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Enlargement Over Happiness

Enlargement Over Happiness

One of the many reasons I read books and blogs is to find insights to the question of what it means to fully live. Sounds deep, I know. But I figure that I could use some guidance on this, and what better way to learn than hearing from the people that have gone before you?

Recently, I stumbled across this idea from Austin Kleon’s blog, which referenced a piece by writer Oliver Burkeman called eight secrets to a (fairly) fulfilled life. Burkeman writes,

When stumped by a life choice, choose “enlargement” over happiness. I’m indebted to the Jungian therapist James Hollis for the insight that major personal decisions should be made not by asking, “Will this make me happy?”, but “Will this choice enlarge me or diminish me?” We’re terrible at predicting what will make us happy: the question swiftly gets bogged down in our narrow preferences for security and control. But the enlargement question elicits a deeper, intuitive response. You tend to just know whether, say, leaving or remaining in a relationship or a job, though it might bring short-term comfort, would mean cheating yourself of growth. (Relatedly, don’t worry about burning bridges: irreversible decisions tend to be more satisfying, because now there’s only one direction to travel – forward into whatever choice you made.)

It’s tempting to defer to the path of least resistance, which is often a path that leads to pleasures. And so, this idea that we should put aside these short-term pleasures is honestly kind of confronting, despite these pleasures being often pathological. I mean, if you had to choose a pet, a cute, chubby bee seems much preferable than an ugly, hairy caterpillar.

But looking back, it’s clear that some of the best decisions I’ve ever made fell in line with this framework of prioritising enlargement over happiness. Things like speaking up when it was uncomfortable. Leaving my hometown. Creating this blog. Public speaking.

Interestingly, over time these initially difficult decisions have transitioned into wonderful sources of happiness, something akin to a butterfly emerging from a cocoon. It’s just in that one moment, a bee looks oh-so-cute, even though it might very well give you a sting leading to your demise.

Beyond the Very Hungry Caterpillar: What this insect can teach us about  self-care | Marisa Raymond

The article referenced can be found here.

Dropping In

Dropping In

I recently watched a video of people dropping in for the first time (thanks YouTube algorithm). In skateboarding, dropping in is the commitment at the top of the ramp. At the top, you’re standing still, staring into the abyss, and then suddenly you’re flying down the ramp and dancing with gravity.

The most important thing to do when dropping in is to commit. The worst thing you can do is half-ass it. When you only sort of commit, you’re likely to fall.

Learning this reminded me of something my dad used to always say. Decide once. You can choose to say no. But once you decide, commit to it and do it to the best of your ability.

I wish I could ask him what he really meant by that, but here’s my interpretation. One can spend endless hours contemplating a decision. But after a while, you’re better off just committing to something and facing the consequences, especially when excessive hesitation leads to time wasting and decision fatigue. As long as you wear a helmet, the worst possible outcome is you learn from it and leave with a great story. The flipside is that it might just change your life.

Indeed, it seems that in many areas, the decision to drop in is precisely at the heart of the challenge.

To the Lazy Days

To the Lazy Days

Picture this: you’re sitting at your desk at 10:45pm, sleep deprived, fatigued from work, sore from a workout and in the process of mindlessly eating your fourth punnet of strawberries. Your whole body begs you to read a book and go to bed. However, it’s a Thursday and you’re supposed to write. You begin to bargain with yourself. Just a short nap. Then you can write your stupid post. But you don’t trust your body to wake up. Just hold on for 10 minutes, you mutter. So here you are, staring at an empty Word document with no real goal in mind.

Ah, hello there.

Out of sheer desperation, you google, “how to write when you don’t want to” and click the first link. You give it a skim read – you’re too tired to read it in depth – and it’s surprisingly informative. You read about a self-discipline muscle. A muscle that grows with consistency and atrophies with days off. The author, Carter Barnett, encourages you to set the bar low if you need to, so long as you train it. You wonder how low it can be set.

