of administrative work that you often have no interest in, and be incredibly diplomatic.

I noticed the superstar performers were far more efficient than me in administrative work (processing grants or staffing admin briefs).

Deep down, I didn’t like my lack of skin in the game.

How could I truly champion Singaporean enterprises when I have zero entrepreneurial experience?

I knew that I had a fiercely independent streak, craved the freedom to explore ideas, and hated administrative work.

As such, I found it increasingly difficult to spend much of my professional time doing administrative work.

If I stayed in the government out of inertia, I would be a B- player at best. At worst, I would resent myself and be a drag on the team.

I wanted to play in a game where I could be an A+ contributor, but being in the civil service just wasn’t it.

Second, the opportunity cost of transition does not increase linearly.

I'm married but do not have kids and am still relatively young.

This means I have a rare and diminishing window of opportunity to take greater risks and discover how I can marry my passions and competencies in a way that is commercially viable.

When you are 29, quitting your job to start a podcast is admirable.

When you are 35, with kids, quitting your job to start a podcast is irresponsible and delusional.

The best time to take risks is when you are young and cheap.

Finding the Floor

I wanted to lock in and build a podcast that would help my fellow Singaporeans better understand Asia.

I called it The Front Row Podcast because I wanted every conversation to feel like a front-row experience with a world-class Asian thought leader.

I saw it as a PPE (Philosophy, Politics, and Economics) podcast where I would interview people I found to be intellectually interesting.

My larger mission is to make and market Singapore as the intellectual capital of Asia.

I was 100% convinced that the podcast medium would take off and that the ceiling on this podcast (if I persist) would be infinite.

But, you know what?

Everyone dreams of the same best-case scenario as me. But the road to exponential growth is longer than most people imagine.

There is a reason why 90% of podcasts don’t make it past episode 3.

The allure of such a high upside was insufficient to convince me to quit my stable job. I needed to quantify the worst-case scenario.

If everything failed and went to dust, could I not just survive, but could I win?

My answer was to treat this podcast as my brainbulking protocol.

I want to continuously deepen my understanding of the ideas shaping our world and the diverse cultures and economic forces driving Singapore, Asia, and the world. The good thing for me now is that many of the great thinkers and ideas in our orbit are underpriced in the media ecosystem.

This mispricing might mean that the podcast grows slower because many of the guests are not public figures. But I think it gives me time and latitude to explore their ideas more seriously.

This also means I can easily access some of the world's brightest minds.

The podcast format gives me real-time feedback on whether I am maturing intellectually.

Simply put, the podcast is my forcing function.

So, even if after 6 months of work- I am still at 100 subscribers- when I call it quits- I will have boosted my CV a little and bulked my brain substantially.

Do A Beta-Test

Before submitting my resignation letter, I had to test myself.

Did I like podcasting, or did I just like the idea of having one?

The only way to find out is to try.

For my first two interviews, I reached out to Woon Tai Ho (the Founding MD of CNA) and Ambassador Chan Heng Chee (Singapore’s longest-serving Ambassador to the US).

Here is my first video for your reference:

I offered to make it as easy as possible.

With my friend, Barnabas (who was incredibly kind and gracious with me), I would interview them wherever they were.

I did my homework, prepped as hard as possible, and filmed the interviews.

Looking back, I cringed at my performance. I felt too scripted and tentative.

But I was incredibly glad I tried.

Now, I knew that I liked doing the work and what I was getting myself into.

Lose Your Ego

In an ideal world, I could turn this into a sustainable media business. But in reality, I know there are many things beyond my control.

A surefire way to put undue stress on myself was to tie my identity and self-worth to The Front Row Podcast.

This means defining myself purely by the views, subscribers, and followers I get. The result will undoubtedly be chaos in both my personal and professional life.

I cannot help but think of John DeLorean, the famous GM executive responsible for introducing muscle cars like the Pontiac GTO to the American public.

As he became increasingly consumed by his ambition to be seen as a visionary and icon in the automotive world, he built his company, the DeLorean Motor Company around himself. He defined himself by how the company would do.

When the company struggled to succeed, DeLorean resorted to desperate means, including his involvement in a controversial drug trafficking scheme, in an attempt to save his business.

His story is a reminder not to let projects define your identity.

I realised that the more useful frame is to see this podcast as a lifelong project.

A project that I can continue working on even if it is not commercially successful now.

I lowered the stakes for myself and have given myself permission to fail.

If this doesn’t pan out in 2025, don’t sweat it.

I will continue working on this podcast even with a full-time job.

Parting Words

Standing at the end of 2024, I don’t think we can ever escape the disproportionate psychological weight of losses vs gains.

But, if we want a crack at doing something truly great, what we must do is first create a healthy relationship with risk.

In short, this is what I tried when I took the big leap:

• Audited the status quo
• Define the New Floor
• Do a Beta Test
• Lose The Ego

I don't know if the risk will pay off but at the very least, I now know what it feels like to take risk.

I will end this essay in the only way I know how: by quoting a Greek philosopher.

This is Giannis Antetokounmpo, an NBA superstar following his team's elimination from the 2023 NBA Playoffs: