The other day, I watched a recording of a work culture expert ranting about respect. He said that respect is a basic human right.

While I don’t think it should be expected, it cost vanishingly little to offer.

Respect allows someone to show up as a person of potential. Respect gives people choices, which leads to self-agency and ownership. An upwards cycle of growth and the ability to do more.

In the free labour market, where people get to choose their job, especially the ones with skills. And when the best kind of work isn’t done by automatons. Perhaps it’s time to invest in respect and empathy. It is not only more fun, it works better too.


As I hit the big thirty, I took some time to look back. See how I have changed, learn, the people who helped me. Taking that perspective, and see the possibilities that lie ahead. Then, lean into it. 

Personal Evolution

How are you different?

  • I’m an entrepreneur, podcaster and writer
  • I see work-life as a series of projects
  • I am more interested in alignment instead of manipulation
  • I’m in tune with my physical wellbeing
  • I’m more introspective
  • I’m better with words and grammar 
  • I’m giving more compliments 
  • I’m less interested in owning things than experiencing its beauty
  • I eat lesser meals


What were the notable wins, milestones, and experiences?

  • Hit my saving goals of 50K 
  • Hit weight goal of 71kg 
  • Fell in love in Chiang Mai 
  • Wrote an article every week 
  • Wrote a newsletter every bi-weekly
  • Improved relationship with my parents 
  • Started a weekly book reading with my parents 
  • Experimented with moving out for 4 months 
  • Wrist injury is under control 
  • Relaunched the blog 
  • Celebrated my birthday with friends and parents 
  • Began intermittent fasting and got comfortable with the 24 hour fast 
  • Hired a coach and learned about my emotions


What were your key learnings?

  • Good relationships are slow and compounding
  • Habits changes are hard, focus on one at a time
  • Family relationship takes a lot of foundational work. Be prepared to put in one year of work before seeing results
  • Relationship commitment is a trade-off between desire and intimacy 
  • A pause button is useful to prevent argument outbreak
  • 5 language of love can be applied for family and work
  • If you assume someone else’s Love Language is similar to you (without experimenting), you’re probably wrong
  • Writing is thinking out loud, which leads to learning. Publishing is the forcing function
  • Emotions are the basic units of life
  • In order to optimise life, I need to understand my emotion and how each task leads to different emotions
  • It’s okay to feel bored if not doing anything 
  • Doing an (art) project is both a selfish and generous act. It’s selfish because you have the opportunity to engage, learn and dance with possibilities. It’s  generous because the result is a gift that might affect others
  • Happiness is peace in motion
  • I’m living on borrowed time, no one owns me anything
  • Working backwards is the only short cut
  • Ask (to understand and earn trust) before sharing

Expressions of Gratitude

Who helped along the way?

  • Dad for being there at every moment when I needed support 
  • Mum for caring about my diet and her courage to try different things and improve our relationship
  • Jake Chiam for being my partner in crime in gadgetry and Faturday 
  • JR Hinds for being a sounding board and supporting my health journey 
  • Christina Monson for holding up a mirror and believing in the possibilities for me
  • Ilone Grinberg for providing refuge outside my home
  • Alice Zong for putting care in creating a container for my creative endeavours 
  • Ng Yi Qing for inspiring me to be a student of life, bringing the zest to learning
  • Natalie Tan for being a friend and design collaborator
  • Nancy Xu for supporting me through my transition
  • Yasmeen Kassim for being my emotional learning partner as I own up to my emotions 
  • Glo Yong Wei for guiding my movement journey 
  • Marilyn Wo for being generous with her contacts and supporting my website relaunch
  • Michelle Alexis for being a delight to work with and trusting my creative judgement 
  • Elmey Lilaw for being a resilient support when things are falling apart
  • Stella Mandehou for being a friend
  • Vignesh Vasuthevan for being my eyes keeping my writing understandable to everyone else
  • Coco Liu for giving time and holding me accountable to be better
  • My coaching partner for allowing me the privilege to serve and guide you
  • Seth Godin for holding the bar for what an amazing human being could be 


How do you want to show up next year?

