Applying Humanities Skills at Work

Most writing defending the value of the humanities in a world increasingly dominated by STEM focuses on what humanists (should) know. If Mark Zuckerberg had read Mill and De Tocqueville, suggests John Naughton, he would have foreseen political misuse of his social media platform. If machine learning scientists were familiar with human rights law, we wouldn’t be so mired in confusion on how to conceptualize the bias and privacy pitfalls that sully statistical models. If greedy CEOs had read Dickens, they would cultivate empathy, the skill we all need to “put ourselves in someone else’s shoes and see the world through the eyes of those who are different from us.”

I agree with Paul Musgrave that “arguments that the humanities will save STEM from itself are untenably thin.” Reading Aristotle’s Nicomachean Ethics won’t actually make anyone ethical. Reading literature may cultivate empathy, but not nearly enough to face complex workplace emotions and politics without struggle. And given how expensive a university education has become, it’s hard to make the case of art for art’s sake when only the extremely elite have the luxury not to build marketable skills.

But what if training in the humanities actually does build skills valuable for a STEM economy? What if we’ve been making the wrong arguments, working too hard to make the case for what humanists know and not hard enough to make the case for how humanists think and behave? Perhaps the questions could be: what habits of mind do students cultivate in the humanities classroom and are those habits of mind valuable in the workplace?

I wrote about the value of the humanities in the STEM economy in early 2017. Since that time, I’ve advanced in my career from being an “individual contributor” (my first role was as a marketing content specialist for a legal software company) to leading teams responsible for getting things done. As my responsibilities have grown, I’ve come to appreciate how valuable the ways of speaking, writing, reading, and relating to others I learned during my humanities PhD are to the workplace. As a mentor Geoffrey Moore once put it, it’s the verbs that transfer, not the nouns. I don’t apply my knowledge of Isaac Newton and Gottfried Leibniz at work. I do apply the various critical reading and epistemological skills I honed as a humanities student, which have helped me quickly grow into a leader who can weave the communication fabric required to enable teams to collaborate to do meaningful work.

This post describes a few of these practical skills, emphasizing how they were cultivated through deep work in the humanities and are therefore not easily replaced by analogue training in business administration or communication.

David Foster Wallace’s 2005 Kenyon College Commencement speech shows how powerful arguments in favor of a liberal arts education can be when they need not justify material payoff 

Socratic Dialogue and Facilitating Team Discussion

Humanities courses are taught differently from math and science courses. Precisely because there is no one right answer, most humanities courses use the Socratic Method. The teacher poses questions to guide student dialogue around a specific topic, helping students question their assumptions and leave with a deeper understanding of a text than they did when they came to the seminar. It’s hard to do this well. Students get off topic or cite arguments or examples that aren’t common knowledge. Some hog the conversation and others are shy. Some teachers aren’t truly open to dialogue, and pretend the discuss when they’re really just leading students to accept their interpretation.

At Stanford, where I did my graduate degree, History professor Keith Baker stands out as the king of Socratic dialogue. Keith always reread required reading before class and opened discussion with one turgid question, dense with ways the discussion might unfold. Teaching D’Alembert and Diderot’s preface to the French Encyclopédie, for example, he started by asking us to explain the difference between an encyclopedia and a dictionary. The fact this feels like common sense is what made the question so poignant, and, for the French Enlightenment authors, the distinction between the two revealed much about the purpose of their massive work. The question forced us to step outside our contemporary assumptions and pay attention to what the same words meant in a different historical context. Whenever the discussion got off track, Keith gracefully posed a new question to bring things back on point without offending a student, fostering a space for intellectual safety while maintaining rigor.

The habits of mind and dialogue trained in a Socratic seminar are directly applicable to product management, which largely consists in facilitating structured discussions between team members who see a problem differently. In my work leading machine learning product teams, I frequently facilitate discussions with scientists, software developers, and business subject matter experts. Each thinks differently about what should be done and how long it will take. Researchers are driven by novelty and discovery, by developing an algorithm that pushes the boundary of what has been possible but which may not work given constraints from data and the randomness in statistical distributions. Engineers want to find the right solution to meet the constraints for a problem. They need clarity and don’t mind if things change, but need some stability so they can build. The business team represents the customer, focusing on success metrics and what will please or hook a user. The product manager sits between all these inputs and desires, and must take into account all the different points of view, making sure everyone is heard and respected, but getting the team to align on the next action.

Socratic methods are useful in this situation. People don’t want to be told what to do; they want to be part of a collective decision process where, as a team, they have each put forth and understood compromises and trade-offs, and collectively decided to go forward with a particular approach. A great product manager starts a discussion the same way Keith Baker would, by providing a structure to guide thinking and posing the critical question to help a group make a decision. The product manager pays attention to what everyone says, watches body language and emotional cues to capture team dynamics. She nudges the dialogue back on track when teams digress without alienating anyone and builds a moral of collective and autonomous decision making so the team and progress forward. She applies the habits of mind and dialogue practiced in the years in a humanities classroom.

Philology and Writing Emails for Many Audiences

My first year in graduate school, I took a course called Epic and Empire, which traced the development of the Western European epic literary tradition from Homer’s Iliad to Milton’s Paradise Lost. The first thing we analyzed when starting a new text was how the opening lines compared and contrasted to those we’d read before. Indeed, epics start with a trope called the invocation of the muse, where the poet, like a journalist writing a lede, informs the reader what the subject of the poem is about using a humble-boasting move that asks the gods to imbue him with knowledge and inspiration.

So Homer in the Iliad: 

Sing, Goddess, sing the rage of Achilles, son of Peleus—
that murderous anger which condemned Achaeans

And Vergil signaling that the Aeneid is Rome’s answer to the Iliad, but that an author as talented as Vergil need not depend on the support from the gods:

Arms and the man I sing, who first made way,
predestined exile, from the Trojan shore
to Italy, the blest Lavinian strand.

And Ariosto, an Italian author, coyly signaling that it’s time women had their chance at being the heroines of epics (the Italian starts with Le Donne):

Of loves and ladies, knights and arms, I sing,
Of courtesies, and many a daring feat;
In the same strain of Roland will I tell
Things unattempted yet in prose or rhyme…
And finally Milton, who, at the time when Cromwell was challenging the English monarchy, signals his aim to critique contemporary politics and society by daftly merging the Judaic and Greek literary traditions:
OF Mans First Disobedience, and the Fruit
Of that Forbidden Tree, whose mortal tast
Brought Death into the World, and all our woe,
With loss of Eden, till one greater Man
Restore us, and regain the blissful Seat,
Sing Heav’nly Muse…


Studying literature this way, one learns not just knowledge of historical texts, but the techniques authors use to respond to others who came before them. Students learn how to tease out an extra layer of meaning above and beyond what’s written. The first layer of meaning in the first lines of Paradise Lost is simply what the words refer to: this is a story about Adam and Eve eating the forbidden fruit. But the philologist sees much more: Milton decides to hold the direct invocation to the muse until line six so he could foreground a succinct encapsulation of the being in time of all Christians, waiting from the time of the fall until the coming of Christ; does that mean he wanted to signal that first and foremost this is a Christian story, with the Greek tradition, signaled by the reference to Homer, only arriving 5 lines later?

Reading between the lines like this is valuable for executive communications, in particular in the age of email where something written for one audience is so easily forwarded to others without our intending or knowing. Business communications don’t just articulate propositions about states of affairs; they present facts and findings to persuade someone to do something (to commit resources to a project, to spend money on something, to hire or fire someone, to alter the way the work, or simply to recognize that everything is on track and no worry is required at this time). Every communication requires sensitivity to the reader’s presumed state of mind and knowledge, reconstructing what we think they know or could know to ensure the framing of the new communication lands. Each communication should build on the last communication, not using the stylistic invocation to the muse like Homer, but presenting what’s said next as a step in a narrative in time. And at one moment in time, different people in different roles interpret communications differently, based on their particular point of view, but more importantly their particular sensitivities, ambitions, and potential to be threatened or impacted by something you say. Executives have to think about this in advance, write things as if they were to be shared far beyond the intended recipient with his or her point of view and stakes in a situation. Philology training in classes like Epic and Empire is a good proxy for the multi-vocal aspects of written communications.

Making Sense of Another’s World: The Practice of Analytical Empathy

In 2013, I gave a talk about why my graduate work in intellectual history formed skills I would later need to become a great product marketer. As in this post, my argument in that talk focused not on what I knew about the past, but how I thought about the past: as an intellectual historian focused on René Descartes’ impact on 17th-century French culture, I sought to reconstruct what Descartes thought he was thinking, not whether Descartes’ arguments were right or wrong and should continue to be relevant today or relegated to the dustbin of history (as a philosopher would approach Descartes).

Doing this well entails that one get outside the inheritance of 400 years of interpretation that shape how we interpret something like Descartes’ famous Cogito, ergo sum, I think, therefore I am. Most philosophers get accustomed to seeing Descartes show up as a strawman for all sorts of arguments, and consider his substance dualism (i.e., that mind and body are totally separate kinds of matter) is junk in the wake of improved understanding about the still mysterious emergence of mind from matter. They solidify an impression of what they think he’s saying as seen from the perspective of the work philosophy and cognitive science seeks to do today. As an intellectual historian, I sought to suspend all temptation to read contemporary assumptions into Descartes, and to do what I could to reconstruct what he was thinking when he wrote the famous Cogito. I read about his upbringing as a Jesuit and read Ignatius of Loyola’s Spiritual Exercises to better understand the genre of early-modern meditations, I read the texts by Aristotle he was responding to, I read seminal math texts from the Greeks through the 16th-century Italians to understand the state of mathematics at the time he wrote the Géometrie, I read not only his Meditations, but also all the surrounding responses and correspondence to better understand the work he was trying to accomplish in his short and theatrical philosophical prose. And after doing all this work, I concluded that we’ve misunderstood Descartes, and that is famous Cogito isn’t a proposition about the prominence of mind over body, but rather a meditative mantra philosophers should use to train their minds to think “clear and distinct” thoughts, the axiomatic backbones for the method he wanted to propose to ground the new science. And Descartes was aware we are all to prey to fall into old habits, that we had to practice mantras every day to train the mind to take on new habits to complete a program of self-transformation. I didn’t care if he was right or wrong; I cared to persuade readers of my dissertation that this was the work Descartes thought the Cogito was doing.

A talk I gave in 2012 about why my training in intellectual history helped be become a good product marketer, a role that requires analytical empathy.

This skill, the skill of suspending one’s own assumptions about what others think, of not approaching another’s worldview to evaluate whether its right or wrong, but of working to make sense of how another lives and feels in the world, is critical for product management, product marketing, and sales. Product has migrated from being an analytical discipline focused on triaging what feature to build next to maximize market share to being an ethnographic discipline focused on what Christian Madsbjerg calls analytical empathy (Sensemaking), a “process of understanding supported by theory, frameworks, and an engagement with the humanities.” This kind of empathy isn’t just noticing that something might be off with another person and searching to feel what that other person likely feels. It’s the hard work of coming to see the world the way another sees it, patiently mapping the workflows and functional significance and emotions and daily habits of a person who encounters a product or service. When trying to decide what feature to build next in a software product, an excellent product manager doesn’t structure interviews with users by posing questions about the utility of different features. They focus on what the users do, seek to become them, just for one day, watch what they touch, what where they move cursors on screens, watch how the muscles around their eyes tighten when they get frustrated with a button that’s not working or when they receive a stern email from a superior. They work to suspend their assumptions about what they assume the user wants or needs and to be open to experiencing a whole different point of view. Similarly, an excellent sales person comes to know what makes their buyers tick, what personal ambitions they have above and beyond their professional duties. They build business cases that reconstruct the buyers’ world and convincingly show how that world would differ after the introduction of the sellers’ product or service. They don’t showcase bells and whistles; they explain the functional significance of bells and whistles within the world of the buyer. They make it make sense through analytical empathy.

Business school, in particular as curriculum exists today, isn’t the place to practice analytical empathy. And humanities courses that are diluted to hone supposedly transferrable skills aren’t either. The humanities, practiced with rigor and fueled by the native curiosity of a student seeking deeply to understand an author they care about, is an avenue to build the hermeneutic skills that make product organizations thrive.

Narrative Detail Helping with Feedback and Coaching

It’s table stakes that narrative helps get early funding and sales at a startup, in particular for founders who lack product specificity and have nothing to sell but an idea (and their charisma, network, and reputation). But the constraints of the pitch deck genre are so formulaic that humanities training may be a crutch, not an asset, to succeeding at creating them. Indeed, anyone versed in narratology (the study of narrative structure) can easily see how rigid the pick deck genre is, and anyone with creative impulses will struggle to play by the rules. 

I first understood this while attending a TechStars FinTech startup showcase in 2016. A group of founders came on stage one by one and gave pithy pitches to showcase what they were working on. By pitch three, it was clear that every founder was coached to use the exact same narrative recipe: describe the problem the company will address; imagine a future state changed with the product; sketch the business model and scope out the total addressable market; marshal biographical details to prove why the business has the right team; differentiate from competitors; close with an ask to prospective investors. By pitch nine, I had trouble concentrating on the content beyond the form. It reminded me of Vladimir Propp’s Morphology of the Folktale.

20th-century Russian literary theorist Vladimir Propp analyzed the formal structure common to folktales. My sensitivity to literary form makes me cynical about the structure of startup pitch decks and yearning for something creative and new.

This doesn’t mean that storytelling isn’t part of technology startup lore. It is. But the expectations of how those stories are told is often so constrained that rigorous humanities training isn’t that helpful (and it’s downright soul-destroying to feel forced to adopt the senseless jargon of most tech marketing). In my experience, narrative has been more poignant and powerful in a different area of my organizational life: coaching fellow employees through difficult interpersonal situations or life decisions.

A first example is the act of giving feedback to a colleague. There are many different takes on the art of making feedback constructive and impactful, but the style that resonates most with me is to still all impulses towards abstraction (“Sally is such a control freak!”) and focus on the details of a particular action in a particular moment (“In yesterday’s standup, Sally interrupted Joe when he was overviewing his daily priority to say he should do his task differently than planned.”). As I described in a former post, what sticks with me most from my freshman year Art History 101 seminar was learning how to overcome the impulse towards interpretation and focus on observing plain details. When viewing a Rembrandt painting, everyone defaulted to symbolic interpretation. And it took work to train our vision and language to articulate that we saw white ruffled shirts and different levels of frizziness in curly hair and tatters on the edges of red tablecloths and light emanating on from one side of the painting. It’s this level of detailed perception that is required to provide constructive feedback, feedback specific enough to enable someone to isolate a behavior, recognize it if it comes up again, and intentionally change it. When stripped of the overtones of judgment (“control freak!”) and isolated on the impact behavior has had on others (“after you said that, Joe was withdrawn throughout the rest of the meeting”), feedback is a gift. Now, no training in art history or literature prepares one to brace the emotional awkwardness of providing negative feedback to a colleague. I think that only comes through practice. But the mindset of getting underneath abstraction to focus on the details is certainly a habit of mind cultivated in humanities courses.

A second example is in relating something from one’s own experience to help another better understand their own situation. Not a day goes by where a colleagues doesn’t feel frustrated they have to do task they feel is beneath them, anxious about the disarray of a situation they’ve inherited, confused about whether to stay in a role or take a new job offer, resentful towards a colleague for something they’ve said or done, etc… When someone reaches out to me for advice, I still impulses to tell them what to do and instead scan my past for a meaningful analogue, either in my own experience or someone else’s, and tell a story. And here narrative helps. Not to craft a fiction that manipulates the other to reach the outcome I want him or her to reach, but to provide the right framing and the right amount of detail to make the story resonate, to provide the other with something they can turn back to as they reflect. Wisdom that transcends the moment but can only be transmitted in full through anecdote rather than aphorism.

Leadership Communication

I’ll close with an example of an executive speech act that humanities education does not help prepare for. A constructive and motivating company-wide speech is, at least in my experience, the hardest task executives face. Giving an excellent public speech to 2000 people is a cakewalk in contrast to giving a great speech about a company matter to 100 colleagues. The difficulty lies in the kind of work a company speech does.

The work of a public speech is to teach something to an audience. A speaker wants to be relevant, wants to know what their audiences knows and doesn’t know, reads and doesn’t read, to adapt content to their expectations and degree of understanding. Wants to vary the pace and pitch in the same way an orchestra would vary dynamics and phrasing in a performance. Wants to control movement and syncopate images and short phrases on a slide with the spoken word to maximally capture the audiences’ attention. There are a lot of similarities between giving a great university lecture and giving a great talk. This doesn’t mean training in the humanities prepares one for public speaking. On the contrary, most humanists read something they’ve written in advance, forcing the listener to follow long, convoluted sentences. Training in the humanities would be much more beneficial for future industry professionals if the format of conference talks were a little more, well, human.

The work of a company speech is to share a decision or a plan that impacts the daily lives and sense of identity of individuals that share the trait that, at this time, they work in a particular organization. It’s not about teaching; the goal is not to get them to leave knowing something they didn’t know before. The goal is to help them clearly understand how what is said impacts what they do, how they work, how they relate to this collective they are currently part of, and, hopefully, to help them feel inspired by what they are asked to accomplish. Unnecessary tangents confuse rather than delight, as the audience expects every detail to be relevant and cogent. Humor helps, but it must be tactfully displayed. It helps to speak with awareness of different individuals’ predispositions and fears: “If I say this this way, Sally will be reminded of our recent conversation about her product, but if I say it that way, Joe will freak out because of his particular concern.” People join and leave companies all the time, and a leader has to still impulses towards originality to make sure newcomers hear what others have heard many times before without boring people who’ve been in the company for a while. The speech that resonates best is often extremely descriptive and leaves no room for assumption or ambiguity: one has to explicitly communicate assumptions or rationale that would feel cumbersome in most other settings, almost the way parents describe every next movement or intention to young children. At the essence of a successful company talk is awareness of what everyone else could be thinking, about the company, about themselves, and about the speaker, as one speaks. It’s a funhouse of epistemological networks, of judgment reflected in furrowed brows and groups silently leaving for coffee to complain about decisions just after they’ve been shared. It’s really hard, and I’m not sure how to train for it outside of learning through mistakes.

What This Means for Humanities Training

This post presented a few examples of how habits of mind I developed in the humanities classroom helped me in common tasks in industry. The purpose of the post is to reframe arguments defending the value of the humanities from knowledge humanists gain to the ways of being humanists practice. Without presenting detailed statistics to make the case, I’ll close by mentioning Christian Madsbjerg’s claim in Sensemaking that humanities students may be best positioned for non-linear growth in business careers. They start off making significantly lower salaries than STEM counterparts, but disproportionately go on to make much higher salaries and occupy more significant leadership positions in organizations in the long run. I believe this stems from the habits of mind and behavior cultivated in a rigorous humanities education, and that we shouldn’t dilute it by making it more applicable to business topics and genres, but focus on articulating just how valuable these skills can be.

The featured image is of the statue of David Hume in Edinburgh. His toe is shiny because of tourist lore that touching it provides good fortune and wisdom, a superstition Hume himself would have likely abhorred. I used this image as the nice low-angle shot made it feel like a foreboding allegory for the value of the humanities. 

What makes a memory profound?

Not every event in your life has had profound significance for you. There are a few, however, that I would consider likely to have changed things for you, to have illuminated your path. Ordinarily, events that change our path are impersonal affairs, and yet are extremely personal. - Don Juan Matus, a (potentially fictional) Yaqui shaman from Mexico

The windowless classroom was dark. We were sitting around a rectangular table looking at a projection of Rembrandt’s Syndics of the Drapers’ Guild. Seated opposite the projector, I could see student faces punctuate the darkness, arching noses and blunt hair cuts carving topography through the reddish glow.

“What do you see?”

Barbara Stafford’s voice had the crackly timbre of a Pablo Casals record and her burnt-orange hair was bi-toned like a Rothko painting. She wore downtown attire, suits far too elegant for campus with collars that added movement and texture to otherwise flat lines. We were in her Art History 101 seminar, an option for University of Chicago undergrads to satisfy a core arts & humanities requirement. Most of us were curious about art but wouldn’t major in art history; some wished they were elsewhere. Barbara knew this.

“A sort of darkness and suspicion,” offered one student.

“Smugness in the projection of power,” added another.

“But those are interpretations! What about the men that makes them look suspicious or smug? Start with concrete details. What do you see?”

No one spoke. For some reason this was really hard. It didn’t occur to anyone to say something as literal as “I see a group of men, most of whom have long, curly, light-brown hair, in black robes with wide-brimmed tall black hats sitting around a table draped with a red Persian rug in the daytime.” Too obvious, like posing a basic question about a math proof (where someone else inevitably poses the question and the professor inevitably remarks how great a question it is to our curious but proud dismay). We couldn’t see the painting because we were too busy searching for a way of seeing that would show others how smart we were.

“Katie, you’re our resident fashionista. What strikes you about their clothing?”

Adrenaline surged. I felt my face glow in the reddish hue of the projector, watched others’ faces turn to look at mine, felt a mixture of embarrassment at being tokenized as the student who cared most about clothes and appearance and pride that Barbara found something worth noticing, in particular given her own evident attention to style. Clothes weren’t just clothes for me: they were both art and protection. The prospect of wearing the same J Crew sweater or Seven jeans as another girl had been cruelly beaten out of me in seventh grade, when a queen mean girl snidely asked, in chemistry class, if I knew that she had worn the exact same salmon-colored Gap button-down crew neck cotton sweater, simply in the cream color, the day before. My mom had gotten me the sweater. All moms got their kids Gap sweaters in those days. The insinuation was preposterous but stung like a wasp: henceforth I felt a tinge of awkwardness upon noticing another woman wearing an article of clothing I owned. In those days I wore long ribbons in my ponytails to make my hair seem longer than it was, like extensions. I often wore scarves, having admired the elegance of Spanish women tucking silk scarves under propped collared shirts during my senior year of high school abroad in Burgos, Spain. Material hung everywhere around me. I liked how it moved in the wind and encircled me in the grace I feared I lacked.

“I guess the collars draw your attention. The three guys sitting down have longer collars. They look like bibs. The collar of the guy in the middle is tied tight, barely any space between the folds. A silver locket emerges from underneath. The collars of the two men to his left (and our right) billow more, they’re bunchy, as if those two weren’t so anal retentive when they get dressed in the morning. They also have kinder expressions, especially the guy directly to the left of the one in the center. And then it’s as if the collars of the men standing to the right had too much starch. They’re propped up and overly stiff, caricature stiff. You almost get the feeling Rembrandt added extra air to these puffed up collars to make a statement about the men having their portrait done. Like, someone who had taste and grace wouldn’t have a collar that was so visibly puffy and stiff. Also, the guy in the back doesn’t have a hat like the others.”

Barbara glowed. I’d given her something to work with, a constraint from which to create a world. I felt like I’d just finished a performance, felt the adrenaline subside as students’ turned their heads back to face the painting again, shifted their attention to the next question, the next comment, the next brush stroke in Syndics of the Drapers’ Guild. 

After a few more turns goading students to describe the painting, Barbara stepped out of her role as Socrates and told us about the painting’s historical context. I don’t remember what she said or how she looked when she said it. I don’t remember every class with her. I do remember a homework assignment she gave inspired by André Breton’s objet trouvé, a surrealist technique designed to get outside our standard habits of perception, to let objects we wouldn’t normally see pop into our attention. I wrote about my roommate’s black high-heeled shoes and Barbara could tell I was reading Nietzsche’s Birth of Tragedy because I kept referencing Apollo and Dionysus, godheads for constructive reason and destructive passion, entropy pulling us ever to our demise.[1] I also remember a class where we studied Cindy Sherman photos, in particular her self portraits as Caravaggio’s Bacchus and her film still from Hitchcock’s Vertigo. We took a trip to the Chicago Art Institute and looked at few paintings together. Barbara advised us never to use the handheld audio guides as they would pollute our vision. We had to learn how to trust ourselves and observe the world like scientists.

Cindy Sherman’s Untitled #224, styled after Caravaggio’s Bacchus
Cindy Sherman’s Untitled Film Still 21, styled after Hitchcock’s Vertigo

In the fourth paragraph of the bio on her personal website, Barbara says that “she likes to touch the earth without gloves.” She explains that this means she doesn’t just write about art and how we perceive images, but also “embodies her ideas in exhibitions.”

I interpret the sentence differently. To touch the earth without gloves is to see the details, to pull back the covers of intentionality and watch as if no one were watching. Arts and humanities departments are struggling to stay relevant in an age where we value computer science, mathematics, and engineering. But Barbara didn’t teach us about art. She taught us how to see, taught us how to make room for the phenomenon in front of us. Paintings like Rembrandt’s Syndics of the Drapers’ Guild were a convenient vehicle for training skills that can be transferred and used elsewhere, skills which, I’d argue, are not only relevant but essential to being strong leaders, exacting scientists, and respectful colleagues. No matter what field we work in, we must all work all the time to notice our cognitive biases, the ever-present mind ghosts that distort our vision. We must make room for observation. Encounter others as they are, hear them, remember their words, watch how their emotions speak through the slight curl of their lips and the upturned arch of their eyebrows. Great software needs more than just engineering and science: it needs designers who observe the world to identify features worth building.

I am indebted to Barbara for teaching me how to see. She is integral to the success I’ve had in my career in technology.

A picture that captures what I remember about Barbara

Of all the memories I could share about my college experience, why share this one? Why do I remember it so vividly? What makes this memory profound?

I recently read Carlos Casteñeda’s The Active Side of Infinity and resonated with book’s premise as “a collection of memorable events” Casteñeda recounts as an exercise to become a warrior-traveler like the shamans who lived in Mexico in ancient times. Don Juan Matus, a (potentially fictional) Yaqui shaman who plays the character of Casteñeda’s guru in most of his work, considers the album “an exercise in discipline and impartiality…an act of war.” On his first pass, Casteñeda picks out memories he assumes should be important in shaping him as an individual, events like getting accepted to the anthropology program at UCLA or almost marrying a Kay Condor. Don Juan dismisses them as “a pile of nonsense,” noting they are focused on his own emotions rather than being “impersonal affairs” that are nonetheless “extremely personal.”

The first story Casteñeda tells that don Juan deems fit for a warrior-traveler is about Madame Ludmilla, “a round, short woman with bleached-blond hair…wearing a a red silk robe with feathery, flouncy sleeves and red slippers with furry balls on top” who performs a grotesque strip tease called “figures in front of a mirror.” The visuals remind me of dream sequence from a Fellini movie, filled with the voluptuousness of wrinkled skin and sagging breasts and the brute force of the carnivalesque. Casteñeda’s writing is noticeably better when he starts telling Madame Ludmilla’s story: there’s more detail, more life. We can picture others, smell the putrid stench of dried vomit behind the bar, relive the event with Casteñeda and recognize a truth in what he’s lived, not because we’ve had the exact same experience, but because we’ve experienced something similar enough to meet him in the overtones. “What makes [this story] different and memorable,” explains don Juan, “is that it touches every one of us human beings, not just you.”

This is how I imagined Madame Ludmilla, as depicted in Fellini’s 8 1/2. As don Juan says, we are all “senseless figures in front of a mirror.”

Don Juan calls this war because it requires discipline to see the world this way. Day in and day out, structures around us bid us to focus our attention on ourselves, to view the world through the prism of self-improvement and self-criticism: What do I want from this encounter? What does he think of me? When I took that action, did she react with admiration or contempt? Is she thinner than I am? Look at her thighs in those pants-if I keep eating desserts they way I do, my thighs will start to look like that too. I’ve fully adopted the growth mindset and am currently working on empathy: in that last encounter, I would only give myself a 4/10 on my empathy scale. But don’t you see that I’m an ESFJ? You have to understand my actions through the prism of my self-revealed personality guide! It’s as if we live in a self-development petri dish, where experiences with others are instruments and experiments to make us better. Everything we live, everyone we meet, and everything we remember gets distorted through a particular analytical prism: we don’t see and love others, we see them through the comparative machine of the pre-frontal cortex, comparing, contrasting, categorizing, evaluating them through the prism of how they help or hinder our ability to become the future self we aspire to become.

Warrior-travelers like don Juan fight against this tendency. Collecting an album of memorable events is a exercise in learning how to live differently, to change how we interpret our memories and first-person experiences. As non-warriors, we view memories as scars, events that shape our personality and make us who we are. As warriors, we view ourselves as instruments and vessels to perceive truths worth sharing, where events just so happen to happen to us so we can feel them deeply enough and experience the minute details required to share vivid details with others. Warriors are instruments of the universe, vessels for the universe to come to know itself. We can’t distort what others feel because we want them to like us or act a certain way because of us: we have to see others for who they are, make space for negative and positive emotions. What matters isn’t that we improve or succeed, but that we increase the range of what’s perceivable. Only then can we transmit information with the force required to heal or inspire. Only then are we fearless. 

Don Juan’s ways of seeing and being weren’t all new to me (although there were some crazy ideas of viewing people as floating energy balls). There are sprinklings of my quest to live outside the self in many posts on the blog. Rather, The Active Side of Infinity helped me clarify why I share first-person stories in the first place. I don’t write to tell the world about myself or share experiences in an effort to shape my identity. This isn’t catharsis. I write to be a vessel, a warrior-traveller. To share what I felt and saw and smelled and touched as I lived experiences that I didn’t know would be important at the time but that have managed to stick around, like Argos, always coming back, somehow catalyzing feelings of love and gratitude as intense today as they were when I first experienced them. To use my experiences to illustrate things we are all likely to experience in some way or another. To turn memories into stories worth sharing, with details concrete enough that you, reader, can feel them, can relate to them, and understand a truth that, ill-defined and informal though it may be, is searing in its beauty.

