on-going mostly unedited stream of thoughts


I was chatting with one of my co-workers and someone asked her how she got into tech. She said she was inspired as a user of livejournal, and memories started flooding back to me.

I have six years of my memories archived at livejournal, from 2001 to 2006. I almost wish it had existed earlier, because I have almost no record of my thoughts and emotions prior to 2001. Back then on livejournal, nobody cared who we wrote for, whether it was getting any traffic. We simply wrote our hearts out and broadcasted our moods.

I wrote for myself back then, and I still want to write for myself now. I think this is why I am back to writing whenever I have the space and time to write, because my memories are precious to me. I don’t realize how precious they are to me until more than a decade later I am sitting here trying to recollect and you have no idea how thankful I am to my past self for consistently writing during those six years.

I gradually moved to more topical writing, but I really miss those livejournal days when I’m just really just journaling without any agenda or purpose. Those entries are like a time machine for me.

I still smile at my old dramatic ridiculous self, and it amazes me how far I’ve come. And here lies one of the most important lessons I’ve learned about my self and life and general. Our past selves are not a great indicator of who we can become.

The people who knew me when I was 21 (including myself) would laugh their toes off if I told them I would be the person I am today. This is what I tell myself now, that I have absolutely no idea who I will be or what I will be doing in ten years time.

How would my 43 year old self react to the 33 year old me? I hope I will make her proud. I laugh at my 20s self, but there were things that remained constant – my desire to question and analyze every single bit of my life.

Thinking of my current self and the one in my early 20s, even though it seemed like a quantum leap if you put them both side by side, I could find intricate details in my accumulative journal entries that showed the early trajectory of the person I am today. This is from an entry on May 6th, 2002:

What is real, really? Who are we to define what is real?

I am anticipating all that amusement that I will derive from looking back at all my writing, decades from now, over and over again.

the power of words

One of my old Medium posts, “The power of your writing” has been blowing up in traffic again, thanks to the official Medium accounts re-sharing it again:

I wrote it over year ago, and it was the only post I have written in probably my entire life that took more than a day to write. I have written intense posts that take six to seven hours in one sitting, and the thing is I don’t actually like writing in more than one sitting. I like sitting here and just letting my thoughts flow into my hands and transform into the written word. Obsessive editing and agonizing over presentation is really not my thing.

But this post was special. It took me hours to write the first draft, and I let it sit for two weeks, before editing that first draft heavily. It is the only post I sent to multiple people for feedback (including a real writer – thanks @verbagetruck!).

It meant a lot to me back then, it still means a lot to me today. I took it upon myself as a personal mission to make more people take their writing seriously, and I in turn took my mission very seriously.

Yet that post took so much out of me, that I never really wrote a post like it again. I went back to writing posts straight from my heart and onto the screen without putting a filter in between. Most of the time I am really just wanting to write for myself. So this may strangely be the only post that I would ever write that could carry this sort of resonance and impact:

Words have this magical way of being in existence. They will find their way to people who need them, at the most uncanny time. Our job is just to write them out and let the universe distribute their power. I knew this is one of the posts I had to write and it was worth the time, and I am thankful that it reached people the way it was intended to be.

I still feel warm fuzzies whenever I receive notes or tweets on the impact of this post and it serves as the best affirmation of the power of words to myself – why I truly love writing and how it has thoroughly transformed me.

contrast between worlds

I’m in Nicaragua right now, surrounded by astounding beauty:

I can see why this is an up and coming tourist spot. But I am unable to truly immerse myself in the beauty, because of the obvious contrast I see.

I see buses packed with children, and I wonder how long do they have to travel to attend school. I wonder what do they learn, how much can they learn, how much they will have to do in order to get even a decent chance at a better life. I think of the life I have had growing up back in Singapore, and no matter how much grouse I may carry with the political system, ultimately I admit my luck of having being born in a country where at the very least I could still weld some freedom of choice in what I want to learn and who I want to be.

I learned that Nicaragua was once occupied by the United States and they fought hard for their independence. I ask myself what is true freedom and independence, and at what cost does it come? I think about what Singapore had to do to fight for her independence, and I think about the tradeoffs she had to make, and I ask myself constantly if the price was worth paying.

I spent hours talking to my good friend Spencer, about the role of governments, on countries where the governments provide so much that the people no longer seem to desire progress and innovation. We talked about basic income, on what is that balance we have to find in order to ensure our fellow human beings are well taken care of and yet foster the environment for creativity and ambition.

I don’t think we have found the answer but we have to keep on finding. Yet in my heart I struggle, because it is hard to think about creativity and ambition, when so much of the world is still left behind. I am sad, because I know the little girl I see on the street of Nicaragua will barely experience any sort of life I have had. I feel so much like a hypocrite, because I think about this so much and yet I feel so helpless.

It is so very paralyzing.

But as I’ve asked myself and written a thousand times before – I can choose to feel all this guilt of having a much better life than the children I see growing up in sheer poverty just by the virtue of my birth, or strive to maximize my privilege in the way I know how.

It is better to think of solving the problems I can solve in my immediate capacity, than to live in a life of paralysis and denial – knowing that millions of children are out there denied a basic human right of water, much less education. I may not be able to do much about it, even if I spent the rest of this life trying to, but they very least I can do is to keep the awareness of this injustice, at the core of my mind and heart with every step of the way I move forward.

I am sad, but I need to experience this over and over again, so I may never forget what many of my fellow humankind have to go through, simply because they drew a bad hand in what we call the ovarian lottery.

The people who insist that luck do not exist in this world, and claim that everything is based on the merit of sheer hard work, have probably never experienced much out of their own privileged worlds.


Days like today make me feel really blessed. I hung out with a dear friend visting from Vancouver. We talked for hours, sitting on a grass patch at Dolores Park. I haven’t seen him in a year, and in between we don’t really keep in touch.

Yet we carried on the conversation as though it was left off from yesterday, despite both of us having evolved significantly between the gaps. He is one of the very few people whom I can engage in a blatantly honest conversation about the world with.

I know I am blessed, because I have a really tiny but growing group of people I can have similar conversations with. Conversations that never get pivoted into anything lightweight even when they make us uncomfortable. It is now my filter when I meet new people. I think life is extremely transient, and I want to get to the depth of things quick. I don’t really want to spend time talking about how I spent my weekend (please don’t ask me this question if you ever see me in real life), instead I would like to talk about how we can empower humanity even if it means we are just popping bubbles into the wind.

I used to feel bad that I cannot tolerate small talk, or I’ll pretend to fade into some corner just to fit in. Something changed in the past few months or so. I just don’t give a shit anymore.

The world continued spinning, life carried on and overall it is just really better that I am just upfront with who I am and where I want to go.

I am blessed to have people I can deeply connect with, and I am really thankful that I’ve found out relatively early in my life that I really don’t have to give a shit about things I don’t care about. I wish it was much earlier, but at the very least, it wasn’t when it was too late to start living.

things I think about

So I mentioned in my last entry that I was writing four days in a row, and that I should write whenever I want, because I have no idea when I’m going to stop writing. I think I should stop cursing myself, for I developed a migraine the very next day.

Migraines are a mixed bag for me. Don’t get me wrong. I hate them. It is one of the worst things that can happen to someone who actually enjoys thinking. The powerlessness I feel when I retain all bodily function except the capacity to think. I had one of those migraines that were lingering but yet not debilitating – which lulled me into believing that I could still function.

I ended up sitting in front of a screen for the entire day feeling like shit because I thought I could do some work, but in reality I couldn’t, so it ended up being really unproductive because it would have just been better for my overall well-being if I had just taken the day off and rested.

But. The day I started to get better, I experienced a profound sense of joy. It was having lost the capacity to think temporarily and then having it back again. This sounds perverse but I would welcome a migraine once a while just to have a stark reminder of how not to take my health for granted. Being able to think, to write, and to express myself is a huge human privilege that I often take for granted.

I remember biking down Valencia street that day and having this huge smile on my face. This is how it feels to be well, I thought to myself. The problem with us is that we don’t know how huge a miracle it is just to be alive and functioning well. How much did we have to evolve in order to develop into a stable set of genes that empowered an entire species like us? I didn’t realize how much of a wonder it is to be capable of thought, imagination and creation. Imagine if some part along the way we mutated instead into creatures that had the capacity to think but unable to express ourselves because we had no limbs or voice? Yes, this is what I spend time thinking about.

It is really difficult to manage one self. I know how fleeting health can be, so that’s the exact same motivation that is behind my conflict between wanting to be a workaholic and yet having enough space and time just to be. I want to do so much because I have no idea when I’ll lose my capacity to think. But it is worse when I become the primary driver of my self-destruction if I burn out. That’s what I think about too, trying to find the right balance.

I biked to the Golden Gate park on both days this weekend. Maybe it was partially because of the migraine. The awareness that sitting at a desk all day does not do much to oxygenate my brain. Partially because I think exercise is one of those things that feels really tedious just to think about it, but becomes really enjoyable once there is an opportunity to set a positive feedback loop. I know people who will literally suffer if they do not do some long bike ride or climb some wall every other day, unfortunately I don’t have that impulse built into me. I have always disliked physically moving, because just thinking alone tires me out.

But it perpetuates a vicious cycle, because I did experience it first hand before – it is true people, that more physical energy does translate into more mental energy. It is simple science, but I was in total denial about it. For people who like to think, thought comes so easily that it seems almost unbelievable that it requires a source of energy.

In other news, I have been having conversations with interesting people out of internet serendipity. It energizes me in a very different way when I am able to meet peers that I can ask questions like – “do you think our rate of change will be quick enough to circumvent our rate of destruction?”, or “why is the human species capable of such intelligence but yet we’re still fighting wars?”

One last thing that has been on my mind a lot lately – the idea that the Stellar protocol can be used to power innovative credit systems. The latest one I thought of during a conversation today – what if one day we can pay for our college education with credit that is amassed not financially, but through performing volunteer work? I am really intrigued bridging different ecosystems and empowering micro-communities with micro-economies.

If we want the world to be different, we have to start thinking different, and acting different.

notes people send me

This is the fourth day in a row I’m writing, ever since I decided I should just write whenever I want. I am not sure how long I can keep up with this, but as long as I feel the impulse to write, I should write. Who knows when the words will dry up?

I received a couple of emails today among other notes left on my Medium post, telling me how much it meant to them. They tell me it is like I am ghost-writing in their place. I know what they mean because I have felt the same way reading people’s stories. It is as if someone found a way to retrieve the voice you’ve thought you’ve lost and then proceeded to soothe your soul.

It is very human to seek a sense of belonging, and we find it through the stories we share. When someone shares a story we identify with, it is a very powerful realization to know that we are not alone. This is what to me, humanity is all about. Lighting up each other’s way, lending each other shoulders to cry on, smiling from the heart when we see others in joy.

It means the world to me to have that capacity to help people tell the stories they cannot tell through my own stories. I may not be doing the best job, but it is a very sincere and desired effort. Days like today remind me why I have to keep on doing this.

I wouldn’t exchange this for anything else in this world, really. To be able to bring back just a little bit of light to someone’s eyes.

Same broken

This was one of my favorite tweets today:

I can’t emphasize this enough – I don’t know how I’ll be without the internet. I may not exist. Imagine growing up believing that you’re everything possibly wrong, only to realize there’s an entire world out there who are just as wrong. Then you start to question, what exactly is right?

I remember feeling butterflies in my stomach the day I first experienced the internet. I couldn’t feel a sense of community locally, but there it was on the internet. Tons of people trying out crazy shit in the brave new world.

It is the same sense of community that I try to reach out to when I publish posts like the one I did Sunday. I was thinking to myself that it is okay if not many people would read it, as long as those who need to will read it. This is what I tell myself every time I write posts like that. It doesn’t matter if nobody reads it. I have fulfilled my end of the bargain.

Unexpectedly it has become my most popular post on Medium in just three days, only exceeded by the power of your writing, but that post accumulated all that traffic after an entire year. I do think part of it is the network effect of Medium compounding, but based on the ratio of recommendations, I would say that people really resonated with the subject. More than I actually wish it to be.

I have been the receipient of many similar stories when I was going through my darkest times. Stories of survival, love and surmounting odds. I remember reading a story about a woman who was sexually abused by a relative, and not only did she rise above and thrive – she shared her story in public. Then I thought to myself, if she could share such a private story publicly, my stories are nothing to be private about.

I have a lot of feedback that people think I am brave, but the truth is, I no longer feel like it is an exceptional effort to share such details of my life. It was nail-biting at first, but I have been writing this way for six years now, the difference is my older blogs were never as widely read. But the traffic is not the point. The moment you publish something like this to the world, you become like an open book to the internet, widely read or not.

The impact of being my true authentic self everywhere is huge. I am who I am. Nobody expects me to be perfect or some shiny object. I don’t have to be afraid that one day people are going to discover my dark self. It is there on the internet for everyone’s consumption pleasure. In turn I get people sharing their selves and stories with me. I get to develop a real community, a community based on a common shared narrative. There are people out there who have been reading such long-winded writing of mine for six years (more for those who started reading on my livejournal and earlier). People are naturally drawn to truth.

