Thinking about design, and a redesign

I’ve been meaning to redesign this blog for several months. The blog design has remained unchanged since I relaunched it in early 2018.

The initial aesthetic and design was somewhat arbitrarily chosen – I knew I wanted something clean, minimalist, and designed for longform reading, but I can’t say that I gave much more thought to it. I always considered the initial design to be a 1.0 version of an evolving project, but the words themselves (and frankly, not blogging) took precedence over a focus on intentional design.

Like many, I came into my design consciousness through the work of Jony Ive and Steve Jobs, initially as an unwitting user of early Macintosh products through multiple iPod generations, the iPhone, the Apple Store and the greater Apple aesthetic revolution. Reading Walter Isaacson’s biography of Jobs unlocked my understanding of the intention and importance behind these product’s designs.

College was my first attempt at dabbling in hands-on design, where I volunteered to produce an academic journal that a couple friends and I had founded. Playing around in Adobe Indesign opened my eyes to a world of choices that I had previously considered arbitrary or unconscious—margins, placements, breaks, typeface—a seemingly limitless series of choices striving towards greater readability an aesthetic enjoyment on the part of the reader (discounting self-satisfaction by the designer).

I’ve long admired the world of design, almost entirely from a distance. Today, the closest I get to engagement with design is thumbing through the design section of a bookstore, a long linger in the modern art section of a museum, or through the discipline of design thinking, an adaptation to the designer’s mentality retrofitted to the worlds of business, policy, and other seemingly unrelated domains, as popularized by Stanford’s and the consulting firm IDEO. (Recommended: Steven Johnson’s recent profile of Stanford’s, which goes a level deeper than the typical fawning appreciation.) Interacting with design often feels like hearing a Romance language – I recognize the essential building blocks, but it feels entirely ungraspable and beyond me.

Even today, reading the brief blurb on the typeface chosen for a book (normally located on the back page) mostly alludes me.

An example from a recent read: Working, by Robert Caro:


This book was set in Janson, a typeface named for the Dutchman Anton Janson, but is actually the work of Nicholas Kis (1650-1702). The type is an excellent example of the influential and study Dutch types that prevailed in England up to the time Williams Caslon (1692-1766) developed his own incomparable designs from them.

Composed by North Market Street Graphics, Lancaster, Pennsylvania

Printed and bound by Berryville Graphics, Berryville, Virginia

Designed by Cassandra J. Pappas

My reaction to the above is a recognition of the deep labor of love and appreciation for the history and painstaking design process and its predecessors in practice. But candidly, it reads like a secret code written for the initiated, people with cool glasses frames and well composed outfits, rather than the broader public engaging with Robert Caro’s words.

A serendipitous series of blog posts reawakened my long-dormant blog redesign project. Several weeks ago, designer Frank Chimero announced that he would be redesigning his own blog, in an open and ongoing process via his own blog. For long-running followers of my blog, I initially became acquainted with the work and writing of Frank Chimero in October 2018 via his viral posts MVP Soundsystem and Modest Guide to Productivity.

In Frank’s first few posts, he explored ideas around what he hoped to convey and express via his site, using high-level concepts, feelings, and adjectives that he proceeded to boil down into tangible characteristics of his website’s design. For someone unacquainted with the design process, following his process and creative train of thought has been a revelation.

Frank’s blog posts also motivated me to expand my inquiry into design (certainly an impulse towards inaction, but nonetheless) via his book, The Shape of Design. The book reads as a philosophical treatise on design, a manifesto that delves into his motivations and ultimate purpose behind design, rather than a step-by-step guide through the design process. It’s highly applicable and inspiring.

Chimero’s redesign process and book both emphasize the importance of bringing intention to one’s projects rather than immediately digging in: the need to start with Why.

Per Chimero: “Why is usually neglected, because How is more easily framed”

Therefore, Why do I have a blog?

The Why (WIP):

  • I want to inject more creativity into my life
  • I want to explore outside of the defined parameters of my day-to-day, with more permanence than a text or email thread
  • I want a “portfolio,” a means to be discovered and a portal into my thinking and interests

Only after establishing and grasping the Why does the What and How come into play. leads to objectives: What am I hoping to accomplish with my blog?

The What (WIP):

  • A notebook for my thoughts, mostly in-progress
  • A diary of expression and discovery
  • A place to explore and be creative

Inspired by Frank (who was initially inspired by another designer’s redesign pursuits), I’m going to try and catalog my wholly-unprofessional attempt at redesigning my own site over the course of a series of blog posts, now that the table (and my intentions) are set. Meta, no?

“Hunting for Heartbreak”

Happy 2020.

I spend a substantial amount of time on email (despite resolutions otherwise) or Linkedin reaching out to folks that I find inspiring or interesting.

I’ve had this habit for a long time, borne of a feeling that reaching out to the right person, and catching them at the right serendipitous moment, might lead to some unknowable opportunity, or a kernel of wisdom based on their own success / experience that would provide immediate clarity and a path forward.

I’ve had varying degrees of success cold-reaching out to people. A small portion respond, gracious and appreciative of my interest, but unsure what to do with me and my humble inquiries. However, a large portion of my emails sit dormant in the inbox of busy people inundated with similar emails from equally passionate people.

My rate of success has improved ever-so-slightly since beginning at Harvard Business School (HBS) in August, although I’ve mostly self-selected HBS or MBA alumni as subjects of my reach-out, counting on feelings of obligation / service towards their alma mater/degree, or empathy towards me as a younger version of themselves: chasing opportunity, ambition, and the unknown.

This routine was thrown completely on its head in late 2018, when I opened my inbox to see an email from Shawn Askinosie, author of the memoir-cum-business book Meaningful Work (pretty darn great title) and purveyor of ethically-sourced, service-minded, and transparently-operated Askinosie Chocolate.

The week prior, I had written a capsule review of Meaningful Work on this site, and Shawn reached out to thank me for reading and sharing my thoughts on the book. I seized the opportunity to strike a correspondence with Shawn, asking questions about direct trade (I was exploring the coffee business at the time while in Brazil), and general advice about life and work.