This post features two excerpts from my warrior-traveler album, both from my time as an undergraduate at the University of Chicago. I ask myself: if I were speaking to someone for the first time and they asked me to tell them about myself, starting in college, would I share these memories? Likely not. But it’s a worthwhile to wonder if doing so might change the world for the good.

When I attended the University of Chicago, very few professors gave students long reading assignments for the first class. Some would share a syllabus, others would circulate a few questions to get us thinking. No one except Loren Kruger expected us to read half of Anna Karenina and be prepared to discuss Tolstoy’s use of literary from to illustrate 19th-century Russian class structures and ideology.

Loren was tall and big boned. A South African, she once commented on J.M. Coetzee’s startling ability to wield power through silence. She shared his quiet intensity, demanded such rigor and precision in her own work that couldn’t but demand it from others. The tiredness of the old world laced her eyes, but her work was about resistance; she wrote about Brecht breaking boundaries in theater, art as an iron-hot rod that could shed society’s tired skin and make room for something new. She thought email destroyed intimacy because the virtual distance emboldened students to reach out far more frequently than when they had to brave a face-to-face encounter. About fifteen students attended the first class. By the third class, there were only three of us. With two teaching assistants (a French speaker and a German speaker), the student:teacher ratio became one:one.[2]

A picture that captures what I remember about Loren

Loren intimated me, too. The culture at the University of Chicago favored critical thinking and debate, so I never worried about whether my comments would offend others or come off as bitchy (at Stanford, sadly, this was often the case). I did worry about whether my ideas made sense. Being the most talkative student in a class of three meant I was constantly exposed in Loren’s class, subjecting myself to feedback and criticism. She criticized openly and copiously, pushing us for precision, depth, insight. It was tough love.

The first thing Loren taught me was the importance of providing concrete examples to test how well I understood a theory. We were reading Karl Marx, either The German Ideology or the first volume of Das Kapital.[3] I confidently answered Loren’s questions about the text, reshuffling Marx’s words or restating what he’d written in my own words. She then asked me to provide a real-world example of one of his theories. I was blank. Had no clue how to answer. I’d grown accustomed to thinking at a level of abstraction, riding text like a surfer rides the top of a wave without grounding the thoughts in particular examples my mind could concretely imagine.[4] The gap humbled me, changed how I test whether I understand something. This happens to be a critical skill in my current work in technology, given how much marketing and business language is high-level and general: teams think they are thinking the same thing, only to realize that with a little more detail they are totally misaligned.

We wrote midterm papers. I don’t remember what I wrote about but do remember  opening the email with the grade and her comments, laptop propped on my knees and back resting against the powder-blue wall in my bedroom off the kitchen in the apartment on Woodlawn Avenue. B+. “You are capable of much more than this.” Up rang my old friend imposture syndrome: no, I’m not, what looks like eloquence in class is just a sham, she’s going to realize I’m not what she thinks I am, useless, stupid, I’ll never be able to translate what I can say into writing. I don’t know how. Tucked behind the fiddling furies whispered the faint voice of reason: You do remember that you wrote your paper in a few hours, right? That you were rushing around after the house was robbed for the second time and you had to move? 

Before writing our final papers, we had to submit and receive feedback on a formal prospectus rather than just picking a topic. We’d read Franz Fanon’s The Wretched of the Earth and I worked with Dustin (my personal TA) to craft a prospectus analyzing Gillo Pontecorvo’s Battle of Algiers in light of some of Fanon’s descriptions of the experience of colonialism.[7]

Once again, Loren critiqued it harshly. This time I panicked. I didn’t want to disappoint her again, didn’t want the paper to confirm to both of us that I was useless, incompetent, unable to distill my thinking into clear and cogent writing. The topic was new to me and out of my comfort zone: I wasn’t an expert in negritude and or post-colonial critical theory. I wrote her a desperate email suggesting I write about Baudelaire and Adorno instead. I’d written many successful papers about French Romanticism and Symbolism and was on safer ground.

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Ali La Pointe, the martyred revolutionary in The Battle of Algiers

Her response to my anxious plea was one of the more meaningful interactions I’ve ever had with a professor.

Katie, stop thinking about what you’re going to write and just write. You are spending far too much energy worrying about your topic and what you might or might not produce. I am more than confident you are capable of writing something marvelous about the subject you’ve chosen. You’ve demonstrated that to me over the quarter. My critiques of your prospectus were intended to help you refine your thinking, not push you to work on something else. Just work!

I smiled a sigh of relief. No professor had ever said that to me before. Loren had paid attention, noticed symptoms of anxiety but didn’t placate or coddle me. She remained tough because she believed I could improve. Braved the mania. This interaction has had a longer-lasting impact on me than anything I learned about the subject matter in her class. I can call it to mind today, in an entirely different context of activity, to galvanize myself to get started when I’m anxious about a project at work.

The happiest moments writing my final paper about the Battle of Algiers were the moments describing what I saw in the film. I love using words to replay sequences of stills, love interpreting how the placement of objects or people in a still creates an emotional effect. My knack for doing so stems back to what I learned in Art History 101. I think I got an A on the paper. I don’t remember or care. What stays with me is my gratitude to Loren for not letting me give up, and the clear evidence she cared enough about me to put in the work required to help me grow.

[1] This isn’t the first time things I learned in Barbara’s class have made it into my blog. The objet trouvé exercise inspired a former blog post.

[2] I ended up having my own private teaching assistant, a French PhD named Dustin. He told me any self-respecting comparative literature scholar could read and speak both French and German fluently, inspiring me to spend the following year in Germany.

[3] I picked up my copy of The Marx-Engels Reader (MER) to remember what text we read in Loren’s class. I first read other texts in the MER in Classics of Social and Political Thought, a social sciences survey course that I took to fulfilled a core requirement (similar to Barbara’s Art History 101) my sophomore year. One thing that leads me to believe we read The German Ideology or volume one of Das Kapital in Loren’s class is the difference in my handwriting between years two and four of college. In year two, my handwriting still had round playfulness to it. The letters are young and joyful, but look like they took a long time to write. I remember noticing that my math professors all seemed to adopt a more compact and efficient font when they wrote proofs on the chalkboard: the a’s were totally sans-serif, loopless. Letters were small. They occupied little space and did what they could not to draw attention to themselves so the thinker could focus on the logic and ideas they represented. I liked those selfless a’s and deliberately changed my handwriting to imitate my math professors. The outcome shows in my MER. I apparently used to like check marks to signal something important: they show up next to straight lines illuminating passages to come back to. A few great notes in the margins are: “Hegelian->Too preoccupied w/ spirit coming to itself at basis…remember we are in (in is circled) world of material” and “Inauthenticity->Displacement of authentic action b/c always work for later (university/alienation w/ me?)”

[4] There has to be a ton of analytic philosophy ink spilled on this question, but it’s interesting to think about what kinds of thinking is advanced by pure formalisms that would be hampered by ties to concrete, imaginable referents and what kinds of thinking degrade into senseless mumbo jumbo without ties to concrete, imaginable referents. Marketing language and politically correct platitudes definitely fall into category two. One contemporary symptom of not knowing what one’s talking about is the abuse of the demonstrative adjective that. Interestingly enough, such demonstrative abusers never talk about thises, they only talk about thats. This may be used emphatically and demonstratively in a Twitter or Facebook conversation: when someone wholeheartedly supports a comment, critique, or example of some point, they’ll write This as a stand-alone sentence with super-demonstrative reference power, power strong enough to encompass the entire statement made before it. That’s actually ok. It’s referring to one thing, the thing stated just above it. It’s dramatic but points to something the listener/reader can also point to. The problem with the abused that is that it starts to refer to a general class of things that are assumed, in the context of the conversation, to have some mutually understood functional value: “To successfully negotiate the meeting, you have to have that presentation.” “Have that conversation — it’s the only way to support your D&I efforts!” Here, the listener cannot imagine any particular that that these words denote. The speaker is pointing to a class of objects she assumes the listener is also familiar with and agrees exist. A conversation about what? A presentation that looks like what? There are so many different kinds and qualities of conversations or presentations that could fit the bill. I hear this used all the time and cringe a little inside every time. I’m curious to know if others have the same reaction I do, or if I should update my grammar police to accept what has become common usage. Leibniz, on the other hand, was an early modern staunch defender of cogitatio caeca (Latin for blind thought), which referred to our ability to calculate and manipulate formal symbols and create truthful statements without requiring the halting step of imagining the concrete objects these symbols refer to. This, he argued against conservatives like Thomas Hobbes, was crucial to advance mathematics. There are structural similarities in the current debates about explainability of machine learning algorithms, even though that which is imagined or understood may lie on a different epistemological, ontological, and logical plane.

