Category: art of gig

Over the short history of this newsletter, I’ve been rather sloppily referring to distinctions among 3 kinds of gig economy workers: indie consultants, indie contractors, and under-the-API gigworkers, who I’m now relabeling platformers (people who find work via things like Uber or Upwork and who I can’t, with a straight face, attach the adjective indie to). I’m overdue for cleaning up my definitions of these 3 important categories and their structural relationships to each other, so here we go. First, here is the basic structure:

You’re an indie consultant if you don’t have to deal with purchasing departments (or sometimes, HR departments) as gatekeepers.

You may still need to do paperwork with them, but they have little control over whether to hire you because sufficiently senior managers or executives are making that call. In particular, if hiring freezes/cost control measures are in place, they are senior enough to authorize exceptions, OR are irreplaceable enough to get such exceptions made on their behalf via their chain of command (often this is mission-critical technical people).

You’re a contractor if a purchasing department has significant power to say no based on a variety of considerations, and the client principal can’t override that decision.

You’re an under-the-API platformer if you get work mostly on autopilot from a demand aggregator platform, with little to no human gatekeeping (you might get some procedural human attention while signing up, and during exceptional situations, but that’s it).

How are these 3 layers different? The overall difference is that you take on more risk, for more return, in the higher layers, and gain more independence if you succeed. Much of the changing risk/return profile comes from having to sell yourself to generate your own demand. The increased independence manifests as increasing control over contract terms.

This basic difference leads to all the other differences. Here are 10 important dimensions of the differences, illustrated. I’ve tried to be pretty black-and-white for clarity, but of course, there’s blurred edges along all 10 dimensions.

The ten dimensions (detailed for the 3 layers above) are:

1. Competition mode

2. Social perception

3. Contracting structure

4. Rate-setting

5. Haggling/bidding dynamics

6. Demand structure

7. Selling model

8. Positioning

9. Generic strategy type

10. Branding

For most of you, the ambiguity in who you are is likely to be between contracting and consulting. The easiest way to tell the two apart is whether or not you haggle (dimension 5). I discussed that in detail in my Aug 15, 2019 newsletter: When is a Gig an Engagement? Important point: as I noted in that article, contractors can often make more money per hour than comparable consultants. Haggling does NOT mean being paid less.

But platformers generally are paid less (far less) than either contractors or consultants, because they’re generally participating in a relatively lower skill sector. Uber-for-X generally involves low-$/hour kinds of X.

The simplest way to understand the logic of these distinctions is via Michael Porter’s famous generic strategies model (dimension 9).

• Indie consultants use a strategy of differentiation,

• Indie contractors use a strategy of focus,

• Platformers use a strategy of low-cost leadership.

These things are hard to mix effectively, which is why “hybrid” strategies are dangerous unless you’re absolutely forced into them. They require incompatible operating practices and models, so if you hybridize, you’ll often find yourself making zero-sum tradeoffs. Moves that strengthen you as a contractor will weaken you as a consultant, and vice-versa. This is also why upward mobility is rare in the gig economy. You’re likely to stay at the level you’re at unless you pull a high-effort stunt to move up (for the contractor to consultant move, a good stunt is to write a book).

I imagine very few of you are in the platform layer, or if you are, it’s a temporary way to backstop cashflow shortfalls while you get the game going at either the contracting or consulting levels. But the reason I pay a lot of attention to the platform layer is that it is the strongest manifestation of “software eating the world” in the gig economy. The biggest trends in the gig economy are unfolding at the platform layer.

So you need to be paying attention to it, and open to participating in it if it opens up the right possibilities for you.

Another 101 type reference post, which I hope is also useful for seasoned indie consultants, on basic consulting diagrams. The kind that you should be able to instinctively judge as appropriate to a discussion, and rapidly whiteboard without thinking too hard. I’ve picked 16 of my favorites to get you started, but you should develop your own vocabulary.

Recent chats with some friends have made me realize that my approach to consulting is based on what academics call ethnomethodology, and this particularly applies to how I use diagrams in conversations.

Loosely, ethnomethodology means taking the modes of thought and problem solving of “lay” people seriously, and in my case, actually making them my own.

A great deal of business thinking runs on diagrams drawn on whiteboards, or inserted into presentations/briefings. There is a reason actual working people doing serious work rely on these diagrams to frame and structure conversations.

You’re not a good consultant until you understand the logic and appeal of every major popular diagram type, and learn to use each tastefully, with good “form”.

A word on the relationship between diagramming approaches and indie consulting brands.

Many beginning consultants have a weird kind of insecurity that leads them to invent and rely on over-complicated, bespoke constructs that they can name after themselves. While these can sometimes be useful, especially ones that are developed and refined over many years, across hundreds of applications, such as Wardley maps, in general, they are fragile visual bullshit. You’re much better off learning to use the basic commodity diagrams well than trying to make up and sell your own in most cases.

Many consultants also seem to take a weird kind of pride in avoiding the basic tools of the consulting trade like 2×2 diagrams, almost as though they are afraid they won’t be taken seriously if they use such familiar constructs. To me, this is a clear tell that you don’t have confidence in your basic thinking, and so are wary of commodity packaging.

That or you’re exhibiting a kind of snobbery towards vernacular visual business language that will lead to people distrusting you and refusing to think with you.

Of course, a few people genuinely have objections to one or other diagramming approach as representing dangerously sloppy thinking (Simon Wardley and I have a long-running good-natured beef about 2x2s for example, but he’s also the creator of one of the best 2x2s I’ve seen: openness versus level of strategic play).

Basic diagrams are basic for a reason. They’re like free weights in the consulting gym. Sure they can be used in cringe-inducing ways that are vulnerable to parody, but used with good form, they blow complicated name-brand machine weights and fancy equipment out of the water. So whatever the kind of consulting you do, it pays to master basic consulting diagrams.

What is common to all of these is that you do not need external data or measurements, or generally, even a brainstorm. These are ways to capture your existing situation awareness of what’s going on, and structure the conversation in a way that participants can pool their beliefs, with the right dominant mood (conflict, cooperation, analysis, synthesis).

All 16 of these diagrams also have a very special and useful feature: they can usually be described with 5-9 chunks of information. This fits Miller’s famous Magic Number argument that we can hold 7±2 in short-term memory. This means good discussions tend to stay in that range and avoid the meeting getting stupid.

So without further ado, let’s take a quick tour of the 16 basic diagrams.

1. The 2×2

The 2×2 is the barbell squat in the business gym. Basic, dull, but a full-brain workout that forces you to think, pay attention, and practice good form to avoid injury. It can be used to break out of a zero-sum situation by adding a dimension, relate archetypal cases, etc.  One of its most interesting and unexpected uses is as a conflict de-escalation tool. When 2 people are arguing about mutually exclusive options, or a single spectrum, moving the conversation to a non-conflict mode (if that’s what you want to do) can be as simple as adding an axis that makes the unspoken conflict variable explicit. The 2×2 is also a natural sweet spot, so resist the temptation to go 3×3 or 2x2x2. It almost never works. Get good at the 2×2.

Miller Complexity: 11 (2 axis labels, 4 limit labels, 4 quadrant labels, 1 title)

Examples: The BCG Growth Share matrix, Johari window.

2. The Ranked Cut

If the 2×2 is the squat, the ranked cut is the deadlift. A simple list is just a data capture structure, but what makes the ranked cut a proper diagram is the addition of a single line, to model a cut-off or threshold. Usually you get to a ranked cut by brainstorming a list, ranking it in some priority order, and then having a discussion about where to draw the line and why (which can lead to revision in the prioritization logic). The line usually marks a proposal dividing different regimes of action (in the simplest case, do versus don’t).

Miller Complexity: 4 (above the line, below the line, meaning of the line, ranking criterion)

Examples: Feature prioritization, candidates shortlisting.

3. The Pyramid

The pyramid is used to illustrate a leverage hierarchy of some sort. It is perhaps the most familiar diagraming technique and is synonymous with organizations themselves. The basic use of the pyramid is to create a hierarchical structural scaffolding to identify levels of abstraction in analysis, description, and prescription. It’s a blank map template for anything. I of course, love pyramids. My entire consulting career is based on an essay about one: Hugh MacLeod’s sociopaths/clueless/losers cartoon.

Miller Complexity: 3-7

Examples: Capability Maturity Model, Maslow’s pyramid, MacLeod hierarchy.

4. The Pick-2-of-3 Triangle

The pick-2-of-3 is probably my own favorite after the 2×2, but is not very commonly used, and this is primarily because it is among the most difficult to use. It requires thinking about interacting real-world constraints that model real tradeoffs. It is an excellent tool to use when people seem to be forgetting constraints that matter and are going wild with too-sloppy brainstorming. As with 2x2s, there seems to be a natural limit, and a sweet-spot value to the 2-of-3 case, and attempts to create n-of-m discussions generally don’t work, so don’t go nuts trying. The combinatorics just get too out of hand and exit the Miller 7 +/- 2 zone fast.

Miller Complexity: 3-6. Three basic constraint variables, three pairwise-active regimes.

Examples: The original pizza triangle, the Mundell-Fleming trilemma, the CAP theorem.

5. The 3-Circle Venn Diagram

The Venn diagram is a way to create an interference pattern, and add resolution to a basic structure by creating a set of fill-in-the-blank complexities. The 3-circle Venn diagram is the most common one for a good reason: all possible intersections create zones. When you get up to 4, you can’t intersect opposite pairs pairwise visually. It is particularly useful for archetype analysis, where traits intersect in interesting ways that create evocative role descriptions, like the famous nerds/geeks/dweebs/dorks Venn diagram.

Miller Complexity: 10 (7 mutually exhaustive regions, plus 3 basic circle labels)

Examples: Nerds/geeks diagram, data scientists, Drew Conway data science diagram.

6. The Flywheel

The flywheel is a visualization of a system that creates compounding effects via a positive feedback loop or virtuous cycle. It is a diagram that is powerful in inverse proportion to the number of blocks in the positive-feedback circle. A 2-block flywheel is more powerful than a 3-block flywheel. Negative feedback flywheels are also useful to visualize draining momentum/vicious cycles.

Miller Complexity: 2-7 (one per block in the circle)

Examples: Customer acquisition loops, Amazon flywheel.

7. The Spectrum

The spectrum is probably the single most commonly used business diagram, but is easily my least favorite, because it tends to suck people into a no-exit, zero-sum frame. Often, people use sets of spectra to characterize a large decision space, or flesh out the feature space of a product category. This is a slightly better way to use spectra. Spectra can be binary or continuous, and the resulting “product spaces” of spectra sets can be mixed discrete/continuous.

The spectrum is probably more useful in discussions about design problems than analysis problems.

Miller complexity: 3 per spectrum (end points, pointer position)

Examples: feature set descriptions for disruption debates, persona models.

8. The Bounding Box

The bounding box is one of my favorites, and I rarely see non-engineers use it. It is a loose, qualitative generalization of the idea of a “design” space illustrating the zone where you have freedom of choice. Each edge — and I recommend drawing this as an irregular polygon — represents one boundary with an adjacent zone that can affect what you do, but is outside your control. These could be supply chain partners, etc. For example, in the semiconductor industry, if you are a chip design outfit, you might have a bounding box with foundry, device manufacturers, and IP partners as your edges.

Miller Complexity: 4—9 (3-8 labeled boundary edges, with an interior label for your in-scope design space.

Examples: Any sort of supply chain discussion, discussion of physics constraints.

9. The Stack

The stack is another diagram inherited from engineering, with the archetype being the stack diagram of a computer. It looks a bit like the pyramid, but has equal size layers. It is great to use for discussing actual stacks involved in engineering, design, and architecture discussions, as well as more abstract things like industry sector structure, and market structure.

Miller Complexity: 3-7 (I’ve rarely seen stack diagrams with more than 7 layers)

Examples: Industry structure diagrams, software architectures.

10. The Pillars

The pillars are, to me, one of the most interesting diagram types because I almost never use them. Their sweet spot is values-based reasoning. This does not necessarily mean ethics at a human level. It can be a dogma for highly opinionated engineering design. The vertical orientation suggests a cutting-through of a stack or pyramid, and each pillar suggests a “present at every level of abstraction” concept. So pillars necessarily have to be somewhat abstract, because they’ll be embodied differently at different levels. With 3-pillar diagrams, you can also discuss stability questions, since a 2-legged stool will fall over.

Miller Complexity: 3-6 (more than 6 pillars and you have a caterpillar)

Examples: “Core values” diagrams, equilibrium diagrams.

11. The Breakdown

The breakdown is a special kind of top-down tree, where a large ambiguous thing is progressively broken down into component parts that are bite-sized chunks ready for resource allocation, responsibility assignment, or functional coverage in a design. They can be used in formal, technical ways in some engineering disciplines, but are commonly used in much more informal ways.

Miller complexity: 9-15, but with some chunking by branch and level lowering the cognitive burden to single digits.

Example: project breakdown, root cause analysis, org charts.

12. The Directed Spokes

The directed spokes are a set of arrows arranged along the spokes of an imaginary wheel, with a labeled hub. In an inward pointing orientation, they usually represent environmental forces you must respond to. In the less common outward orientation, they represent some sort of impact analysis. Where a flow (see 14 and 15) is a controlled, directed pattern of unfolding action and consequences, the outward spokes are good for thinking about relatively uncontrolled impact patterns, such as thinking about the effects of a major press release.

Miller Complexity: 4-5 (1 per spoke, 1 central concept)

Examples: Descriptions of environmental factors affecting a company, convergence/divergence in trends, impact analysis, fallout patterns.

13. The Turnpike

The turnpike is an idealized pattern of growth where two evolving variables are in a healthy dynamic balance. In the simplest, somewhat degenerate case, the x-axis is simply time, while the y-axis is something like capability. The turnpike — the term is from economics — is the vector of optimal growth. Below the line and above the line you get some sort of suboptimal (and possible unstable) out-of-balance condition. On the turnpike, you get some sort of idealized pattern of evolution or growth.

Miller Complexity: 7-9 (1 per axis, turnpike label, above/below line region labels, 1 per “milestone” box)

Examples: Product development roadmaps, capability maturation path, business evolution stages.

14. The Sequential Flow

The sequential flow is simply a single set of arrows going from left to right, representing the temporal gestalt. The more detailed (and in most cases, less useful and possibly harmful) version is the Gantt chart. The sequential flow serializes the necessarily complex detailed behavior into a set of phases or gears. Often separated by stage gates with go/no-go decision points, in which case this is the horizontal, temporal version of the ranked cut.

Miller complexity: 3-8 (a per arrow, and optionally, one between each pair of arrows, and a pair of bookends, along with a overall flow label)

Examples: Project phase structure, narrative structure, causal hypotheses.

15. The Parallel Flow

Parallel flow diagrams are useful when you need to talk about synchronized efforts. Unlike the vertically oriented cousin (Pillars) which represent timeless values, the parallel flow represents the most precisely timed artifact in business: the synchronization point. Things that have to line up at a single point in time.

Usually it is used to talk about an all-or-nothing outcome with several necessary  conditions (a large AND gate basically), but with some practice, you can also use it easily for talking about hedged option sets (an OR gate).

Miller complexity: 3-8 (a per arrow, synchronization point label, overall flow label)

Examples: Launch conditions modeling, go/no-go necessary/sufficient conditions.

16. The Concentric Circles

The last of my 16 basic diagrams is a focusing tool. Concentric circles are usually used to think about fuzzy structural boundaries, with a stepped transition from inside to outside. A common example is modeling an ecosystem, or a set of prioritized concerns with a coarse partial ordering. Interestingly, the concentric circles are closely related to the basic linear spectrum. The radial axis of a concentric circles diagram is a directed spectrum. The tangential direction represents a sort of unsorted residual direction of “everything else”.

Miller Complexity: 3-5 (one per ring)

Examples: Ecosystem models, partitioning of concerns along a focal to peripheral spectrum.

Using Visual Language

There are plenty more, but I’ll stop at 16. If you have any favorites that aren’t on my list, do comment. I might eventually make a flashcard deck of these.

Diagrams are like any other language. You get better with practice, and your vocabulary expands expands as you gain both experience and theoretical knowledge. So long as you never use diagrams simply for the sake of using them, and focus on improving your ability to pattern match contexts where a particular type of diagram is useful, your command of the language will improve, and you will become more eloquent and useful as a discussion partner.

Don’t turn your nose up at the basic stuff. Don’t invent or use unnecessary, bespoke, complex stuff. Use what works, pay attention when and how it works, and use it better next time. If people you’re talking to seem to have an aversion to particular bits of your vocabulary, don’t waste too much time trying to convince them. Just switch to mutually preferred vocabulary. The point is the discussion, not displaying your diagramming prowess. It’s not complicated unless you want to make it complicated.

We talk a lot about 4 types of economic entities in this newsletter: big organizations, startups, under-the-API gig workers (such as rideshare drivers), and finally our core class — independent consultants. The superficial structural differences are obvious, but what are the real, deep differences that account for their different economic roles and mutual relationships? I’m going to try and explain it with 2 pictures.

The first picture is a generic Venn diagram of organizational behavior modes that applies to all 4 (considering free agents to be 1-person organizations). All organizational behavior can be understood in terms of the intersections of problems, resources, and surprises, which intersect to create 7 behavioral zones like so.

I’ll let you think about my 7 behavioral zones on your own, but I want to make a couple of general comments before zooming in on the indie consulting version.

The first thing to recognize about this diagram is that problems and resources don’t have to match/overlap much, but do need to be approximately equal in magnitude, which allows for solving them via creative trade and commerce. Bullshit work usually indicates underutilized capacities that can be sold to others. Futile gestures and signaling generally indicates real problems that could be solved by third parties. If the scope of opportunities to spend/make money are well matched, there is the possibility of increasing the efficiency zone.

But if your problems sum to $1 billion and your resources sum to $100k, there’s a basic mismatch that cannot be solved without some true innovation and probably brute-force capitalization. More likely, you will simply try to shrink the scope of the problems you accept to match the resources you have, or die trying.

The second thing to recognize is the role surprises play in shaping organizational behavior. Good/bad doesn’t matter. Sometimes unexpected gifts turn out to be curses. Other times, making lemonade from lemons turns out to be a huge win. What matters is that something unexpected has entered your world from the vast unknown outside.

I’m something of an extremist on this point. I believe nothing truly significant ever changes in an organization without the injection of a surprise from the external world, followed by a creative and imaginative internal response to it. Surprises are necessary (but not sufficient) fuel for growth and change.

Without a stream of external surprises in the picture, the problems-resources relationship is generally in a zero-sum gridlock and doesn’t offer much opportunity to break out of bad situations. All you can hope for is slow, painstaking growth or decline driven by conscious discipline.

But external surprises can break the gridlock. Whether in positive or negative ways is partly, but not entirely, up to you. Organizations differ in their “surprisal surface area”, both in terms of the scope of generally salient surprises, and the degree of direct overlap between the stream of surprises and the resource/problem gridlock picture.

Varieties of Surprisability

The trick to understanding different types of organizations is recognizing that these circles and intersection zones are sized differently for our 4 basic types. And of course we can plot them on a 2×2 😎. What I’ve plotted here are typical representatives of each class.

See what’s going on here?

Big organizations and under-the-API gig workers are both process constrained. This means relatively low scope of relevant surprises (small green circle), and weak ability to respond to them (small overlap zone).

Startups and under-the-API gig workers are both resource limited, which means there is a significant mismatch between the scale of problems they have to take on and the resources they have available to address them (red circle bigger than blue circle). This means the situation is unsustainable long term without some differential growth or shrinkage to balance the two. Startups and gig workers are both in grow-or-die mode, and the growth is required as much to right-shape their economic roles as to make them profitable.

But indie consultants are unique among the four types in having a much bigger surprisal surface area, and overlap zones, than the other three. Because we are neither process constrained like under-the-API gig workers, nor faced with a severe mismatch between resources and problems like startups. So we have a very significant openness to surprisal, and a much higher ability to solve problems in ways besides arguing over resources with others.

The Art of Being Surprisable

A trivial example: if you’re reasonably smart and broadly curious and interested in stuff, almost any item in the news can be fodder for something like a blog post, or quick-turnaround expertise acquisition if you want to invest more time.

