Thanks to quite a few of you who have reached out to me regarding my last post. Your comments not only continued my thinking about memorability and how it relates to my value framework, but also helped me realize how many of us are thinking through similar questions. I want to share how I’ve been thinking about these questions and ask about your philosophical processes – how have you arrived at the beliefs you hold today, and (more importantly) the questions you wonder about today?

For me, I suppose that each person lives according to some framework or value system (which may change), and within each framework each person has some goal or objective function. My goal is to optimize my self-chosen values; for others, the goal could be to discover some fundamental truth about the workings of the world or to serve as a mirror image of God. Throughout life, each person is trying to best achieve this goal.

I personally view achieving my goal as a reinforcement learning problem. I best achieve my goal by pursuing exploration (i.e. gathering information to figure out which activities would best achieve my goal) and exploitation (i.e. gathering immediate reward from activities that I already know achieve my goal pretty well, even if they’re not globally optimal). Although this tradeoff is an entire fascinating discussion in of itself, I am more interested in discussing exploration here because I feel that exploitation is something that is personally specific and straightforward (i.e. everyone knows of activities and experiences that accord with his or her own framework, and it’s pretty intuitive to figure out how to keep exploiting those activities) while exploration is a less straightforward pursuit filled with common challenges.

In exploration, I am Bayesian updating, i.e. I have some prior belief on which activities achieve my goal and update my belief with each new incoming piece of information or experience, hopefully honing in (accurately) on “best” activities as time goes on. Now each of my updates has two steps: 1) retrieving the new piece of information and experience, and 2) incorporating that into a new belief on best activities. To borrow words from Confucius, doing 1) and 2) is akin to “learning” and “thinking.” I first learn things: I observe how my friends’ reactions differ when I walk up to them smiling instead of frowning; I swim in a pool and capture sensory details from my environment; I go to topology lecture and finally have some (vague) understanding of manifolds; I notice that I feel less sad after my second house move than my first; etc. Then I think about these things, subconsciously or not; I somehow incorporate these learnings into my beliefs about which activities best achieve my goals of self-enriching and achieving.

It’s intuitive why and how I should do step one of learning. To again draw on machine learning analogy, the more data I have, the more informed I am to (generally) make better decisions and have a closer approximation of the optimum. If learning is good, how do I learn more? I try new things; I have different conversations everyday, explore different cuisines everytime I move to another city, go to college to expose myself to diverse people and pursuits, etc. Especially as babies, humans exhibit these learning tendencies by putting everything in our mouths or touching anything in sight; I think these learning inclinations are innate to all of us.

I also think we innately know why and how they should do step two of thinking. However, it’s much harder for me to articulate how I think in the same way that I just articulated how I learn. I could again offer the Bayesian analogy and say that when I think, I calculate the probability that what I just learned is actually true given my prior belief on optimal activities, and use that to update my beliefs (the improbability of each of my “learnings” correlates with how drastically I should shift my beliefs). But that calculation step is still a black box, both in actuality and in my attempt to explain it intuitively.

From personal experience, I’m going to offer intuition on how this black box works. In some ways, I think of the input-output process of this updating black box – which turns learning input into new belief output – as I would think about solving a math problem – which turns an input set of assumptions or conditions into an output set of answers or implications. More often than not, I start with techniques I already know that might help me get part of the way to the answer (e.g. draw the figure out on paper); then in the likely case that I still need to do more, I start experimenting with simple and intuitive or related approaches, often with many unfruitful trials, until finally I get that “aha” intuition, however fuzzy or hand-wavy it may be. Then I spend the rest of my effort trying to precisely explain that intuition and mold it exactly into an answer. In my mind, updating proceeds similarly. If I observe a learning input that is already very consistent with my prior beliefs, I can just leave my existing prior untouched (akin to using my existing “techniques”). If I see a novel learning input, subconsciously I try to connect it with previous related thought processes or learning experiences, with many of these attempted connections striking no personally resonant chord until I get some “aha” connection that for some reason “feels right” to me. Once I get that “aha”, I spend time consciously thinking or writing about this connection until I can articulate it precisely and make it consistent with the rest of my newly updated beliefs.

