The Art of Gig, Volume 1

Metadata

• Author: Venkatesh Rao, Grace Witherell, and Jenna Dixon
• Full Title: The Art of Gig, Volume 1
• Category: #books

Highlights

• Uncritical adoption of career advice is significantly more hazardous in the gig economy than it is in the paycheck economy. (Location 85)
• Solve for industry-level questions, not organization- or world-level answers. (Location 127)
• Never accept a deliverable request from an intermediary who can’t act on it. (Location 128)
• Create choices, not recommendations. (Location 129)
• The work ends when the story ends, not when the last check clears. (Location 133)
• Keep your client-facing identity normie. (Location 134)
• Don’t trust your situation awareness in a gig after six months of inactivity. (Location 137)
• Learn the sector’s paper-napkin math and unique measures of itself. (Location 138)
• Cost-plus accounting over value-based accounting. (Location 142)
• In billing, bundle and unbundle line items for at-a-glance auditability. (Location 143)
• Learn more from every client than they learn from you. (Location 145)
• Never let the truth get in the way of a good story. (Location 147)
• obfuscated chess postman is applying learnings from one gig to another in real-time by creating suitable abstractions to port your new learnings without compromising confidentiality. (Location 161)
• as an indie consultant, you’re very unlikely to be selling happiness (Location 167)
• the problems external consultants solve always fall into two basic buckets: insufficient systematic confidence and insufficient systematic doubt. (Location 170)
• Any consultants present will be seen as parasites to be exterminated rather than utilized more. (Location 172)
• The Explorer is a client who wants to build capacity for systematic doubt at an outer-world locus. They do this by constantly considering possibilities, alternative perspectives, and refactorings of worldviews. They tend to hire a sparring partner type of consultant who can constantly stress test their thinking and actions, and undermine their assumptions from unexpected new directions. (Location 180)
• Achiever is a client who wants to build systematic confidence at an outer-world locus. They typically hire consultants who take on roles as teachers or coaches, helping them develop specific functional capabilities and skills, such as public speaking, survey methodology, being more productive, architecting databases, running Kickstarter campaigns, applying for government grants, or sourcing things from China. (Location 183)
• The Explorer Organization tends to be future-oriented and is likely to have people or departments devoted to activities such as scenario planning, futures, and market modeling (often called strategy operations). Explorer organizations hungrily consume forecasts and trend information, as well as historical analyses and industry reports. They believe they are curious organizations. (Location 199)
• The Integrator Organization tends to be employee mental health and culture focused. They love things like employee-engagement programs, well-being initiatives, and diversity and inclusion programs. You will find a strong culture of listening habits inside such organizations: town-halls, manager-employee 1:1s, and effective communication training. They believe they are compassionate organizations. (Location 206)
• depending on how much they are actually winning or losing, the organizational self-images may be more or less deluded in different ways. That’s where people like us come in, and where management jokes are born, but that’s a story for another day. (Location 215)
• I suspect, in terms of sheer population size, Achiever organizations are the most common. I’d guess as high as 70%, followed by Integrator, Explorer, and Tester organizations. (Location 218)
• The tell of the Explorer in Need is a sense of staleness and being in a rut evident in ways of talking, distractibility, and arbitrary pursuit of Next Shiny New Things. (Location 253)
• Achiever in Need is energy being dissipated in random acts of X where they are thrashing and improvising behaviors in an area where skilled and disciplined behavioral precedents exist. (Location 255)
• Integrator in Need is endemic mental health issues across activities. There is too much anxiety. There are communication problems everywhere. Relationships are fraying all over the place. Morale is plummeting. (Location 257)
• Tester in Need is toxic arguments that go nowhere, disagreements over facts and data that get weaponized along lines of control, big ego conflicts, and ideological battles. Behaviors are driven more by the need to feed ongoing beefs than accomplish missions. (Location 259)
• you classify the organization by looking for a locus of futile energy expenditure. That futility is your opportunity. (Location 262)
• both individuals and organizations can have two polar opposite reasons for hiring a consultant: to build on a strength or to mitigate a weakness. (Location 263)
• It usually takes a crisis situation to drive an individual or organization to seek external help for a weakness. (Location 265)
• consultant addresses both the symptoms and root causes is by injecting a much-needed dose of disinterested systematicity in the right place. (Location 268)