After a while, the author ends with: The best way to write when you don’t want to is to just write when you don’t want to.

Exactly what you don’t want to see.

However, reading the muscle analogy reminds you of the importance of consistency. The importance of just showing up. That writing something trash is far better than not writing anything at all. So, you decide to jot this experience down, even if it’s the worst thing you’ve ever written.

Alas, here’s to the lazy days. To the days that seem long, heavy and suffocating. To the days where your eyelids feel like lead. To the days where you wish the Earth could just swallow you up. Here’s to facing these crazy forces and saying, “look, I surrender but just hang on for a sec –” and quickly rushing off to your responsibilities. Like an Asian kid throwing rice in the rice cooker right before the mum arrives. It could be disgraceful. You could end up doing the poorest job you’ve ever done. But at least you showed up and tried. And who knows? Maybe next time, it won’t be so hard.

You glance at the clock and realise it’s 11:22pm. Over 30 minutes since you started. Oi, you only said 10 minutes, your tired self mumbles. Sorry. But you guess it’s time for bed.

Audience of One

Audience of One

In 2014, Maria Popova, the writer of brainpickings.org, did an interview with Tim Ferriss which remains one of my favourite conversations of all time. For context, Brain Pickings is a collection of beautiful and profound musings described as a ‘one-woman labor of love exploring what it means to live a decent, substantive, rewarding life.’ Maria also writes a biweekly newsletter which consistently brighten up my week.

In this particular interview, Maria discusses her blog and who she writes for:

Tim Ferriss: The quote that I heard you cite that I wanted to dig into a bit was the Kurt Vonnegut saying, “write to please just one person”. So, my question to you is, when you write, is that still the case? And if so, who is that person that you are writing for?

Maria Popova: It is very much the case. I still write for an audience of one, and that is myself. It’s like I said, it’s just a record of my thought process, my way of just trying to navigate my way through the world and understand my place in it, understand how we relate to one another, how different pieces of the world relate to each other and create a pattern of meaning out of seemingly unrelated, meaningless information, and the intersection or transmutation of information into wisdom, really, which what learning to live is. It’s about wisdom.

It’s interesting, too, because when I started Brain Pickings – like I said – almost eight years ago, it started very much as a private record of my own curiosity and I shared it with seven co-workers that I had at the time just as an email newsletter thing. Now, to think that there are about 7 million people – strangers – reading it every month… [it’s so] surreal that I still feel like I’m writing for one person, one very inward person.


When I started this blog back in March 2019, I intended it to be something like an online journal – a place for me to record my thoughts and reflections. But as my readership has grown over the last year, I occasionally feel the urge to adjust my content for a wider audience.

But the more I write, the more I experience this wonderful reminder by Austin Kleon: to write the books you want to read. Sure, I could write about the latest current affairs and topical issues to be ‘safe’. But frankly, the stuff I write about, I’d like to read about – and chances are, someone out there would like reading it too.

Like Maria, writing is ultimately my way of navigating through the world to understand what it is to live. And so no matter the spectators, I write for an audience of one: myself.

Here’s how artist Marc Weidenbaum put it in his celebration of blogging on the twentieth anniversary of his blog, Disquiet.com:

And don’t concern yourself with whether or not you “write.” Don’t leave writing to writers. Don’t delegate your area of interest and knowledge to people with stronger rhetorical resources. You’ll find your voice as you make your way. There is, however, one thing to learn from writers that non-writers don’t always understand. Most writers don’t write to express what they think. They write to figure out what they think. Writing is a process of discovery. Blogging is an essential tool toward meditating over an extended period of time on a subject you consider to be important.

The Good Enough Parent

The Good Enough Parent

I recently listened to a podcast episode on the Tim Ferriss Show called Books I’ve Loved: Alain de Botton. Alain is a bestselling British philosopher and author, and the co-founder of the School of Life. He is also one of the narrators for the School of Life YouTube channel and has a phenomenal reading voice. One message Alain shares comes from D.W. Winnicott’s collection of essays Home Is Where We Start From, called the ‘good enough parent’.