Several months later, I shared with Shawn the news of my admission to Harvard Business School. Given the privilege of being accepted to one of the world’s top business schools, and the time and space to think about the next stage of my professional life, I asked Shawn: how should I think about prioritizing and balancing what’s important to me with what the world needs, and how I’ll feel fulfillment, or at least contentment with the path I’m on.

Shawn’s response was as follows:

“remember that some misery is part of the life we lead. I know you’ve seen my TEDx, but I talk about that very thing. Misery and heartbreak. You want a life in which you go hunting for heartbreak. Ouch.

I’ve now sat on Shawn’s email for several months. At some innate level, I deeply understood what Shawn was getting at, but found it too abstract and intangible for me at that stage, time, and place.

Early in the experience, HBS students are inundated with the messaging that anything is possible, that simply by being accepted and sitting amongst your 900-person cohort that you’ve gained entree to a society of high-achievers, and that HBS is the place to unleash your ambition onto the world. Even the early curriculum spans the worlds of sport, medicine, industry, and science, inviting students to opine and insert their opinions on these diverse pursuits, as if any and all are possible simply by virtue of membership.

Sitting one semester into my experience, with the physical and mental distance of a long winter break and the need to begin taking action towards an eventual post-MBA career, Shawn’s advice has returned.

But rather than returning as words, it’s surprisingly manifested itself physically – the feeling of heartbreak. At the risk of sounding dramatic, as I’ve begun “putting myself out there” – reaching out, applying for opportunities, and asking for work in pursuit of next steps in my career and stage of my life, I’ve felt deep pangs of disappointment mixed with uncertainty and unknown. While I don’t know if this is ‘heartbreak’ exactly, it certainly feels as if it comes from the same place.

Rather than running from this feeling, I’ve taken Shawn’s words to heart – that a life spent chasing heartbreak (and feeling it often) is an indicator that I’m on the right path. As much as the heartbreak and related emotions are difficult, I recognize that this means that I’ve bypassed insecurity and leaned into my self-confidence in the pursuit of heartbreak. Deep down, I feel as if I’m going for it.

One of the key insights that I’ve felt in my first semester at Harvard Business School was in a leadership and organizational behavior class. The professor/researcher explained that individuals with an achievement-orientation tend to externalize their day-to-day success as a series of ups-and-downs – feeling especially low in moments of disappointment or discontent, and very high in (momentary) success and goal-reaching. The conclusion of the academic study was that this psychology should be avoided, and changed to a more even-keeled mindset, a constant feeling of “6/7” in lieu of alternating “1/2″ and “9/10” on a scale from 1 to 10.

By all means, the last few months have been plenty of “1/2” days, with a few “9/10″s sprinkled in. How to achieve this contentment and ongoing growth mindset, while chasing heartbreak, is the next stage of my journey, what I hope to work towards in my coming semester, and beyond.

Thoughts on working and work

Work will be a major part of my life over the next several decades, and is likely to consume a great deal of my mental energy and time.

The older I get, the more I recognize the luxury of being able to spend one’s time as I please, with whom and on what I care to pursue.

As a result, being intentional about the work I pursue, and some of the skills, perspectives, and qualities that I hope to build during my working hours, is worth contemplating in some detail.

What follows are some (point-in-time) thoughts on what I see as the most important aspects of my working life and career.

Principles to lead with

I’ve tried boiling down the key principles behind how I hope to lead in the following bullet points. I’ve tried to elaborate a bit on each as well below, though the goal is for each of these phrases to exist on its own:

Humanity – Seek to unite around a common humanity, and work towards deeply understanding those around me via this lens of humanity, while inviting others to gain a similar understanding of myself.

Dignity – Treat those around me with a base level of dignity and respect regardless of hierarchy, division, or potential dissension, and ensure that those around me feel a strong sense of self worth.

Curiosity – Work in the direction of my curiosity — continue to seek out the challenging and uncomfortable in the pursuit of learning and growth.

Community – Commit to bettering the environment that I work and live in by leaving it a better place than the one I entered, and build community whenever and however possible.

Humility – Internalize the role of luck in all outcomes, and recognize that any success or failure is most often not the result of any one person’s efforts (or even effort at all).


Human connection must be a central part of my day-to-day working life. I believe that each person has a unique set of experiences and a perspective to draw on, and that actively seeking out engagement with people on a constant basis is crucial to my engagement and happiness (read: success) in my work.

Each of us exist in our own personal realities as individuals, with complicated histories, aspirations, and home-lives to juggle. By trying to conform individuals to a single work-culture, or maintain a concrete set of expectations, I believe it is very easy to lose sight of the complex, psyche-driven motivators behind why we choose to work in the first place. However, by trying to deeply engage with one another, by trying to better understand these “realities,” I believe a trust can be formed, leading to more honest and productive relationships. Work should always be centered around the human being, rather than around arbitrary financial, production or other performance indicators.

I believe that humanity is at the center of idea-generation, iteration, and improvement. I have personally experience instances where ideas that live in my head for weeks and seem perfect in the comfy confines of my brain can immediately be exposed as shallow or (potentially) worthy when subject to the judgment and input of a fellow human being. Human interaction – with people of all types – must be embraced and actively sought out, sometimes at the expense of cheaper technological solutions. I believe that this ultimately stands to the benefit of my thinking, perspective, and appreciation for the world around me.


In business, I believe it is very easy to allow for ego to seep into one’s psyche, causing harm to relationships and warping one’s perspective on reality. In the absence of true break-through, innovation, or altruism in work, a net worth or an annual take-home figure can easily take the place of self-worth. As a result, fluctuations in financial success become fluctuations in personal happiness, and feelings towards others can be overtaken by transactional relationships or others’ net worth.

I believe that developing a strong sense of my own self-worth, while seeking to build that sense of self-worth in others, is a crucial component to my happiness and success at work. Divisions created by competitive relationships or arbitrary hierarchies exist to create distance between human beings, and detract from self-worth. As a leader and in my work-life, I hope to help instill a sense of dignity and self-worth in all of those around me, and ensure that they feel secure in their position at work to express themselves and not feel constrained by horizontal, vertical or other organizational splits.

I also believe that I have the most to gain from being around those who feel, see, and think differently than I do. Surrounding myself with a group of individuals with a similar set of experiences only stands to reinforce my currently held beliefs, and stands in the way of growth and evolution, as a person and professional. As a result, I believe that it is important to work even harder to ensure the dignity with those who I deeply disagree with, to create environments conducive to the difficult but constructive conversations that come from difference.


I strongly believe that learning in its many forms must be at the center of my work. The uncomfortable and sometimes-painful growth that comes from learning something new has compounding effects on my ability to create solutions and identify problems. Evading this growth must be avoided at all costs, despite the relative comforts and ease that comes from a predictable routine and work-life.

An analogy that I come back to often regarding curiosity and learning and its role in my work is the difference between the Google and GMail. I am a habitual GMail user, and oftentimes begin my day at the top of my inbox, allowing the latest receipts and information to take up my brain and define my next steps. While there is value in being responsive and aware of the latest information, I strongly believe that this creates a false prioritization, and prevents the real learning and curiosity that I hope to integrate into my work-life. I hope to strive to treat my days similar to the blank page, or the Google Search Bar – defining my own priorities in pursuit of this curiosity and continued growth.

I believe it is important to continually reevaluate the intellectual fulfillment that comes from work, and try to redefine what this growth and curiosity means in the context of work on a regular basis.


As working adults, I’ve been mentored, taught, supported, and “made” by those around me – my community. It is important for me to recognize this and commit to providing the same (and more) that my community has given me to my community in the future. It is important to me to feel a deep connection and communal sense of ownership to the place that I choose to work – to pledge to make the workplace (and surrounding community) a better place than the one I initially found (even if from “nothing” to “something”).

A sense of rootlessness and a lack of connection to my community / environment where I spend my time makes me feel empty and unfulfilled. On the other hand, actively seeking out opportunities to provide service to my community – to mentor, to help others find meaning and purpose in their work, and to work towards making the immediate environment around me a better place helps create meaning, and helps to expand my perspective beyond my immediate self and my (mostly) trivial problems. Amidst the noise of our day-to-day work lives, maintaining this commitment to my community helps to remind me what’s truly important.


There is no way to feel fulfilled and content in one’s work without a strong sense of humility. Defining success as a byproduct of one’s output in work or life discounts the massive role of chance and luck in any outcome, good or bad. In addition, tying back this success to the result of the efforts of any one person discounts the input and impact of all of the individuals in the past and present who have contributed in some way to support me. There is no way to experience success alone – we are all byproducts of those around us, and I believe in living and working in full appreciation of that fact.

I feel strongly that leaning into this humility is crucial to helping to ensure that my time is spent in the pursuit of a fundamental good, rather than the need to keep up appearances (in my mind or others’). Returning to my own imperfections, and maintaining perspective on my own insignificance will help steer my work and goals.

Some other thoughts on work and life


As much as I would prefer to exclude money from this conversation, the inescapable fact for me is that I don’t believe I would work if not for want of money. Or, at least, that there are much more engaging / important ways to spend my time that (our current, American) society doesn’t necessarily value enough to make them worthy of a living wage, so they are left to the especially privileged / altruistic / selfless or monk-like among us.

The unfortunate reality is that to support myself, and eventually to support a partner and family and achieve much of what I want from my life, some sufficient and predictable compensation is required to provide for basic necessities (food, shelter, healthcare, transportation, etc.) as well as other important expenses (education, travel, etc.).

Reading between the above lines should make clear that I’m not necessarily after some sort of windfall salary or certain number to justify my existence or define my success. However, at a certain point the opportunity cost of justifying one’s time working must be commensurate (with some discounting for other factors) to a salary one might receive “in the market.”

Feeling sufficiently valued in the form of reward (i.e., compensation) is a vapid, but unfortunately necessary aspect of work to maintain psychological wellbeing and continue to feel motivated to continue to pursue a level of excellence in a defined line of work.


I believe it is important to create a line in the sand, to delineate between one’s working life from non-working life..

As much as I hope to seek validation, meaning, learning, and reward from work, I recognize that there is much to be gained in life that is likely to have very little to do with work. Being an active and involved father, husband, and participating member of my community and broader family, as well as continued intellectual pursuits and the practice giving back more broadly, are all important values that serve no direct purpose to my work. However, to truly commit to these overarching goals, time and space need to be created and maintained by establishing firm boundaries between “work” and “non-work.”

In an idealized and imagined future, this division takes the form of set working and non-working hours with minimal exception – to be able to “unplug” both literally and figuratively from the issues and anxieties of the workplace. Without defining the set hours, my assumption would be this would take the form of nights and weekends, with some set weeks of vacation, though of course this balance would wax-and-wane over time, and should be constantly reevaluated and updated to reflect the respective states of work- and non-work.

To maintain an invigorated and energetic approach to work, I believe this division is crucial. Beyond a healthy working life, making sure that dedicated times are set aside for reflection and reappraisal of aspects of this document will ultimately create better business outcomes that are well-considered and made in full consideration of the various tradeoffs, opportunity costs, and choices that come from making difficult decisions in high-stakes contexts.

Unfortunately, maintaining a distance (mental and physical) between work and non-work life is usually the first thing to be sacrificed in the pursuit of [more, better, and sustaining] at work. Hopefully, by putting my commitment to “non-work” front and center, I can continually remind myself of its importance to me, and allow me to be frank with myself when I’m failing in my commitment to this balance.

It’s time to rethink my approach to email

Email checking is an obsessive and distracting habit of mine, a constant and simultaneous yearning and dread for the next email to arrive in my inbox.

In my obsessive mindset, the next email could come from anywhere, and could be the key to unlocking or exposing me to the information, people, or opportunity that will inform my ongoing and future direction.