• Positioning school takes its intellectual cues from economics and uses formal models and numbers as the ultimate foundation for everything, while the People school takes its intellectual cues from sociology and psychology and uses narrative as the ultimate foundation for everything. (Location 276)
• the opposite of every Great Playbook is also a Great Playbook. (Location 296)
• Take an inventory of actual named players in the situation, sorting them into rings by their level of agency and ability to influence the situation. Make up a story to account for the recent history of the situation, using abductive reasoning3, to uncover what the actual players are up to, and why. Start “nudging” the situation to test your narrative, and start forming live, evolving judgments about the actual players: who matters, who doesn’t, how they align/don’t align, what futures they are working towards. Pick the group of players you think is both right about the future, and capable of winning the future. Help them win. If such a group doesn’t exist, or you’re on the wrong side, exit the situation or switch sides. Keep retelling the story and nudging the action according to the current narrative logic, monitoring the evolving situation for narrative violations and disruptions. (Location 303)
• The Great Truth of the People school is that subjective, internal realities (note the plural) are everything and objective reality is a matter of evolving consensus and dissensus. (Location 318)
• For the People school, formal models and data, if used at all, are like specialized forensic investigative tools to be used when the process of repeatedly retelling the story while nudging it along runs into show-stopping mysteries and puzzles. People school practitioners are essentially storytellers at heart, who believe in truth-by-narrative, but sometimes make what they think of as concessions to empiricist insecurities by including data and graphs. (Location 324)
• Being a consultant is about staying in a state of dynamic balance, evolving your own game with the shifting balance of power between Great Truths and Great Playbooks. (Location 360)
• Knowing which nut to tighten to resolve a mysterious noise is a simple example of a knowledge asymmetry. (Location 385)
• the principal-agent problem is particularly acute in any relationship where the typical principal has a need that is rare enough that there is no incentive for them to get systematically knowledgeable about the domain, while fulfilling the need is so common an activity for the agent that they have incentives to learn to do it very cheaply, systematically, and efficiently. (Location 404)
• Any employee with a very unique, opaque, and illegible skill is a huge risk for an organization. (Location 432)
• Often a uniquely skilled but underutilized employee, despite being compensated enough to make dishonesty uninteresting, will end up leaving and becoming a consultant simply to find more things to do. (Location 434)
• I’ve used the relative phrase reasonable-seeming rather than the absolute reasonable to describe the perception of effort in tasks done by employees. (Location 436)
• In either case though, one of the tells of an organization working very hard to stabilize a dissonance between internal and external realities is resistance to consultants: When the internal reality is deluded, consultants might inject an entirely unwelcome reality check. When external reality is deluded, consultants might contaminate a fragile island of deeper truth by injecting bad external thinking. In either case, we consultants represent informational risks and threats to the organizations we try to help and it’s generally up to us to manage the risk. (Location 446)
• Crisis-only consulting policies: Organizations will simply resist retaining consulting services unless there is a crisis, and the costs of not bringing in outside expertise to help become unacceptable. These organizations simply leave certain knowledge-gap risks unmanaged. Ecosystem competency: Organizations will consciously develop competency in managing an ecosystem of consultants via specialized monitoring mechanisms—think certification programs. Externalize the risk explicitly: Many organizations will require consultants and contractors to carry specialized insurance policies, as some of you will know. I’ve never yet taken such a gig. Relying on exceptions: Many organizations will have default no-consultant policies, but allow senior executives to make exceptions based on special needs, and the existence of trusted relationships. This of course, is an entry point for a lot of cronyism. (Location 456)
• Build relationships that allow you to be an exception to anti-consultant rules/barriers. So long as you keep yourself honest by resisting the lure of cronyism, and only taking gigs where it is clear that you’re bringing genuine external knowledge or relationships to the party, it is the best way to address the legitimate principal-agent concerns of clients, without bearing too heavy a burden of externalized risk-management costs yourself. 1 en.wikipedia.org/wiki/Principal%E2%80%93agent_problem 2 en.wikipedia.org/wiki/Transaction_cost (Location 469)
• Indie consultants need to be aware of their operating epistemology, in order to avoid buying their own bullshit, and turning into unconscious grifters. (Location 483)
• If you’re an entrepreneur or an indie consultant, whatever else you might be, you are not a scientist. (Location 492)
• There is no such thing as an evidence-based startup or gigup. In the world of gigups and startups, only failures can be evidence-based. (Location 494)
• how do you know the important things you think you know?Through fiction, through simulation, and through thick description (a fancy word for anthropology). (Location 500)
• Indie consulting is speculative and/or story-driven. (Location 502)
• Calculating how the ball bounces is valuable for Great Yak Enterprises because x. . . . you inevitably, and inexorably, go from science to something else. Whatever that is, to call it science is a distortion of it, and a disservice to it. But in that X lies the core of how you do know things and add value. (Location 511)
• When you try to “science” a system, you don’t carve out pieces that are important, interesting, or useful. Those are merely nice-to-have features you can hope for in a carved-out piece, but essentially unrelated to whether or not you can science it well. The chances that you can “carve reality at the joints” in ways that conform to the contours of practical concerns are low. You carve out a part that offers potential for systematic ambiguity reduction, and hope that when you go back (if you can go back) and integrate it into an understanding of the whole, some of that lowered ambiguity will pay dividends in some unpredictable way. (Location 521)
• Simulation, storytelling, and thick descriptions are integrative modes of knowing. When you’ve taken something apart and scienced what you can science (and that subset might be “nothing”), the real work of a startup or gigup begins. (Location 527)
• I concluded that what I deal with poorly is the combination of high risk and high time pressure. (Location 534)
• Indie consultants naturally fit in where the capability gap is either small enough and oddly-shaped enough to be filled by a few individually contracted people, or where the gap is large, but can be filled by a fairly generic type of labor without the help of a labor-aggregating counterparty. (Location 542)
• I offer Strategy for Explorers. You might be in Preventive Care for Integrators or Surge Capacity for Testers. Here’s a handy 4x4 table for you to think about. (Location 549)
• What is perhaps less obvious is that the lack of systematized capability (either in-house or outsourced) is generally rational. (Location 556)
• many struggling consultants seem to believe that the lack of in-house capacity for the services they offer is irrational. That their work ought to be a job and that they ought to be hired as an employee to do it. This belief leads to weird and potentially crippling mental blocks that put you in the worst of both worlds. (Location 558)
• preventative care, surge capacity, strategy, and first response. (Location 561)
• This is the kind of consulting offering (often made up by laid-off mid-career middle managers who have succumbed to up-or-out pressures) that best fits the accusation that consultants are people who help solve problems that wouldn’t exist in the first place without them. (Location 564)
• If you’re in this quadrant, chances are you’ll struggle to brand and position yourself uniquely. You’ll also struggle to set your own price or differentiate yourself from contract labor supplied by contracting companies. One test: you have a blog, portfolio site, or other marketing asset, but most of your work still comes through gig sites like Upwork. You’re unable to actually attract any work at your preferred bill rate, and are forced to work at prevailing market rates. (Location 575)
• High risk and low time pressure is generally the combination of conditions that makes anything strategic. (Location 583)
• Strategy-centric offerings are usually based on a track record that induces trust, and idiosyncratic personal mind-melds of taste and intellectual style between client and consultant. (Location 585)
  • Note: Who do i have this with
• A good strategy consultant is often simply someone who is good at just being present in a situation without becoming yet another part of the problem. This can be surprisingly hard to do. (Location 589)
• You have to be able to pattern-match and generate appropriate responses much faster. Not just that, you have to be good at dealing with clients in abnormal states, like patients in ICUs. (Location 596)
• If you think of organizations as cars, a good mental model of the politics (not economics) of work is that capital is the accelerator, labor is the brake, and middle-management is the gearbox. And we gigworkers? We are the clutch. We help disengage/re-engage the drivetrain during gear-shifting, as operating regimes change and organizations need to adapt behaviors. (Location 624)
• The defining characteristic of a scab is striking a self-interested independent bargain with the capital-owning/managing/leading class that breaks from any larger collectively bargained deal. (Location 633)
• A graphic designer or independent strategy consultant is fundamentally a more mobile type of economic actor than a welder or an auto-assembly specialist. We work with our own cheap tools: laptops and notebooks for the most part, rather than with million-dollar machine tools or billion-dollar factories owned by investors seeking returns. We serve broad rather than narrow patterns of demand. (Location 651)
• Because the gig economy, especially the indie consulting corner of it, relies on production capabilities that are 5% based on owned capital equipment and 95% based on affordances of the free internet. (Location 661)
• But from the perspective of a 2020s digital economy, we are members of the clutch class who largely own our means of production, have too high a degree of agency in shaping our own lives to be part of labor, and too little wealth to be part of capital. (Location 664)
• The rare corners of the gig economy where organizing like traditional labor is meaningful—actors are a good example—typically exist where the demand is concentrated enough that it can be targeted by collective action. (Location 674)
• Mechanisms do matter, but the ones that we actually employ towards political ends are adapted to our political ends, not those of either capital or labor. (Location 701)
• We swap notes, we share leads, we pitch in to help each other out on specific gigs, we put ourselves in crucible groups to rapidly learn skills far faster than labor or capital, we serve as market makers in an economy of referrals, we do what needs to be done. And we do an end run around the stale battles of the 20th century. (Location 706)
• Push come to shove, where we stand depends on where we sit. And in almost all cases, we sit right next to management and capital, serving as clutch players, helping shift gears where necessary, helping with surge actions, helping break out of stalemates. (Location 716)
• Clutch Time is evenings and weekends. With apologies to Chris Dixon,4 what the clutch class does on evenings and weekends, everybody will be doing in ten years. (Location 726)
• Clutch time is when capital and labor both try to rest and relax and gigworkers get going. That’s the time when those of us in the clutch class really come into our own. We go to meetups, we get coffee with each other. We scan the social streams for openings, seek out room to maneuver, ways to deploy high-leverage cheap assets, learn breakout skills, and dream up hacks and arbitrages. (Location 729)
• And we sneak one-at-a-time into the future, through gaps on the economic frontier, rather than marching rank-and-file in slogan-chanting cohorts. (Location 732)
• First-principles analysis would suggest that in general, the smaller a business, the more fragile it is likely to be. And nothing is more fragile than a one-person business operating in the gig economy. (Location 772)
• Many lines of business that indies like getting into do not allow for easy scheduling of breaks, interruptions of service, or service-level degradations. Passive income is mostly a myth. (Location 788)
• If the opportunity spike coincides with an emergency spike, you get hit with a double jeopardy: you lose the income opportunity and you have to deal with the emergency-related expenses. It’s what Charles Perrow labeled a normal accident—a condition in a complex system (like nuclear reactors or the modern gig economy tech stack) where two unrelated and ordinary risk events coincide to create extraordinary risk conditions. (Location 796)
• This finding jibes with the observation, in Bill Janeway’s book on the startup economy, Doing Capitalism in the Innovation Economy, that what gets startups through turbulent times is simply cash and control. (Location 816)
• being a Lindy Indie really just boils down to building up reserves. (Location 837)
• The brute force answer is to simply cut down expenses till they are half the after-tax income, saving the other half in conservative reserve form (cash). (Location 844)
• Just focus on making money any way you can, and acquiring your own idiosyncratic understanding of how the game is played. (Location 877)
• At this level, you’re basically learning to run your indie consulting life as a business, and acquire and refine basic instincts around pricing, supply and demand for your services, and negotiations, all driven by an understanding of your own needs, lifestyle costs, and operating margins. (Location 885)
• To last longer, you have to discover who you are, by doubling down on things you like to learn, while working on gigs. (Location 889)
• It’s a bad mistake to separate your learning interests from your working interests. (Location 890)
• At the learning flywheel level, you should strive to say yes to gigs where you’ll learn more of what you want to learn, and no to gigs where you won’t. It’s as simple as that. (Location 895)
• it’s the opposite of passive income. This is as active as income gets. You’re not looking for shortcuts. You’re looking to make the long way the fun way. (Location 897)
• This is effectively indistinguishable from what you’re learning the fastest, which in turn is almost entirely a function of what behaviors you are repeating most frequently and enjoying in your gigs. In other words, the iteration rate of mindful deliberate practice. (Location 898)
• Finding and staying in the maximal iteration/learning rate zone of what you enjoy is a pretty subtle challenge. It took me nearly three years to figure out that it was “conversational sparring” for me. (Location 901)
