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.


People don’t want what you make. People want what they want.
People don’t really like you. People like how you make them feel.
People don’t do charity because they are altruistic. People enjoy the pleasure of pleasing others.

In case you’re wondering, we are all selfish. But what if it’s okay to be selfish? What if we can all be selfish while making others happy? Of course we can, that’s the best kind of selfishness.


It’s something we choose and we rarely benefit from it.

The flip side is gratitude.

Whenever we feel confused or wronged, stop the heartache with gratitude. For our breath, for the ability to contribute, for awe of life.

A simple way to think about it: We’re not grateful because we’re happy. We’re happy because we’re grateful.


One of the insurmountable challenges is to convince any parent to go for family therapy. And this is how I did it. 

It has been 6 months since we’ve embarked on our monthly “family dinners”. I put time away to discuss our challenges, triggers and wants, hopefully, to improve our relationship. Yet, my only reliable strategy for a delightful dinner was to shut my mouth. 

I’ve read books (Non-Violent Communication, Why You Won’t Apologize), listened to interviews with renowned therapists (Esther Perel, Brene Brown), and implemented learnings into these dinners. Everything sort of works until one of us would get triggered and that’s the end of dinner. 

On this day, I had a new perspective. Perhaps it is not the message, it’s the messenger. Time to bring in the professional, the family therapist, the person with years of experience resolving deep-rooted issues. A person with a wall of certificates and success stories to share.

Now, the plan is to convince my parents for therapy.
1) Align common goals: A better family relationship.
2) Agree that the current approach is not achieving results: Monthly dinners
3) Seek advice for possible reasons
4) Actively listen to them
5) Suggest my solution: family therapy
6) Conclude and execute on the new approach

“Mom, what do you think could be possible reasons why we are not progressing in our relationship after months of dinners?” I asked. 

Mom got silent and replied, “Bryan, I think you have depression.”

My jaw dropped. “Oh… okay. Well, what about you? Maybe you’re the one who has depression? We should go to the doctor together!” I’m surprised by my reply. 

And there we go, sitting outside the polyclinic waiting for our number to be called. 

After a round of questions with the doctor, he concluded, “Bryan, you don’t have depression. You’re too productive to be depressed.” 

“Well, I know that already. Now you just need to convince my mum,” I smiled. 

My parents got invited back into the room and were debunked of their concern that I have depression. Out of possible reasons, that’s how my mum got roped into the family therapy.  

Often times, we have a certain way of seeing the world. Instead of a verbal argument to change someone’s mind, or worse, using power to instruct or name -call which is not at all effective, the next best thing might be to let reality do its job.  There is no need for power, logic or debate. It’s simply an embrace of the opinion of others, treat it as an experiment and let reality do its teaching. Perhaps, this is the best way to change someone’s mind and even better, be beside them like the kind teacher we all hope for. 


Putting your worst foot forward turns out to be a great negotiation tactic, but more importantly, an excellent thinking process to get what you want.

That is how Rufus Griscom raised $3.3 million dollars from investors, and eventually sold his company to Disney for $40 million dollars.

Instead of flaunting his strengths and minimising his weaknesses, he leads meetings with “top five reasons not to invest in my business” and “Here’s Why You Should Not Buy Babble.”

This way of selling doesn’t only make him seem sincere and empathic, but also smart and realistic.

Unbridled optimism can come across as slimy salesmanship, making us seem dishonest and as a consequence, met with skepticism. It is a form of delusion, the inability to look at reality without bias. Too much of it can be catastrophic.

Ironically, by acknowledging and thinking about the most serious problems, Rufus disarms the investors, opens the possibility to plan for business risk, and get people on his side to solve these problems together.

Of course, being optimistic makes us happier. But every once in a while, it’s time put away those rose-tinted glasses and look at reality for what it really is.


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