A brief summary of my current approach to email, mostly recounted below as a way to self-shame and hopefully course correct:

  • Emails that require multi-step actions or thoughtful responses are mostly left unresponded to. This often results in a loss of conversational momentum, especially with people I don’t know personally and who have been gracious enough to reply in the first place.
  • Emails are attended to and revisited in chronological order, with the most recent and not-yet archived/deleted emails reread and reviewed first. Older emails further down in my inbox are left unseen for long stretches, further compounding the build-up of my inbox and lengthening my response time on the aforementioned “tough” emails.
  • I often set about my day hoping to achieve, a once-in-a-lifetime inbox zero event, after which I will responsibly and sanely manage my email for the rest of time, without any further compulsion and without a similar buildup of emails in the future. For over 10 years, I have never achieved inbox zero.
  • Following a digital detox spurned by Cal Newport’s Digital Minimalism (reviewed here), I made an active effort to unsubscribe from the vast majority of email newsletters and subscriptions, reducing my “email clutter” significant, and running the risk of missing out on potentially interesting information. However, I wasn’t able to divorce myself from email newsletters altogether, and still find myself overly beholden to links and text from the “essential” newsletters that I’ve deemed too important to miss out on.
  • I’m a complete sucker for email organization  / process improvements articles online, and consume them up ravenously. As a result, my inbox has no shortage of ‘GMail hacks,’ making extensive use of the Labs and Labels functions. No auto filters, however.

The Problem: I treat email like a job (which it mostly isn’t), and like something I’m beholden to, rather than a tool, and something to be used and exploited only as needed!

Given the fact that I currently find myself in a state of transition, with a looming experience that will only further inundate me with more emails and more to-do’s, I am hoping to make use of this strategically significant time to review and replace my bad habits around email.

Potential solutions, as brainstormed by me:

  • Remove the GMail app from my phone, preventing compulsive checking and rechecking (or make it harder to access)
  • Create a minimum number of ‘actions’ (e.g., responses, archives, deletions, etc.) per email session, with some implemented penalty if the minimum is not met?
  • Shorten email responses, and always include calls-to-action. Oftentimes, my emails can take the form of an open-ended conversation, and can get especially long in the absence of a direct next step or action. If there’s not an obvious call-to-action at the end of an email correspondence, create one, or send a kind, but short response and move on!
  • Move actively disconnect from email during weekends. Even reading weekend roundups and digests meant to be pleasurable, like the FT Weekend or NYTimes special sections, can feel like work if they’re left unread and unresponded to. If there’s an especially interesting article, it will likely organically make its way to me. Otherwise, use the app/site if desired, or even better, buy the papers themselves if time permits. Otherwise, forget it!



The challenge, and where to go from here: How to effectively implement these ideas, and ensure their ongoing adoption?

A Trip to the Amazon

Despite my long-held desire to visit and experience the vast diversity of the Brazilian land mass (nearly a continent in its own right), the Amazon has always felt out of reach – so wild, sprawling and alien that it felt necessary to relegate any visit to another point in my life altogether.

Even most Brazilians are ignorant to the Amazon and its massive rainforest, given its distance and remote location relative to the more populous and wealthy South and Southeast regions of Brazil. Given the option, those with the means to travel mostly prefer to venture out of the country to Europe (London, Paris) and the US (Orlando, Miami, NY) over a trip sure to include its share of discomforts and difficulties.

With my current year-and-a-half stint in Brazil coming to a close, I resolved to ensure that a trip to the Amazon was one of my final excursions, placing it above similarly vaunted destinations like Fernando de Noronha or the Pantanal as a can’t miss opportunity.

After resolving to visit the Amazon, the choices for the intrepid traveler only get more numerous from there. First, whether to begin in the more interesting city of Belem or the more remote, mouth-of-the-jungle city of Manaus. Once in the jungle itself, the decision becomes how one wants to experience it: whether via river cruise, a chance to see much of the Amazon River itself, but likely less of its encompassing jungle and the wildlife therein, or a stay at a single or series of jungle lodges, which have been erected everywhere from just outside of the major Amazonian cities to deep into the jungle, in both luxurious splendor and more “rustic” versions, at seemingly every price point. Even the duration of one’s stay was an open question, from a short trip offering a “taste” of the jungle and minimizing the Amazon’s less desirable aspects (heat, mosquitos, etc.), to an overstay which risks succumbing to one-to-many mosquito bites, sweaty and sleepless nights, or feelings and deprivation and isolation from civilization.

As a notorious over-researcher and -optimizer, I was fortunate that my girlfriend served as a crucial ultimate decision-maker after our shared researched into the wide range of options available. We ultimately landed on a six day, five night stay across two jungle lodges (spending one night in the jungle, which I imagined would be plenty for us) led by a private guide to lead, teach, and enable our adventure (hopefully without the need to provide protection).

We arrived in Manaus on a Saturday afternoon, with a half-day to spare before our next morning’s venture into the jungle. Consulting my handy guide books on the four-hour plane ride from São Paulo to Manaus, it became clear that my interests in our arrival city were mostly food-related – including:

  • The Amazon’s unique fruits, most of which are either too delicate or otherwise impractical to be transported too far from their origins, including the bacuri, sapoti, graviola, cupuaçu, etc. etc. etc., as well as tasting authentic açai, which is mostly eaten in highly sweetened and diluted forms throughout the country
  • The wide diversity of fish that call the Amazon River (and its many tributaries) its home, including the pirarucu, tambaqui, tucunaré and the infamous carnivorous piranha
  • Other culinary specialties of the region, such as the mouth-numbing tacacá soup

Other than seeking out foodstuffs, the other requisite destination of the Manaus leg of our trip was to the Teatro Amazonas, the ornate European-style opera house built at the height of the Amazon rubber boom almost entirely from materials imported from Europe (thankfully, excluding the beautiful lumber of Brazil, the country’s literal namesake). The beautiful opera house was most famously portrayed in the Werner Herzog film Fitzcarraldo as the inspiration for the eponymous main character’s own opera house even deeper into the Amazon. Despite the end of the rubber boom, and the departure of its European benefactors, the Theatre continues to host an annual month-long opera festival, as well as an assortment of other concerts throughout the year (most notably to me being the White Stripes’ 2005 performance there.)

Luckily, we were able to score tickets for a performance of the Italian Opera Maria Stuarda upon a our return from the jungle, which, with little in the way of fancy clothing and sure to be exhausted from our adventure, was going to be a unique experience.

After a meal of the giant tambaqui ribs (so large that they could be easily mistaken for pig or beef ribs, with a grilled barbeque flavor to boot), it was off to bed for an early morning pickup and the beginning of our Amazon adventure.

19 in 2019

An idea that my girlfriend shared with me – 19 goals / aspirations for 2019 … better late then never, no?