• Believe it or not—and this is heresy to doerists—a life of pure learning and new personal records is not satisfying. If you get stuck at the learning level, you will burn out in about three years. To survive longer, you have to explore how you create value for others. (Location 903)
  • Note: This was me
• When you’ve bootstrapped this level of mindful ongoing interrogation of your working life, you will be able to more readily see the world from the point of view of your clients, critically interrogate your own evolving identity, and become aware of your blindspots, rationalizations, and limiting self-perceptions. (Location 908)
• you can get sucked in from there into perennial agonizing and fine-tuning of your work, in an attempt to find a Grand Unified Theory of Guaranteed Value Addition. This is a utopian trap. You’re actually doing far better than average if you can claim that you are adding value in one out of two gigs. A more typical rate I suspect is one in five (below that, you’ll likely feel like you’re participating in a bullshit-work economy). The corresponding dystopian trap is coming to believe that nothing can ever get better, and slowly succumbing to the temptations of fraud, bad faith, and corruption. (Location 914)
• One of the reasons many indie consultants fail to do this, and get trapped at the value theory level is that they fail to distinguish learning (one level below) from growth (one level above). They think the value-theory level is the top of the pyramid. (Location 920)
• You can learn without really growing, and many people do exactly that. (Location 923)
• A fad is basically an uncritical, fixed, widely shared value theory that only dies when it starts to fail miserably, triggering utopian or dystopian yearnings and behaviors. (Location 925)
• Growth is the result of integrating your experiences, figuring out what they mean, healing any scars, and evolving beyond them. (Location 927)
• How do you know when the lessons are the right ones? When they point the way to continuing the game in the most interesting way possible, instead of adding more details to the map of whatever value-addition rut you are in. (Location 929)
• You will compensate for cognitive decline by seeking out skilled hobbies and interests and narrow paths of personal accomplishment with feedback loops of strengthening high-integrity behaviors. (Location 961)
• You will compensate for chronic social anxiety by investing increasing energy into premium mediocrity1 (looking more successful than you actually are). (Location 963)
• You will compensate for overwork and exhaustion with hedonistic excess. (Location 966)
• you have to pick two of three, but you don’t have to make the same choices in all situations and at all times. (Location 985)
• Make your choices. Accept the consequences in the short term, but resist them in the long term. Make new choices when and where you can, in order to avoid degenerating. (Location 997)
• Freedom is for what Samo Burja calls live players.3 If you act dead, you will eventually die for real in an unpleasant way. (Location 1000)
• Up until the Great Recession, the perception of the Big-Three 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. (Location 1053)
• A good part of the consulting market is a corporate assisted-living facility for geriatric companies. (Location 1067)
• That’s the most important thing you have to understand about the Big-Three consulting world: it selects for intelligent, high-energy grinders, not snowflake philosophers driven by foundational curiosities. (Location 1076)
• 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. (Location 1079)
• 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 manageable grinds. (Location 1100)
• They are the organizational equivalent of expensive medical imaging equipment. (Location 1103)
• 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 (Location 1110)
• 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. (Location 1118)
• 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. (Location 1122)
• The DEI and ESG theaters are the latest examples of such boutique sectors, where you are more likely to find grifters or power-tripping political opportunists than people sincerely engaging with the actual ethics issues supposedly in question. (Location 1138)
• Hanlon’s razor: never attribute to malice what can be adequately explained by unexamined philosophical commitments. (Location 1155)
• ethics in consulting is simple: it’s a matter of saying no to things. Which usually means lowering some topline or bottomline expectations, and being content with less. Ethics are a form of self-imposed taxation. (Location 1167)
• TINA assumptions—There is No Alternative. (Location 1174)
• indie consultants, indie contractors, and under-the-API gigworkers, (Location 1204)
• You’re an indie consultant if you don’t have to deal with gatekeeper organizations, such as purchasing or HR. You may still need to do paperwork with them, but they have little control over whether or not to hire you because sufficiently senior managers or executives are making that call. (Location 1207)
• For the contractor to consultant move, a good stunt is to write a book. (Location 1244)
• 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. (Location 1251)