For all the stories that lighted my way, I hope by telling my stories and living my life for everyone to see, I can be at least one example of a human being who is extremely broken and yet found a part of the world to belong to. Perhaps one day, there will be more people unafraid to share parts of themselves, and we will evolve to become a society less judgmental of ourselves and one another.

Because this is what I’ve learned. Everyone is fucked up in their own ways. We just cover it up really well. But if everyone realizes that everyone else is as fucked up, perhaps we can be a lot more compassionate to one another and stop standing on our moral high ground. Then, perhaps we’ll stop our senseless power struggles in pursuit of never-ending validation, because we’re all the same broken. Then perhaps, we can really start building this world for what it is. For connection.

I can have a dream. Thanks internet, for letting me find my same broken kind of people. I like them a lot. Where we break, is where the light gets in.

Blogging, again

Apparently there is a blogging renaissance going on and the premise is that you can write anything you care about. The problem with me is that I care about a lot of things, so I confuse myself when I feel the impulse to write.

There is something really attractive about writing on Medium (And it is really not because I used to work there). For me it isn’t the beautiful editor or the brand, but the very visceral feedback you get when you see little faces appearing in your notifications. It gets especially endearing when it is someone you know. But every piece I write there is significant to me, so for now I don’t really want to dilute the content I have there with my ongoing public monologue with myself here.

What is the point of blogging then? I don’t know. I’ve been doing it since those days when you had to run a perl script to generate your blog entries. I was blogging before blogger existed. I was writing both inane and contemplative ephemeral thoughts before ephemeral became a buzz word.

The other part is that I’m obsessed with self-quantifying and keeping a record of almost everything I do, just in case in 2080 I am still alive and want to create a memoir for myself. I have no idea what technology exists in the future, but the worst thing to happen is to have some amazing creation tool and a lack of data. I am already regretting not keeping proper backups of my Greymatter blog.

I just want to write whenever I feel the impulse to write. So many thoughts and moments uncaptured, and forgotten. It is also a recent thing that I no longer care about my professional image (not sure if I ever had one), so it doesn’t really matter if people read this entry with no obvious objective except for the simple pleasure of writing. Know me for me, not just purely for the work I do.

So, I want to embrace the opportunity to possibly write about my ongoing and ever-evolving opinions, biases, contradictions, neuroses and whatever tidbits I care to share with you.

Here’s a list of what’s been on my plate recently:

Writing about my depression

It is not the first time, and will not be the last. I wrote about recovering from chronic depression on Medium, it was something I had to put out there without knowing what will return. I wrote it because not enough people write about it, the stigma will not be reduced if we keep hiding it in the closet. The shame and guilt builds, there is not enough empathy, and the next thing you know, another suicide happens. I want to keep on writing about it, no matter how much distance away I am standing now. This will remain one of the core issues I will spend the rest of my life raising awareness for. What matters is the community of people I discover through these posts – having a powerful shared narrative and mutual resonance bonds two strangers like nothing else.

Consciously moving

I love being alone surrounded by four walls so much that it is starting to turn unhealthy. I managed to make myself bike all the way to the Richmond today, and I was rewarded with plenty of beautiful observations:

Little things amuse me so much and bring me so much joy, I don’t really know why I have to will myself so much to get out of the house.I constantly have to schedule things to force myself to break out of my own routine. It is a lot of positive reinforcement and repetition to build new habits, but I am relatively hopeful.


I finally bought the Vitamix blender I was supposed to buy with the birthday money I’ve gotten when I was still at Medium (yes, amazing perk – I used the rest of the money to buy the rest of my co-workers Amazon gift cards which they were supposed to buy a book with). Hence, I’ve been making delicious green smoothies for myself as meal replacements. I feel a subtle energy difference already, and again, I am relatively positive about this change.

And I keep thinking about…

Balance. And decentralized networks. More on this later, but it’ll probably end up being long essays on Medium.

I’ll probably be writing a lot more. I’ve been thinking about it since I discovered Fred Wilson writes every day. I had spurts when I used to write almost everyday, one such spurt was my first trip to San Francisco, and till today I still look back at those entries with great fondness. Also, I want to put it out there – if you follow me on twitter expecting some great dropping of knowledge on design, please do feel free to click on the unfollow button. The difference between me and most other designers is – I care about design, it is just that I care about 10,000 other things along with it. And I no longer feel bad about it.

