Entrepreneurship is Metaphysical Labor

“Businessmen are our only metaphysicians…”

–Walker Percy, The Moviegoer

We were days away from closing a fresh fundraising round when our CFO pulled me aside to tell me the company did not have enough cash to cover the next payroll run.

“Never miss payroll” is the most uncontroversial of all the startup advice out there. We held this hard-and-fast rule in mind and used our gross payroll figure as a fixed expense in forecasts. Black-and-white issues are rare in startups, yet once you get down to practice, you find that even this simple advice is not so black-and-white.

We called an urgent meeting of the executive team to discuss our cash emergency. The solution we came up with was for everyone on the management team to take a drastic pay cut, but leave all other employee salaries the same, allowing payroll to squeak through at just under our current cash balance. A week later we closed our round and soon things returned back to normal.

So, were we faithful followers of the startup maxim? Did we still “make payroll,” even though several management employees got paid less than their usual wage?

Even if you answer in the positive, the best you could say is something like “Yeah, you made payroll, but…” It’s not 100% clear cut. We only just made payroll because we redefined what it meant to make payroll, and shifted some atoms in the world (that month’s salary calculations) to make the outcome “Did employees get paid?” come out true.

In the annals of entrepreneurship, this tale is a dime a dozen. Every entrepreneur worth their salt can relate with a story of their own company’s near-death experience. In fact, because this story is so common, I believe it sheds light on the defining skill set of entrepreneurship.

Just as emotional labor is arguably the foundation of work in the service industry, I posit that the shared work domain of entrepreneurs the world over is one of metaphysical labor.

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The Strategy of No Strategy

Strategy is everywhere in our society. But strategy in practice seems to be a cruel and even silly joke. I learned that the hard way when I went to college long before I ever studied strategy formally. My own “strategy” about how to get through college collapsed virtually the moment I set foot on campus. I was living on my own for the first time and had never been outside of California’s perennial summer weather environment before. I was a poor fit for an East Coast school and didn’t last a full year, getting ill from the cold temperature and transferring out to a California school. At the time, I felt like a failure.

Ensō (c. 2000) by Kanjuro Shibata XX. CC BY-SA 3.0

Like many people of my generation and my socio-economic bracket, my teenage years were eventually consumed by the looming issue of where to go to college. I tried to get the best grades, study hard for the SAT, and make whatever connections I could with alumni to get into colleges I wanted. I applied to many of them, recycling and modifying personal statement letters like the individual payloads and sub-payloads of a MIRV’d nuclear missile. Once I got to college, the clarity and structure that routine provided evaporated. I had to make my own. It was certainly very difficult.

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Rolling Your Own Culture and (Not) Finding Community

This is a guest post by Timothy Roy.

In economically advanced democracies, whose universities teach some sort of Enlightenment tradition and technocratic specialty, societies often do not share in common (and do not teach) certain important cultural cores.

These cores, which I think of as modules, include personal conflict resolution (how do we disagree? how do we apologize?), personal finances (how do we spend our money? how luxuriously should we live? how much should we save?), personal fitness (how do I maintain my body? what athletic skills should be practiced to promote health and strength?), and emotional or spiritual growth (more on this later).

rollyourown

These cultural modules are important because they address large parts of day-to-day life and overall lifestyle. They are also important because each module or chunk of teachings/practices can be fairly extensive, and hard to derive from scratch. Individuals, and entire societies, may take a long time to rediscover some of these helpful practices.

Fortunately for those of us bred in educational systems which run light on these cultural modules, there are lots of gurus around which are not too hard to discover. By taking a guru here and a guru there, you can form a complete personal culture, a complete lifestyle.

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The Computational Condition

Over the past few months I read Hannah “Banality of Evil” Arendt’s difficult and idiosyncratic (somewhat unnecessarily so) but highly rewarding 1958 classic The Human ConditionThis slide-deck is a deep-dive attempt to apply her philosophy to the post-software-eats-world human condition, which I call the computational condition. Maybe digital condition or post-technological condition would be better, but I like alliteration.

This deck should serve as a decent introduction to Arendt’s philosophy of action, which is already part of the zeitgeist to a much greater degree than you probably recognize. It is dense and wordy, 88 slides long and full of big (thematically bucketed and curated) block quotes along book-ended and interrupted by my own heavy-handed commentary and summary sections, but trust me, it’s a 100x easier to digest than the book itself. But that’s not my main purpose in creating it.

The main purpose is this: With some significant augmentations and modifications (a few of them drastic enough to alter her basic philosophical posture in an irreversible and unforgivable way, the irony of which she’d have appreciated as you’ll see), her ideas actually work really well as a foundation for constructing what I think Silicon Valley needs badly right now: a solid political philosophy built on the foundation of the folk philosophy that already defines tech culture: doerism. So here’s my stab at it. Post a comment if you are interested in a sort of video salon on the topic, in either seminar or discussion format (specify which interests you more). I haven’t yet decided whether to do one, or attempted to present this deck. I suspect it would take me 2-4 hours to present this depending on how prepared people are.

In my own modest way, what I’m trying to do here is get a stone soup going, to cook up a political philosophy for Silicon Valley that is not embarrassingly juvenile/sophomoric. If you’re interested in that kind of thing, this should be a good starting point for you. Even if you dislike doerism (in the sense of the lived political philosophy of Silicon Valley), dislike Arendt (there is much to dislike about her), and are suspicious of any attempt to combine the two, this is in a way the most obvious steel-manning of what is already the tacit political philosophy of Silicon Valley. So your alternatives to it should probably understand what it might possibly be right about.