(In no particular order)

1) Sit more in silence
2) Journal out my anxieties, evolving thoughts, and pending decisions
3) Don’t be a slave to email and news – use it as a tool, or not at all
4) Write more on the blog, creating “structured but flexible repetition” (per Patrick O’Shaughnessy)
5) Reach my blue belt (note: done), and keep going
6) Cook more, and work through cookbooks
7) Plan less, relish more
8) Be more open-hearted and understanding in all conversations
9) Keep emails and related correspondence as short as possible
10) Unplug before bedtime, and when waking up
11) Be more intentional – with actions, with time
12) Be less afraid of difficult conversations, and put them off as little as possible
13) Share ongoing feelings and anxeities more with others, especially loved ones – don’t shut them out
14) Don’t succumb to peer pressure – but also don’t avoid new and different people and experiences
15) Go to bed earlier
16) More spirituality, less cynicism and skepticism
17) Start more books, and quit more books
18) More, and longer walks
19) Take more pauses

The Ongoing Battle Over Data in Creative Industry Decisionmaking

It seems like everywhere you look, you can’t escape ‘data.’ Once obscure arguments about the data accumulation and handling of “free” technology services like Facebook and Google have exploded into the mainstream. Data Science has become an increasingly popular field, as has the use of data-driven “analytics” in a wide ranging number of fields, from healthcare to sports, to city planning and wealth management. The primacy of data (especially “big data,” or the accumulation and synthesis of vast amounts of data enabled by increasing computing power) seems to be a near-consensus: more data will improve our lives, and make us happier, healthier, and more informed.

However, the one area where data’s supremacy remains in doubt is in the creative industries, including the arts, film and television production, and book publishing. Whereas many industries have leaned into data head-first as a key (if not sole) determinant behind decision-making, the creative industries have taken a more cautious approach, wary of confronting the artists and their creative (and oftentimes highly analog) processes and (in my view) inherently skeptical of the power of “data” to yield a breakout success. Whereas data may be helpful in determining the correct number of stoplights per square mile or the perfect amount of risk in one’s portfolio, leaving a computer to assign cultural importance, popularity, and commercial success to an unknown and volatile combination of artist, author, actor, director, designer, etc. remains a task mostly left to human beings.

Yuval Noah Harari’s 21 Lessons for the 21st Century (my review here) takes on this issue head-first, arguing that rather than an inherent inability for computers to create or select art that resonates with people on an emotional basis, it is merely a question of time and data. One of the central theses of his book deals with the merging of biotech (data about our bodies, emotions, neurology), and infotech (data about the rest of the world), and computers’ ability to synthesize that data into actionable and/or tangible outcomes.

As Harari explains: the long run no job will remain absolutely safe from automation. Even artists should be put on notice. In the modern world art is usually associated with human emotions. We tend to think that artists are channeling internal psychological forces, and that the whole purpose of art is to connect us with our emotions or to inspire in us some new feeling. Consequently, when we come to evaluate art, we tend to judge it by its emotional impact on the audience. Yet if art is defined by human emotions, what might happen once external algorithms are able to understand and manipulate human emotions better than Shakespeare, Frida Kahlo, or Beyonce?

After all, emotions are not some mystical phenomenon –they are the result of a biochemical process. Therefore, in the not too distant future a machine-learning algorithm could analyze the biometric data streaming from sensors on and inside your body, determine your personality type and your changing moods, and calculate the emotional impact that a particular song–even a particular music key– is likely to have on you.”

Netflix was long seen as the leading vanguard of this data-first movement in the entertainment industry. Netflix has become famous for its fealty to algorithms in recommending content for its users to watch, and even created a million dollar prize (known as the “Netflix Prize”) to create a tool to accurately predict user’s ratings of films and television shows. Over time, this approach extended to Netflix’s content acquisition strategy – upfront investment for exclusive rights to television shows and movies. Famously, the algorithmic combination of the popularity of the UK political series “House of Cards,” director David Fincher, and Kevin Spacey led to the adaptation and subsequent break-out success of House of Cards, Netflix’s first high-profile content acquisition.

With its center of operations in the tech-based San Francisco as opposed to the power center of Hollywood, Netflix has been seen as a rebel to the traditional Hollywood studios, with its ingrained ecosystem of agents, actors, and studio heads. Further, Netflix’s reputation as a ruthlessly meritocratic place to work, with a high rate of turnover and emphasis on producing results, gave further credibility to its status as a innovative company with start-up roots. Investors eager to load their portfolios with disruptive and highly profitable technology companies have driven up Netflix’s stock price, leading to its inclusion into the FAANG acronym of ‘must-own’ stocks (Facebook, Apple, Amazon, Netflix, and Google). Comparing Netflix’s 5-year stock performance against traditional entertainment companies (Viacom, Comcast, Disney) is a telling indicator – in the minds of investors, Netflix is the future of entertainment, while its immediate industry competitors are poorly equipped to handle this ongoing ‘disruption.’

netflix vs competitors

However, in Netflix’s continued pursuit of subscriber growth and improved financial results, as well as growing competition for licensed content from the film and television studios that initially produced the data, as well as Amazon, Apple, HBO, Hulu, and other company’s entrance into the film and tv-streaming platform business, Netflix has increasingly moved towards producing its own content. In order to meet the growth and profit demands of its investors, Netflix could no longer rely on expensive acquisitions of existing content that included pricey royalty payments to the producer and short rights windows subject to renewal negotiations. Suddenly, Netflix began acquiring and producing hundreds of different films and tv shows, including awards-focused fare and commercially-driven projects alike. In order to sate its consumer, Netflix has chosen to focus on quantity more than quality, to grow its catalog of shows and ensure that consumers paying a monthly subscription fee would never run out of things to watch (this year, Netflix will produce ~700 “original” shows and movies). In the process, Netflix has racked up more than $6.5B in long-term debt, using bonds to finance this spree of content investment.

As a result, Netflix has transformed into a traditional Hollywood studio, mostly unrecognizable from its immediate competitors. Every week, Netflix seemed to poach executives from media and entertainment companies to join its ranks (just search “Netflix hires” on Google to bring up a spate of Hollywood press releases), bringing the entrenched and systemic mindset of Hollywood with them. In the process, Netflix has bifurcated its path forward between its religious devotion to data and innovative approach with its need to build credibility and work within the traditional Hollywood system (or generously, a balance of the two) in the continued pursuit of subscriber growth and financial returns.