[5] People tell me that one reason they like my talks about machine learning is that I use a lot of examples to help them understand abstract concepts. Many talks are structured like this one, where I walk an audience through the decisions they would have to make as a cross-functional team collaborating on a machine learning application. The example comes from a project former colleagues worked on. I realized over the last couple of years that no matter how much I like public speaking, I am horrified by the prospect of specializing in speaking or thought leadership and not being actively engaged in the nitty-gritty, day-to-day work of building systems and observing first-person how people interact with them. I believe the existential horror stems from my deep-seated beliefs about language and communication, in my deep-seated discomfort with words that don’t refer to anything. Diving into this would be worthwhile: there’s a big difference between the fictional imagination, the ability to bring to life the concrete particularity of something or someone that doesn’t exist, and the vagueness of generalities lacking reference. The second does harm and breeds stereotypes. The first is not only potent in the realm of fiction, but, as my fiancé Mihnea is helping me understand, may well be one of the master skills of the entrepreneur and executive. Getting people aligned and galvanized around a vision can only occur if that vision is concrete, compelling, and believable. An imaginable state of the world we can all inhabit, even if it doesn’t exist yet. A tractable as if that has the power to influence what we do and how we behave today so as to encourage its creation and possibility.[6]

[6] I believe this is the first time I’ve had a footnote referring to another footnote (I did play around with writing an incorrigibly long photo caption in Analogue Repeaters). Funny this ties to the footnote just above (hello there, dear footnote!) and even funnier that footnote 4 is about demonstrative reference, including the this discursive reference. But it’s seriously another thought so I felt it merited it’s own footnote as opposed to being the second half of footnote 5. When I sat down to write this post, I originally planned to write about the curious and incredible potency of imagined future states as tools to direct action in the present. I’ve been thinking about this conceptual structure for a long time, having written about it in the context of seventeenth-century French philosophy, math, and literature in my dissertation. The structure has been around since the Greeks  (Aristotle references it in Book III of the Nicomachean Ethics) and is used in startup culture today. I started writing a post on the topic in August, 2018. Here’s the text I found in the incomplete draft when I reopened it a few days ago:

A goal is a thinking tool.

A good goal motivates through structured rewards. It keeps people focused on an outcome, helps them prioritize actions and say no to things, and stretches them to work harder than they would otherwise. Wise people say that a good goal should be about 80% achievable. Wise leaders make time reward and recognize inputs and outputs.

A great goal reframes what’s possible. It is moonshot and requires the suspension of disbelief, the willingness to quiet all the we can’ts and believe something surreal, to sacrifice realism and make room for excellence. It assumes a future outcome that is so outlandish, so bold, that when you work backwards through the series of steps required to achieve it, you start to do great things you wouldn’t have done otherwise. Fools say that it doesn’t matter if you never come close to realizing a great goal, because the very act of supposing it could be possible and reorienting your compass has already resulted in concrete progress towards a slightly more reasonable but still way above average outcome. 

Good goals create outcomes. Great goals create legacies.

This text alienates me. It reminds me of an inspirational business book: the syncopation and pace seem geared to stir pathos and excitement. How curious that the self evolves so quickly, that the I looking back on the same I’s creations of a few months ago feels like she is observing a stranger, someone speaking a different language and inhabiting a different world. But of course that’s the case. Of course being in a different environment shapes how one thinks and what one sees. And the lesson here is not one of fear around instability of character: it’s one that underlines to crucial importance of context, the crucial importance of taking care to select our surroundings so we fill our brains with thoughts and words that shape a world we find beautiful, a world we can call home. The other point of this footnote is a comment on the creative process. Readers may have noted the quotation from Pascal that accompanies all my posts: “The last thing one settles in writing a book is what one should put in first.” The joy of writing, for me, as for Mihnea and Kevin Kelly and many others, lies in unpacking an intuition, sitting down in front of a silent wall and a silent world to try to better understand something. I’m happiest when, writing fast, bad, and wrong to give my thoughts space to unfurl, I discover something I wouldn’t have discovered had I not written. Writing creates these thoughts. It’s possible they lie dormant with potential inside the dense snarl of an intuition and possible they wouldn’t have existed otherwise. Topic for another post. With this post, I originally intended to use the anecdote about Stafford’s class to show the importance of using concrete details, to illustrate how training in art history may actually be great training for the tasks of a leader and CEO. But as my mind circled around the structure that would make this kind of intro make sense, I was called to write about Casteñeda, pulled there by my emotions and how meaningful these memories of Barbara and Loren felt. I changed the topic. Followed the path my emotions carved for me. The process was painful and anxiety-inducing. But it also felt like the kind of struggle I wanted to undertake and live through in the service of writing something worth reading, the purpose of my blog.

[7] About six months ago, I learned that an Algerian taxi driver in Montréal was the nephew of Ali La Pointe, the revolutionary martyr hero in Battle of Algiers. It’s possible he was lying, but he was delighted by the fact that I’d seen and loved the film and told me about the heroic deeds of another uncle who didn’t have the same iconic stardom as Ali. Later that evening I attended a dinner hosted by Element AI and couldn’t help but tell Yoshua Bengio about the incredible conversation I had in the taxi cab. He looked at me with confusion and discomfort, put somewhat out of place and mind by my not accommodating the customary rules of conversation with acquaintances.

The featured image is the Syndics of the Drapers’ Guild, which Rembrandt painted in 1662. The assembled drapers assess the quality of different weaves and cloths, presumably, here, assessing the quality of the red rug splayed over the table. In Ways of Seeing, John Berger writes about how oil paintings signified social status in the early modern period. Having your portrait done showed you’d made it, the way driving a Porsche around town would do so today. When I mentioned that the collars seemed a little out of place, Barbara Stafford found the detail relevant precisely because of the plausibility that Rembrandt was including hints of disdain and critique in the commissioned portraits, mocking both his subjects and his dependence on them to get by. 

Of Thread and Mermen

I bought a dress Tuesday evening. It’s silk and it billows, the cut loose, elegant, harkening flappers and 1930s France. The print seems sampled directly from a Wes Anderson film. Featured in the image above, it has a Jerry Garcia merman with sunglasses and a ping pong paddle rippling regularly across the silk. The design house, La Prestic Ouiston*, hails from a family that maintains a traditional oyster farm in Brittany. The brand’s manifesto celebrates “craft, tradition, virtuosity, always [seeking] to work and to hightlight** the craftsmanship of artisans by producing unique pieces such as garments with embroideries hand-made in Rwanda or clogs made in Brittany and painted in Paris by an artist.” It’s a small brand that proclaims the local, that “dedicates itself to the return of slow fashion.” The silk is infused with mists from the nearby salt marshes in Guérande, it billows brine gusts and ocean raked into flat white squares. Eyes closed, I imagine walking in merman silk barefoot, bare legged, over the desiccated marshes, shaved salt embedded flake by flake into foot arches, falling flake by flake back to a new place of rest, ever migrant with the opalescent tides. Oysters turgid under rugged shells, their taste reminiscent of our common ancestry as ocean. Sweat and blood betokening a past too old to be remembered but by cortisol and heartbreak.***

The salt marshes in Guérande, just south of Brittany, where you can find the La Maison Mer oyster farm affiliated with La Prestic Ouiston. I visited the marshes in the summer of 2009, learning that the fleur de sel is the crystal crust that forms atop the rectangular marshes. They still use rakes to shave off the salt, collecting it into piles like those in the photo.

I purchased the dress at GASPARD, my favourite clothing boutique in Toronto. The owners are attentive and visionary; they comb the world to find designers with beautiful clothing backed by stories and introduce their unique clothing to Toronto. The first time I visited, I immediately felt the ease and grace of a new relationship. I told Ayalah, who was working at the boutique when I bought the dress, that I speak in public frequently and was excited to wear such a rad dress on a panel the next day. She invited me to send photos in the dress to Richard, one of GASPARD’s owners, as it was currently his favourite. And then she asked if work ever paid for my wardrobe, given my public-facing role. I laughed the idea off as absurd, as I work for a small startup and can only imagine what our controller would think if I included a line item for a merman dress on my January expense report.

But her suggestion sparked an idea. How awesome would it be to collaborate with a design house like La Prestic Ouiston on a wardrobe for talks and public appearances, to design an identity either tailored to or able to challenge an audience, in the same way that, as speaker, I shift my approach, content, and tone depending on whether I’m addressing a super technical artificial intelligence research audience, a super practical business audience who need just enough technical detail to feel empowered but not so much as to feel alienated, a passionate and righteous sociology and critical theory audience who want to unpack the social implications of new technologies and do something to fix them, or a muted, constrained policy audience fascinated by the potential of a new conceptual framework to think about what it might mean to regulate AI but trapped within the confines of legal precedent and the broad strokes of the electorate?

What I imagine isn’t sponsorship à la Tiger Woods or pick your favourite athlete. It isn’t trendsetting or luxury branding à la pick your favourite actress wearing Alexander McQueen or Dior or Armani or Gucci or Carolina Herrera on the red carpet at the Oscars. It’s more like Bowie or Lady Gaga or Madonna, Protean shapeshifters whose songs and performances embody a temporary persona that vanishes into something new in the next project. I imagine a collaboration with an artist or designer. Couture not as fitting a dress to individual proportions but as context, each performance exposing its roots, not just measuring bust and waistlines but identity and persona, my providing constraints and parameters and abandoning myself to the materials, shapes, patterns, folds, twists, buttons, sleeves, lengths, tones, textures the designer felt appropriate for a given performance. Not unlike the dance between authorship and abandonment Kyle McDonald experiences in algorithmic art, where the coder sets the initial parameters of the algorithm and experiences what results. Design a mode of creation girding both fashion and product marketing, both ethnographies of what exists today, techniques to tweeze out mental models that guide behaviour and experience and emotion, but that always go beyond observation, that infuse empiricism with the intuition of what could be possible, of how today’s behaviours could be improved, changed, optimized to create something new.

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Kyle McDonald has been working a lot of algorithmically generated music of late, and featured this image on a recent post about using neural nets for music.

I knew from the outset the idea would be polarizing. Fashion and brand sponsorship is at home in sports because athletes are more than athletes; they are cultural icons. It’s at home in entertainment, where physical appearance and beauty are part and parcel of stardom, whether we like it or not. But it’s not at home in math, quantitative fields in academia, or technology. Which is why the topic is thorny, uncomfortable, interesting.

I was concerned about the potential negative reaction to the very post I’m writing (you’re reading) so shopped the idea with a few people to tally reactions.****

Those in fashion were non-plussed: “Fashion x public figures is as old as bread, it’s just a question of finding someone up for a collaboration.”

The way I engage with my younger, technical, male colleagues inspired a presentation of the idea as an act of badass empowerment. They saw and heard what they normally see and hear from me. I could have been talking about research. I could have been talking about speaking on cybersecurity to a bunch of generals. They didn’t hear me speak about fashion. They heard the persona I embody when I work with them, one where I am at once trusted mentor and role model for the leadership positions they want to occupy someday. My being a woman in amazing clothes on stage was a means of embodying something empowering for them, perhaps even masculine.