Concretely, I think that the “aha” intuitions happen mostly subconsciously and are brought out by events mostly beyond my control – during discussions with friends, a certain question or comment may spark revelation; a new pursuit like photography could help me notice something new and groundbreaking about the subject; or during free-writing I might let my consciousness stream and end up on a topic I never would’ve chosen to write about. Once I get these “ahas”, I try to talk through them with my friends or think and write about them explicitly in order to articulate them into my new belief set.

Some might then conclude that these “ahas,” not articulation ability, are the limiting factor to this updating because we can’t control them and therefore they must be some rare, magical occurrences. But “ahas” are only a limiting factor if few of them occur, and while we cannot directly control our “ahas,” we can affect the number of belief updates that we have to do by increasing the amount of learning we do, so that we update more frequently and more easily (with each new learning, we just have so many more things we can use to make those “aha” connections!).

This formulation of exploration has led me to balance my amount of learning (i.e. undergoing new experiences without necessarily thinking about how they help me achieve my values) with thinking (i.e. converting my learning into an updated set of beliefs and prediction machine). I used to think it incredibly important to think about things before learning or experimenting with them. After all, isn’t it much more efficient and powerful if I can predict something by thinking about it rather than having to actually conduct an experiment? It turns out that thinking, both in process and input, thrives on existing data (i.e. learning), and that thinking without learning can lead to fruitless mind-racking and “dangerously” wrong conclusions, to quote Confucius.

To accelerate my exploration process, I also ask myself how to increase “ahas.” We unintendedly do so in our daily (often bilateral) conversations and active pursuit of novelty (see post on memorability). But can we specifically design situations that would bring out lots of “ahas”? I think one way to do so is to have multilateral conversations through which we can broadcast and collect our learnings and beliefs in a many-to-many model rather than one-to-one discussions or self-contained thought processes. That many-to-many conversation is what I hope to spark with my thoughts and questions here on this blog. I encourage you to help initiate and participate in the discussion as well!


Many of my friends know I consciously live my life according to a value system – I choose pursuits that optimize two values, self-enrichment and achievement. I’ve picked these values based on what I’ve (perhaps subconsciously) noted about myself and my priorities over the past decade or so. Then I’ve built in rituals into my daily life that facilitate me fully pursuing these pursuits that optimize my values, including physical enrichment (working out in the morning, with lifting MWF and swimming TSa), intellectual enrichment (allocating half an hour to read for leisure every night), and even a set of times and places during the day when I work exclusively on startup or school. I adhere to rituals because once I get used to them, it takes little energy to “be disciplined” and follow them, and I spend less time wondering what I’m going to do next or how my rituals contribute to my grander value system.

I’ve been confident that this is the best way to live my life. When I say “best,” I mean according to this framework of optimizing for self-enrichment and achievement. But yesterday, while reading Joshua Foer’s Moonwalk with Einstein, I came across a passage that led me to reexamine my framework. The book documents Foer’s experience of training for the US Memory Championship, and the specific passage that provoked me describes Grand Master of Memory Ed Cooke seeking to make his life maximally memorable by packing his life with memories. Foer suggests that because we remember events relative in time to other events in our lives (e.g. I had my first kiss after that Flight Deck ride at Great America, after getting soaked on the Logger ride, etc.), we can make our lives more memorable just by increasing the number and novelty of experiences (e.g. the number and novelty of “afters” in the above sequence).

After I read this, the idea of maximum memorability began to resonate with me. One of Foer’s statements in particular articulates this seemingly strange resonance:

Like the proverbial tree that falls without anyone hearing it, can an experience that isn’t remembered be meaningfully said to have happened at all? Socrates thought the unexamined life was not worth living. How much more so the unremembered life?