• 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. (Location 1269)
• If we wallow in nostalgia for creaky, century-old constructs, all we’ll do is reproduce old models with cosmetic tweaks, and undermine the gig economy rather than strengthen it. (Location 1278)
• people have lately been talking about the passion economy3 as the evolutionary descendant of the gig economy. (Location 1294)
• Gigworkers? We leap into opportunity spaces. Not just once, but repeatedly. In the most extreme case, every new gig is a leap, and since you ideally have many gigs going in parallel, you are always leaping on some track. (Location 1319)
• there’s no such obvious ceremonial starting point for scripting a leap into the gig economy. Only a joke one—getting business cards. (Location 1332)
• Well, actually, there is one real starting point: getting and staying married to someone with a job, who is willing to support your risk-taking and backstop your first leap with their own stability. (Location 1333)
• The first mistake you can make in launching a gig economy career is to think it is pure improvisation. (Location 1344)
• The second mistake you can make is thinking the kind of scripting that works for job-searching will also leave you prepared for the gig economy as a bonus. (Location 1347)
• The third mistake you can make is to treat the gig economy as a natural and predefined Plan B you automatically land in if you fail at the other two. (Location 1349)
• computing your unmanaged leap risk, as illustrated in the diagram on the next page. Our goal with this exercise is to first estimate your income replacement horizon (in months) and from that, your unmanaged leap risk (in dollars). Let’s make up acronyms for these, why not: IRH and ULR. (Location 1379)
• A good way to think of this is in terms of a time advantage. You’re hoping to make up for this 10-year-long, dumb, no-risk preparation time with sheer strategic cleverness. You’re trying to leap ten years into your own financial future somehow. You’re trying to disrupt yourself. (Location 1417)
• favorable exit conditions, a parental factor, a spousal factor, and a transient lifestyle cost-down (Location 1425)
• Figuring out how to close risk gaps with cunning rather than money is essential early training in gig economy resourcefulness. Because remember: the gig economy is not a single leap, but repeated leaping. (Location 1454)
• every cycle of brain time you spend playing defense you’re not playing offense, so it is hugely valuable to have somebody else take care of that, allowing you to focus on the top line rather than the bottom line. (Location 1481)
• Don’t be snobby about parental support. Your parents’ generation probably didn’t have to try making it en masse in the gig economy, so give yourself a break, courtesy of your parents (or in-laws), if you can. Intergenerational wealth transfer is a major dynamic in civilized life and most parents are more than willing to help as much as they are able. (Location 1501)
• It’s not actually a strategic cheat if you have to pay for material support with your mental health. (Location 1508)
• here at the Art of Gig, we are solving for a non-minimalist, non-spartan lifestyle: just on your own terms rather than those of a paycheck employer. (Location 1524)
• The best high-cunning exit condition is one in which you’ve created a live asset, out in the open, that can be turned into a viable foundation for a gig-economy business with the flip of a switch. (Location 1552)
• Marketing assets like a blog or newsletter where you can start to look for and create opportunities. I had both. Product assets that can be turned into a money-making thing on Day 1. I had a nearly complete book that I was able to finish and put up for sale within a month of quitting. Instant spike of cash flow right when it was most useful. Live, hot leads that can be converted to starter gigs before you quit. I had two consulting gigs and a writing gig lined up a month before I quit. They didn’t amount to much, but having any cash flow going was a big deal. (Location 1556)
• All you win is the opportunity to leap yet again. And again. And again. (Location 1574)
• Lifestyle design is robot design. (Location 1592)
• Timothy Gallway’s Inner Game of Tennis (Location 1608)
• The inner game is hard enough that you could argue the best way to tackle it is to not even realize how hard it is before diving in, and then working it all out under live-fire conditions. Then you can look back and marvel at your own survival. (Location 1624)
• When you are in a job, you are unaware of the extent to which you rely on other people to manage you. (Location 1646)
• Most people need a certain amount of structure in their lives.1 When the structure falls apart, they don’t do well. As a gigworker, you have to build structure for yourself. (Location 1658)
• Think of self-structuring as creating an operating system around yourself. (Location 1665)
• I like A. G. Lafley’s definition of leadership as “interpreting external reality for the organization.” This is not an objective, dispassionate description, but an opinionated, emotional understanding that makes a particular direction of movement seem inevitable and aesthetically necessary, rather than merely logical. (Location 1672)