Meta-Skills, Macro-Laws, and the Power of Constraints

Nearly every science-fiction novel seems to agree on one thing: in the future, work will be indistinguishable from art. Such wide agreement suggests that work is far more than a means of income generation. Even in a robot servant utopia, with all our practical needs taken care of, human work will still have a purpose. To find or make meaning, to know thyself, to create beauty or value in the world. Productivity is helpful in these deeper pursuits because the fundamental questions it seeks to answer—how order arises from disorder, complexity from randomness, and ends from means—are the very same questions essential to understanding sentience, life, the universe, and everything.

It’s been noted that the best writers know the rules of writing well enough to break them in creative ways. The rules in this way are more than rules. In the beginning, they are crutches. Later, they become guides and useful defaults. Eventually, they become springboards. They crystallize the moments where a writer has to decide what she believes, who she isn’t, and by process of elimination, who she is.v7.001

This is the same role, I believe, that “tips and habits” play in productivity: rules that are designed to be broken in a journey of self-discovery. They resist a little bit, asking “Are you sure you want to choose your own adventure?” Which is helpful, because many times you shouldn’t. This changing role makes it irrelevant whether a piece of productivity advice is “right” or “wrong.” What matters is how fruitful of a domain it circumscribes, and thus whether it’s worth the effort to redesign it. It’s not important whether you “believe in it” or not, but whether you can articulate how it fits (or doesn’t) within your personal system of truths.

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Examining the Accidental Life

I only have two basic moods accounting for most of my waking hours: one marked by mild to severe ennui, and the other by a rushing energy. Refractory state and burst state. I seem to have largely random-walked through an accidental life so far, imposing barely any discipline on this basic, ungoverned, binary life process. I have no thoughtfully constructed scaffolding of habits and rituals in my life, just a few accidentally set ways. My biggest adult achievement in that department is learning to floss regularly.

I do have a rare third state though, one that only seems to appear only when I am in certain kinds of places, like off-season beach resorts. Like Cannon Beach, on the Oregon coast, a couple of weeks ago. Or the Outer Banks several years ago (which inspired my 2009 post, How to Think Like Hercule Poirota personal favorite).

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By definition, off-season means most humans don’t like these places during these times. Most waterfront businesses are closed. There are no peak-season activities on offer. You’re out on a mostly empty, slightly chilly, grey, and cloudy beach. It’s a satisfyingly atemporal environment.

Something about such outings deeply relaxes me. And after years of doing such trips, I think I am beginning to understand why. I think it is because my natural home state is being peacefully lost. Going to a place that, temporarily, doesn’t know what to do with itself,  is one good way to be at peace with being lost. An environment that doesn’t know what to do with itself, and is in no particular hurry to find out, is an an environment that doesn’t know what to do with you. And much of the stress of being lost, after all, comes from the environment pestering you to do stuff.

I like not knowing where I am, where I am going, why, or how I am going to get there. And I like it when the environment leaves me alone in that state.

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A Framework of Experimental Habit Formation

One of the key challenges of living and working in the future will be continuous learning and experimentation. I’d like to propose a framework for guiding these efforts that is both feasible and focused on the individual: experimental habit formation. I believe it can help resolve one of the fundamental paradoxes of modern life: how to balance our need for stability and routine with our thirst for novelty and exploration.

Experimental habit formation is a precursor and gateway to behavior change. The question “ How do I change?” is not enough, because it presupposes that you know which behaviors to adopt; even if you do, that these behaviors will lead to the outcomes you expect; and even if they do, that these outcomes will remain personally relevant and meaningful forever. By replacing these risky assumptions with tests, experimental habit formation provides a sandbox to “debug” new behaviors before wider deployment.

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The Holy Grail of Self-Improvement

The holy grail of self-improvement in modern times is a framework for individual experimentation and learning that can be used by the average person. The key question such a framework would have to answer is “How do people change?”

The-Holy-Grail-of-Online-Engagement

In this essay I will suggest possible answers to this question by looking at the recent history and theory of behavior change, the main obstacles this framework would have to address to be feasible, and a few promising directions from research and practice.

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Productivity for Precious Snowflakes

We’ve been told for years now that what our parents and kindergarten teachers told us is not, in fact, true — we are not each and every one of us special unique snowflakes destined for greatness. In this essay I want to offer a new theory of productivity for those of us who, despite all the evidence to the contrary, still believe there is something valuable about our particular point of view. I will argue that the fundamental driver of creative work today is not values, goals, or processes, but unique states of mind.

Two identical snowflakes, via the NYT

Let’s start by taking this idea to unreasonable extremes: hyper-advanced aliens and digital souls.

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Inbox Zero versus Flow Laminar

The world of stream-metaphor workflows in tools like Slack and Github — with strongly emphasized temporal structure, and the realistic probabilistic expectations of chat replacing the illusory deterministic expectations of email — has made me reconsider how I think about information processing. In particular, I’ve moved from an Inbox Zero mental model to a Flow Laminar mental model, as illustrated in this picture.

Inbox Zero, while a great concept within the limits of email and paper (“Clean Desk policy”), is a fundamentally authoritarian high-modernist concept. It creates a strong, bright line between profane and sacred regimes of information, and encourages you to get to illusory control (a clean inbox) by hiding precisely the illegible chaos that’s tempting and dangerous to ignore (if you use folders, you likely have one or more misc folders even if you don’t call them that). This is dangerous because you’re just moving unprocessed chaos from a procrastination zone with strong temporal cues (the Inbox) to a denial zone with broken temporal cues (the set of de facto misc folders).

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