Another explanation for my resonance with maximum memorability is its natural interpretation as maximizing psychological lifetime, or subjective experience of time, if we merely measure this “time” by number and novelty of experiences. I find subjective time a natural personal value to optimize. For one, I think this desire to maximize subjective lifetime could be the reason that I (and many humans in general) seek novelty and change in pursuits. This idea that humans measure subjective experience of time by novelty of life rather than by physical, objective time comes up everywhere. In Duane Michals’s Now Becoming Then, Michals tells stories of twisted relationships, mystical and religious occurrences, and even entirely different worlds (“Empty New York”) by capturing snapshots of “points of novelty” in each story’s trajectory – the points at which the story changes most significantly – rather than by taking snapshots at constant time intervals. Why are these points of novelty so much more interesting to us as chronological markers of subjective time than time itself? In finance, one problem that traders commonly encounter is how to index “time” in the market, given that incredible volatility and trade volume can be concentrated into such short times of day while the remainder of the day trudges slowly along. One approach to indexing time is by counting specific changes or events in the market, which suggests that change or novelty gauges the subjective time we’re interested in. In computer vision, a common approach to identifying objects in an image is to scan across the image and detect significant changes in pixel values, which correspond to one object disappearing and another beginning, suggesting that novelty is an index of objects’ very existence. All of these modes of thinking imply that we seek novelty because we seek to lengthen our psychological experiences of time, i.e. make our lives more memorable.

So I think it’s natural to value memorability; I certainly place some value on it. (I should be clear that I value memorability in the sense that I value the mere number and novelty of memories that I possess and thus am continually influenced by, however subconsciously, rather than some efficient system for fetching these memories by rearranging my neural connections or any other type of conscious recall.) And if I value memorability, I should incorporate it into my value framework, but how? I could add “memorability” as another value, but that seems unnatural because I don’t view it as a competing priority that I should optimize. Rather, I should use memorability as a metric and choose to measure how greatly an experience or activity achieves my two values of self-enrichment and achievement based on its memorability, i.e. its subjective impact on me, rather than based on any other criterion. For example, in my self-enrichment value, memorability is already naturally encoded, because by definition self-enrichment emphasizes pursuits that have self-impact. But as for my achievement value, until now I have had in the back of my mind some external metric for achievement (e.g. number of people impacted) that felt less genuine to me. What I really value in “achievement” is that subjectively experienced (“memorable”) magnitude of achievement. I can’t truthfully say that my 14-minute TEDx talk to 100 Gunn students was a more memorable, impactful achievement for me than 14 minutes of fixing certain bugs in my pathway identification algorithm in a cubicle, even though in many standard definitions of “achievement” the former would be greater than the latter. And because memorable achievement is genuinely what I value, that’s how I should evaluate how each of my actions optimizes achievement.

Thanks to Kanjun Qiu and Carl Gao for their thoughts on this.


I spend twenty minutes every morning freewriting before the daily onslaught of startup work and college. My only rules for freewriting are that I don’t stop writing and that I don’t erase. Here is one of my (revised) freewrites that I found surprisingly helpful for my thinking.


Walking back from a morning swim without contacts is an interesting experience. I’m tired but content, wearing short swim trunks that reveal the whites of my thighs. I’m passing people in the gym and weight room, in the dining hall, and even on the stairwell up to my dorm. But I can hardly see them. My lack of contacts obscures the details from me. And in this part of my daily routine, that might be a good thing.

For some weird reason, I used to think that others judged me as I walked back from my morning swims. “Look at those short shorts.” “You don’t even swim, yet you get up at 8am to do so? Why?” These are obviously exaggerated, but I used to think that others were thinking these things; even I was sometimes thinking along these lines, so they had to be!

As it turns out, when I take off my contacts, I become oblivious to any judgment from the passerby. I only see a big fuzzy picture, without the nuances of people’s slight eyebrow raises that would imply judgment. I can’t even see if I know the people I pass, and I end up not caring about how many human blobs appear on my path. But for some reason, I still hear the criticisms. Where are they coming from? Then I realize that the voices are just me.

Now it’s not exactly a mind-blowing revelation that my insecurities often stem from my own attitudes rather than others’ judgments. Rather, what I find more interesting here is that I can learn new things from the same daily experiences by viewing them in less detail. Occasionally, taking off my contacts opens my eyes to the bigger picture and filters out noise that obscures underlying truth.

In general, I wonder what I could learn by running my life without contacts. How comfortable would I feel to let the details fall away and only see the big picture? Would this new perspective help me focus on greater vision in my life philosophy, and put me above day-to-day vicissitudes?

What would it be like to see only a big green-brown mass instead of a tree? To be surrounded by a mahogany space rather than a dining hall filled with ornate chairs and tables? Maybe details help me form stories and rationalize. Take the dining hall. How were these chairs designed? With a slight natural back arc, maybe the designer thought to support good posture. The chairs are wooden, yet light enough to be moved around, perhaps for the sake of intermingling. The tables part along a central walkway through which I can rush to class or stroll and catch up with everyone I know. The tables seat eight; maybe that’s the optimal amount of people for a nice dinner conversation?

Are these the details – the stories – I would miss by shedding contacts and a closer examination? Would I learn more or have clearer direction if I missed these random details and focused on the bigger picture? Of the random and coincidental details I’ve noticed already, of course I appreciate the stories behind them. But now that I’ve understood them, can I wrap them up in a nice black box since I know the lower level implementation?

Maybe that’s how vision, both figurative and literal, should proceed. Upon first sight, I study the fine details, then abstract them away and leave a fuzzy picture in my mind. Then every so often I put on my contacts and refocus these fuzzy pictures, as I gain more life perspective that helps me reinterpret the updated details.

25th Floor

I’m amazed by the things I notice when I stop what I’m working on to actually take a look outside. It’s especially cool to observe so many details about life on State Street and The Loop in Chicago just by looking out the window of my apartment on the 25th floor.

It’s noon on a Saturday and people are out and about, sporting their summer clothes that they bought just for this occasion. From up here, the pedestrians look like calm ant troopers – not scurrying around in any rush, but carrying on confidently in single file to their weekend haircuts or grocery shopping. Some travel in small packs – families or bands of brothers – but many walk alone, the women with their shades up and black purses tucked under their arms, and the guys wearing anything from button-ups with jeans to deadmau5 tees with shorts and flip-flops. Every now and then you have joggers with their headphones locked in determinedly weaving through the sidewalk pedestrians, listening to some motivational Kanye or getting into lock step with LMFAO’s beats (you can tell from their jogging pace). The joggers come mostly in singles, although occasionally there is the couple trying to stay in shape together. Even though it’s the weekend, you can tell Chicago is a mix of fast- and slow-walkers, of East and West Coast – you have your New Yorkers with quick, big strides (it’s like they can’t get it out of their system, even on a Saturday) and then your dilly-dallying Californians always blocking the paths of the impatient New Yorkers behind them. I almost laughed when I saw a New Yorker plow through a crosswalk in half as many steps as the Californian behind him.

Of course, there are a few people chatting away on their phones – making last-minute weekend plans, getting unexpected calls from friends they haven’t seen in a while, or (still) discussing work with demanding bosses unable to detach from office life. (You can see who’s doing which by the facial expressions.) And the jaywalkers never cease to amuse me with their creativity and audacity, especially the jaywalkers who simultaneously talk on the phone and wind between cars at an intersection that’s about to go green.

And then there are the many species of cars traversing the grid-like jungle of Chicago streets and skyscrapers. Taxi cabs of different sizes drive by every now and then, sporting pizza ads from their rooftops. You have your fair share of typical sedans and (to a lesser extent) SUVs cruising up and down State Street for as far as the eye can see, as if they’re on a never-ending assembly line that disappears into the horizon. This serenity lasts for 30 seconds; then, suddenly, a big rectangular bus breaks up the homogeneity on the street, invading the bike lane and blocking out multiple lanes on left turns. As if to compete in size, a white Hummer limo steps out from behind the Hotel Palomar tower and is joined by a fully stocked supply truck just turning onto State.

I raise my eyes and gaze out further into Chicago, to the sight of towering construction cranes planted squarely at the centers of city blocks. Skyscrapers edge each other out of the way for the city’s best vantage points. Like dwarves among giants, the 5- and 10-story buildings put their rooftop gardens, fans and ventilation systems, and even swimming pools on full display for their taller brothers to see. Under the overcast sky, a cute girl sunbathing by one of the pools eerily reminds me of the opening sniping in Dirty Harry, but the large McDonald’s in the background with its happy yellow arches puts these thoughts away.

I’ve never paid too much attention before to these shorter buildings, or to the rather ugly cranes and industrial rooftop fans, or to any of these interesting details in the local passerby for that matter. I’ve always had the habit of getting home from work rather late and taking a minute to gaze out through these same windows at the same barrage of pretty city lights as if gazing upon the same stars. But I’ve never had the opportunity or urge to count the number of steps a young child takes to cross the intersection at State and Grand, nor to observe the variety of 5-person walking formations that people try on Chicago’s sidewalks. The unchanging black night sky awaiting me when I get home – the black city background – has obscured the fact that there is so much detail and human substance behind that visage of flashing lights, of city thrill and architectural grandeur. But now, taking an hour just to observe – to part the curtains of night and see the mundane backstage behind the dazzling theater of nightlife – is a truly enriching diversion.

Oddly enough, I notice these details more profoundly now, 25 stories high and behind the isolation of glass windows, than when I am surrounded by people on the packed bus to work, or when I am eating out in a crowded restaurant surrounded by others doing the same. Seeing Chicago now and knowing that it will be so different 9 hours later – or even 5 hours later – and knowing that this cycle continues day by day and week by week reminds me of Monet’s paintings of the same stack of wheat across all times of day and all seasons. What must have captivated him to paint the same subject in so many different settings is exactly that there are so many undiscovered nuances in even the things we think we know intimately, and such a wealth of information to be captured by observing one object at a different time, from a different perspective, or even with an entirely different sensory capability.

Why Blog?

Due to my over-preparedness, I find myself at my gate at the Paris Charles de Gaulle airport two hours before my flight. I have no internet and nothing else to do – I guess this is the perfect time to start writing and recap my trip. But before I do that, let me explain why I am beginning anew my attempt to journal, blog, and otherwise record and analyze parts of my life for my own processing as well as (hopefully) others’ enrichment.

Life moves too fast. It’s a cliche – I know – but especially as a college student (even one on summer break), I find myself reaching into so many things – a startup/research project outside of class, an associate role at a VC, somewhat interesting classes, multiple friend groups and student organizations within Harvard and without, and relationships with VCs and entrepreneurs. All of this is partly for enjoyment, partly to develop skills, but mostly to “discover my passions.” That’s the priority I wrote out in big blue marker on a motivational poster for myself this freshman year, and it’s a focus I’m still happy about pursuing. The idea is that I can dabble in a variety of interests, figure out which ones really engage me (i.e. my passions), and then pursue those passions to the fullest. Right now, I’m still dabbling.

In my dabbling I feel like a computer’s task scheduler, compartmentalizing each of my interests into a process and constantly context switching between these processes. The problem is that I only have one CPU and I can’t actually multitask. Unlike a scheduler, I can’t make split-second switches between processes – as a human, I can’t accomplish something without first putting in substantial time investment, plus I can’t just turn interests on or off on a whim. Yet this is exactly the multitasking approach I have to take to explore so many exciting things on such a tight schedule. Imagine the opportunities for distraction at a place like Harvard – late night conversations learning about your roommates (and even understanding the motives of English majors), interviews and talks with tech and finance companies about their business and engineering challenges, meals and coffees with entrepreneurs and VCs to understand the problems they’re solving and their world visions, and brilliant, fast-paced lectures delivered by Professor Edward Glaeser.

The result is that it’s impossible to focus on any one thing to gain enough depth in it.

But I don’t want to stop exploring! I don’t think I’ll ever stop. Exploration keeps things interesting and it’s fun, and in many cases I find that it yields complementary undertakings – rather than time tradeoffs – to my main pursuits. How, then, can I keep track of what I’ve learned even as I explore so many interests simultaneously? As long as I’m exploring, I’d better explore purposefully. I’d better solidify what I learn or risk forgetting it all. More importantly, I’d better think more deeply about my learning rather than merely absorbing information, to begin to make sense of what I am exploring and be able to determine my next area of pursuit with more insight.

That is the very long explanation for why I am writing this blog for myself, first and foremost. To not only record my learning, but also to analyze it in writing and produce theses and direction for my life.

And I want to blog publicly to engage with others who I believe are making this same journey, albeit along different paths. There’s only so much I can explore as one person, but I’ll happily exchange lessons with others so that I can cover an expanse orders of magnitude larger, even vicariously. Hopefully I can contribute to others seeking their own direction by sharing these reflections.