This contrast and conflict between Netflix’s technology-based, data-driven origins and its increasing turn to becoming a traditional media company was reported on by the Wall Street Journal in interesting detail, in an November 10th article entitled “At Netflix, Who Wins When It’s Hollywood vs. the Algorithm?” (again, doubling as this week’s Best Thing I Read This Week.)

The article provides an interesting look at how decisions across the company are made with competing considerations pitting “the data” against the more human- and art- and business-driven parts of the company. The article leads with the decision whether or not to exclude one of the two main actresses from the sitcom Grace and Frankie in major promotional and marketing materials (“the data” said that images excluding Jane Fonda, and solely featuring Lily Tomlin resulted in more clicks), but expands into broader and more existential concerns, including whether or not to “green-light” projects or renew television shows, how to incorporate actor/director input, maximizing the effectiveness of film/show titles and trailers, and even whether or not to spend on billboards and other traditional advertising outlets. In each of these cases, Netflix has run up against the complex calculations whether or not to placate agents and their representatives (the “creatives”), or to trust the algorithms and their cold, “rational” calculations.

The Wall Street Journal piece cites several examples where the Hollywood “arm” has won out over the Silicon Valley arm, further underlining Netflix’s continued shift in focus from Northern to Southern California. As the article explains:

Some shows at risk of being canceled due to poor performance have gotten a reprieve because netflix doesn’t want to damage relationships with key producers or actors, people familiar with Netflix’s deliberations say.

At times, the efforts to appease stars don’t sit well with the company’s technology and product teams, triggering heated discussions between the Hollywood and Silicon Valley arms of the company, the people say.

While no doubt Netflix still prominently features data as central to many of its audience-focused experimentation and other key decisions, it’s interesting to see where Netflix’s seemingly all-powerful algorithms have limits. While computers may have gotten better at sniffing out under-the-radar topics and given further credence to the popularity of beloved actors and actresses, it has yet to capture the nuance and importance of interpersonal relationships, and how to navigate the dynamic, highly interconnected Hollywood environment.

On the other hand, the majority of Netflix’s kowtowing has been to established and renowned Hollywood players in an attempt to win them over and convert them to seeing the tech giant as a worthy home for its work. Recent projects by the Coen Brothers (The Ballad of Buster Scruggs) and the restoration and resuscitation of Orson Welles last project, The Other Side of the Wind, as well as the related marketing and promotional spend, are moreso vanity projects than ones expected to generate a significant return. In both cases, the films were released in theatres via short runs in select theatres, hardly the reception that would accompany a similarly high profile release by an established studio. One could argue that over time, as Netflix and other streaming-first services continue to grow in power and incidence, that there will be fewer and fewer auteurs and agents to win over, leading to a reversion to the algorithms and data that will only get better and more accurate over time.

As engineers and product heads likely argue, over the long-term, the results of the algorithm are likely to win out and result in more successful outcomes. However, it’s fascinating to think through the (temporary) limits of these algorithms, and/or whether this is yet another aspect of life that is at risk of being supplanted by machines in the future.

Refugees, Immigration, and You (and Me)

One of the (very few) upsides of living in a city with poor public transportation is the opportunity to converse with cab / Uber / ride sharing drivers. Unlike the unspoken rule of leaving everyone else alone on the subway / metro, cab drivers are normally eager to chat a bit, with limited refuge in the quieted radio, and a near-constant presence of traffic to slow things down further.

One particularly memory encounter of late via a hellacious 2-hour jaunt to the municipality of São Bernardo do Campo (onetime homebase of Lula, as well as the highly recommended Cantina do Zelão) to resolve some Brazilian bureaucratic nightmare and meeting a second-generation Japanese-Brazilian driver. He told me about his experience growing up in outer São Paulo alongside hundreds of other Japanese immigrants sent to Brazil, and we chatted about the baseball-playing Brazilian population, mostly of Japanese descent. This was a conversation I would’ve never had if not for the inviting nature of the cab ride chat.

Over the weekend, I took an all-too-short trip back to the United States to visit an ailing grandparent and help out however I could. My Uber driver back to JFK was named David, who informed me shortly after we set off on the 1.5-2 hour trip that his English wasn’t very good, as he was from Venezuela. Seizing the opportunity, we began chatting in Port-onhol-glish — a hybrid of the three languages which enabled us to understand one another.

The story that he shared with me was one that I was familiar with from the newspapers, but had never heard in person. David was a civil engineer in his native country, previously working on Caracas’ metro system. However, two years ago he fled his country, immigrating to the US and joining an Uncle of his wife’s in New Jersey. Along with David, many in his family had left Venezuela, dispersing across South America, the United States, and Europe, joining millions of others who have fled the failed state as its leader, Nicolas Maduro, continues to rob the country of its resources while creating civil, social, and fiscal disfunction.

As he shared stories of living with hyperinflation and empty supermarkets, rationing, starvation and senseless and pervasive violences, oftentimes crying or fighting tears, I began to reflect a bit on refugees and our common responsibility to the suffering of individuals succumbing to state failures across the world.I pushed David on some of the latest news out of Venezuela: who did he believe was behind the drone-bomb-assassination attempt against Maduro? (Maduro himself, who had previously regulated drone flight and seemingly orchestrated the parade for such an event.) What of Trump’s rumored support of a military coup against Maduro, and the United States’ history of supporting coups against democratically elected leaders in favor of military strongmen promoting stability and rooting out communist influence? As previously recounted, David pointed out that the military are just as corrupt as Maduro, and deeply involved in the illegal drug trade. Better to round them all up and start over, leaning on the pre-Chavez Venezuelan Constitution. Would he go back? In a heartbeat.

While I could hardly argue against David’s answers, I felt like answers to the situation were somehow incomplete (sidenote: useful editorial in the NYTimes for thinking through the situation.) In addition to driving for Uber, David had risen within the ranks of his day job to become a supervisor, and was building a life for his wife, two children, and himself in just two short years in the United States. But David was fortunate to have skills and a college education, and even luckier to know someone to support his immigration to the United States, and the means to get there. Millions of venezuelans are not as lucky, and are either stuck in the country (and starving) or fleeing to neighboring countries. In one example, after seeing hundreds of Venezuelans crossing the border into the quiet Brazilian town of Pacaraima over the past year+, and given support by the Brazilian government, the citizens of the town pushed back against the massive influx of Venezuelans and their strain on the small town, destroying migrant camps and other acts of violence against the Venezuelans trying to survive.