  • Understand my emotion and use that to make decision 
  • Find comfort in saying no 
  • Serve people with their emotion in mind 
  • Deepen my skill to listen
  • Create a practice for creative projects 

[Thank you Steve Schalfman for inspiring this post]


I noticed this from my coach. After the end of my sharing, she added a beat and looked me in the eyes. It is as if she is asking (in her head) “is there anything else you want to share?” Then she took a breath and said “thank you for sharing.”

I felt seen. I wanted to share and connect more. Maybe I even teared a little.

During my family meeting, I tried on the posture of my coach, saying “thank you” and adding an extra beat. It was awkward. It was time-consuming. And we did not get through everything I wanted.

The extra beat created a pause, enough for me to recall lessons from books. And instead of blurting it as an edict, I seek permission to share (“Something came to mind as you were sharing your thoughts that I think might be helpful. May I share it?”)

Sure, we did not get through everything I wanted. But that hour was magical. We shared more deeply than we have and it laid the groundwork for a different way of engagement.

This takes emotional labour and you’ll be tired. It might not be for everyone. But for someone important, it might be worth it.

[Thank you, Christina Monson]


Some people, not all people, want more of whatever gave them happiness the last time.

Jeff Bezos has a thousand times as much money as someone with 10 million dollars. Do we think Jeff is a thousand times happier than someone with 10 million dollars?

I was lucky to have experienced traveling in places with not a lot of money. When I was in the US, with a combination of Couchsurfing, whole roast chicken and Indo Mee, I lived happily with a budget of SGD$1,000. And that has cemented the idea that I don’t need a lot of money to be happy.

So when I got back, I thought hard about how much I really need to be happy. How much do I need a month? How much is rent if I move out? How much do I need for food? How much to live a happy and a “good enough” life? I put in the work to figure all that out.

Rent: $1,200
Food: $500
Utilities: $200
Transportation: $200
Insurance: $200
Total: $2,200

In a year, I would need ($2,200*12 months) S$26,400. And if I’m getting a 5% annual return from the investment, I would need $550,000 to effectively stop working for money. That also means I could be a barista and my salary would be a bonus to my living expense.

I think a lot about this idea of “good enough” and applied it to food, work and health. Yet, I find myself turning it up to 11 again. This time it is with friendship, romantic relationship and projects.

As I look at taking on a new project, I generate a lot of ideas but fearful to decide on one. I went on 50 dates this year, and yet to double down on one. I made a lot of friends, but I couldn’t name my top 5 friends.

Am I happier? I don’t think so.
Am I satisfied? I don’t think so.

I haven’t yet thought hard about what is “good enough” for my projects, romantic relationships and friendship.

Part of having a happy and satisfied life is never turning up to 11, but that part of being human is trying to get it up to 11. This is the first step in us understanding that we are always playing this game with ourselves and we have the opportunity to put ourselves on a different track to create outputs that we can be proud of.


No one can keep every promise they make. And what do you do when we’ve broken a promise? Do you say sorry and move on?

Consider this: “Shane, before we get going, I want to cover that I’m out of integrity with you. I made an agreement to be on the call at 8:00, and I wasn’t there. So I want to take responsibility for that, and I want to see if there is anything I can do to clean that up with you?”

How would you feel if someone starts a conversation with that? Would you trust him or her more?

Notice in doing that, you’re not making excuses or justifying. You’re not explaining. You’re just taking responsibility. And that act of taking responsibility is the commodity of trust.

Don’t fall into the trap of rushing the apology when it is about the trust and reputation that you’ve worked so hard to build.

[HT Jim Dethmer]


Each day, I am fighting against biology.
To be comfortable.
To procreate.
To eat fats and sugar.
To live in the moment.