• The mere existence of any default interpretation of reality and direction of movement is enough to fill the need to be led. (Location 1676)
• Charlie Munger for instance, is the de facto CEO of thousands of free agents. (Location 1680)
• Think of self-directing as making and maintaining your own maps, location awareness, and movement. Don’t underestimate how hard it is. The easy part is drawing a map and picking a logically coherent direction to go. The hard part is doing it in a way that you’ll actually care about going in that direction enough to take step after step, indefinitely. (Location 1685)
• The point of self-ceremonialization is to close a sensory-cues feedback loop to manage your psyche. (Location 1706)
• Think of self-ceremonializing as creating an effective UI for your new life. (Location 1715)
• The difference between armchair strategy and non-armchair live action often boils down to a ticking clock. The clock is the bridge between strategy and execution. (Location 1727)
• If your clock is no more than the sum of billing clocks in your gigs, you’ve come temporally undone. Don’t come temporally undone. Build an inner clock. Set your own pace with reference to the state of your own inner game. (Location 1731)
• The hard part of self-socializing is understanding how you depend on other people, who they are, and the extent to which they recognize the role they play in your new life, and then rearranging things if they seem to be unhealthy and limiting rather than healthy and enabling. (Location 1741)
• Self-Management: Learning to program yourself Self-Structuring: Creating an operating environment Self-Direction: Sense-making external reality by making your own maps Self-Defining: Architecting a permissions identity for yourself Self-Ceremonializing: Creating a UI and packaging for your new life Self-Pacing: Sense-making time by making an internal clock for yourself Self-Socializing: Architecting a network identity for your social environment (Location 1750)
• If your robot suit is visible (in the form of formulaic behaviors that mark you as an easily identified “type” for instance, or as a “personal brand” robot that is put together with preternatural poise), it is a badly designed robot suit. (Location 1761)
• On the other hand, if you seem painfully all-too-human, but your behaviors seem whiny, overly vulnerable, and low-agency, you haven’t in-sourced enough of your psychological support environment yet. Like a starving artist who produces no art, but is very loudly human about it, playing the part of a sensitive soul being tossed about by a cruel world. (Location 1766)
• That is performative learned helplessness. (Location 1768)
• Illogical though it might sound, you have to pick a date or leap event (such as a certain critical meeting going a certain way), and then do the best job of preparation you can before that. The rest will have to be done under live-fire conditions after the leap. (Location 1784)
• preparedness, risk appetite, opportunity, and depressors. (Location 1788)
• There is a tide in the affairs of men. Which, taken at the flood, leads on to fortune; Omitted, all the voyage of their life Is bound in shallows and in miseries. On such a full sea are we now afloat, And we must take the current when it serves, Or lose our ventures. (Location 1819)
• 0<N<1: You’re in launch ramp zone. Count the number of friends outside your work you interact with regularly outside of work and increase that. They will be more valuable in the short term than shallow “networking” contacts or current at-work colleagues (who may feel betrayed and not inclined to help when you leave). Double or triple your investment in outside high-frequency friendships. If you’re in a line of work that allows for creating outside-of-work artifacts, identify a small warm-up pre-gig like a pro bono project for a nonprofit or a contribution to an open-source project. And most importantly, ramp up your performance at work. Exiting on a high note creates a lot of positive externalities. And of course, start saving aggressively, on a war footing. (Location 1872)
• The correct answer is that they each pick a beef worth picking, but not too strongly. The Gervais Principle picked a beef against feel-good “nice” management thinking that dominated the pop-business literature at the time.5 Entrepreneurs are the New Labor picked a beef against people in the tech sector shilling what has come to be known as “hustle porn” and flattering founders with a hero self-image that blinds them to industry dynamics and debilitating behaviors. Fat Thinking picked a beef with the lean six-sigma crowd in big corporations, and the lean startup crowd in the startup scene. (Location 1963)
• In both cases, I stand by my criticism and believe they are bad books. But the point is, the reviews were 100% beef. I didn’t reject selected premises and build something else better on an alternative foundation. In both cases, it would have been possible; I just didn’t bother to do it. (Location 1983)
• spotting a widespread pattern of disillusionment in the margins identifying the prevailing orthodoxy driving the disillusionment analyzing its foundations rejecting one or more flawed premises fueling the disillusionment adding imaginative alternative premises running with it to see where the whole thing can take you becoming conscious of what and who you’re for and against articulating it out there in public and standing behind it. (Location 2002)
