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.

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.