The day when I don’t need to work anymore, I can choose to lay in bed for another hour. I can make breakfast and enjoy it slowly. I can scroll through unlimited videos on my phone. I can click on never-ending links on social media.

Or to do something fun, useful or cool. To face the abyss of choices. To do work that I’m proud of. To contribute to someone.

The truth is that I can’t do them all.


Some culture changes happen really fast and some take way too long. 

Consider the buzz around the migrant worker’s condition in Singapore and contrast it with the gay rights movement where Lee Kuan Yew has openly stated that it would eventually happen

Overnight, the topic of migrant worker became a thing. Except, Cai Yinzhou has been helping the migrant worker by giving free hair cuts since 2015. 

One thing in common is that it all started in the grassroots by people who care. As the stories spread, more people come to steal your idea, copy copy copy, then it becomes safe. Then your job is not on the line when you propose something. That radical idea is not so radical anymore because it has been de-risked. 

The opportunity is that we don’t need to wait for the government/culture/system to change. We can lead, organise and make the change that we care about. The opposite would be complaining and outsourcing our self-agency, that is a trap. 

[4/10/20 update: TWC2 has been supporting migrant workers since 2008.]


The people we listen, the professionals that we choose, the folks we talk about are often at the extremes. After all, if you need a lawyer, accountant, or even a Pizzaman to make you dinner, why wouldn’t you pick the best one?

If you are a Jack or Jane of all trades, you are somebody, by definition, who is pretty good at a lot of things. How then to show up in the market place of ideas? How to show up in the gig economy?

There are a few choices. The first one is to realise being pretty good at a lot of things is in itself an edge of a skill that is worth talking about. The Swiss Army knife is worth talking about because most knives don’t come with a can opener. The Swiss Army knife should not go head-to-head with a chef knife in a fancy restaurant kitchen. But if you can only carry one thing in your pocket, carrying a chef’s knife is probably not the right answer.

So what that means is that you have to get very good at being pretty good at a lot of things. You have to get very good at context switching. That what it means to be a handy person is that the answer to almost any question is “no problem.” It means that you carry with you the tools of your trade. It means that you have figured out what you need to to do pretty good work on a moment’s notice. Because an expert is more brittle than you. You, by being an expert at a lot of things, are flexible.

The second alternative is to seek out gigs where it’s not necessary to be an expert. It’s necessary to be steady, to be resilient, to be a flexible, enthusiastic, positive, easy-to-work-with person, cause you can become the best in the world at that.

The third alternative is to start your own thing. By being a connoisseur at many fields, you can weave ideas together from separate places and connect them to interesting problems. You see possibilities of making things better, put together a directory of experts and weave together a system that works.

What’s not available is to say “I’m 3.5 stars at 40 things, I come in fourth place at every ranking, please pick me because I really need a gig.” Cause no one is going to pick you up that reason.

What we can do is to lean in to the fact that we are good at a lot of things.

[HT Akimbo Podcast]


During the pandemic, schools are forced to move online. The top students who were entering their school of choice, many decided to postpone their enrolment. Understandably so. With the rise of good online resources, the value of school has shifted from learning to connection.

Moving school online took out the fun, the water cooler conversation and most importantly, the lifelong connection of a cohort that is travelling to the same destination.

Some ideas of creating collision space as learning moved online:
– Public profile page of students (with interesting prompts)
– Breakout room during class for discussion
– 24/7 study together (quiet) zoom room
– 24/7 water-cooler zoom room
– Each room are staffed to make sure people don’t enter a lonely room

It might not replace the magic of getting ice-cream together, the hope is that the connection would be enough to make things happen in real life.


Putting together a plan is scary. It’s a negotiation with our future-self to do something uncomfortable. A promise we’re making now.

Sometimes when we’re stuck in a seemingly unachievable dream, a plan is exactly what we need. It is to own the uncomfortable work that needs to be done. Alternatively, give it up.

What’s not a good idea is dreaming it, not making it happen, then beating yourself up when it’s not happening.

Don’t let your dream be a goal without a plan.


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