The idea is, many parents are obsessed with being perfect. They want to set the best example for their kids. To cook the healthiest meals. To show the purest love. To have highest moral standards. And what’s more, they do this so their children can have the best upbringing, attend the best school and be the happiest child possible.

The problem is, perfection is very dangerous concept to strive for. It’s much better – and practical – to be simply a good enough parent. Alain says, referring to Winnicott’s writing:

Another great idea from Winnicott is the concept of the good enough parent. Many parents came to Winnicott very worried that they weren’t doing a good enough job as parents. They wanted to be better. They were worried that they weren’t educating the kid right, or there was some eating problem, or school problem, etc. And Winnicott could see that these worries were actually getting in the way of the parents doing the fairly good job that they were doing. And so Winnicott made a fascinating intervention. First of all, he told parents, no child needs a perfect parent. Indeed, a perfect parent is very dangerous. It’s a one way route to psychosis, a psychotic incident because essentially the job of a parent is to disappoint a child bit by bit and induct them into adult realities. If the parent is perfect, how can the child grow used to living in the world that we all have to live in, which is a deeply imperfect one?

So in an ideal world, a good parent is able to break bad news well to the child until the child can accept the whole panoply of difficulties of adult life, amounting ultimately into the fact that we are all mortal and we are all going to have to die.

Alain then suggests that this ‘good enough’ attitude can be applied to other domains such as friendship and learning. There’s no use trying to be a perfect friend, for screwing up occasionally is how a friendship grows. There’s no use striving to be a perfect student, for not knowing things is how you develop a sense of wonder. Being good enough to do the job, but allowing some gaps for maturity and growth, is what we should strive for.

In other words, our imperfections expose the inadequacies of life. And it is through these inadequacies that one understands the world clearer.

What a liberating message: that really, we don’t want to be perfect, for perfect is boring, unnatural and ultimately, unattainable. That being good enough is, in fact, perfect.

The Downward Spiral

The Downward Spiral

A few days ago, I was on the way to buy some groceries when I encountered a homeless man. He was slouched against a wall, wearing worn out clothing and broken sandals. He sat on the bare veranda with a grey duffel bag on his right and in front of him was an empty 7-11 coffee cup. I saw no blanket or rug for him to sleep on. As I walked closer, he looked up and our eyes met. Oh, his eyes. The homeless man had the most glassy and lifeless eyes I have ever seen, as though someone had sucked out the very essence of his soul.

“Excuse me, do you have any change?” he asked in a rough, tired voice.

I slowed down a little, hesitated, and said I had no cash on me.

“No worries. Have a good day.”

As I looked closer into his eyes, I felt a knot coming up in my throat. What stared back at me looked like someone who had been abandoned by the world. Who had lost everything dear to him. Who had lost a reason to live. How could a person look so lifeless? I found it disturbingly difficult to hold eye contact.

“Well, can I get you some water or food? Woolies is right around the corner.”

“Ah no, that’s okay. Thanks, though.”

I paused, contemplating whether to move on and to continue with my day. But curiosity got the better of me. I had to know this man’s story. I squatted down and looked further into his eyes.

“How did you end up here?”

The following story is my recount of the homeless man’s story, who I’ll name H.  


H grew up in regional Victoria and dreamed of becoming a banker. He had never known his father, who had left his mother before he was born, and he lost his mother to cancer when he was six. He spent the majority of his life with his maternal grandparents, who were both alcoholics.

H was a smart and resilient kid. Although there were a lot of shady dealings with in his neighbourhood, he never got caught up in the wrong crowd. His mother, while she was alive, instilled in him a strong and correct moral compass. A compass that would come crashing down in his adult years.

Despite all odds and expectations, H fulfilled his dream and became a banker. On the way, in his final year of studies, he met a woman. It was love at first sight. They dated for a few months and got married within the year. They had stable jobs amidst the pandemic and loved each other. It was heaven.