My ambitious, female colleague, passionate about diversity and inclusion and also interested in clothing and style, said, “gosh, can I do that too?” She and I inhabit our positions as strong women in technology differently. A jack of all trades, she owned branding efforts early on and got excited about the prospect of our having bright pink business cards. I was appalled, as I couldn’t imagine myself giving a bright pink business card to the scientists and executives I typically engage with at conferences. At the time, I felt it was important to deliberately embody androgyny, but elegant androgyny, to wear a-lines and black and neutral professional clothing, but nonetheless extremely feminine clothing, this subtle dance that both erases and underlines gender, but that is so much different from the direct statement of hot pink. Grappling with the difference teases out the subtleties here.

Friends who openly eschew gender essentialism commented on the thorniness of the issue, likely engaging with my own hesitation, which muted the brazen excitement I embody with my younger colleagues. Here conversations waxed consequentialist, focusing on the fact that, whether intended or not, deliberately collaborating with a designer would reinforce stereotypes aligning women with clothing, while brogrammers perform nonchalance in, well, standard brogrammer garb or icons like Steve Jobs perform aestheticism that indexes the life of the mind by donning plain black sweater uniforms. I worried.

Some admonished me for pursuing the project, commenting on my responsibility to the brand identity of the various organizations with which I am associated professionally. This harkened the split ethical imperatives I explored in Censorship and the Liberal Arts. For indeed, as professionals we sign a social contract where we trade unadulterated free speech and expression for the benefits of collaborating with others to build something and do something we’d be unable to accomplish ourselves. But the line between personal and professional brand is anything but clear, and varies greatly between companies and contexts. As evidenced by his world-class out-of-office emails*****, my partner John Frankel at ffVC falls a few standard deviations from the norm, while also insisting on rigour and consistency on the firm’s positions on investment theses. Friends in government rarely express their personal opinions, ever beholden to their duties as representatives of a public body. This forces the question of how much the brand, for example, stands for personal expression. The nuances here are as delicate as those related to feminine identity: it’s our responsibility to embody the brand that supports our business goals, but I’ve always found that success emerges from the breath of fresh air promoted by authenticity.

What do I think?

I doubt the collaboration will come to be, at least not anytime soon. I spent a few days inhabiting an imaginary potential, thinking about how fun it would be to co-create outfits for different performances, one day a boxy Yamamoto, the next a flowery Dior, the next a Katharine Hepburn-inspired pants suit to index a potential future in politics. I remembered all the articles about Marissa Mayer’s style back in 2013, the fact that her having style was news for the tech industry. I reread Susan Fowler’s post about her disgusting experience at Uber and found another very touching post she wrote about what it feels like to be someone who “wants to know it all,” who lacks a singular destiny. I imagined peppering this post with myriad quotations from Ellen Ullman, my new hero, whose Life in Code I devoured with the attention and curiosity spurred by feeling prose so much in line with my own, by reading a vision of what I’d like to write and become.******  I thought about the responsibilities I have right now as a pseudo-visible woman in technology, as a pseudo-visible woman in venture, as a woman who doesn’t write code (yet!!) but serves as translator between so many different domains, who struggles with her identity but wouldn’t have it any other way, who wants to do what’s right for the thousands and thousands of young women out there watching, dreaming, yearning, ready to do amazing things in the world. I just want them to be themselves and not to fear and to create and to be free to become. To have a voice to shape the world. And to fucking wear beautiful clothing if that makes them happy, and alive.

I wore my merman dress on Wednesday on a panel with my friend Steve Woods and the CEO of Wysdom.AI. The audience comprised mostly men; I felt they paid attention to what I said, not what I wore. On Friday, another strong female leader in the Toronto AI community told me she admires my style, and asked where I buy my clothes. I referred her to GASPARD, delighted to support local entrepreneurs making the world more beautiful.

* It took some digging to find the primary designer behind La Prestic Ouiston. Her name is Laurence Mahéo. She looks unabashedly at the camera in the photos various media outlets have posted about her and her spectacular, singular existence. Her head often tilts slightly to the side. She doesn’t smile widely.

**Typo in the original (English translation from the original French).

***Isak Dinesen understood our oceanic roots, as in one of my favourite quotations: “The cure for anything is salt water: sweat, tears or the sea.” I remember hikes up Windy Hill in 2009 and 2010, mourning the loss of my first real love, tears, and sweat, and sea all needed to get back on my feet, love that broke me, that altered my course in life, that changed my emotions ever forward, instilling both negative patterns I still struggle with eight years later and positive patterns, widening my heart and permitting expressiveness I hadn’t known possible there prior. Memories fixed solid in my synapses, of such heightened emotional importance I will carry them with me intact until the day I die. He always knew that the self he saw and enlivened wasn’t the current me but the me he saw I might one day become, knew I was helplessly addicted to this promised self, as I knew he was helplessly addicted to the child I recovered in him, personhood long silenced, but for which he desperately yearned and was grateful to remember existed as a kernel of possibility.

****I had a hell of a time writing One Feminine Identity exactly one year ago today (curious how those things work; my father had a heart attack exactly one year after his father died, as I commemorate in this post). I was dating an ardent feminist at the time, who criticized me for the lack of rigour and systematicity in my approach to female empowerment. His critique lodged itself in my superego and bastardized my writing. I hedged so as not to offend anyone with what I assumed were offensive positions. Then, two other friends read the piece and criticized the hedging! I learned something.

*****This week, John’s out-of-office email featured this poem, which I sent to two colleagues as I felt they’d appreciate it:

Life is like a grain of sand;
it can slip through your fingers
at any time and be lost forever.
We must enjoy every minute
while we have it
in case that too
slips through our fingers.
Love is a fleeting thing
that passes all too quickly through our lives
unless we grasp it tightly
never letting it go.
Our lives are like a grain of sand
and will slip through our fingers
before we get to enjoy it thoroughly.
A Grain of Sand by David Harris

******Here is Ullman giving a talk at Google.

I took a photo of the featured image last Tuesday evening with my iPhone. The shadows arise from the ill-fit black plastic cover that partially covers the lens, tailored for a previous iPhone release. The tag on the dress indicates that the merman’s name is Seb le Poisson. Seb is in the closet, awaiting his next appearance. I write in my pyjamas. 

On Mentorship

On Tuesday, together with four fellow eloquent and inspiring women, I addressed an audience of a hundred and fifty (I think?) odd young women about becoming a woman leader in technology.

I recently passed a crucial threshold in my life. I am no longer primarily a seeker of mentors and role models, but primarily a mentor and role model for others. I will always have mentors. Forever. Wherever. In whatever guise they appear. I have a long way to go in my career, much to work on in my character. Three female mentors who currently inspire me are Maura Grossman (a kickass computer science professor at Waterloo who was effectively the founder of using machine learning to find relevant documents in a lawsuit as a former partner at Wachtell); Janet Bannister (a kickass venture capital partner at Real Ventures who has led multiple businesses and retains a kind, open energy); and Venerable Pannavati (a kickass Buddhist monk and former Christian pastor who infuses Metta Meditation with the slave spirit of Billy Holiday, man it’s incredible, and who practices a stance of radical compassion and forgiveness, to the point of transforming all victimhood-including rape-into grounded self-reliance).

I’m in my early thirties. I have no children, no little ones whose minds and emotions are shaped by my example. I hope someday I will. I live every day with the possibility that I may not. The point is, I’m not practiced in the art of living where every action matters, of living with the awareness that I’m impacting and affecting others, others looking to me for guidance, inspiration, example. And here, suddenly, I find myself in a position where others look up to me for inspiration every day. How should I act? How can I lead by example? How might I inspire? How must I fuel ambition, passion, curiosity, kindness?

What a marvelous gift. What a grave responsibility.

I ask myself, should I project strength, should I perform the traits we want all women to believe they can and should have, or should I expose vulnerability, expose all the suffering and doubts and questions and pain and anxiety I’ve dealt with-and continue to deal with, just tempered-on this meandering path to this current version of me?

There is an art to exposing vulnerability to inspire good. Acting from a place of insecurity or anxiety leads to nothing but chaos. I’ve done it a zillion times; it’s hurt a zillion and one. Having a little temper tantrum, gossiping, breaking cool in a way that poisons a mood, enforcing territory, displaying sham superiority, all this stuff sucks. Being aware of weaknesses and asking for help to compensate for them; relaying anecdotes or examples of lessons learned; apologizing; regretting; accepting a mess of a mind for the moment and trying one’s damnedest not to act on it out of awareness of the damage it may cause, all this stuff is great.

I believe in the healing power of identification and of embracing our humanity. Being a strong woman leader in tech need not only be about projecting strength and awesomeness. It can be about sharing what lies under the covers, sharing what hurt, sharing the doubts. Finding strength in the place of radical acceptance so we can all say, “Nevertheless, she persisted.”

This is me saying something at Tuesday’s event.

Many of the audience members reached out over LinkedIn after the event. Here is the message that touched me deepest.

It was great to meet you and hear you speak last night. Thanks for taking the time to share your experience. It is comforting to know that other women, especially ones as accomplished as those on the panel, have doubts about their capabilities too.

As sharing doubts can inspire comfort and even inspiration, I figured I’d share some more. As I sat meditating this morning, I was suddenly overcome by the sense that I had a truth worth sharing. Not a propositional truth, but an emotional truth. Perhaps we call that wisdom. Here’s the story.

I had a very hard time in the last two years of my PhD. So hard, in fact, that I decided to leave Stanford for a bit and spend time at home with my family in Boston. It was a dark time. My mind was rattled, lost, unshackled, unfettered, unable. My mother had recommended for a while that I start volunteering, that I use the brute and basic reality of doing work for others as a starter, as yeast for my daily bread, to reset my neurons and work my way back to stability. Finally, I acquiesced. It was a way to pass the time. Like housekeeping.

I started working every day at the Women’s Lunch Place, a women’s-only soup kitchen located in the basement of an old church at the corner of Boylston and Arlington streets in Boston. Homeless and practically homeless women came there as a sanctuary from the streets, as a safe space after a night staving off unwanted sexual advances at a shelter, as a space for community or a space to be left alone in peace. Some were social: they painted and laughed together. Some were introverted, watching from the shadows. Some were sober. Some were drunk. I treated the Women’s Lunch Place like my job, coming in every morning to start at 7:00 am. The guests didn’t know I needed the kitchen as much as they did.

Except for one. Her name was Anne. When I asked her where she was from, she told me she was from the world.

Anne was one of the quiet, solitary guests at the kitchen. I’d never noticed her, as she hung out in a corner to the left of the kitchen, a friend of the shadows. One afternoon towards the end of my shift she approached me, touching my shoulder. I was startled.

The first thing Anne did was to thank me. She told me she’d been watching me for the better part of a month and was impressed by my diligence and leadership skills. She watched me chop onions, noticing how I gradually honed my knife skills, transferring the motions to a more graceful wrist and turning the knife upside down to scrap the chopped pieces into the huge soup pots without dumbing the blade. She watched how new volunteers naturally flocked to me for directions on what to do next, watched how I fell into a place of leadership without knowing it, just as my mother had done before me. She watched how I cared, how deeply I cared for the guests and how I executed my work with integrity. I think she may have known I needed this more than they.

For then, out of the blue, without knowing anything about my history and my experiences beyond the actions she’d observed, she told me a story.

“Once upon a time,” started Anne from the World, “there was a medieval knight. Like all medieval knights, he was sent on a quest to pass through the forbidden castle and save the beautiful princess captured by the dragon. He set out, intrepid and brave. He arrived at the castle and found the central door all legends had instructed him to pass through to reach the dragon’s den, where lay captured the beautiful princess. He reached the door and went to turn the knob. It was locked. He pulled and pushed harder, without any luck. He tried and struggled for hours, for days, bloodying his hands, bruising his legs, wearing himself down to nothing. Eventually he gave up in despair, sunk with the awareness of his failure. He turned back for home, readying his emotions for shame. But after starting out, something inspired him to turn around and scan the castle one more time. His removed vantage point afforded a broader perspective of the castle, not just the local view of the door. And then he noticed something. The castle had more than just the central door, there were two others at the flanks. Crestfallen and doubting, he nevertheless mustered the courage to try another door, just in case. He approached, turned the knob, and the door opened, effortlessly.”

This wonderful gift I’ve been given to serve as a role model for other women did not come easily. It was not a clear path, not the stuff of trodden legends. It was a path filled with struggles and doubts, filled with moments of grueling uncertainty where I knew not what the future might hold, for the path I was tracing for myself was not one commonly traced before.

I’ve been fortunate to have had many people open doors for me, turning knobs on my behalf. My deepest wisdom to date is that we can’t know the future. All we can do is try our best, always, and trust that opportunities we’ve never considered will unfold. When I struggled hopelessly at the end of graduate school, I never imagined the life that has since unfolded. I was so scared of failing that I couldn’t embrace what it might mean to succeed. Finally, with the patient support of many friends and lovers, I gained the ability to step back and find a door that I could open with less effort and more joy.

Since I earned my PhD in 2012, I’ve spoken to many audiences about my experiences transitioning from literature to technology. I frequently start my talks with this story, with this gift from Anne from the World. God only knows why Anne knew it was the right story to tell. But she did. And her meme evolves, here as elsewhere. She is one of the most important mentors I’ve ever had, my Athena waiting in the shadows, a giver of wisdom and grace. I will forever be grateful I took the time to listen and look.

I can’t figure out where the featured image comes from, but it’s the most beautiful image of Telemachus, Odysseus’ son, on the web. The style looks like a fusion between Fragonard and Blake. I love the color palette and the forlorn look on the character’s face. A seemingly humble and unimportant man, Mentor was actually the goddess Athena, wisdom donning a surprising habit, showing up where we least expect it, if only we are open to attend. 

The Value of Culture

For without culture or holiness, which are always the gift of a very few, a man may renounce wealth or any other external thing, but he cannot renounce hatred, envy, jealousy, revenge. Culture is the sanctity of the intellect. William Butler Yeats, 1909

Culture is one of those slippery words everyone talks about but no one talks about in the same way. The etymology stems from the Middle French culture, meaning “the tilling of land,” itself from the Latin cultura (which shares roots with colony)It wasn’t until 1867 that culture was regularly used to describe the collective customs and achievements of a people. I haven’t confirmed this, but suspect this figurative use of the word occurred so late in history because what we currently call culture used to be called mores, the habits and customs that define the ethical norms of a community. Note that culture connotes activity, cultivation, education, the conscious act of shaping one’s activity to embody a certain set of values; mores connotes manners, customs, habit, the subconscious adoption of patterns set and reflected by others and ancestors. It’s possible-but again requires further research-that culture became the word used to describe the how of human activity in tandem with the rise of the autonomous, capitalist individual.

In the workplace, culture often gets reduced to the fluffy stuff of the HR department. At its most vapid, culture is having a cool office full of razor scooters, organic smoothies, and, as Dan Lyons mordantly and hilariously describes in the prologue to Disrupted, an aesthetic that “bears a striking resemblance to [a Montessori preschool]: lots of bright basic colors, plenty of toys, and a nap room with a hammock and soothing palm tree murals on the wall. The office as playground trend that started at Google and has spread like an infection across the tech industry.” Work as lifestyle, where every sip of Blue Bottle coffee signals our coolness, where every twist of wax on our mustaches imbues our days with mindful meaning as we hack our brains and the establishment (ignoring, for the time being, the premium we pay for those medium roast beans). At its most sinister, culture is overlooking implicit and even explicit acts of harassment, abuse, or misogyny to exclusively favor the ruthless promotion of growth (see Uber’s recent demise). At its most awkward, culture is the set of trust- and bond-building exercises conducted during the offsite retreat, where we do cartwheels and jumping jacks and sing Kumbaya holding hands in a circle once a year only to return to the doldrums at our dark mahogany corner offices and linoleum cubicles on Monday morning. At its most sinuous, culture is the set of minute power plays that govern decisions in a seemingly flat organization, the little peaks of hierarchy that arise no matter how hard we try to proclaim equality, the acrid taste we get after meetings when it’s obvious to everyone, although no one admits it, that deep down our values aren’t really aligned, and that master-slave dialectics always have and always will shape the course of history.

hubspot candy
The candy wall is considered a perk for the millennial workforce at Hubspot.

But culture can be much more than craft beer at hack night and costumes on Halloween. The best businesses take culture so seriously that it shifts from being an epiphenomenon to weaving the fabric of operations. The moment of transubstantiation takes place when a mission statement changes from being a branding tool to being a principle for making decisions; when leadership abandons micromanagement to guide employees with a north star, enabling ownership, autonomy, and creativity; when the little voices of doubt and fear and worry and concern inside our heads are quieted by purpose and clarity, when we feel safe to express disagreement without suffering and repercussion; when a whole far greater than the sum of its parts emerges from the unique and mystically aligned activities of each individual contributor.

This post surveys five companies for which culture is an integral part of operations. Each is inspiring in its own way, and each thinks about and pragmatically employs culture differently at a different phase of company history and growth.

Always Day 1: True Customer Obsession at Amazon

On April 12, Jeff Bezos released a letter to shareholders. Amazon is now 23 years old, and has gone from being an online bookstore to being the cloud infrastructure making many startups possible, the creator of the first convenience store without checkout lines, and one of the largest retailers in the world. Given its maturity and the immense scope of its operations, Amazon risks falling into big company traps, succumbing to the inertia of process and the albatross weight of the innovator’s dilemma. Such “Day 2” stupor is precisely what CEO Jeff Bezos wants to avoid, and his letter presents four cultural pillars to keeping a big company running like a small company: customer obsession, a skeptical view of proxies, the eager adoption of external trends, and high-velocity decision making.

Bezos states “true customer obsession” as the fulcrum guiding Amazon’s business. While this may seem like a given, in practice very few companies succeed at running a customer-centric business. As Bezos points out, businesses can be product focused, technology focused, or business model focused. They can be sales focused or lifestyle focused. They can focus on long-term strategy or short-term revenue. The popularity and design thinking stems from the fact that product development methodologies historically struggled to take into account how users reacted to products. In Creative Confidence, Tom Kelley and David Kelley show multiple examples of how feature prioritization decisions change when engineers leave the clean world of verisimilitude to enter the messy, surprising world of human reactions and emotions. One of my favorite examples in the Kelleys’ book is when Doug Dietz, an engineer at GE Healthcare, overhauled his strategy for building MRIs when he realized the best technical solution created a horrifying experience for children. The guiding architecture for MRIs henceforth became pirate ships or space ships, contextual vessels that could channel the imagination to dampen the aggressive clanging of the machine, and create a more positive experience for sick children.

pirate ship MRI
GE’s pirate ship MRI, designed to make tests less horrifying for children.

Bezos astutely remarks that a customer-centric approach forces a company to stay innovative and uphold the hunger of Day 1 because “customers are always beautifully, wonderfully dissatisfied, even when they report being happy and business is great.” This is Marketing with a big M. Not marketing as many people misunderstand it, i.e., as the use of catch phrases or content to shape the opinions of some group of people in the hope that these shaped opinions can transform into revenue, but marketing as a sub-discipline of empiricism, where a company carefully observes the current habits of some group of people to discern a need they don’t yet have, but that they will willingly and easily recognize as a need, and change their habits to accommodate, once it’s presented as a possibility. Steve Jobs did this masterfully.

Using customers as an anchor to design and build new products is powerful because truth is stranger than fiction. Many product managers and engineers fall into the trap of verisimilitude, making products as they would write a play, where each detail seems to make sense in the context of the coherent whole. I’ve seen numerous companies spend months imagining features they think users will want that arise logically from the technical capabilities of a tool, only to realize meager revenues because users actually want something different. User stories built on real research with real people-even if it’s a sample set of a few rather than the many that support A/B testing methodologies at consumer companies like Netflix-have Sherlock Holmes superpowers, leading to insights that aren’t obvious until reinterpreted retrospectively.

Bezos ends his letter with the importance of high-velocity decision making, which involves the courage to make decisions with 70% of the information you wish you had and “disagreeing and committing” when consensus is impossible. Disagreeing and committing requires radical candor and the courage to embrace conflict head on. Early in my career, I failed on a few occasions by not having the courage to voice disagreement as we made certain important decisions; after the fact, when we started to observe the negative impacts of the decision, I wanted to stand up and say “I told you so!” but couldn’t because it was too late. This breeds resentment, and it certainly takes culture work to make employees feel like they can voice conflicting or dissenting views without negative repercussion.

(A couple of my readers pointed out that Amazon has been reported to have a cutthroat culture. This reminds me of Ferdinand Céline and Martin Heidegger, two men who supported Fascism and Nazism, and yet left us quite valuable writings. Should we pay attention to the idealized version of a man or company, the traces left in letters and prose, or the reality of his lived life and actions? Can we forgive the sinner if he leaves us gold?)

Soul as a Recruiting Tool at

While Amazon is a massive company whose cultural challenge is to avoid inertia and bureaucracy, is a brand-new startup whose challenge is to attract the right early talent that will make or break company success. Inspired by his experience at Facebook, CEO & Founder Steve Irvine decided the surest way to recruit top talent-and avoid hires whose values were misaligned-was to make it a priority to build a company with soul.

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While we easily recognize that Ray Charles has more soul than Justin Bieber,                    we struggle to quantify soul in company culture.

In a recent presentation, Irvine explains how soul is the hard-to-explain, intangible aspect of a business people struggle to pin down in words, one of those things you know when you see it but can’t really articulate or describe. He says it’s “what you do when no one is looking and when everyone is looking, what gives people in your company purpose and makes them brave in the face of long odds.” Underlying soul is a set of common values: Irvine believes its crucial that everyone in a company share values and mission, even if they approach different questions with a plurality and diversity of perspectives. Soul, here, is different from the spiritual essence of an individual, the self that remains after our corporeal bodies return to dust. It’s the least common denominator uniting a group of diverse individuals, the fulcrum that keeps everyone engaged when things aren’t going well, the life force sustaining interest and passion in the midst of doubt and dismay.

Perhaps most interesting is how effective commitment to soul can be. Irvine is at the very beginning of building his company, so soul, for the moment, is an abstract promise rather than an embodied commitment. But it’s extremely powerful to love what you do. To embrace work with passion, not just as a job that pays the bills. To be excited about weathering storms together with a group of people you care about and in the service of a mission you care for. The trick is to transform this energy into the hard work of building a business.

IKEA: The Best Company Mission Statement Ever

If there’s anyone who has managed to transform soul into successful operations, it’s IKEA founder Ingvar Kamprad. The Testament of a Furniture Dealer, which he wrote in 1976, is the most powerful company mission statement I’ve ever read. It’s powerful because it shows how the entirety of IKEA’s operations result, as if by logical necessity, from the company’s core mission “to create a better everyday life for the many people.”

Just after stating this core mission, Kamprad continues that they will achieve this mission “by offering a wide range of well-designed, functional home furnishing products at prices so low that as many people as possible will be able to afford them.” These two initial phrases function like axioms in a mathematical proof, with subsequent chapter in the Testament exploring propositions that logically follow from the initial axioms.

The first proposition regards what Kamprad calls product range, the set of products IKEA will and won’t offer. As the many people need to furnish not just their living rooms but their entire homes, IKEA’s objective must, as a result, “encompass the total home environment, [including] tools, utensils and ornaments for the home as well as more or less advanced components for do-it-yourself furnishing and interior decoration.” The product design must be “typically IKEA,” reflecting the company’s way of thinking and “being as simple and straightforward as ourselves.” The quality must be high, as the many people cannot afford to just throw things away.

To keep costs low, of course, requires “getting good results with small or limited resources.” Which, by logical necessity, leads to subsequent propositions about the cost of capital and inventory management. Kamprad says that “expensive solutions to any kind of problem are usually the work of mediocrity.” Rigorous pragmatism, and having a sense for the entire supply chain of costs to create and distribute a product, is a core part of IKEA’s culture. Considering waste of resources to be “one of the greatest diseases of mankind,” Kamprad builds the cultural mindset that leads to the compact, do-it-yourself assembly packaging for which IKEA is famous.

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IKEA created this Poäng series in 1976, the same year Kamrad wrote   The Testament of a Furniture Dealer

And the brilliance continues. Kamprad pivots from simplicity in design and production to simplicity as a virtue in decision making, claiming, like Bezos, that “exaggerated planning is the most common cause of corporate death” and extolling a rigorous curiosity that always asks why things are done a given way to open the critical curiosity required to identify opportunities to do things differently. He extols concentration, the discipline required to focus on the specific range of products that defines core identity, the type of focus Steve Jobs instilled to usher Apple to its current level of success. And finally, Kamprad closes his mission by celebrating incompletion and process:

“The feeling of having finished something is an effective sleeping pill. A person who retires feeling that he has done his bit will quickly wither away. A company which feels it has reached its goal will quickly stagnate and lose its vitality.

Happiness is not reaching your goal. Happiness is being on the way. It is our wonderful fate to be just at the beginning. In all areas. We will move ahead only by constantly asking ourselves how what we are doing today can be done better tomorrow. The positive joy of discovery must be our inspiration in the future too.

The word impossible has been deleted from our dictionary and must remain so.”

Note that he wrote this in 1976, a good 35 years before the current new-age thinking focusing on the joy of the process was commonplace wisdom. Note the parallels with Bezos, how both leaders focus on creativity, discipline, and the ruthless awareness and avoidance of biases as a means to keep innovation alive. IKEA has grown from being a low-cost furniture provider in Europe to being a global franchise business with operations in many markets. Time will tell what it will mean for them to serve the many people in the future, and how they will expand their product range while adhering to the focus and discipline required to keep their identity and mission intact.

Commitment to Diversity at Fast Forward Labs

On February 23, 2017, Hilary Mason, the founder and CEO of Fast Forward Labs, sent the following email to our team:

Subject: Maintaining a Respectful Environment


It’s very important to me that our office is respectful and comfortable for everyone who works here and for our visitors, many of whom we are trying to engage as customers and collaborators.


There is writing on the seat to remind you.

Thank you,

Diversity can easily become a compliance checklist item or a pat-yourself-on-the-back politically correct platitude. Practicing it fully takes vigilance and effort. Mason actively promotes diversity and equality in just about every aspect of her professional (and private) existence. Fast Forward Labs is a small company, but there are many women on the leadership team and research interns from international creeds, races, and backgrounds. I’ve sometimes overlooked gender equality (even though I’m a woman myself!) when recommending speakers for conferences, only to have Mason remind me to be mindful in my choices next time around to help build the future we want and can be proud of. We make sure to include a section on ethics in each of our machine learning research reports and have actively turned down business with organizations whose values contrast highly with our own.
The vast majority of the technology world is still run by white men, leading to narratives about the singularity and the superintelligent future that distract us from the real-world ethical problems we face today. We need more women-run companies like Fast Forward Labs to bring more voices to the table and, pragmatically, to make sure character traits like empathy are keeping us on track to solve the right problems and encourage AI adoption (as I discussed in a recent interview on TWiML). This is certainly not to say that empathy is a uniquely feminine trait; but it is to say that no large enterprise will adopt AI successfully without navigating the emotional and people challenges that attend any change management initiative.
(Mason read this post, and told me she doesn’t consider herself to be promoting diversity, but to be creating the world she wants to live in.)

Culture as Product at Asana

The final example focuses on practices to make culture a critical component of a business as opposed to an office decoration or afterthought at the company party. Asana, which offers a SaaS project-management tool, has received multiple accolades for its positive culture, including a rare near-perfect rating on Glassdoor. Short of using Putin-style coercion and manipulation techniques, how did they achieve such positive employee ratings on culture and experience?

According to a recent Fast Company article, by “treating culture as a product that needed to be carefully designed, tested, debugged, and iterated on, like any other product they released.” Just as Amazon analyzes feedback from their external market, so too does Asana analyze feedback from their internal market, soliciting feedback from employees and “debugging” issues like false empowerment as soon as they arise. The company also offers the standard cool office perks that are commonplace in the valley, offering each employee $10,000 (!!!) to set up customized workplaces that can include anything from standing desks to treadmills.

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Asana states its cultural values on its company page.

It’s likely risky to adopt Asana’s culture as product model given the gimmick of hacking phenomena-like our minds and cultural practices-that aren’t computer code. But the essence here is to manage culture using the tools you know well. Agile software development practices aren’t universal across all companies, so it would be a stretch to apply them in environments where they’re not a great fit. But if we take this to a more abstract and general level, it does make sense to treat culture as a living, moving, dynamic product that requires work and discipline just like the products a business offers to its customers, and to manage it accordingly.


The older I get, the more I’m convinced that the how of activity is more important to happiness than the what of activity. Culture is the big how of a company that emerges from the little hows of each individual’s daily activities. When norms were mores, the how was inherited and given, habits and manners we had to adopt to align civil interaction. Now that norms are culture, we’re empowered to create our how, to have it trickle down from mission into operations or work actively to build it and debug it like a product. This requires vigilance, mindfulness, responsibility. It requires humbleness and, as Ingvar Kamprad concludes, “the ambition to develop ourselves as human beings and co-workers.”

The image is from Soup Addict’s recipe for a wild yeast sourdough starter. It’s valuable for us to remember the agricultural roots of the world culture, to bring things back to earth and remember the hard work required to care for something larger than and different from ourselves, which, once it reaches maturity, can feed and nourish us.