There is just something about writing without giving a shit and not make a single edit. Except typos, of course.


I was sharing with a bunch of good friends earlier, on how going for a meditation retreat changed my life. They laughed, because I seem to be having these life-changing moments all the time.

I do have these transformative moments frequently. I actually think I don’t have as many of them as I would like to. There is a reason why I love new experiences and tons of solitude. I thrive on periods of forced contemplation. It is really easy for me to get into a routine, fall back into old behavioral patterns and simply live on auto-pilot mode – wake up, work, get home, sleep. Rinse and repeat.

I stop looking at my big picture, the snowball I want to build, all the learning opportunities I want to pursue. Work can be empowering, but it can also be an effective distraction if we only focus on the day to day tasks and forget to question why are we working on a particular cause in the first place?

I am not afraid of making big life decisions. I am only afraid of letting myself down after making these decisions. Do I have the will and determination to carry out my ambitions, or do I allow “busyness” to take charge of my life again? How can I increase the level of consciousness I have on a daily basis?

The news of Robin William’s passing impacted me more than I thought it would, just like the passings of Chloe Weil, Aaron Swartz, Ilya Zhitomirskiy and the many others that were not as public. I don’t know these people personally, but I can’t help but feel bound to them in some ways, as though a part of me would die along with each of them. But these are the ones we see, how many of us we don’t see, and how many of us are living as though we are living dead?

It kills me on so many levels inside in ways I cannot describe. That I am never safe from myself, that each time this happens instead of feeling like my old self is miles away I actually feel her close to me again. That I get why. I envy. I grieve. All at once. I can no longer differentiate whether I am grieving for them or for myself. Whether I grieve because I wanted to be dead or that I am now still living.

It makes me rethink myself and the way I live. What is the point of all this technological advancement and progression if the society we are building is fundamentally so broken? The events of the past week or month have not helped.

I have a very dysfunctional relationship with my species. I love and resent us so much. Why are we a species capable of so much resilience and change, and yet so self-destructive?

Some people have asked me why I am able to write so bravely about myself. I tell them that I don’t have an intellectual choice. I must, or I cannot live with myself. I cannot live with knowing that we are so broken and yet we pretend we are not. I cannot live with knowing that everyone of us is broken in some way and yet we make so much judgment on how other people are more broken and less deserving than us.

I want to be publicly broken and yet demonstrate that I can thrive with all the breakage I have suffered, and that being unafraid to be broken is a sign of strength and that it can be tremendously empowering. What power do people have over me, when I am unafraid to break myself?

My regret is not being able to do even more than I already am. That I am not speaking louder about the issues I care about. That I am not living as much as I want to. That I am not making full use of my lucidity and consciousness as a human being and I am taking my ability to think and create for granted. That I am not acting more like the person I want to become. That some days I just want to lie in bed and pretend that the weight I carry does not exist. That sometimes I get really, really tired of wanting to care about the greater whole and I just want to live like a hermit where nobody can ever find me.

But I still try. I try to live on for the rest of us because I know every one of us counts. Everyone who battles daily with their darkness and yet live on just one more day matters to the rest of us who are still struggling. I light my way in order for the ones after me to find their way.

Perhaps I live on in the hope of proving myself wrong. That as a species we are really capable of so much more, that we will eventually work towards building a world where all of us can thrive together, that we can really see beyond the futility of power struggles when there wouldn’t be much of a world left to struggle for if this goes on.


I was on a plane to New York from Boston. There was some rough turbulence, and that is a given if we fly frequently enough. But each time it happens for me, I ask – what if this time is going to be that one time?

I think about my death a lot, but choosing to think consciously about it is really not the same when one is being forced to think about it.

It got real really quickly when the plane shook violently, especially with the knowing that my earlier flight was cancelled due to “inclement weather” and there’s a hurricane we were trying to avoid by taking an extended flight path that looked like tiny circles around Massachusetts.

I took a quick mental and emotional audit of my life, critically analyzing if there was anything I would have regretted doing or not doing. I don’t think I could have tried to be more alive than I was already attempting to be, with all factors and context considered.

Travel, the one thing that magnifies the paradox of quickening the urgency of how we live and yet provokes the neccessity to slow down and let go.

I hope to never lose my desire to keep on questioning myself, and that I will be blessed enough to keep on encountering opportunities for myself to face my own mortality right in the face, to always be reminded that it is really there with us all the time, we are just not very good at recognizing it.