But the problem with love is that while it is wonderful to have, it is equally terrible to lose. And H lost it. One day, H’s wife left him for another man and left him alone. This catalysed a downward spiral for H. A spiral which led to substance abuse, getting fired from his job, bankruptcy, depression and finally, getting evicted from his apartment. He had applied for social housing but for whatever reason, his application wasn’t being accepted. That left him no other option but the streets, where he has been for two weeks.

Over the last few years, H started smoking and often numbs his pain with alcohol – when he can afford it. In his darkest moments, H considers ending his own life. He keeps a blunt piece of glass in his rucksack and sometimes rubs it against his skin, wondering why life had done this to him.


H sighed and looked into my eyes. “That’s life,” he said. “Just one moment can mess you up like that. Never think your life is perfect. It only takes one thing to tear it all down again. For me, it was my wife. For you, it could be something else. But once that thing hits you, you better stop it early. Because if you don’t, it will consume your life like a downward spiral, until you end up on the streets like me.”

I didn’t know how to respond. I murmured something about my condolences and my surprise at Victorian social housing. H looked down sadly, muttering a quiet “yeah.” The conversation was over.

The Four Digital Horsemen

The Four Digital Horsemen

Jim Kwik’s book Limitless: Upgrade Your Brain, Learn Anything Faster, and Unlock Your Exceptional Life sounds like a scam but is one of the best books I’ve read this year. While I don’t typically read personal development, I found myself highlighting line after line on the kindle. One concept I’ll share from the book is the ‘four digital horsemen’, or four dangers that the digital age brings.

Digital deluge. There is too much stuff. The average person consumes 3x as much information as we did in the 1960s and a 2015 report indicated that respondents spent eight hours a day consuming media. As time goes on, this problem will only get worse. The problem is, according to Jim,

“There is a growing body of evidence that suggests that if we never let our mind wander or be bored for a moment, we pay a price – poor memory, mental fog, and fatigue.”

Digital distraction. We are too connected to our devices. These devices are shiny, addictive and are endless. Dopamine heaven! But this means we are never present and become unhappy as a result. Furthermore, shifting attention from one thing to another is very energy costly. As Jim writes,

“Asking the brain to shift attention from one activity to another causes the prefrontal cortex and striatum to burn up oxygenated glucose, the same fuel they need to stay on task… and the kind of rapid, continual shifting we do with multitasking causes the brain to burn through fuel so quickly that we feel exhausted and disoriented after even a short time.”

Digital dementia. We rely on technology to do so much these days. We use it to navigate maps. Remember phone numbers. Autocorrect wrong words. This overreliance results in the breakdown of cognitive abilities. As Jim puts it,

“Too often, we outsource our brains to our smart devices, and our smart devices are making us, well, a little bit stupid.”

Digital deduction. A ubiquity of information results in a ubiquity of opinions about everything. If you want to inform yourself on an issue, just go on reddit to find some opinions. The problem is that the process of deduction – a blend of critical thinking, problem solving and creativity – is becoming automated. Jim writes,

“We’re letting technology do the deduction for us. And if technology is forming our deductions, then we are also ceding much of our problem-solving ability something so important and something we will discuss at length later in this book.”


So, here are the four digital horsemen.

  • Digital deluge: We have too much to process -> we get tired.
  • Digital distraction: We are too connected in a noisy digital environment -> we are unhappy and cannot focus.
  • Digital dementia: We are relying too much on technology -> we get dumber.
  • Digital deduction: There are too many opinions -> we cannot think for ourselves.

Jim also includes a fifth emerging horseman: digital depression: there is too much comparison -> we feel bad. However, since the book is ultimately about productivity, he doesn’t go into this in much detail.

Reading about these horsemen (and writing them here) serves as a personal reminder: technology is great, but there are some serious dangers. Personally, I can relate to all of the symptoms above. And yeah, it’s concerning. However, this is simultaneously encouraging: that the antidote might lie in just a simple airplane mode once in a while.