Across the world, refugees seem as unwelcome as they’ve ever been. Nicaraguans fleeing the right wing repressive regime of Daniel Ortega have flooded into Costa Rica, leading to more than 200 asylum cases per day. Today, Nicaraguans make up 1/10 of all people in Costa Rica, putting strain on the country and its civic systems. Hundreds of thousands of other Central Americans have fled violence in El Salvador, Guatemala, and Honduras, mostly heading north via Mexico to the United States, and meeting President Trump’s no tolerance policy towards the border (short of an actual wall.)

As This American Life exposed in an incredibly powerful and informative episode called Let Me Count the Ways, Trump is not only trying to limit immigration via US’ Southern border. Refugees from Haiti, Syria, Sudan, and other war- and weather-stricken parts of the world, and even talented STEM workers (yes, the “best and brightest”) have been turned away from the United States through well-oiled US immigration routes, met with Trump-appointed bureaucrats empowered to delay, obfuscate, and generally make the United States a less welcoming place to those in need.

Unfortunately, this anti immigrant environment is far from limited to the United States. In Sweden, notoriously one of the most refugee-friendly countries in the world (welcoming 163,000 Syrians in 2015 alone), the misleadingly folksy, “keep Sweden Swedish” far-right Sweden Democrats party has grown into a formidable political force, forcing one of the country’s more moderate political parties to build a coalition with a party with Neo-Nazi roots, lest the centre-right and left band together (gasp.) Across Europe, from Germany’s emboldened Alternative for Germany, to France’s National Front and Italy’s Five Star Movement, we are seeing a widespread backlash against refugees, and immigration in general.

I have many more question than answers in this post, but I’m left contemplating the stark reality that in today’s society, with global warming continuing apace and natural disasters damaging cities and claiming lives across the world, how the world will accommodate the continued (and likely growing) influx of refugees with compassion for their hardships, and recognition for the passion, intelligence, and perseverance, not to mention skills, that these people are bringing to their adopted countries. People like my Uber driver, David, and millions of others.

On Wrestling Failures, and (Momentary) Ju-Jitsu Successes

I think I was the worst wrestler in the history of my high school. Like, 1-30 terrible. Over my two season-long wrestling ”career,” I lost to everyone: boys and girls alike. And I remain convinced that the unsuspecting freshman that I beat was in his first few days of learning the sport. The opening bell would sound, and before I knew it, I would find myself on my back, struggling to avoid being pinned.

Despite the constant losing and the draining weight loss regimen, I enjoyed my wrestling experience, namely for the team’s camaraderie and training. While wrestling is an individual sport, each team trains collectively, and work together closely to improve each teammate’s individual prowess. Rather than being an embarrassing footnote in my life’s story, my high school wrestling failures have proven incredibly consequential, even life-changing.

When I made the decision to accept a job in Brazil, I did so despite not having any friends in the country, let alone family. With a newfound surplus of free time, I decided to take up Brazilian Ju-Jitsu (BJJ), a grappling-based martial art that has become one of the country’s biggest cultural exports. With my wrestling failures front-of-mind, I sought to approach my ju-jitsu training from a clean slate. ju-jitsu has become an instrumental part of my life since taking up the sport, and has re-enforced many of my closely held values.


After several weeks of settling into my new position, I found a nearby BJJ gym, hopeful that the gym’s proximity would give me little excuse to avoid going. From my first class, I was introduced to an entirely foreign experience, with specific rules and customs to attend to. As a white belt, I was relegated to the back of the gym, reserved for the most junior members of the gym. Surrounded by individuals with years and decades of experience, it is hard not to feel humbled every time I enter the gym, to this day. This humility serves as the basis for much of my learning and progression – my “novice” status enables me to ask basic or “dumb” questions, actively seek out opportunities to learn and improve. This humility drives my willingness to learn, and to not miss any opportunities to get better. This means constant, near-daily training, and pangs of guilt when I do decide to take a day or two off.


The gym is filled with students of all levels, from minimally experienced white belts to black belts with decades of experience. Inside the gym, age, physical prowess, social standing, and one’s profession, things that serve to divide us in the “real world,” especially in a place as unequal as Brazil, go away. As a white belt at the beginning of my journey in ju-jitsu, my primary objective is to act as a sponge – to “soak up” the actions and mannerisms of those around me. Each member of the academy has something for me to learn from. As a result of my willingness to learn, I’ve developed a strong camaraderie with the men and women of the gym, who have acted as a surrogate community for me and have embraced me as the token “foreigner” of the group.

Self improvement

As the weeks progressed, I joined the ranks of my fellow students in the gym: individuals on a personal journey of self improvement, but committed to working together to elevate their own craft and the success of the gym. My initial feelings of humility have not dissipated, but are momentarily accompanied by mommentary recognitions of progress.

One of my all-time heros, Anthony Bourdain, was a humble student of BJJ, a challenge he took up at the ripe age of 58 and partially based in the inspiration of his now ex-wife, Otavia Busia-Bourdain, a dedicated BJJ practitioner and competitor (here’s an article written by Busia-Bourdain on ‘how jujtisu changed her life’).

In an interview with Charlie Rose, Bourdain explained how BJJ has reengaged a long-dormant part of his brain:

I started at 58. It’s the last thing in the world I could’ve ever imagined wanting to do or enjoying. I’ve never hung out in a gym, I’ve never really cared about those things.

I think it can best be explained by, at my age, to entirely learn a new skill is deeply satisfying. To recreate the feeling of being the lowest person on the totem pole, being in a kitchen when I was 17, knowing nothing, in a very hard world. The incremental, tiny satisfactions of being a little less awful at something, every day, it’s like that with ju-jitsu for me. I’m learning an entirely new skill, a very difficult one, a very physically demanding one, but one that I think about for the rest of the day. They call it “physical chess” because it’s something you think about […] there’s a lot of engineering involved.