These can then be turned into money fairly easily, with mechanisms ranging from subscription newsletters to online classes, to corporate workshops, and spec work for appropriately targeted clients. This means you can respond to a LOT more of what’s going on in the world than the other 3 types of organizations. This is the reason the main product a lot of indie consultants sell is surprises transformed into customized/personalized action optionality for clients. Because we have surplus capacity to respond to surprises ourselves, we sell that capacity to others who have a deficit, due to reasons of either process limitation, or resource limitation, or both.

Startups are equally process-unconstrained, but their capacity for surprisal is limited by the fact that they are trying to build out one very specific ambitious thing with very scarce resources, so their green circle of relevant surprises is smaller. Otoh, big companies have a lot of resources, but too constrained by their processes to ingest significant surprisal. Under-the-API gig workers of course, are the most constrained of all.

You need 5 things going on to turn surprisability into economic leverage:

1. Openness to experience: You have to be paying attention outside your focal zones, and ideally, actively provoking parts of the environment to generate surprise-fuel for yourself.

2. Depth of curiosity: A surprise by itself is like rain. Without adequate forest cover or porous soil, it just rolls off like a flash flood. To “trap” surprise in the form of an asset, you need a rich and broad awareness of the world, so you can integrate surprising things to things you already know/do in interesting ways.

3. Lack of missionary lock: Your life should NOT be built around a single overarching mission to the degree that you can’t opportunistically in ways unrelated to other things you are doing. If you have that kind of lock, you need to turn yourself into a startup.

4. Imagination: Ability to see the possibilities latent in a surprise that are within your zone of actionability. Nobody else can do this for you. This is a kind of connecting of dots that relies on your private knowledge.

5. Boldness: The ability to overcome doubts and just act to be the agent of whatever the environment has enabled to happen. The ability to say: this connection is just waiting to be made, somebody has to make it, why not me?

That’s ODLIB if you like mnemonics: Openness to experience, Depth of curiosity, Lack of missionary lock, Imagination, Boldness.

If you think your surprisability is weak, you might want to start a “surprise log” in a notebook, or even as an evolving thread of tweets. Sensitizing yourself to surprise is not hard. Be careful not to turn it into an “idea log” though. It’s important to learn to see the surprise itself, and the potential it opens up, and not jump too quickly to a way to do something with it (and most of the time you won’t be able to). That’s the only way you’ll train your surprisability.

Pro-tip: a surprise doesn’t have to be a new development or seem obviously surprising at first glance. It just has to be newly surprising to you, via an insight. It can even be something that didn’t happen (“the dog that didn’t bark”). A surprise stream is not a news feed.

Apologies for taking two weeks off on the newsletter instead of a planned one week. A bad cold rendered me incapable of doing anything more complex than shitposting on Twitter for the last 10 days. I meant to do an end-of-year roundup, but now I’m deferring that to the one-year anniversary of this newsletter in April, since I’m not actually at a good retrospective point. In the meantime, the archives page is reasonably browsable if you’re a recent subscriber.

Back next week with a real newsletter issue. In the meantime, do send in any thoughts on what you’d like to see me cover in the coming year, and what you’d like to see more or less of.

Happy new decade, gig on!

🤧

I’ll keep it short and practical this week. If you’re in the gig economy, or planning to be, I suggest doing some sort of relatively structured end-of-year review/planning exercise heading into 2020, and taking it seriously. Here are some resources to help you do that.

One of the best ways to take such exercises seriously is to undertake them with a partner. Pamela Hobart has kindly volunteered to run a blind-date matching process to pair people up to do their annual planning/review cycles together (ht Tom Critchlow for the idea).

If that’s of interest, sign up on this google form to be assigned a partner.

If you think you could use more structured support, with processes and models, a few options to consider include:

1. Taylor Pearson’s goal-setting masterclass

2. Pamela Hobart’s coaching (she has office hours coming up)

3. Tiago Forte/David Perrell annual review workshop

4. Malcolm Ocean goal-crafting 2020 intensive

While I haven’t tried any of these myself, they are all offerings from people I know, and trust to do a thoughtful job with their models and processes. They’re all gig economy people themselves, so they have a sense of the peculiar challenges we face. So check them out.

The only resource I have to offer myself is a link to this blog post I wrote in 2008, half in jest, How to Make New Year’s Calibrations.

If you have additional resources to suggest, or general thoughts/reflections on annual reviews/planning, or simply want to share something about your own process, reply to this tweet to share.

A few thoughts on the stakes seem called for though.

Regular paycheck people tend to march into the New Year with a good deal of ceremony. It’s practically a parade. But their lives are typically structured and safety-netted enough that doing it poorly doesn’t matter much. The stakes for things like resolutions rituals are pretty low, and the typical cost of getting it wrong is on the order of an unused gym membership.

We in the gig economy on the other hand, tend to stumble unceremoniously into the new year via a back alley, rather than marching into it down Main Street. And usually, there is some actual non-ceremonial reorientation debt piled up to pay off. So your review/planning rituals matter, and this is one of the rare predictable windows of opportunity you have available to do them in.

And the stakes are higher. We have no default structure or safety net to yank us back to safety if we get it wrong.

Full disclosure, I’m personally not very disciplined about end of the year observances, or structured processes, so that’s one reason I’m pointing you to other people.

But I do tend to take a sort of mental vacation (if not an actual vacation) and do some sort of thinking I don’t normally do. Some years, I dabble in a hands-on learning activity during the holiday week, like trying out a new programming language. Other years I just binge-watch some comfort TV. This year, my project is a little different: building a wooden pendulum clock from a model kit.

Whatever your approach to navigating the 2019-20 transition, try and make it a mindful, conscious one. Week-long opportunities to step back from the fray and make course corrections are scarce and valuable in the gig economy.

Happy holidays, and happy reviewing/planning!

It’s newbie-consultant vaccination week here at the Art of Gig (and booster-shot week for the experienced ones who may have learned and forgotten the lesson I want to talk about). The vaccine comes in the form of this triangle, and is meant to protect you from an operational hazard of indie consulting: charges of parasitism.

More specifically, the vaccine is meant to protect your psyche against the constant gaslighting and broad-strokes scapegoating of consultants by other kinds of economic actors, making you doubt your own economic worth relative to theirs, and wonder whether perhaps you are in fact morally inferior to them, as they insidiously keep suggesting, with their holier-than-thou sermonizing.

It’s particularly worthwhile getting your immune defenses strengthened right now, since McKinsey’s sketchy practices, which I did some commentary on last week, remain in the news cycle with the story about their work with the City of New York to reduce violence at Rikers (tldr: it seems they failed and violence actually increased). And reports like this paywalled article titled How to Avoid the Startup Trap of the Parasitic Consultant (I only read the lede).

Parasitic Competition

The gaslighting and scapegoating of consultants is most likely to be led by two species of parasite that compete with parasitic consultants (who do exist) to feed on weak organizations: charismatic but weak leaders, and unaccountable bureaucrats.

To vaccinate yourself, you must learn to identify and counter the trash-talk from these two wonders of organizational ecosystems. You must learn to firmly defend your worth, especially to yourself. And even go on the offensive in internal battles if necessary, if you believe you are being unfairly maligned as a parasite, when you are in fact a Good Gigster fighting the Good Fight against the actual parasites.

Here’s the basic dynamic you have to understand.

As organizations weaken, all three species in their non-parasitic forms become subject to the morally hazardous incentives that lead to parasitic behaviors.

Usually two of the species will appear together, and act to lock out the third, making it a two-way duel. And sometimes, only one of these species will appear, and cut off the other two.

But in seriously weakened organizations, all three are often present, leading to a sort of Mexican standoff among them, with shifting alliances as the situation unfolds. This is the situation I’ve illustrated above in the cartoon (the locust, ladybug, and caterpillar in the diagram above are pests rather than parasites, but oh well, you get the point).

Consultants, as outsiders with no locus standi in the official narrative, and biased towards public silence by both long-term business model considerations and contractual obligations, are naturally vulnerable to being blamed for the effects of parasitism, whether or not they are actually being parasitic in a particular case.

Basically, because you don’t want to gain a reputation for throwing your clients under the bus under stress, and because non-disclosure and non-disparagement clauses probably make it legally risky to do so anyway, you are easy and safe to blame. Perversely, this can make angry consultants, who feel unfairly maligned, turn parasitic even if they weren’t previously. The tempting line of reasoning goes: might as well be hanged for a sheep as a lamb, and get yours while the getting is good.

Charismatic-and-weak leaders and unaccountable bureaucrats aren’t the only ones who like to preach anti-consultant sermons, and score cheap points by tarring our noble trade with a broad brush. But they are the ones who matter, because they are in a position to affect the roles consultants might be playing, and also know enough to be effectively disingenuous in their anti-consultant sermonizing.

Others who join in, especially in the media, tend to have no idea what they’re talking about. Their unaided criticism (sincere or disingenuous) tends to be so wide off the mark, it does little to no damage. But competing parasites can sometimes co-opt these less effective critics and target their outrage to be more effective.

In the ongoing McKinsey saga for instance, while clearly McKinsey is guilty of a degree of parasitism, it is equally clear that weak leaders and unaccountable bureaucrats are throwing McKinsey under the bus. The media reporting on this either isn’t well-versed enough in these dynamics to see what’s going on, or they do, but are playing along because they think McKinsey is worth throwing under the bus anyway, and an easy target, even if the other two species of parasites are possibly more to blame.

Assuming you’re among the good players who aren’t actually being parasitic in your gigwork (if you’re subscribed to this list, I think it’s a fair assumption, hence the headline), vulnerability to undeserved charges of parasitism creates two problems for indie consultants in particular.

The easier problem is making yourself practically immune to accusations of parasitism and structurally distancing yourself from actually parasitic consultants.

The harder problem, and the one the triangle vaccine is meant to address, is hardening your psyche against the gaslighting, making you philosophically immune to it.

Let’s tackle the harder problem first, because it will make the easy problem even easier.

Philosophical Immunization

The key to philosophical immunity is to firmly call bullshit on the holier-than-thou moral posturing that usually lies behind accusations of consultant parasitism. The key to this is understanding who feels threatened by the presence of consultants (whether honest or actually parasitic), when, and why.

Organizations are vulnerable to three kinds of parasites when they are in poor health.