You can find Limitless here.

On Joy and Sorrow

On Joy and Sorrow

I’ve always struggled to articulate the dynamic between joy and sorrow. Luckily, I can benefit from wiser writers who have undergone this journey before me. The following is taken from Kahlil Gibran’s The Prophet, which beautifully illustrates the dichotomy between joy and sorrow.

Then a woman said, Speak to us of Joy and Sorrow. And he answered:

Your joy is your sorrow unmasked.
And the selfsame well from which your laughter rises was oftentimes filled with your tears.
And how else can it be?
The deeper that sorrow carves into your being, the more joy you can contain.
Is not the cup that holds your wine the very cup that was burned in the potter’s oven?
And is not the lute that soothes your spirit the very wood that was hollowed with knives?

When you are joyous, look deep into your heart and you shall find it is only that which has given you sorrow that is giving you joy.
When you are sorrowful, look again in your heart, and you shall see that in truth you are weeping for that which has been your delight.

Some of you say, ‘Joy is greater than sorrow,’ and others say, ‘Nay, sorrow is the greater.’ But I say unto you, they are inseparable. Together they come, and when one sits alone with you at your board, remember that the other is asleep upon your bed.

Verily you are suspended like scales between your sorrow and your joy.
Only when you are empty are you at standstill and balanced.
When the treasure-keeper lifts you to weigh his gold and his silver, needs must your joy or your sorrow rise or fall.


Related: On Children

Glorious Contradictions

Glorious Contradictions

I recently listened to a podcast episode between Malcolm Gladwell (my favourite non-fiction author) and Jay Shetty (my favourite interviewer). While the conversation was wide ranging, there was this one section on contradictions that blew me away. I’ve put the transcript below, lightly edited for clarity.

Shetty: “I love what you’ve said that as human beings, we exploit our contradictions. Can you elaborate on that?”

Gladwell: “I’ve always found that when you get to know someone, what you discover is that they’re full of contradictions. And that being contradictory is one of the defining points about being human…

In my case, my father was English, my mother is Jamaican and I am Irish. I have my foot in two very different heritages. When people ask me which way I identify, my answer is, “I don’t. I’m both.” And being both is a contradiction! … One of the reasons I’m drawn to [racial issues] is I see both sides of them. There’s a part of me that’s white and sees the world through the lens of a privileged white man. And part of me is black and sympathises with the other side of the equation very readily and appreciates it. These two things exist inside of me and my attempt to make sense of this apparent contradiction is what makes me a writer.”


Contradictions are glorious. They reveal a truth about us that we sometimes forget: that people are a vat of unique experiences; experiences that make up a unique human being. When viewed as a byproduct of glorious complexity, contradictions can be quite beautiful.

To slap a singular label on someone is not only incorrect, it’s dehumanising. Not all Marxists are the same. Not all Christians are the same. Not all politicians are the same. When we observe behaviour from another that seems odd, perhaps it’s our expectations that require examination, not the other person.

As someone who tends to struggle with contradictions, this message was a great gift. Rather than responding to inconsistencies with annoyance, it’s more productive to embrace people for who they are – a hot mess of experiences that are inherently contradictory. A mess which can be strange, yet hauntingly beautiful at the same time, evidenced by the work of Malcolm Gladwell.

If you want to listen to the episode, you can find it here.

Conformity, Reason and Hope

Conformity, Reason and Hope

The following stream of consciousness is largely derived from an article on brainpickings called Kierkegaard on Nonconformity, the Individual vs. the Crowd, and the Power of the Minority. Would highly recommend.


‘Conformity’ is a bit of an ugly word. I’ve always associated it with a sense of loss and giving up a piece of yourself to comply with a broader standard. Don’t get me wrong – solid, universal guidelines are important for any well-functioning society, but the loss of individuality – an inevitable consequence of conformity – is unfortunate nonetheless. As Eleanor Roosevelt put it more poetically,

“When you adopt the standards and the values of someone else, you surrender your own integrity [and] become, to the extent of your surrender, less of a human being.”