Recently, I’ve reflected a bit on my aptitude for ju-jitsu, especially in comparison to my tenure as a horrible wrestler. As I’m still reminded by my training companions, ju-jitsu is oftentimes about patience – about establishing your position, thinking about your next move, and conserving your energy, versus wrestling’s rule of constant motion.

This patience extends to my training more broadly. Time and time again, through injuries (a couple of undiagnosed deeply bruised/broken ribs, fingers, and toes), humiliating defeats, and periodic moments of retention, I am pitted with the enormity of the journey ahead of me and the need to maintain this perspective throughout this lifelong journey of advancement and improvement.

In August, I received my first examination result, adorning my white belt with two stripes, signifying my (minimal) advancement. Now several months in, I’m no longer at the far, far end of the gym, replaced by younger newcomers just a few months behind me. But far from any overconfidence or feelings of deservedness, I continually remind myself that the process continues, learning is lifelong, and I have decades to go before my jujitsu journey is complete.

Designing Puzzles, Games, Worlds

Over the past two weekends, I’ve devoted hours of my free time playing Myst III: Exile for the first time, after its ported re-release to modern machines by the venerable (formerly

With a bit of remove since playing Riven, a game that I had been initially introduced to as a child, I feel like I can reflect more clearly on the incredible pleasure I get from playing these games – exploring the individual levels created, working through the puzzles put forth, and immersing myself in the broader worlds created by the folks at Cyan.

exile-02exile-03exile_1Screenshots from Myst III: Exile (2001)

As a younger person, the concept of video game designer is an abstract one, most likely conceived more so as video game “player” (which now, coincidentally, is actually a real job) than designer – of worlds, levels, mechanics, and stories. What’s so incredibly pleasurable about playing games from the Cyan canon, and especially in the progression from Myst to Riven to Exile, is how much care and attention was given to the design of these games, and how much these games were created with the “player” in mind.

As I’ve come to innately learn through playing their games, the game designers expect an active and observant player (with some baseline knowledge of physics concepts). These are not games to be mindlessly played through on a couch – one must be willing to be challenged and occasionally frustrated. In exchange for these ‘asks,’ the game designers have gorgeously constructed worlds filled with areas to explore and puzzles to be solved.

Unlike Riven (and Myst before it), I’ve made a conscious effort to work my way through the game without the assistance of walkthroughs or obvious hints that would take the thinking out of my hands. As a result, I’ve gone through momentary bouts of getting stuck, and several frustration-/exhaustion-quits (the lesser known cousin of the famous “rage quit.”) However, this has also led to intense, pleasure-filled sequences as I figure things out, either while playing the game itself, or via a stray thought on a particularly thorny area passing through my head over the course of my non-gaming day.

Cyan’s puzzles are not meant to “break” you, nor are they reserved for only the most mathematically astute codebreakers. Rather, they are mostly rely on the player’s power of observation, the ability to insert oneself into the world(s) constructed by the designers to orient oneself, learn the world’s rules, and play within the confines of the game’s “sandbox.” From there, it’s mostly a question of connecting the dots between these in-game observations (I use a notebook to jot things down), with necessary patience and reflection in between.

One of the interesting byproducts of playing these games has been the exercise of thinking like a designer to try to draw logical connections, and make progress within the game. In my view, this requires the perspective of an adult – the ability to actively place yourself in the shoes of another (in this case, a grown-up game designer), to logically work backwards and make progress with the “game.” This is something that I could have never reasonably done as a pre-teen clicking through the various art panels of Myst with mouth agape. One stray thought that I’ve returned to often as an adult is the “limits” of videos games themselves, whether due to graphics, computer processing power, or the concept of a video game itself. As a younger person, these games (even the most basic MS-DOS games) felt like they had almost unlimited potential if I was good/smart/adept enough at unlocking them, able to blur the lines between the game and reality, and the possibility of deeper secrets underneath the surface of the game.

Like a director’s mise-en-scene, a novelist’s detail, or an artist’s choice of color, subject, or style, every element of the worlds being explored within the Cyan’s video games were considered by the designers, and in turn left to be interpreted by the players – why was this put here? What question is this meant to solve? In Cyan’s games, which oftentimes include minimal dialogue and no narration, rooms are strewn with tools and artifacts with no broader purpose other than to further immerse the player in these strange worlds, as well as notebooks that take you into the minds of the characters (protagonists and antagonists alike). This, combined with goregous art and immersive sound design, gives a game like Exile, released all the way back in 2001, a timeless quality, and elevates it from a mere video game into a world of art, in my mind (though it appears as if MoMA agrees).

Aside from continuing to refine game mechanics and further improve the game’s intuitive connection between player and game, the game’s principal technological leap from its predecessor (released four years prior) is the use of a panoramic, VR-like perspective to allow the player a full perspective on what’s below, above, and next to him. Today, more than 17 years since Exile’s release (and even longer since its design), the concept of VR has sought to replicate this sensation, adding a more immersive video headset and motion controllers as well as more photo-realistic graphics, but otherwise not changing the core concept in any major way.

In my mind, Cyan’s immersive worlds, and their ability to unlock the innate human pleasure of exploring and figuring things out represented the best use case for VR, in video games or otherwise. It’s no surprise that Cyan’s upcoming release, Firmament, is being designed to be played in VR, and deemed “a new VR experience” by Cyan. Interestingly, its predecessor, Obduction, was given a VR-release after its initial design, which ultimately proved ambitious but underbaked. Back to the drawing board, I have the utmost confidence that the next game will draw on the lessons learned from Obduction, and potentially be the first great VR game, As Cyan founder Rand Miller recently said in an interview regarding the transition from Obduction to Firmament:  “We definitely jumped in, and realized that this was going to work, but it also allowed us to get a nice head start on what’s coming next. It definitely seems like what we do, making these worlds, is definitely going to be amplified by VR.”

Obduction_01A goregous screenshot from Cyan’s latest, Obduction (2016), to be played at some point

One day, I’ll spend the money to update my machine to be able to play some of these newer games. In the meantime, I will continue to maintain that a masterpiece stands the test of time no matter when it was created, and is oftentimes more innovative and engaging than the flashier, better looking new releases. For now, good old games will have to do.