1. Charismatic but weak CEOs/leaders who function by creating strong reality distortion fields around gaps in their weak leadership. They are vulnerable to their reality distortion fields being punctured by skeptical, informed scrutiny. Think the WeWork CEO Adam Neumann, or Theranos’ Elizabeth Holmes.

2. Unaccountable bureaucracies that quietly control the organization from the inside and are vulnerable to their internal monitoring and inspection processes being revealed as ceremonial shams protecting inefficiency, ineffectiveness, incompetence, or profiteering by skeptical, informed scrutiny. Think the career leadership at the government agencies involved in the McKinsey cases. Or most old-economy big companies.

3. Hard-to-fire consultants who get their hooks into organizations, and make themselves indispensable to the day-to-day-functioning once they are in. They are vulnerable to their work being exposed as self-serving and against the interests of the organization by skeptical, informed scrutiny. Think McKinsey.

For each of these bad-actor species, the other two kinds of bad actors represent competition in the feeding frenzy, but the bigger threat is good-actor types at the other two vertices because they are the ones who can direct the skeptical informed scrutiny at them, and lead efforts to resist and reverse the parasitized organizational condition:

1. Strong effective CEOs who don’t need to distort reality to cover up weaknesses in order to either lead the organization or profit personally.

2. Professional, high-integrity bureaucracies whose processes can pass internal or external scrutiny with flying colors.

3. Good consultants who can cast an unflattering light on internal realities and self-congratulatory narratives through pointed, detailed, and specific external comparisons.

Notably, Steve Jobs (though he had his share of weaknesses) distorted reality primarily to create missionary motivation at Apple rather than cover up his own weaknesses, and equally notably, his is among the rare criticisms of consultants that is fair, based on the breadth-over-depth tradeoff we consultants must make, rather than glib charges of default-parasitic evil tendencies (his opening line in the clip above: “I don’t think there is anything inherently evil in consulting”).

The key to immunizing yourself is to tag the primary source of the accusations in a give case, reject their default claim to the moral high ground (and default insidious suggestion that the consultant must necessarily be the parasite, kinda like a Butler Did It default), and uncover the actual pattern of parasitism going on.

Which might lead on to…

Fighting the Good Fight

Once you’ve uncovered it to your satisfaction, the actual pattern of parasitism in a weak organization is not necessarily information you need to act on. The organization may be naturally defending itself, and you may be able to add value without getting involved. You just need to become aware of it to protect your psyche against gaslighting, and dodge scapegoating attempts.

But if need be — and such need indicates the gig has turned into a war zone at a seriously weakened organization — you can choose to direct skeptical scrutiny where you think something is actually going on.

What weakness or fraud is a charismatic-but-weak leader hiding?

What processes are career bureaucrats protecting from skeptical inspection?

These questions are weapons with which you can go on the offensive if you feel things are going beyond generic knee-jerk gaslighting of consultants and you’re actively being set up for unfair blame.

That is, of course, if it is worth your while to stay and fight at all, not just at a personal level, but at the level of your sense that the organization has value to the world, is worth curing of its parasitic infestations, and that you can be a meaningful part of the cure.

This philosophical immunity is necessary if you want to survive as a consultant, because it is very rare for consultants to be hired to help completely healthy organizations, and very easy to buy into hostile “evil mercenary” perceptions of yourself.

Chances are there is a little bit of parasitic infection of all three kinds (in a large organization, even if you are playing a clean game, doesn’t mean other consultants in the organization are).

Internal Allies

Not every gig is a Mexican standoff of three-way competitive parasitism, and you don’t have to stay and fight in all of the ones that are.

But chances are you, you won’t have the luxury of always working for healthy organizations. Some fraction of your gigs will involve parasite-fights, and of those, you’ll have to pick a few to actually fight, because they are Good Fights.

If you walk away from all of them, not only will you forgo a big slice of the consulting pie, you will fail to grow in courage and integrity as a consultant. So you must pick a few fights. Every gig need not be an anti-parasite fight, but a few should be.

Still, it’s hard to fight the good fight to save an organization when nobody within it seems to want to. This means, it’s only worth fighting when you have effective and sufficiently powerful internal allies who are fighting for what’s worth saving about the organization.

Assuming you’ve philosophically immunized yourself against charges of parasitism, the three most common allies who make for a fight worth fighting in an unhealthy organization are:

1. An effective CEO/leader against an unaccountable bureaucracy.

2. A effective and competent bureaucracy against an unprincipled predatory weak-charismatic CEO/leader trying to feed on the organization.

3. An effective senior leader who is not the top leader/CEO but has enough personal credibility and sophistication to lead a reform campaign even despite an unaccountable bureaucracy and/or weak-and-charismatic top leader.

That third pattern is surprisingly common.

One of the tells of a weak-but-charismatic CEO is that they tend to allow high-level exceptions in their reality distortion field to make room for competent subordinates they cannot do without.

While their general leadership posture is demanding unquestioned loyalty from their inner circle, and cult-leader like reverence from employees and customers, who don’t see them close-up, they tend to compromise that posture where they must.

A good principle to remember this pattern is John Boyd’s advice: if your boss demands loyalty, give him integrity, if he demands integrity, give him loyalty.

Let’s call a senior leader who plays by this rule a Boydian Lieutenant. A holy warrior willing to lead the Good Fight internally. These make great allies and clients.

Extremely weak leaders, or ones preparing to exit with their loot (possibly killing the organization in the process), tend to demand loyalty and accept nothing but loyalty. But the ones with better survival instincts (who might have some genuine desire to keep the organization alive mixed in with profiteering motives), tend to make exceptions for indispensable Boydian Lieutenants.

They are the only ones excused from having to pretend to believe in the reality distortion field. They are the only ones excused from frequent and fervent inner-circle displays of loyalty towards the Dear Leader. They are the ones equipped to lead a Good Fight.

In summary: philosophical immunization against charges of parasitism amounts to recognizing the pattern of competitive parasitism that infects weakening organizations, correctly attributing unfair charges and gaslighting to competing parasites, and being prepared to go on the offensive and bring skeptical scrutiny to their behaviors when you feel the fight is a Good Fight, and you have the right internal allies.

If you have that mindset, the practical immunization is easy.

Practical Immunization

Once you have the mental models for philosophical immunization in place, are able to deflect routine gaslighting, and are armed with the information to go on the offensive if necessary, you are actually equipped to do some good in your gigs.

But there’s a matter of practical immunization. It is not enough to have the philosophically hardened mindset. You must structure gigs tactically for defensibility against false charges, insinuations, or perceptions of parasitism.

Here’s the key trick: make yourself hard to hire, hard to retain, and easy to fire.

(Hard to retain as in, hard to keep you paid, benched, and available without actually giving you things to do).

Most consultants and consulting firms do the exact opposite. They strive to be easy to hire and retain, and hard to fire.

Worse, they do all they can to structure gigs with hooks for passive income, unnecessary maintenance work done on autopilot, and front-loaded non-optional work as a precondition for working with a client. That last item is a particularly clear tell of a potentially parasitic consultant.

Example: a publicist firm I once worked with on a project many moons ago insisted on front-loading a $7500 item into the contract (we negotiated it down to $2500 and a cross-promotional barter clause) for taking a month to prepare a “Master Marketing Plan” before they did any actual publicity work. This sounded like bullshit, and what do you know, it turned out to be bullshit. That whole engagement was a huge waste of money. It generated no useful publicity. Classic parasitic consultants.

Being easy to hire and retain, and hard to fire, and acting to lock down your own income regardless of project outcome, makes you vulnerable to accusations of parasitism. And it creates the kinds of moral hazard that make such accusations likely to become true, even if they aren’t initially.

But it doesn’t make such accusations automatically true, just easy to level.

Hard to hire, hard to retain, easy to fire translates into this structural heuristic:

Rely only on inbound leads to get gigs, and within gigs, never do billable work that you’re not explicitly asked to.

For the latter part of the principle, you can always suggest options for various ways to achieve an end (including using your services) that might solve a problem the client has, but the choice is theirs. And you can always give them freebies at your discretion to build trust and goodwill, but the choice to ask for more of the same with pay is theirs.

The client should never be surprised by an item on an invoice, or feel like they were forced to sign off on it to get what they actually wanted done (unwanted bundling basically).

If you are able to follow this principle 100%, you’ll basically be 100% structural immunity to charges of parasitism, because you’ll be able to say with honesty (though I’ve never had to):

“You guys sought me out, I’ve done nothing you didn’t ask me to, I’m making no money on autopilot, I’m not bundling in shit you don’t want, and you can kick me out any time you like. How am I the parasite?”

If you cannot hit 100%, you’ll be vulnerable to the extent you’re forced to deviate from it.

At 100%, you are also well-armed to go on the offensive and cast a spotlight on parasitism elsewhere if the situation calls for it. This can be hard (but not impossible) when you are at less than 100%. Basically putting yourself in the role of “let he who is without sin cast the first stone.” Engineering a condition of “no skin in the parasitism game” makes you an honest witness of it.

Should you aim for 100% practically immunity in every gig? Depends on the weakness of the organization and risk profile. You can take calculated risks (and remember this is reputational risk that you pay for with character/integrity perceptions that might dog you for years, not mere financial risk within a single gig).

Every outbound pitch, every uninvited speculative proposal, every suggestion within a gig that could be perceived as manufacturing unnecessary billable work for yourself, exposes you to possible accusations that you are exploiting gullible leaders/managers (or colluding with corrupt ones) to parasitically feed on a weak organization.

I personally don’t like to play risk management games when it comes to reputation, so I’ve pretty much stuck to 100% inbound and 100% do-only-what’s-asked consulting, with no passive or bundled billables.

I let clients know upfront that they entirely control the pace of the engagement and volume of work. I do not set an expected frequency of meetings, a minimum number of hours, or structure gigs to include fixed costs like non-negotiable initial discovery research hours or ongoing “maintenance” hours, though in many gigs I’ve had the leverage or trust to demand such terms, and the cash flow pressures to make it tempting to do so. Occasionally I let clients pay for a block of hours upfront to ease their budgeting, but that’s about it as far as deviations from my pay-as-you-go model go.

The only real control I maintain over a gig is prioritization of work requests: I prioritize client requests based on overall volume. So if they want deeper, faster engagement from me, they have to choose to rely more on me overall. The more you actually rely on me, the more I prioritize what you ask of me, which usually leads to more reliance on me. A virtuous cycle of increasing meaningful entanglement. Conversely, the less they rely on me, the less I prioritize them, a cycle of gradual disengagement.

All this is neither about noble ethics (I’m not particularly noble) or some sort of subtle rainmaking stunt (as far as I can tell, this rule is a self-imposed tax that lowers my potential income). It is simple self-preservation. As an independent consultant, your reputation for integrity is pretty much the only kind of capital you have.

And if that gets tarnished, you’re done.

You have to either quit the game, or go over to the dark side of self-consciously parasitic consulting.

But I don’t want that, and neither do you. Because you and me, we’re in the game for the intellectual challenges it offers. We’re not parasites.

Whatever actual parasites say.

In my September 19th post, The Price of Freedom, I wrote:

When you give up integrity of methods (in terms of skilled discipline and/or ethics) you break the feedback loop of mindful practice and growth that keeps your cognitive abilities and procedural-ethical judgments strong and growing. So you experience cognitive decline.

I want to revisit this point a bit, in light of recent “news” about McKinsey. For those not keeping up, Pro Publica, the non-profit journalism outfit, along with the NYT, co-published a major feature about McKinsey’s work with the Trump administration on ICE (the US immigration police for those not in the US).

My scare quotes are because these “revelations” aren’t really news, in the sense of being even remotely surprising, to anyone who knows how the consulting industry works. So what is actually news is that this counts as news for the broader public.

The interesting question for me is: what exactly does the general public think firms like McKinsey do, that this counts as news?

That they work this way, and are not too picky about who they work for, is not exactly a secret. So it is unclear what illusions, held by whom, are being shattered here.

The question is important for us in the indie consulting world. In many ways McKinsey is something of a bellwether for perceptions of consulting in general, including the indie and boutique varieties. So the fates of the two sectors are coupled, and shifts in sectoral perceptions matter to us.

The big difference is that the kinds of incentives and pressures firms like McKinsey navigate as a company, you and I navigate as individuals (albeit at a much smaller scale). This means the mindfulness feedback loop I refer to above is much easier for us to maintain in a healthy state. It is also much harder for us to ignore problems with the feedback loop.

For big consulting firms like McKinsey, much of the responsibility for big decisions rests with senior partners, rather than with the rank-and-file who do much of the grinding on engagements, so the feedback loop is vulnerable to being broken.

As independent consultants, you and I cannot blame senior partners for poor judgment, or rank-and-file grinders for failures in execution. We are responsible for both judgment and execution. If the feedback loop breaks, it’s our own fault. If we are held accountable for behaviors of clients we are complicit in, our options for deflecting the blame are limited.

So it is worth understanding what’s happened at McKinsey, and using it as a lens for examining your approach (implicit or explicit, tested or untested) to ethics in gig work. Because believe me, if you last, your ethical commitments will in fact be tested under live fire. It’s not abstract.

Knives Out

The latest news is yet another chapter in almost a decade of bad optics and brand tarnishing for McKinsey and its ilk. It started in 2012 with the conviction of then-CEO of McKinsey Rajat Gupta for insider trading, and the spotlight on Bain thanks to the presidential bid of Matt Romney. It was followed more recently by a harsh media spotlight on McKinsey for its work with the Saudi Arabia. And now this.

Perceptions of the big-firm consulting sector in 2019 are now a far cry from the high regard it enjoyed as recently as a decade ago, though students in MBA programs appear not to have caught on yet.

The reaction to this latest chapter has been swift and harsh. Matt Stoller has a scathing indictment. Louis Hyman, a historian of capitalism at the Cornell School of Industrial and Labor Relations has a twitter thread blaming McKinsey (somewhat unfairly) for inventing the modern, precarious gig economy. Others are gleefully jumping in with whatever pent-up hostilities towards the sector they’ve been harboring.

The knives are out in earnest.

None of this is news of course, which is why many of us are puzzled. Nobody ever pretended the Big 3 consulting firms were not what these sensational “revelations” are showing them unambiguously to be.

What has changed is the public mood in relation to elite institutions, and what Walter Kiechel called the literary-industrial complex, which includes, (besides prestigious consulting firms), elite universities, labs and research centers like the MIT Media lab, business book publishing, and events like TED and Davos.

The mood has shifted from tolerant and indulgent to harsh and unforgiving. It is not a good time to be affiliated with the literary industrial complex if you care about perceptions.

In 1999, the Mike Judge comedy Office Space portrayed consultants as unprincipled sociopaths, but still people to be regarded more sympathetically than the clueless fat-cat executives and managers they supported. People who genuinely relished the intellectual challenge of whipping a struggling company back into shape, and who did meaningful, if not always pleasant, things towards that end. Big Consulting has generally not been regarded as bullshit work. For better or worse, it has been too consequential and self-aware to dismiss with that particular criticism.

So what changed? Why are consulting firms suddenly being held accountable, in the court of public opinion, for the decisions of their clients? Why has the get-out-of-jail-free card stopped working?

Up until the Great Recession, the perception of the Big 3 large-scale consulting industry was largely positive, as cunning rascals you had to grudgingly admire. They were seen as bagmen doing the dirty work bankers and CEOs made necessary. Deliverers of harsh messages. And at their best, pragmatic mercenary foils mitigating missionary tendencies towards ideological excess. They were seen as aware of, and complicit in, high-level governance in all parts of the institutional landscape, but ultimately not primarily responsible for moral matters.

These perceptions matter to us in the indie consulting world because they trickle down to shape how we are perceived as well, which for the most part we’ve welcomed as a positive. In some cases, I’ve made direct reference to them in explaining what I do, as in “I do the same sort of stuff McKinsey does, just on my own, and at a lower price.” It’s not actually a very accurate self-characterization, but it is a convenient starter perception, at least initially, while you establish your actual modes of delivering value.

But these perceptions have changed, and with them, the consequences of positioning yourself relative to the Big 3. The cost of co-marketing convenience has changed.

Now, increasingly, the big consulting firms are seen as directly responsible for the moral failures of client organizations. Even perhaps more responsible than client leaders. They are seen as predatory organizations that exploit the general stupidity and incompetence in prey firms to capture them for profit, by making themselves indispensable to running them, but without any accountability for running them well. It’s a cousin of regulatory capture.

And there is some justification there that favors the consulting firms. Many large organizations are so dysfunctional, they effectively have to be run by the big-firm consultants who service them. They are too brain-dead to run themselves unassisted (a condition the big consulting firms had a hand in creating). A good part of the consulting market is a corporate assisted living facility.

But that justification begs the question to some extent. If the organizations are so brain-dead they need to be on consulting-firm life support to function by themselves, it is a little disingenuous to claim that ethics decisions on matters of mission and values are entirely the client’s problem. A generalized zombie is obviously also specifically a moral zombie, incompetent to stand trial.

Who is asking whether the zombie clients should exist at all? Why should such relationships be viewed as anything other than pure scavenging or parasitism in the guise of guardianship?

Turns out, there’s actually an interesting answer here.

Grinder Selection Effects

I’ve been largely sympathetic to McKinsey and its peers through most of my adult working life. Many of my classmates and friends have spent time with McKinsey, Bain or BCG. I actually interviewed with McKinsey in 2003, while finishing up my PhD, but got rejected in the second round. I didn’t mind though. It was so obvious that I did not fit the grinder profile they were recruiting for, it made me respect rather than resent their selection process.

Because that’s the most important thing you have to understand about the Big 3 consulting world: it selects for intelligent, high-energy grinders, not snowflake philosophers driven by foundational curiosities. Tiger Kids if you like. People who set out early in life to win the game as it is presented to them, rather than question, subvert, or change it. Which is not ipso facto a bad thing. If the game presented to such people is a good one, they will play it well, and a good time will be had by all. The world runs on grinders. When it runs at all.

What the critics miss, in their eagerness to call out the unsurprising fact that relatively inexperienced college grads are rented out at a high mark-up (not in itself problematic as far as I am concerned), is just how hard and effectively these people are willing to work, compared to the complacent and comfortable managers at the organizations they serve. I’d be dead in a month if I attempted to work at the pace I’ve seen young Big 3 consultants work. 100 hour weeks are not uncommon. And that lifestyle of constant, stressful travel and living out of hotels takes a toll too. Whatever their sins, taking it easy isn’t one of them. And whatever my virtues, working that hard isn’t one of them.

I was clearly not cut out for their approach. Eight years later, when I struck out on my own, that rejection helped me define the kind of consulting I could actually be good at, and could sustainably do at the level of effort I am capable of putting out (which is about 0.1G, where 1G = 1 Grinder). I could position myself in a differentiated way around conversational sparring, and avoid anything that looked like a Big Three 100-hour grind. I could benefit from the perceptions of the consulting industry, but not be bound, limited, or defined by them.

That selection-for-grinders model that dominates the Big 3 world is at once its greatest strength and greatest weakness.

As a strength: there are few forces in the world comparable to the raw mid-grade aggregated intellectual horsepower that can be unleashed on organizational problems by the likes of McKinsey, Bain, and BCG. And it’s easy to underestimate it because what an individual junior associate does can seem like unimpressive grinding. But a dozen such people grinding in the right places can move mountains. Or Fortune 100 companies.

As Matt Stoller notes in his criticism, the problems these firms solve are not exactly difficult, and the advice they end up offering are not exactly breakthrough flashes of genius. But the point is, it does require fairly intelligent grinding at scale to generate that advice with the right numbers and specific details attached.

Finding cost-cutting opportunities in a large corporation is rarely about elegant strategic insight and 2x2s. It is usually an exercise in sending a small army of Excel-armed young associates into every corner of the company, documenting costs, and figuring out where to make cuts by crunching the numbers. And that’s not an activity that trains you much in asking the hard questions about why you’re trying to make cuts in the first place, or why the organization exists in the world, and whether perhaps it should not. Grinding mainly teaches you to grind in more efficient ways.

To be clear, this is work that large companies and organizations are generally not actually capable of doing for themselves. They are too compromised by infighting and self-serving delusions and blindspots. What the big consulting armies are selling is not genius brainpower, stellar imagination, reserves of courage, philosophical insight, or even skilled labor time. They are selling the distance that enables them to look in places internal eyes cannot look, and turns impossible problems into grinds.

At scale.

They are the organizational equivalent of expensive medical imaging equipment. To complain that inexperienced young graduates are being paid big bucks to “run” the playbook is like complaining that medical technicians rather than doctors are operating medical imaging equipment. The value lies in the machine, or in this case, the scalable procedural machine defined by the playbook, not the operators running it.

But as a weakness: selection for grinders is a selection of people with little philosophical interest in matters of principle, impatience with doctrinal thinking, disdain for reflection, and a bias towards hard-driving action.

People with those devalued cognitive strengths within these firms (if they get into these firms in the first place) tend to get sidelined into functional expertise areas where they might write modest little white papers and books that don’t rock the boat, provide occasional injections of spot expertise on special topics, and do thought leadership work, rather than frontline consulting work. Those miscast on the grinder frontlines, or with too much maladaptive talent for the devalued kinds of thinking, tend to burn out early and drop out. They typically don’t last long enough to make partner or execute a smart sideways shift into a VP role on the client side.

So there is a strong adverse selection process at work here. At the tops of these firms, there is not just a disciplined tendency to stay away from doctrinal matters, but a systematic functional weakness in the capacity to think about them in the first place.

The problem with firms like McKinsey isn’t that they aid and abet organizations pursuing unaccountable missions that the broader public might find problematic.

The problem is that grinders aren’t philosophers. Which is not to valorize or demonize either. Just an observation that the two are not the same thing, which is a problem if you believe, as I do, that both have a role to play, and either pretends to be both.

Strategy sans Ethics

The self-labels the Big 3 firms use are interesting and revealing.

All bill themselves “strategy” firms, and “strategy” is a coveted aspirational label for second tier IT and marketing consulting firms eyeing their market from a middle-layer position. The cachet of “strategy” also continues to attract aggressively competitive and ambitious graduates of elite universities determined to grind their way to the top of elite institutional society, and be counted among the movers and shakers of the world at Davos some day, fluidly navigating the top echelons of global power.

But what does “strategy” mean for these firms?

Historically, for McKinsey it has meant being present in boardrooms and C-suites, and participating in decisions at that level, but not getting involved in execution.

For Bain it has meant specializing in shareholder value hacking.

For BCG it has meant brainiac “insights” for framing big moves.

Or as I like to think of it, Gryffindor, Slytherin, and Ravenclaw (Hufflepuffs are the strategy-wannabe second-tier IT and marketing firms).

What is missing across the board in this sector is a sense of “strategy” that includes genuine, deeply considered doctrinal, ethical, or philosophical elements (which to me are indispensable components of strategy) driven by real curiosity on those fronts. For the Big 3, those are regarded as the client’s concerns, and decoupled from strategic considerations proper. They are also generally regarded as matters of cosmetics and optics, rather than legitimate concerns worth taking seriously.

And of course, in practice, 90% of top executives don’t want to be holding the ethics and philosophy balls either, and tend to quietly drop it when nobody is looking.

One side-effect of this eschewing of the moral dimension by both C-suite leaders and their prestige-firm consultants is that matters of ethics devolve down to HR and legal departments, whence they are further farmed out to a boutique gig economy cottage industry of what I think of as “ethics grifters”. This is people who gleefully go around creating workshops, training regimens, compliance bureaucracies, and rules around every aspect of individual and corporate behavior. All mostly aimed at creating plausible deniability and cushy jobs for internal ethics czars.

So the cost of abdicating responsibility for the moral dimension at the top is a bloated ethics-grifter bureaucracy in the middle, which has the potential to eventually grow into a cancerous drag that threatens the organization without particularly elevating its ethics game. But that’s a topic I’ll save for another day.

The party line in the consulting world is: the client sets broad objectives based on their CEO values, corporate values, missions, and so forth, and we help figure out how to operationalize it in strategy, by doing the detailed research, creating the justifications necessary, and recommending effective paths.

It is something of a lawyerly stance: the client is something like a defendant in a court of law and it’s the consultant’s job to build the most effective case allowing them to do what they want to do. Passing judgement and doling out punishments and rewards is for juries and judges. For the private sector, that means the court of public and market opinion. For government agencies and politicians, it means the voting public. In any case, it’s not the consultant’s job.

This is a convenient position to take if your goal is to accept the widest range of moneyed clients possible. Work for a dictatorship and a democracy at the same time? No problem, we’ll do both and let the political philosophers work out the meanings. You want to solve for sustainability, profitability, or lowering the cost of incarceration of prisoners or illegal immigrants? No problem, we’ll make you a spreadsheet model for any and all of it, and dig up the numbers necessary to populate it.

It is tempting to conclude that this is an ethically malicious position to adopt out of convenience, and an aspect of the moral hazards of the principal-agent relationship inherent in consulting. Why take responsibility for stuff you don’t have to? There’s clearly no upside.

The real explanation is more sobering: the adverse selection mechanisms by which these firms staff themselves with grinders ensures that the majority of people working in them are genuinely not capable of processing such questions meaningfully.

It’s a cousin of Hanlon’s razor: never attribute to malice what can be adequately explained by unexamined philosophical commitments. In this case, we’re talking about a sort of adversely-selected disinterest in philosophical foundations on the consulting side, and a deliberate abdication of moral responsibilities (accompanied by devolution of the responsibilities to middle-management staff functions) by client leadership.

Either way, the outcome is that the judgement of the court of public opinion, and eventually, the market, is harsh. And when times turn dark, the knives come out.

My own judgment is perhaps less harsh, mostly because I don’t expect anything different from the big consulting industry, and don’t share the illusions that many apparently have (or are conveniently pretending to have) about the sector. They are what they are, and they do what they do.

I don’t have any bright ideas for how the Big consulting companies can change, or whether they even should attempt to do so, since we’re talking about features rather than bugs in their core DNA.

But then, I’m not entirely sure the sector needs to exist at all.

My null hypothesis is that organizations that are zombified enough that they cannot run themselves without Big Consulting support perhaps shouldn’t continue to exist, and deserve to be disrupted and displaced by organizations that can do the necessary thinking on their own (with some modest help from us indie consultants of course 😎). And if the market left over when you eliminate the zombie-life-extension segment isn’t big enough to sustain Big Consulting, perhaps Big Consulting needs to shrink.

To me, ultimately, ethics in consulting is simple: it’s a matter of saying no to things.

Which usually means lowering some topline and bottomline expectations, and being content with less. Ethics are a form of self-imposed taxation. Perhaps you can creatively make up for these tax losses with growth elsewhere, but you can’t magically transform the tax-like nature of the beast. You just have to decide that you believe in the things the taxes pay for, and hope that paying those taxes benefits you in unknown ways in the future. If you knew the actual incentives and payoffs for behaving in “ethical” ways, it would be part of strategy, not ethics.

That’s a decision that’s easy to make as an indie consultant, but quite hard when you’re a huge company staffed by an army of grinders all expecting to climb to the top, and led by people who have been grinding so hard, for so long, they can’t see past grinding as an end in itself to existential questions about themselves or their clients.

They live in a world of TINA assumptions — There is No Alternative. A world of elites that has always been run a certain way, around a set of sacrosanct institutional compromises. A way in which they have an indispensable and well-paid role to play; a role that takes hard work to fill. A role they cannot imagine being fulfilled any other way. If you could imagine a different way, you wouldn’t be working in that world.

We’ll see if they’re right in the next few decades, as the world continues to get eaten by software.

Lessons for Indies

To return to my opening self-quote, the mindfulness feedback loop for staying ethically grounded is much easier for us indies to maintain than for big firms, but it’s not trivial.

The big lesson for independent consultants is that strategy decisions are always also moral decisions. Every client you accept, every task you accept, has both strategic and moral implications for you and the client. And even if you both operate in strictly legal ways, and perfectly within the bounds of the contracts that govern your relationships, you’re still going to be held morally accountable for the work you chose to do.

And as I pointed out in the opening, as an independent, you will never have the luxury of blaming someone else for your choices, the way people in big firms do.

The only excuses that will ever be available to you as an indie consultant, for anything you choose to do, are “I needed the money” and “it was perfectly legal and above-board.” Neither excuse has a history of flying well in the face of hostile public scrutiny.

So doing the right thing is, in the long term, the easiest thing if you’re in the indie consulting world, and want to be able to withstand hostile scrutiny with nothing to apologize for or be ashamed about. You don’t have enough maneuvering room to do anything else. Big firms get themselves into trouble largely because they have the maneuvering room to do so, not because they are morally worse than independent consultants.

This is not abstract theory for me. I’ve said no to potential clients when I’ve been in need of money. I’ve said no to doing specific tasks long-term clients have asked of me. But I’m also no saint. After all, my reputation is based primarily on writings recommending slightly evil sociopathic behaviors. But I’m happy to own that.

The point is, whatever you do, and wherever on the spectrum from absolute saint to absolute sinner you choose to land, you can actually choose to own it in a way big companies generally cannot. So make your choices. Carefully.

Hmm. I received this mysterious package that I apparently secretly ordered from some sort of game-building site when I wasn’t looking. I think I’m up to something, but the part of my brain that appears to be doing whatever the hell this is appears to be NDA’ed off from the rest.

The haul appears to include a deck of 100 cards with consulting tips, some yak coins, a yak zodiac 24-tile set, and some yak zodiac stickers. Now why would I have had all this made? 🧐

Any ideas? I’l probably have to go on some sort of vision quest powered by yak butter tea to figure it out.

***

In other news, it’s Thanksgiving here in the United States, so Happy Thanksgiving, and a big thank you to all of you for supporting my first experiment in subscription email newslettering. We’re just over six months in, can you believe it?

A special shout-out to Tom Critchlow, Paul Millerd, Corissa Nunn, and Tom Kerwin, who all have been especially helpful in developing this project through its initial awkward months. I recommend following all of them (and of course @artofgig) on Twitter to level up your gigging game.

I’m still mulling various ways to make this a more social project, and connect what I’m doing here with what fellow explorers on the gig economy frontier are doing. Those of you who know me from my blog are probably aware that an interesting community grew up around that over the last decade (largely by accident, and despite my reluctance to cultivate it). I’d like to develop a more deliberately conceived community element here, but in an imaginative new way. A do-over of traditional blog-style communities seems a bit boring. Been there, done that.

Plus, the gig economy is a bigger, broader phenomenon than the blogosphere; and a more all-subsuming way of life. So it needs a more daring conceptualization of a community/social aspect. Meetups and conferences might be good enough for blogs, but won’t cut it for meaningfully leveling up the gig economy.

***

This list now has 300 odd paying subscribers, generating annualized revenue of almost $16,000 (😱😨🤯), which I totally didn’t expect. Again, thank you. It’s now the equivalent of a medium-sized consulting gig, and is just past the threshold where I feel like I can afford to think somewhat expansively to come up with interesting and imaginative ways to develop it further.

More than the money itself, which is nice to have, this measure of validation feels like permission to think at a meta-level about consulting and the gig economy. We’re not just a bunch of delinquents living a life comprising one damn thing after another. There’s a bigger story developing here, and we’re all part of it.

When you’re in the trenches pursuing leads, chasing down invoices, and riding the cash-flow roller coaster, it’s hard to step back and take the pressure off of yourself without feeling guilty about it. It always feels like available time could be spent more productively on concrete activities related to actual or potential gigs, or things like lead-gen.

Even as I write this, I feel a bit guilty about doing this rather than finishing up some notes I owe clients.

For an essentially shadowy sector of the economy, it feels self-indulgent to spend time thinking about general principles, doctrinal aspects, and philosophy. And dare I say it, exploring the seams of fun and games that are naturally present in the lifestyle, just as office parties and happy hours are a natural part of the paycheck lifestyle.

Writing this newsletter, for the first time in 8 years, I feel like I’m above the weeds, able to look at what we all do from enough of an altitude to provide meaningful perspective.

***

I plan to invest some of this incoming $$ into developing something more substantial under this newsletter, to help the gig economy develop and mature. The game-like assets in the picture are my own first idea in this direction. I’m sure many of you will have more ideas for me.

I’m not exactly sure where I’m going with the game assets. Mainly I wanted them for myself, to play with. So I got myself this prototype set to help me think about what to do with them.

My initial thought when I started this list was to eventually compile the content into books (which I might still do for the nonfiction essay-like) parts, but I figured I ought to experiment with tabletop gaming as a new publishing medium for exploring, teaching, sharing, and learning consulting and gig economy concepts.

For those who came in late, the Yak Zodiac is described here, the consulting tips deck is from my tip tweets, compiled in this series. The yak coins feature prominently in the consulting fiction I was sharing over the summer, and made their first appearance in the pilot issue of this newsletter. We’ll pick up the fiction and world-building again in a bit (as you’ve noticed, I like to keep some seasonal variety going here).

I’ll have these things available for purchase in a week or two, and going into the new year, we can all play with them and swap notes and ideas.

***

Speaking of games, holidays, and community, the general drift here for me is towards thinking of consulting and gig work as a full-fledged folkway, which historian David Hackett Fischer defined as:

…the normative structure of values, customs and meanings that exist in any culture. This complex is not many things but one thing, with many interlocking parts…Folkways do not rise from the unconscious in even a symbolic sense — though most people do many social things without reflecting very much about them. In the modern world a folkway is apt to be a cultural artifact — the conscious instrument of human will and purpose. Often (and increasingly today) it is also the deliberate contrivance of a cultural elite.

Gigwork is evolving from a narrow status as an alternative mode of work, into a full-blown folkway that fits Fischer’s definition.

Fischer developed his concept of a folkway in his classic Albion’s Seed, to talk about the early streams of immigration from Britain that made America what it is today. I have found it a useful concept for thinking about more migrations in general, including conceptual ones across non-physical borders. For example, I’ve explored the idea of folkways of globalization, to think about the nature of our emerging cosmopolitan, globalized life (which is still evolving steadily, despite some reactionary backsliding). In fact, I’d argue that the gig economy is one of the major folkways of globalization.

What we are doing here with this list, and what you are all doing in your own corners of the gig economy, constitutes one stream of migration from an Old World — the industrial paycheck economy conforming to the contours of nation-state geography — to a New World, based on gig work as a central economic mode, and conforming to the contours of global digital infrastructure.

But to make the migration successful (which means nudging it to evolve into a full folkway by Fischer’s definition, one that plays a significant role in shaping the future of the economy at large), significant injections of imagination and creative construction are required.

Though they are primarily emergent phenomena, folkways don’t make themselves. Per Fischer, they are the “deliberate contrivance of a cultural elite.” And in the very young modern gig economy, merely surviving for a few years without descending into penury makes you part of the “elite”. Which means you bear a share of the responsibility for this “deliberate contrivance.”

Fischer lists the following components of a folkway, of which only one is about work per se: speech ways, building ways, family ways, gender ways, sex ways, child-rearing ways, naming ways, age ways, death ways, religious ways, magic ways, learning ways, food ways, dress ways, sport ways, work ways, time ways, wealth ways, rank ways, social ways, order ways, power ways and freedom ways.

Fischer’s inventory is effectively a to-do list of social, cultural, and economic construction work that all of us in the gig economy participate in. Some of us do it consciously, others do it unconsciously, via casual advice they hand out, joking, griping and moaning on twitter, and tips and tricks they borrow from peers.

It is tempting to think of this to-do list as an institution-building imperative, but that’s too narrow. Though a folkway is a set of institutions in the broadest sense, when most people talk of institutions for the gig economy, they mean things like unions, coworking spaces, and health insurance.

That’s not only too limited, it’s a case of thinking ineffectively about the new through the lens of the old.

And in general, that has been a disaster, as scams like WeWork, and ill-conceived (though perhaps well-intentioned) legislative efforts like California’s AB 5 show. Things aren’t going to improve unless we in the gig economy take a much broader view of our responsibility for inventing our thread of the future for ourselves. If all we do is look back with wishful nostalgia at creaky, century-old constructs, all we’ll get is misguided attempts to reproduce old models, with cosmetic tweaks, that undermine the gig economy rather than strengthen it. Often instigated by people who are either not part of it, or don’t want to be. Far too much of the conversation around the gig economy is driven by people who seem to be wishing it would just go away.

The idea of a folkway is an invitation to think more expansively and imaginatively, and go beyond formal cargo-cult institutions that mimic industrial paycheck economy institutions. This means thinking in more fluid ways about a much broader class of concerns. Everything ranging from handshakes and greetings — which are institutions by certain definitions — to games, mythologies, histories, and epistemologies.

Otherwise we’ll be eternally caught in the purgatory between predatory politicians, wannabe union organizers, and apathetic paycheck-employee-centric HR departments.

We’ve barely scratched the surface here. While swapping tips and case studies, and how-to playbooks for landing clients is valuable, it is not enough.

In 2019, nearly twenty years into the modern gig economy, constructing our identities primarily in terms of how we relate to the paycheck folkway is no longer good enough. After all, there is a good chance the gig economy will outgrow the paycheck economy, relegating the latter to a minority sector of the economy overall. Imagining our future in relation to the future of paycheck work would be like early industrial age workers imagining their future in terms of the future of farming. Much of the supposed “future of work” thinking I see around the gig economy strikes me as the equivalent of early factory workers worrying about where to park their cows.

So the gig economy needs to outgrow its origin story in the paycheck world. For the gig economy to grow from limited sideshow to full-blown folkway, we need to talk about a lot more, and develop much deeper internal realities and subjectivities.

This process of reimagining and refactoring our world from an internal perspective is already underway. For example, people have lately been talking about the passion economy as the evolutionary descendant of the gig economy. Nice development of an rudimentary inner life, but evolution can’t stop at incorporating a notion of “passion”. That’s merely one more dimension. There’s a couple dozen more to go before we can call ourselves a folkway.

There’s a lot more evolving and designing and contriving to be done here, and by the time we’re done, you and I will be old, and looking forward to whatever the equivalent of “retirement” is for the gig economy folkway (gigway?).

It’s a long journey ahead, and we’re just getting started.

The idea I’ve cited most often in the last few years is Arthur C. Clarke’s “hazards of prophecy” in Profiles of the Future, which asserts that the failure of nerve is a bigger problem than a failure of the imagination. Failure of nerve happens when, despite being given all the facts, and despite the required reasoning being trivial, people fail to draw obvious conclusions about the future. The problem is that the simple reasoning from simple premises leads you towards an unpleasant conclusion that’s hard to face.

This is an important phenomenon for us in the gig economy to recognize. Possibly the most basic level of failure in failed gig economy careers is failure of nerve.

First Leap versus nth Leap

It’s sort of obvious that taking your first leap into the gig economy, especially when you’re not being forced to by circumstances, is an act of courage. In large part though, the courage required there is a kind of dutch courage, except that you’re high on the prospect of freedom rather than alcohol. You don’t actually know much yet about the perils you’re diving into, or what kind of courage you will need, as you plan your first leap (see my 5-part series on that). You’re merely assuming you have it.

The courage it takes is based on a belief similar to “I’m smart enough to graduate college” or “I’m strong enough to lift this weight.” It’s a belief that allows you to try, but it may not be enough for you to succeed. It is a belief that you will have the courage necessary when it is actually called for.

These beliefs fuel a kind of Dunning-Kruger false confidence that relies on ignorance, but can bootstrap you into the real thing. You find out how you actually stack up as tests of such beliefs hit you one after the other. By the time you’re on your nth leap, your courage is real, because it is in response to dangers you do understand.

Training Nerves versus Mitigating Risks

Like intelligence or strength, courage is an attribute that can be trained, refined, specialized, and generally matured into a knowledge-based understanding of what one is actually capable of. As with intelligence and strength, most people are far away from the genetic limit of what they might be capable of.

But training your nerves is not the same thing as reducing the risk itself through risk-mitigating skills.

A good example is the difference between learning to swim and learning to jump off the high board.

Learning to swim takes no courage at all if you do it in the shallow end, under skilled supervision. You can get to swimming safely without ever testing your nerves, or ever having to overcome even a moment of panic, by gradually developing your skills.

On the other hand, assuming you know how to swim, learning to jump (not dive) off the high board takes no skill at all. You just have to step off the board and fall. It’s all about raw nerve. It’s about learning to overcome the fear itself, accepting that knot in your stomach and the sudden rush of weird sensations as you step off. And it’s almost a one-step thing: the second time is far easier, and by the 10th time, you’re actually enjoying the thrill.

Learning to function effectively as a paycheck employee does not take much nerve, but does take a lot of specialized employer-specific skills you can learn in the shallow end of the pool. If the organization is well run, it should be like learning to swim with a good teacher. If it isn’t, you’ll drown.

Learning to function effectively as a free agent, on the other hand, takes a lot more nerve, but generally no additional skills beyond what you already have. It’s like learning to jump off the high board repeatedly till you enjoy rather than dread it.

To the extent there are risks, you don’t actually mitigate them much. You just learn to deal with the consequences of environments with unmanaged, unmitigated risks.

Dimensions of Boldness

Though you can’t train your nerves in the same way you train skills that derisk an activity, you can train them. What you’re learning is to act in certain ways despite unpleasant situational responses getting in the way.

It helps to break it down a bit into aspects. Here’s a spider chart of the “nerves” I think matter most in the gig economy. The purple polygon is a sketch of what I think my own pattern of boldness looks like. The red one is the pattern I think my buddy Arnie Anscombe, data science consultant, exhibits. Relative to him, I’m bolder about trusting my gut, adapting fast, and ending things cleanly, while he’s bolder at committing early and recovering fast from setbacks.

You should try drawing your own.

Along each spoke, there is a dimension of courage associated with a particular pattern of failure of nerve. In each case, you lose opportunities, time, or both. Lose enough of both, and you lose the plot entirely and bomb out of the gig economy.

• Failure to trust your gut: when things seem okay on the surface, but there’s a couple of red flags, and something just seems wrong at gut level, you either trust your gut and poke at the red flags to either confirm or allay your suspicions, or you studiously ignore your gut.

• Failure to recover fast: you will routinely have setbacks with immediate and unpleasant impacts. A gig fails to come through. An invoice gets held up, causing a cash-flow crunch. A sudden medical emergency stresses your reserves. In each case, if your nerve fails, you’ll initially freeze into helpless inaction, wondering why the universe is being so damn unfair to you. The failure of nerve happens when you don’t unfreeze and begin acting again quickly enough.

• Failure to adapt fast: circumstances have changed. The CEO was replaced, and your champion at a client company, who was going to send a nice juicy gig your way, is suddenly out of power, or out of a job. Do you reorient quickly and do something about it, or wait just long enough that the loss becomes irrecoverable?

• Failure to commit early: You have an idea you feel is basically ready to be tried. You’ve workshopped it a bit on Twitter. People are excited and seem positively disposed towards it. But you delay and hedge, and don’t act, and when you’re finally ready, the moment of zeitgeist resonance has passed. You’re too late, or someone else gets there first.

• Failure to end things cleanly: A potential client has been stringing you along for ever. But you don’t cut the conversation short as a waste of time and move on. Or a client who you thought represented 10s of hours a month in billings is only sending 1-2 hours a quarter your way, but demanding a level of support and situation awareness maintenance that you can only justify for much higher volumes. But you’re letting the gig limp along instead of just politely ending it.

All these cases are failures of nerve. The situation is not intricate or hard to read. The outcome on the present course of inaction is obvious and bad. It is obvious what to do instead, to try and make a better outcome happen.

Yet you don’t act.

Failure of nerve.

The horror of recognizing that something isn’t working, or that a comforting belief isn’t true, or that something important has changed.

The good news about failure of nerve is that it cannot become a habit. If your nerve fails you often enough, you’ll just fail entirely and drop out of the gig economy into something else (generally more unpleasant).

What can become a habit is acting with nerve. And that takes no real skill. Just doing the thing that obviously needs doing. And doing it again, and again. Until the panic reaction turns into an exhilaration reaction.

The reason this works is obvious: the riskiest thing you can do is to take no risks at all. Every time you act with courage, and avert a failure of nerve, you rebalance luck in your favor. You start being right more often. You attract more serendipity than zemblanity.

In fact, that’s how you know if you’re acting boldly enough. When you start to feel that you’re getting unreasonably lucky, and more of your bets are paying off than you’d have expected.

The idea that “fortune favors the bold” is not an observation about the nature of divine agency, it is an observation about the interaction of active human agency, luck, and unintended consequences. Fortune appears to favor the bold because the bold are making their own luck by acting in obvious ways in response to obvious imperatives. Failure of nerve is so common, it is almost the default, so even doing marginally better than others pays off.

As Wayne Gretzky succinctly put it, you miss 100% of the shots you don’t take.

There’s a gig economy disease that will likely strike you within a couple of years of going indie, if you succeed by sticking the landing on your first leap. You’ll find that you have periods with plenty of nominally “free” time, but mysteriously, no time for the kinds of personal passion projects, such as writing, independent research, maker projects, or travel, that probably motivated you to quit in the first place. I’ll call this disease sneakoffproofitis.

The problem is, as a free agent, you are your own boss, and you’re likely a bad boss, unable to relax, and driven by fretful anxiety about lining up the next gig. That would be bad enough, except that you’re also an omniscient bad boss. You know all your own tricks, and nothing is hidden from you. You can’t sneak away from yourself.

You have sneakoffproofitis.

Here’s what sneakoffproofitis looks like.

Your bank balance looks healthy for the moment. You have enough work lined up so the cash flow looks good for the next few months. You’ve only committed a modest fraction of your hours — say 10 a week — to deliver that work. You’re temporarily cash rich and time rich. It’s a sweet situation, right?

So why is it so hard to take your time/money surplus and do something interesting with it?

The thing is, fun things are only fun when you sneak off from things that feel like “work” to do them. There is a certain creative freedom that is unleashed when you’re using up “free” time that feels like it is “stolen” from commitments towards “necessary” work. The courage demanded by the time theft fuels boldness in the sneak-off activity.

This is funny because the idea of time-theft is only well-defined for robotic labor where you are paid to execute a production algorithm, with a clear relationship between time and output, rather than apply knowledge. It is incoherent when applied to knowledge work where there is only a weak correlation between time spent at work and the quality/quantity of output.

But our sneak-off instincts are still linked to robotic labor modes of production. Time isn’t high-quality creative time unless it feels a little bit stolen (which is why, paradoxically, fuck-you money can be a creativity killer).

The work of the knowledge worker is never done. You can always do an infinite amount of work for a finite piece of output. There are always more plans you could make, more background research you could do, more skills you could develop, more trends you could stay updated on, more refinements you could add to the slide-deck, more Q&A you could prepare for. Knowledge work is something like insurance, and it can always be made to violate the law of diminishing marginal returns if you’re neurotic enough.

This is as true of the free-agent life as it is of the paycheck life. There’s always more lead-generating blog posts you could write, more pitches you could send out, more tweaks you could make to your website, more spec-work you could do to go gig-fishing with, more RFPs you could respond to, more clever tweets you could put out to draw viral attention to your soundcloud.

And the bad-omniscient-boss side of you knows this. And won’t let the sneak-off-to-play side of you sneak off to do anything else while there are “productive” things you could be doing. That’s sneakoffproofitis.

What’s the cure? Well, you could get brain surgery to separate the omniscient-bad-boss you from the sneak-off-to-play you, and have the latter hide stuff from the former (weirdly, things like this do happen with brain-damaged patients), but there’s an easier way. You ratchet up the boldness of playful-you and sneak off despite the fact that the omniscient bad-boss is yelling at you.

Because here’s the secret: Omniscient-bad-boss-you is all-knowing and all-seeing, but not all-powerful. Omniscience does not imply omnipotence. In fact, omniscient-bad-boss-you is quite impotent compared to your old other-person boss. What are they going to do? Fire you?

You still need a principle to manage your sneaking-off though, and a way to balance sneak-off behaviors against money-making behaviors.

The principle I suggest is this: pay yourself first. You have probably heard that line from financial advisors. The idea is to put money in retirement savings accounts first, before spending money on other things. It’s that idea, except with time, and with sneak-off activities rather than a retirement account being the target.

So when you have some freedom in how to allocate time towards necessary commitments (for example you have 5 hours of work due to a client, but the deadline is a week off, and a to-do item to update your website before a speaking gig two weeks away) versus sneak-off activities, sneak-off and have fun first.

Subtle point: you have to fill up all available time with necessary activities before you can actually sneak off.

So if you typically plan in terms of a 40-hour week, on Monday morning, make a to-do list of “necessary” things that “must” get done “asap” and will take 40 hours. For safety, overcommit, and put 60 hours worth of work on the list.

Then sneak off.

Before attacking that list.

Sneaking off from an under-full to-do list doesn’t work, just as weight-training with no weights doesn’t work. You strengthen your sneak-off boldness by stealing from committed time, not by clearing and occupying “free” time. That’s just a hobby bad-boss-you tolerates.

Sneaking off is how you reveal your own sense of priorities and urgencies to yourself. You don’t know whether or not something can wait unless you try to sneak off from doing it. And unlike carved out “free” time, sneak-off time has no preset boundaries. How long you stay in sneak-off mode is determined by the tug-o-war between your to-do anxiety and the strength of your absorption in the sneak-off activity.

Yes, your omniscient bad-boss side will scream and bully, but you can ignore that. Learning to ignore your own screaming and bullying is the whole point of sneak-off behaviors. Quitting a paycheck job and earning your freedom from others is the easy part. You aren’t truly free until you’ve earned freedom from your own ridiculous expectations of yourself.

The logic of paying yourself first is similar to retirement savings prioritization logic. The things you do in your sneak-off time are the things that have a chance of turning into long-term compound-interest assets (though watch out for a related disease, projectitis: omniscient-bad-boss you will attempt to turn every such activity into a legible “project” the moment they smell a “return”, and ruin both the fun and the possibility of a return; eventually you have to let that happen if the activity grows enough, but delay the onset of projectitis, and stay in sneak-off-and-play mode, as long as possible).

In the short term sneak-off activities are bugs in your self-imposed productivity regimen, but in the long-term, they’re the main feature of the lifestyle you’re constructing, and the most necessary among all the things you must do.

Neglect sneak-off activities at your own peril. All work and no play make Jack a dull paycheck employee, but a dead free agent.