The question must be asked, then: what are ways in which we can independently conform, behaving in such a way that is in line with society’s reasonable standards but protects individual freedom of thought?

The Danish writer and thinker Søren Kierkegaard offers various insights in his journals, starting with a reflection on how one should protect their integrity, emphasizing the importance of quiet communion. He writes,

“One can very well eat lettuce before its heart has been formed; still, the delicate crispness of the heart and its lovely frizz are something altogether different from the leaves. It is the same in the world of the spirit. Being too busy has this result: that an individual very, very rarely is permitted to form a heart; on the other hand, the thinker, the poet, or the religious personality who actually has formed his heart, will never be popular, not because he is difficult, but because it demands quiet and prolonged working with oneself and intimate knowledge of oneself as well as a certain isolation.”

But while it’s helpful to know the role of reflection, another problem arises: how does one know if they’ve broken out of the bubble of conformity?” While this question seems to be unanswerable, Kiekegaard provides another clue in looking towards the majority:

“Truth always rests with the minority … because the minority is generally formed by those who really have an opinion, while the strength of a majority is illusory, formed by the gangs who have no opinion.”

This sentiment echoes that of Anthony de Mello in his short reflections on Awareness, where he vividly describes the moment of enlightenment and separation from the majority:

“Do you know one sign that you’ve woken up? It’s when you are asking yourself, “Am I crazy, or are all of them crazy?” It really is. Because we are crazy. The whole world is crazy. Certifiable lunatics! The only reason we’re not locked up in an institution is that there are so many of us. So we’re crazy. We’re living on crazy ideas about love, about relationships, about happiness, about joy, about everything. We’re crazy to the point, I’ve come to believe, that if everybody agrees on something, you can be sure it’s wrong! Every new idea, every great idea, when it first began was in a minority of one. That man called Jesus Christ—minority of one. Everybody was saying something different from what he was saying. The Buddha— minority of one. Everybody was saying something different from what he was saying. I think it was Bertrand Russell who said, “Every great idea starts out as a blasphemy.”

Indeed, Christ – who could be regarded as the most influential minority in history – echoes this warning through the apostle Paul’s letter to the Romans:

Do not conform any longer to the pattern of this world, but be transformed by the renewing of your mind. Then you will be able to test and approve what God’s will is–his good, pleasing and perfect will. (Romans 12:2 NIV)

But of course, there remains the problem in that truth is rarely obvious. Two people can look at the same world and see two completely different places. One might despair at the injustice, the grief and the lack of meaning governed by death and yet another can be astounded by the beauty and opportunities enabled by life. What do we choose when the truth is uncertain?

The answer to this is up to each individual to decide. This, I believe, was the core question Yann Martel was trying to address in his vivid bestseller, Life of Pi. In the novel’s climax, the protagonist Pi Patel presents a challenge to his interrogators, challenging them to err on the side of faith rather than reason:

“The arrogance of big-city folk! You grant your metropolises all the animals of Eden, but you deny my hamlet the merest Bengal tiger!”

“Mr. Patel, please calm down.”

“If you stumble at mere believability, what are you living for? Isn’t love hard to believe?”

“Mr. Patel– ”

“Don’t bully me with your politeness! Love is hard to believe, ask any lover. Life is hard to believe, ask any scientist. God is hard to believe, ask any believer. What is your problem with hard to believe?”

“We’re just being reasonable.”

“So am I! I applied my reason at every moment. Reason is excellent for getting food, clothing and shelter. Reason is the very best tool kit. Nothing beats reason for keeping tigers away. But be excessively reasonable and you risk throwing out the universe with the bathwater.”

And so, the decision remains open to us all. Will we conform, embracing the majority at the expense of our integrity? Or will we embark on an uncertain, meditative journey in the quest for truth? And if the latter, what weapons will we use to guide us? Reason, hope, or a pinch of both?