The never-ending game

Aug 17, 2023
The never-ending game

Find Your Superpower newsletter 023

Read time: 4 minutes

Topics covered: ikigai, job satisfaction, work-life balance, mental health


There is a very troubling phenomenon in society of overachieving.

Competitiveness. One-upmanship. Kiasu-ism.

Need to find a partner and buy an apartment before your friends do.

Need to get promoted to the VP level before your colleagues do.

Need to earn five digits a month to be considered successful.

All of this reminded me of an amazing book by Simon Sinek, The Infinite Game. According to the book’s description:

In finite games, like football or chess, the players are known, the rules are fixed, and the endpoint is clear. The winners and losers are easily identified. 
In infinite games, like business or politics or life itself, the players come and go, the rules are changeable, and there is no defined endpoint.


The finite-game strategy is flawed

So we work extremely hard in our 20s and we pay our dues. We put in the late hours and guess what… the world reciprocates. We get promoted, we get raises, and we’re now in our 30s and 40s.

Then what? Well I hate to break it to you… that’s when the cracks start to show, and it will most likely catch you by surprise.

The office cliques that used to invite you to meals? They will stop inviting you as you’re the person they are gossiping about now.

The pity parties and complaints about senior management? There’s nobody left for you to complain about as you are the boss now.

Your mental health and physical health which you’ve compromised all these years to get to where you are today? It will come back to haunt you in full force with aches and pains everywhere.

Suddenly, there’s a cognitive dissonance going on.

Do I floor the engine and keep going at it?

Or do I throw in the towel and say, “This cross is too much for me to bear”?


Introducing the never-ending game

To take inspiration from Simon Sinek, the never-ending game is a game that you never want to end. Rather, you elect to keep on playing the game without winning or losing.

I recently celebrated my 40th birthday. I’ve decided to embrace my 40s because right now, I will have all of the financial resources, time and experience that I never did in my 20s and 30s.

Imposter syndrome? Been there, done that. ✅

Please everyone but yourself? Been there, done that. ✅

In my 40s I would therefore like to play a new game, the never-ending game.

Unlike the F.I.R.E. movement, where the goal is to gain financial independence and retire as early as possible, I don’t necessarily want to stop playing this game, ever.

And if the goal is to continue playing or working on my ikigai— what I love to do, what I am good at, what the world needs and will pay me for—then I must change my strategy.

Instead of rushing to peak early, I should try instead NEVER to peak. Here’s how I plan on doing it:


1/ Adopt an abundance mindset

First, I will need to adopt an abundance mindset over a scarcity mindset. A scarcity mindset is what forces us to rush, because we believe we will run out of time and resources. If we open our eyes a little wider, we will find abundance everywhere: opportunity in crisis, lessons from failure, and redirection from rejection.


2/ Protect the vessel

The vessel here refers to our body and mind. If we want to play the never-ending game, we must first prioritize our mental and physical health. Singapore’s Institute of Mental Health conducted a comprehensive nationwide study in 2022 which found that about 21.6% (one in five) of our youth aged 15 to 35 years old have experienced at least one mental health condition. To play the never-ending game, we need to fix that first by talking to a therapist or trusted mentor.


3/ Build a tribe around me

If we don’t have a tribe, we simply don’t stand a chance. As an entrepreneur, I have found a group of entrepreneur friends who act as my peer mentors and informal advisory committee. Assuming all members of my tribe work together to help each other, we would collectively move the sky.


I wish someone had told me this when I was in my 20s and 30s… I would have been such a better player of the game of life.

May all of us get to enjoy playing a never-ending game!


For those of you who are new to my newsletter, this newsletter, Find Your Superpower, is subscribed to by 24,000+ people, and discusses the following three goals: (1) Making a career transition, (2) Professional branding on LinkedIn, and (3) Reinventing ourselves for the future of work.

Thanks for reading issue 023 of my weekly Find Your Superpower newsletter.

See you next week. 



Besides my newsletter:

- Have you taken my masterclass on LinkedIn professional branding? Find Your Superpower: How to Rebrand Yourself on LinkedIn is a simple, 1h on-demand video course that will help you identify your professional brand, write a brand statement from scratch, and create original content on LinkedIn.

- Have you heard my podcast? Subscribe to The Science of Work podcast on Spotify and Apple Podcast and don’t forget to leave me a five-star rating to help others find my podcast! ⭐⭐⭐⭐⭐

- Have you signed up for my newsletter mailing list? Sign up to receive a 10% DISCOUNT coupon code for the masterclass.

Let's stay in touch.

Subscribe to my Find Your Superpower weekly newsletter: