the heart is short-sighted, the mind is far-sighted; it’s the two together that represent reality

The title is an original :D (slowly building my book of quotes, heh heh)

Two topics related to this.

I’d been quoting this to a few people recently  — “when the heart speaks, the mind finds it indecent to object.”

But object it must, sometimes. Because sometimes the mind can see when the heart will be hurt again in the future. The untrained mind lives primarily in the future and past. In fact, it’s considered a remarkable feat to train the mind to live primarily in the present; this is mindfulness.

But there are some benefits to the mind traversing time so easily — it picks up patterns, it forms hypotheses, it can see time as a continuum in which the same things repeat, just with different names.

The heart, on the other hand, knows nothing but the present. It feels what it does and it feels it now. It knows when it’s happy and it knows when it is not. It does not know if that happiness will last a second or a day or a year.

This has obvious benefits as well, of course. As I mentioned in my previous post — I think one should really be careful in choosing to delay joy; you never know if life is going to be a second, a day, or a year more.

Which brings me to the second and more interesting but less eloquent of the two points — I was recently chatting about MBTI with a few friends (speaking of things that repeat…) and decided to re-take the test (for probably the 10+ time…which is fine because the biggest criticism about the test is that the results fluctuate dramatically over one’s life, hinting at just how much of personality is nurture versus nature). I’m pretty borderline on two of the four characteristics and off the charts extreme on the other two. Which makes me wonder…

In the above situation of mind versus heart, which MBTI would call thinking versus feeling, it’s really powerful to be able to see both sides. To will oneself to step over the line to feeling and then back over to thinking just to see the world through different lenses (as an aside, another quote I’ve been tossing around recently is — the world is a tragedy to those who feel and a comedy to those who think. Pretty accurate).

In light of this powerful ability to see both sides, I wish I was borderline on all four MBTI qualities. Because, more than anything, I want to understand. I want to understand how others see the world today…and how those that have come before us saw it and therefore shaped it into the way it is.

the heart is short-sighted, the mind is far-sighted; it’s the two together that represent reality

sometimes it’s ok to eat the marshmallow

I recently received the letter I wrote to myself in the last few days in business school. This was an exercise the school proposes, not something I narcissistically did myself, haha. It’s pretty powerful (if I can say that about my own writing haha). It was written during what is called Bridges, which can be described as the school’s gentle “offboarding” of its students into the real world; it’s supposed to remind us what was really clear to us at this point in time. I hope I remember the contents of this letter indefinitely.

As an aside, the title of this post is one of the pieces of advice one of my favorite professors gave our class.

Dear Wendy,

It’s been three months since the writing of this…I hope it’s been a good three months for you, filled with joy and filled with purpose.

At this point, I hope you remember a few things that were so abundantly clear to me at the time of this writing.

First, I hope you remember to live with joy in mind — be impatient for finding, creating, and cultivating it in yourself and others. It is not something worth delaying.

Second, I hope you stay true to and remember your best self, your values, your purpose. You were entrusted with some positive attributes and opportunities, and I hope you don’t forget to remember to pay the world back — better yet, to pay it forward. I hope every night you go to sleep knowing this is the best you can be and do at this moment.

Finally, I hope you don’t forget the deep well of support of loved ones that surrounds you and that you in turn provide to others. Don’t hesitate to rely on and draw from it, but also don’t forget to replenish it frequently.

I hope these last three months have been all you dreamed of and more.


PS – and if it hasn’t, I hope you’re learning and adapting!


sometimes it’s ok to eat the marshmallow

you are not entitled to your privilege, you are entrusted with it. and then the natural question is – who entrusted you? why? what do you owe them?

Paraphrased quote from Matthew Bannick @ Omidyar who came to speak at one of our classes last fall.

I have two thoughts I wanted to discuss in this post. Now, I know for post / blog / whatever popularity, one needs to segment these thoughts out in different posts. But, as I remind myself over and over again, this is not a “blog for popularity” :P

First – when talking about adult re-education, there’s still, frankly, an unwarranted amount of focus on content. Guys. It’s 2016. There’s the internet and even if there isn’t the internet, there’s the public library, community college, encyclopedias…

The issue hasn’t been content for a long time. The issue is confidence, specifically the confidence that one can learn new things from scratch. As one gets older, the last time this activity happened – which for a lot of people, lamentably, is school – gets further and further away and, much like learning to ride a bike and then not doing it for a decade, one starts to fear getting back on.

Similarly to the analogy, though, it’s very hard to forget how to ride the bike. The brain doesn’t forget to learn. In fact, even for people who don’t do it deliberately, the brain is learning every day. But one forgets that one has the capacity.

How to address this scalably rather than through social services? Let’s discuss.

Second – there’s an Ender’s Game concept (the quote eludes me) that has stuck out in my memory since 8th grade – “No, you don’t understand. I destroy them. I make it impossible for them to ever hurt me again. I grind them and grind them until they don’t exist.”

It’s essentially that if you decide to fight, which you should decide to do very seldomly, then you must decide to indisputably win. In the case of Ender’s Game, you must kill. Otherwise, the thing which you fight will come back at you, more vehemently each time.

I realized on the way to work one day that the same concept applies to ideas. The most extreme example is revolution, as we saw in Turkey recently. If you don’t kill the thought of revolution / coups the first time, you allow it to hide for now and resurface, stronger and more confident about your relative weakness.

I thought of this, though, more in the context of the mundane, specifically about matters of disagreement at work. Now, I think this is quite a different category and more often than not, you need to listen and sometimes even fully adopt the other person’s ideas if they are better than yours. I have no problem with this. However, if you decide to fight hard because you know your idea is right, it is almost always more preferable to win the argument in one fell swoop. Because ideas, once only half killed, come back stronger than before. They fester and spawn doubt that they then feed off. That doubt needs to be eradicated before it makes the idea so strong that you have to fight the fight all over again, this time an even harder fight.

you are not entitled to your privilege, you are entrusted with it. and then the natural question is – who entrusted you? why? what do you owe them?

children begin by loving their parents; as they grow older they judge them; sometimes they forgive them

“Ready, Mom?”

She looked up from the Health magazine she was scanning, glasses pulled down past the tip of her nose to accommodate her worsening farsightedness. “Been ready.”

I grabbed the car keys and wallet off the counter and slipped on flip flops. “Cool, let’s go.”

She got up from the couch. The muscles in her arms appeared and disappeared and appeared again as she held onto the wall while putting on her shoes. The jeans she picked out that day looked baggy, pooling a little at her ankles after she pulled on tennis shoes.

I lock the door after us, giving myself a few seconds to hide my face and allow her a head start towards the car. The lump in my throat threatened to dissolve into my expression, but I distracted myself by doing a mental check for keys, wallet, phone. Check, check, check.

By the time I turned around, she had already opened the passenger side door and had one foot in. “Your dad always likes to sit so close to the dashboard,” she muttered as I slide into the driver’s seat.

I laugh a little. “Dad still gets nervous when I drive.” I hear the click of the seat belt and a soft exhale, an emptying of the lungs, as she settled into the seat next to me. We pull out.

“How’re you feeling?”

In my peripheral vision, I think I see her shrug, but maybe it was just her folding into herself. “Well, you know. I knew this day was coming.”

“We could’ve prevented it, you know,” I state quietly. It seemed a pointless statement this far in, but I couldn’t help myself. The volume of my voice indicated the deafening anger, violently muted by the expansive hopelessness I felt filling my chest, infusing my lungs, making my throat constrict and leaving the taste of the fear of drowning in my mouth. I wanted to say it isn’t fair, but the best I could muster is she didn’t try hard enough.

“Yes, maybe. But now we’re here.” I think she snuck a glance at my profile, her eyes traveling down to my hands, knuckles bleeding white from gripping the steering wheel too tightly. “Relax, Allie. Dialysis is a common treatment.” When my posture remained frozen, she tried again. “It’s just four hours. It’ll be over before you know it.”

I drop my shoulders a little, relenting. “You sure you don’t want me to stay with you?”

“Oh, honey, what’s the point? You’ll be bored out of your mind.”

“That’s ok. I can keep you company.”

She laughed a little. “No, no, you should go be with Alex. Take Joey to the park. It’s nice out.” Again, discomfited by my silence, she added, “You think I ever offered to keep you company when you didn’t want to be dropped off at pre-school? Please. I had so much I had to do!”

And then it clicked. The feeling of misplaced deja vu, the warmth of familiarity mottled by the cool breeze of uncertainty, the depth of attachment I felt to this event that is just the first of its kind for the rest of my mom’s life — over a decade ago, we were here. Our seats were different. My mom was ten years younger. I still couldn’t drive.

How quickly time has flown. How quickly our roles have changed. Or maybe slowly? Imperceptibly. A slow going out of business. One moment she was the pillar of my world and the next moment when I remembered to scan the horizon, the pillar was gone. In its place was a shadow of what was there before. It needed to be meticulously taken care of lest it fades away from relevance as all things less than young, beautiful, or heroic tend to do.

“Allie, I can’t wait to see you grow up.” I remember her telling me. But then she paused and shadows tiptoed onto her face, causing her eyes to dim and the smile on her face to turn inward. “But when you grow up, I will have grown old.”

children begin by loving their parents; as they grow older they judge them; sometimes they forgive them

the saddest aspect of life right now is that science gathers knowledge faster than society gathers wisdom

Quote a la Isaac Asimov.

I chanced upon this tweet many years ago:

Screenshot 2016-07-07 22.09.14

My classmates and I have talked surprisingly little about what we’ve taken away from HBS. It is more often when I chat with HBS hopefuls or HBS skeptics that I take time to reflect on whether or not I really learned anything in business school.

Some of my classmates have attempted to think about this on a fairly micro scale — per class, per session, per semester, per conversation. I admit, for much of my time at HBS, this is also how I thought about it (and, frankly, it’s unsatisfying to think about it this way). Others have a much more macro view, including the one that HBS communicates they’re trying to teach — how to form a view about the world that functions as a north star in ever changing contexts? Most likely, then, we will not know what the impact HBS has had on us until a few years out of school, when some of these hypothetical world views have been given a bit of breathing room to solidify, ossify, or disintegrate.

So this post is a snapshot in time. A few months after HBS and about 1.5 months into the post-work world, though in startup years so maybe that deserves a 3x multiplier. In a management by influence with no formal power + sole responsibility for results position, so maybe that’s another 2x multiplier. This is my current take on what I have learned and not learned at HBS.

(spoiler alert — I wholeheartedly believe it was worth it. It’s a bit pointless to describe, though, because it’s a weird blend of personal journey + widening of perspective + tactical learnings, etc. It’s an experience that molds itself to the individual rather than the current state of K-12 education in the US, which demands that the individual molds him/herself to the experience. Therefore, when describing it, all I can really convey is what takes place in this experience and my best judgment of what you will find there after getting to know you a bit better).

What they teach you at Harvard Business School

Lesson One: Everything that you aspire to achieve, no matter how big your ambition, is within the realm of possibility. Many things are within the realm of probability. Some things are even within the realm of certainty unless you f*** up. 

I tell friends this often — somewhere around the first or second semester of second year, it dawns upon most people — the default assumption of the school is that you are going to be CEO one day. Of course, some people will choose not to be. But if you want it, it’s yours. This assumption is never explicitly stated, but it is ever present in everything that is said (“when you’re talking with your board…”) and unsaid.

Lesson Two: The world is big. Any part of it is fair game.

HBS expands your perspective. Not only is there an explicit class that covers one country per class but 40% of your classmates have a non-US passport. Additionally, business school is made for travel, and travel expands the mind. This is especially true in the format that HBS tends to have for trips — led by people familiar with the country, oftentimes with a particular angle on understanding the broader themes of the country through one in-depth instance (e.g. the Tohoku earthquake / tsunami / nuclear meltdown as a lens into Japanese culture). The experiences and classes convincingly transport you to different parts of the world. Suddenly, it feels very possible that you do something meaningful in Nigeria one day.

Lesson Three: What makes a good leader.

Everything from theory to practice, from organizational level to one on one level, from team building to team disciplining, from delivering results to being loved, from being one of the people to standing apart and carrying more weight. This lesson is too hard to distill into one blog post, but we looked at examples from everywhere — the usual suspects of today’s organizations, governments, movements, but also the leaders in Rome, history, philosophy.

Lesson Four: Every dimension of the business is your job to lead (but not necessarily to manage).

We get a view into every major facet of an organization, from accounting to marketing / sales to finance to government relations to strategy…you get the idea. As people often joked, the spoiler is that everything converges to a class called Lead…that is, by the last third of the semester, every class starts feeling like Lead, a class in which you learn how to act as a leader.

Lesson Five: You can’t be good at everything. Choose what you’re going to suck at.

Choosing what you’re going to be good at is a hugely pleasurable experience. Choosing what you’re going to suck at sucks. But doing the latter guarantees success in the former more than doing the former.

Lesson Six: When you start breaking problems down, you’ll find the issues are often pebbles rather than boulders.

Most things are within our ability to solve. Break it down. And if it’s still overwhelming, break it down further. Very few problems can withstand the combined forces of patience, persistence, hard work, and deliberate care.

Lesson Seven: Always do the pre-work. Then, stay vigilant. And always speak up.

Don’t be lazy and leave things up to chance. But realize that chance has a role in everything, so learn how to observe carefully, especially for anomalies. And never be afraid to speak up. Sometimes it might be for yourself alone, but oftentimes, if done right, it might be in the stead of somebody else who can’t.

Lesson Eight: Whether you choose to formalize it or not, a process exists for everything. Processes are the building blocks of culture. You can’t will culture into existence. And, as Warren Buffett famously said, culture eats strategy for breakfast.

This is more of a lesson for the startup world. Processes will exist whether you choose them or not. Choose them. They, not the 10 commandments you paint onto your walls, are the elements that shape your culture.

Lesson Nine: Your actions are just a manifestation of your theories about how the world works. Try hard to break your theories so you can refine them.

It’s pointless to take an action to repeatedly prove a theory. Theories become better as they repeatedly break and adapt. When you can take the risk, try to break theories, both yours and others’.

Lesson Ten: Know thyself. And ask for help.

The ultimate truth. And in knowing yourself, know when to ask for help. I realize even in these first few months how valuable my classmates are — their depth of knowledge in areas I had never had experience in is really profound and humbling. I also realized how powerful the network is. Not even counting the people who came before us but just those in my class — I realize with a 1-2 step connection and a healthy dose of shamelessness, I can probably intro anybody to anybody.

What they don’t teach you at HBS

Lesson One: You can immediately start taking risks.

While most people understand that one day they will become CEO or one day they can work on a meaningful problem, most also believe that that day is not today. That day is somewhere in the murky future. I think even at graduation, we are all already uniquely privileged to take more than the average amount of risk. And, of course, personal risk only increases with time.

Lesson Two: Make the relevant scope as large as possible.

The scope of care for people varies a lot. Some think in terms of their immediate family. Some think in terms of people like them. Some think in terms of companies. Some think in terms of nations. Some think in terms of humanity. Some think in terms of all living creatures. I think it’s important to make the scope of care as large as possible. The largest that I’m currently aware of is thinking in terms of the universe and optimizing for it, even if it means humans are just a sidebar or an insignificant evolutionary step along the way to something greater.

Lesson Three: Self reflection.

The school doesn’t force this upon you, but it is probably one of the most worthwhile uses of one’s time during the two years. There’s a lot of information and knowledge being transmitted, but, as the saying goes, experience =/= wisdom. You can experience something and still learn nothing.

Lesson Four: Empathy.

Surprisingly very rarely discussed in the school despite that it is one of the most adaptable and powerful tools for living. It’s often brought up by students but I can’t remember having a beyond superficial discussion on the topic.

Lesson Five: What’s right and wrong.

The school never intended to teach this. If you haven’t learned this yet by age ~27 (avg age of class), you probably have some bigger problems…

The school does teach you how slippery the slope is into “wrong” despite that you think you have good and strong values. And it teaches how to create environments where “right” is more likely to thrive than “wrong.”

Lesson Six: How to not believe the hype. And that competition isn’t always the best path.

Business school is a hype machine. There’s so much eyeballing what the other person is doing. There are so many Type A, hyper competitive people. There’s a collective view on what’s “hot” right now and people measure each other against it. The social pressure makes it difficult to remain true to yourself.

I think HBS doesn’t do a good job of communicating that the game lies in how to avoid competition rather than win (a bit bloodied) against intense competition. I think some of my classmates believe you don’t prove anything unless you win and you can’t win without competition.

Lesson Seven: How to satisfice.

HBS accepts people who are overachievers and perfectionists and doesn’t do much to tame that desire. But life is not as forgiving.

Lesson Eight: Patience.

As Siddhartha said in Herman Hesse’s book — I can think, wait, and fast. And with those three skills, one can overcome almost any challenge. People leave HBS with a strong desire to act. Inaction seems wasteful, slothful, and inane.

Lesson Nine: How to be happy.

Nobody can teach you this. People think HBS can teach them this because it arguably teaches you how to be successful in your career, but we all know that doesn’t equate to happiness.

Lesson Ten: How to judge people and multi-faceted situations instead of just data.

The former requires messy experience. The latter is over-emphasized in all classroom settings.

the saddest aspect of life right now is that science gathers knowledge faster than society gathers wisdom

those who have a ‘why’ to live can bear with almost any ‘how’

One of my friends frequently reminds me to write but I have to admit, over the last year or so, whenever I consider what I would write about, my conclusion is often that the activity is pointless. That it is a species of self-aggrandizement that contributes little to others, collects a time tax from those who read it, and provides me with most of the benefits — a psuedo sense of accomplishment, incremental practice on my writing and synthesis, and some temporary exposure on social media.

In my teenage years and early 20s, every new insight felt novel. It tickled the brain to think about the human condition, the potential indifference of the universe, the problems of our present and future — all the topics that make for good rainy afternoon cafe chatter — and each realization seemed to open up entire territories (like in Minesweeper :D). I had just enough aptitude and knowledge to think I knew – or could come to know – everything.

As I read more (and even at a decreasing pace), it is clear that most of what I had previously thought were interesting had been thought a long time ago, in greater depth and conveyed in fewer words. It seems pointless to perform the job of a tweetbot and re-post highlights here; this isn’t my attempt to be a bot, a motivational speaker, or a source of mental donuts. It would be different if I had derived new insights from new information or a diverse perspective on a neglected topic.

With the exception of those cases, I am inclined to keep silent and just observe. If anything, to prune.

My only significant realization in the last few years (and possibly for a long time) is this — life is shockingly simple. Good health, meaningful work, good relationships, and luck. Take care of yourself physically, mentally, emotionally; be vigilant for what has meaning; spend time with loved ones; be grateful.

Interests going into 2016 if you’re interested in discussing–

  • Problems of our present — centralization, climate change, education, aging, inequality of the ability to create value, thoughtless design
  • Problems of our future — artificial intelligence, synthetic biology



those who have a ‘why’ to live can bear with almost any ‘how’

success is never final; failure is never fatal

The only long-term advantage is speed of learning. The assumption is that agility is a good substitute for power and its usual symptoms of size, wealth, etc.

Software measures this by pace of release cycles. Military by pace of the OODA loop (observe, orient, decide, act).

What is the right metric elsewhere and, more generally, in life?

As my classmates and I evaluate which organizations to join, I argue pace of learning is the single most important predictor of an organization’s success, so it is worthwhile to be obsessive about figuring out what the right one is for each organization.

Roughly, the way to decompose this question is

  • Figure out what the organization needs to learn (one of them is probably customer behavior … but there are other important things, too)
  • Figure out what is the key (likely iterative) behavior that enables the organization to learn this information
  • Assess how good the organization is at turning information into insights and adjusting actions (politics come in here!), and
  • Measure how long this whole cycle takes.

For life in general…I agree Drucker’s implication in Managing Oneself — we reflect very poorly, if at all. Thus, natural biases grant us the fuzzy reprieve to conclude we’re more successful than we actually are. As Regina Dugan, former Director of DARPA, once said — it’s ok to fail, but it’s fatal to not realize when you have failed.

Maybe the initial few habits to adopt are

  • At the end of every day, jot down 3 things you’ve learned that day
  • At the end of every week, look over the 21 things you’ve jotted down and decide if there needs to be any behavior change. Pick the most important behavior change and try it for the week; keep track of the other ones you’ve identified
  • For important decisions, write out the OODA loop — 1) what did you observe? 2) how did you orient / analyze the situation? 3) what was the decision? 4) what was the ultimate action? 5) initial reflections? Revisit each major decision monthly to see if there were any errors in the loop. Jot down recurring biases / errors

This stuff is boring. It’s plumbing. And oftentimes, it won’t seem like the most efficient use of time in the short term. It isn’t. It is in the long term.

To my future self — ignore those signals and carry on learning.

success is never final; failure is never fatal

in a world like this, you pay it forward, ’cause more than likely you didn’t deserve it when you got it the first time

It’s around the end of the semester, so we’re filling out a lot of course feedback reviews, many of which ask for advice about things to improve. This made me think of two things, one more commonly accepted than the other.

The first is that, as is so commonly said as to be mocked, feedback is a gift, especially in this setting, where the quality of the feedback doesn’t benefit the person who gives the feedback at all. We’ve already taken the course; any amount of time we contribute to delivering good feedback is a gift for future students. Because of this, I think it’s difficult to see the relevance of the exercise. This is a reflection of the fact that most acts of unkindness in this world aren’t acts of cruelty but rather acts of omission. I would argue, though, that we can be selfishly motivated to provide feedback for, essentially, the betterment of the school, because as long as this brand is associated with us, it is in our best interest to help it thrive.

The second thing that comes to mind is something I try to be as conscious about (and often fail at) as I can — good advice is very hard to give. And yet so many people are so fond of giving advice (myself included), usually as an assertion of ego behind a shoddily made veil of generosity, so bad advice is also, unfortunately, very often given. It’s hard to give advice that is not autobiographical and the way to do it requires listening first, empathizing second, and speaking last. This takes both time and intensive effort and if ever I’m in a situation when I can’t devote that time and energy, I prefer to just tell the person that, rather than give misleading advice — that my advice is biased and irrelevant because I can’t identify with your unique situation enough to be insightful, but there is a person who might have more applicable advice…let me introduce you to…

For the above reason, unfortunately, the advice receiver needs to spend some effort in discerning the quality of the advice. It’s not ideal because between the two, the one with more experience should shoulder this burden. It’s interesting that often the advice people give is one of the clearest windows into that person’s fears, regrets, and values. The only way I can think of remedying this as an advice receiver besides being intensely sensitive to bias and understanding the advice giver’s context (which is good practice but maybe not something you care to get really good at), is to force the advice giver to lay out his or her assumptions. Then you can assess where your assumptions deviate and guide the conversation or discard the advice.

in a world like this, you pay it forward, ’cause more than likely you didn’t deserve it when you got it the first time

you’re learning fast enough if when you look back to a year ago and you think, “I was so f***ing stupid”

Was cleaning out my Evernote and just a few gems from the past year or so that hopefully increases the likelihood of the title. Reminder to self + some synthesis + for the sake of sharing. Hopefully not overly preachy.

  • Be ruthlessly present. Even if it’s “stupid” work like responding to email. Be present enough to think about the task as well as the action of doing the task and how it can be improved. If you can’t get to that level of presence doing something, consider automating it or otherwise removing it from your life. Similarly applies to spending time with loved ones, carrying a conversation, showering, eating, etc. Doing this is extremely tiring, which is why everybody does it so infrequently.
  • Read with purpose. This means forming a hypothesis or rebuttals while reading rather than just consuming information. Doing this is extremely tiring as well. I think it’s fine to start small — just one piece of journalism with purpose a day, rather than 10 pieces without purpose, to build the right muscle.
  • Surround yourself with people you respect. And if that’s not immediately possible, the people can be virtual — thought leaders, historical figures, etc. Nothing accelerates learning as much as the quality of people around you. And it’s the most effortless kind of learning, too. Make these people keep you honest, especially about the following point.
  • It’s ok to fail, but it’s not ok to not know when you have failed. Usually through denial and self delusion. It’s shocking how often this happens. Think about your past — how many months does it usually take you to recognize a failure? A failure can be as small as that you’re not talking to somebody in the way that they want to be talked to, or that you’re not asking the right questions of somebody more experienced than you. Sometimes people never realize these are actually failures because we attribute the fault to the other party.
  • Success is achieved by people who deeply understand reality, not those who choose to ignore it. As a corollary to the above point. What’s interesting is how few people really deeply understand reality.
  • Embed humility in your mindset. Always be asking yourself “what can I learn from this person?” Focus on that rather than every person’s inevitable shortcomings. Also, kindness is egalitarian — everybody deserves it.
  • Take a few minutes each day and jot down three takeaways. To help you synthesize each day. And only three to force you to prioritize.
  • Possibly most importantly, do not get efficient at the wrong thing. Progress in the wrong direction is worse than no progress because it deceives you into thinking you’re making progress. Our environments most significantly affect this. If you don’t want to get better at politicking, don’t be in a highly political company. If you don’t want to get better at responding to email, don’t prioritize your day around getting to inbox zero (guilty). Focus what little time and energy you to the things you want to get better at. Efficiency is not created equal. And you will definitely lose what you don’t practice.

How has the last year been?

you’re learning fast enough if when you look back to a year ago and you think, “I was so f***ing stupid”

in order to achieve a great breakthrough, you must be able to suspend disbelief indefinitely

I’d read a Ben Horowitz post from early 2014 called the Can-Do vs Can’t-Do Culture, from which the title of this post is pulled. I remember this post deeply and it makes me constantly check how I am reacting to people’s thoughts and ideas.

I don’t love VCs, but if there is one thing I admire about them, it is the ability to constantly see the potential in every idea despite a job that is also constantly passing judgment on those same ideas. I find it very difficult to keep an open mind and see potential once my mind is in “judging” mode, so I try my best to not ever be in judging mode. So far, I haven’t found any situation that is worse off because of it.

As I’ve written elsewhere, I think judgment is one of the heaviest burdens we carry with us (and I’m very guilty of carrying it as much as everybody else) — judgment of others, of situations, of ideas, of ourselves. It’s so liberating to be able to step away from that and either to just accept something (like a rainbow — do we say “oh, if only it were a little to the left”?) or, even better, to see what that thing hasn’t even realized yet in itself.

I am reminded of this today because it was Launch Day for FIELD 3, where a bunch of HBS students are required to build micro businesses in the span of ~10 weeks with ~$3,500 and 4-5 teammates. The construct is that we judge these ideas as we are (healthily skeptical) investors and must subsequently trade their stock (though I still haven’t figured out where stock returns factor into anything other than momentary pride). It is so easy to get into a completely judging mindset during this entire half day — every idea seems like it’s bound to fail; it’s, in fact, more admired to be able to see the flaws in an idea than to see the potential in it. We are strangely rooting for our classmates’ failure.

But I think it’s much harder to exercise the muscle of where can this idea succeed. To that end, I will now go through the first 6 ideas presented to my section today (next 12 to come in 2 additional batches) and write a few quick notes on where I think one area of potential is (probably amongst many). Also, it’s a common refrain in venture that nothing is worth investing in unless, at scale, it changes culture in a substantive way. So I will also jot down what I think the world can look like in a best case scenario for these ideas. I do this as a selfish exercise to expand my ability to see potential, but I hope as a reader, you get some optimism as well.

  • Itinehurry – 2-3 day, mobile + paper itineraries that include all details from which is the best transportation to use (subway vs walk vs bus vs Uber) to specific tips on restaurants (e.g. expect there to be a wait, so you can go to x bar nearby)
    • Most obvious complaint – not scalable?? content businesses are not typically considered VC-fundable and it seems like many people are in the business of travel content (though travel content is still very valuable because of the high value advertising). barriers to entry??
    • Potential – 1) trend, especially in taste-related areas like travel / food / clothing, to have a healthy balance between crowdsourced “wisdom” and expert-generated advice + 2) trend towards shorter trips + 3) I love Fodor’s (over Lonely Planet, Trip Advisor, etc.) because it approximates this level of detail (and because it’s an expert who clearly has done these itineraries him/herself and has CLEAR opinions on what is worthwhile and what is NOT). Fodor’s, however, as far as I know, only has a few mainstream itineraries for each destination, not any themed ones like by culture or food or w/e. This company can grow and eventually get bought out by Fodor’s (if not Lonely Planet, etc.). Sure, it might never raise serious VC funding, but it’s a FUN business to build! Part of your job is that you must TRAVEL to create this content. People die trying to get journalist jobs at travel magazines…barriers to entry = not everybody wants to be in this business + content businesses have “economies of scale”
    • If this goes really well, what does the world look like? – we all have perfect itineraries, including when to start the day (8:43AM), which subway to catch, which dish to order, when is the best time to visit attraction x because it’s least crowded or because that’s when the sun is setting on this particular day. Instant re-routing if there’s something unpredicted like oh it’s raining now…
  • Ansel – DIY custom framing that is the quality of custom framing but has the modularity of colors & styles that also allows for easy swapping out of frames (without feeling like you just wasted $100s) –> want to make swapping out a picture on your wall as easy as changing your desktop background
    • Most obvious complaint – price point too high! Currently at $59/frame. Comparative price point at IKEA is about $12.99
    • Potential – can HBS students not KNOW that price point might be too high? If it is, they will just drive that price point lower or compromise on something else. If the team is solid, they’ll find a way. Custom framing is one of those rarely thought of industries that kind of moseys along undisrupted for a long time. I don’t see why Ansel can’t eventually, with full modularity + customization, allow for frames + matting to be any color. From a design-minded person’s perspective, this is really valuable. There are actually really easy and impactful ways to make a picture pop by calling out a certain color in the matting or frame (it’s like how your blue eyes pop when you wear a blue sweater). They can probably easily expand from this to helping you figure out how to best position those photos, maybe helping you figure out what art looks best in your home, maybe eventually helping out with all aspects of interior decor.
    • If this goes really well, what does the world look like? – custom framing dies, each frame is perfectly crafted for each picture, and changing frames / our home decor is just as easy as changing our desktop or mobile background (which, by the way, I do every 2 weeks, out of boredom).
  •  Watch Party – organizes watch parties at local businesses around sporting events and/or other major broadcasting events such as Game of Thrones; charge a small ticket price and bring additional revenue to businesses + give people a way to organize around things they’re excited about
    • Most obvious complaint – why can’t I just organize a watch party for my friends myself? barriers to entry??
    • Potential – because we’re all lazy? And we’re more willing to pay $5-10 to go to a nice venue, see our friends + some other fans we can meet + get a drink discount thrown in there? People’s laziness can rarely be overestimated. Barriers to entry = it’s a marketplace + social network (if all of your friends you this, you will, too)
    • If this goes really well, what does the world look like? – it’s a better Meetup. People with common interests can come together and in the process solve the problem of local business discovery. Alumni organizations get rejuvenated. All cricket lovers find each other. Everybody ends up becoming closer together, in real life.
  • The Perfect Gift – based on a fun survey about that person (e.g. does this person prefer a beach vacation or a cultural vacation), it will give you a catalog of best gifts for that person; you’ll continually rate it (or your receiver will) and it will get smarter
    • Most obvious complaint – why can’t I just find that gift for you and then go buy it on Amazon for cheaper? do you really think you can create a gift-optimizing recommendation engine??
    • Potential – I think this can become really powerful in a couple of ways. The first is if the recommendation engine ends up becoming more powerful than what a human mind can contain. For example, it’s been reported that after 150 likes, Facebook can predict your behavior better than your parents or friends can. If this recommendation engine can get close to that, that’s really powerful. Maybe to jumpstart that, it builds an interaction that allows the gift receiver to allow access to their FB data. Second, if the selection is unique in any way — things that I have trouble finding on Amazon. Third – even Amazon hasn’t made wishlists very successful. If they can figure out where the human disconnect is there, that can be extremely powerful (you can predict purchases).
    • If this goes really well, what does the world look like? – for acquaintances, I’ll probably still give a bottle of wine. For the 3-5 really close loved ones, I’ll probably still make something + get something that is an inside joke. But for everybody else in between, we’d use this. Maybe Etsy buys them to pair unique selection with perfect recommendations (because, arguably, Etsy has a discoverability problem still).
  • Leverage – aggregates your anonymous credit card data to allow you to get credit for being a good shopper at Nordstrom to get Neiman Marcus deals (since Neiman wants you to become a shopper there, too) — allows Neiman to woo you because now it knows you’re worthwhile when previously it didn’t have the data that you are a good shopper at Nordstrom
    • Most obvious complaint – privacy? is this feasible? are brands interested?
    • Potential – credit card companies/banks are already doing this (e.g. Amex, Paypal). Currently they only have their data. If the customer is willing to hand over data to Leverage, then arguably Leverage has an advantage
    • If this goes really well, what does the world look like? – brands can more perfectly target customers and customers get more deals
  • QdPi – books + experiment kits for girls to get them interested in science. First book is Izzy and the Invisible Ink where there’s a story but the reader also is encouraged to experiment with different formulae for invisible ink. Teaches experimentation as well as the fun things you can do with chemistry.
    • Most obvious complaint – unscalable? content…and physical content too, bah! might be a hits driven business (children’s books). barriers to entry???
    • Potential – HUGE trend towards getting girls into science / math. You will reap HUGE PR benefits. Parents will throw money at problems they perceive their children have without a second thought. If you make the experiment a parent-child activity, it’ll kill two birds with one stone – quality time (which is a constant guilty nagging voice parents hear) AND education. I think it’s smart that they’re making it a series (I hope! will help with barriers to entry). Maybe can be the new American Girl / Barbie.
    • If this goes really well, what does the world look like? – girls everywhere realize their full potential for interest in science. Probably there will be Disney / Pixar movies, all sorts of paraphernalia, maybe a theme park (haha), TV show, etc etc etc

Whew! Okay, till next time.

in order to achieve a great breakthrough, you must be able to suspend disbelief indefinitely