• The work is hard because it takes a certain amount of courage and a good deal of taste. (Location 2009)
• Differentiation is the right amount of beef in your positioning; notionally about 20%. (Location 2018)
• You’re offering an irreversible path of political action. You’re making your support for that action mean something by association. You are meaning. (Location 2025)
• I recommend Arendt’s The Human Condition as philosophical background reading (Location 2027)
• Executives typically got where they are not by being exceptional performers, but by being bold and opinionated decision-makers who took interesting risks with a broad but mediocre set of abilities. (Location 2036)
• I learned this when one of my early clients literally introduced me to someone as his “secret weapon.” (Location 2039)
• Add three or four novel elements for every one rejected orthodoxy element. Use the Warren Buffett rule: praise by name, criticize by category. Offer an exit to a better way, rather than a voice in a fight. Bring out the funny side, which is not the same as being haha funny. Reject what you reject with force and clarity, don’t pull your punches. Embrace what you embrace with doubt and qualifications. Follow your truth where it leads you, not your adversaries where they draw you. Openly acknowledge any motivating resentments and set them aside. You don’t have to pick every battle, but you do have to pick a few. Disengage from the rejected way, do not seek to destroy it. Firmly reject resentment-driven supporters who want to fight for you. Be kind. If you forget every other rule, don’t forget this one. (Location 2049)
• The situation is that a high-profile member of the Guild of Assassins is talking to a bunch of contract-muscle types for a job, and one of the contractors uses the word employed to refer to the team’s relationship to the client. He bridled at this. Assassins were never employed. They were engaged or retained or commissioned, but never employed. Only servants were employed. (Location 2096)
• As an indie consultant, you too are always engaged, never employed. A mark of this is that you almost never haggle over your price. (Location 2100)
• Consultants have quasi-social relationships with clients, with nonfinancial aspects you may or may not value. (Location 2107)
• If you’ve successfully positioned yourself as a consultant, you’re in the quasi-social zone and people will either say yes or no to the price you quote. If nobody ever says no, you’ve priced your services too low. (Location 2116)
• Why this dynamic? Because consulting is an intellectual partnership that is too bespoke to easily compare to substitutes, and only works if both parties see each other as fully human. (Location 2125)
• all parties are contributing to the outcome in highly entangled ways that make it hard to break out and accurately value a given individual’s contribution. (Location 2128)
• Their choice is between doing it one way with you in the picture and doing it a different way without you. (Location 2131)
• read my old blog posts The Economics of Pricelessness3 and Bargaining With Your Right Brain. (Location 2138)
• So why do we gravitate to these self-images? Because uncritical imitation is easier than thinking about your own situation. That, plus easy availability of real people to imitate. And the fact that they are familiar images to project to clients, making for easy (if not particularly effective) marketing and sales strategies. (Location 2191)
• Upton Sinclair once observed, “It is difficult to get a man to understand something when his salary depends upon his not understanding it.” (Location 2202)
• rank-and-file workers, served by martial-artist trainer types staff management, served by pattern-language maven types executive leadership, served by storyteller/bard types line management, served by no-bullshit grinder types (Location 2214)
• The pattern-language maven self-image was pioneered by design consulting firms, many drawing inspiration from the work of architectural thinkers like Christopher Alexander, that pandered to the vanities of aesthetes and wannabe autocrats seeking comprehensive “systems” for running little empires. (Location 2224)
• As an indie consultant, your situation is opposite that of salaried consultants. Your livelihood depends on understanding what the traditional consulting industry, in the form of larger firms, actually does. That’s the only way you’ll find a guerrilla niche for yourself in the landscape they’ve carved out. salaried consultant self-images are liabilities for independent consulting. (Location 2250)
• Believing in any kind of kool-aid is an existential risk for you, even though it is a crucial enabler for some breed of salaried consultant. (Location 2256)
• You’re not Christopher Alexander, you’re a dumpster diver. (Location 2260)
• Sometimes that’s a 100-hour work week, sometimes it’s a 4-hour work week, and it’s never a straight line from interviews to spreadsheets to powerpoints. (Location 2264)
• You’ll find that you have periods with plenty of nominally free time, but mysteriously, no time for the kinds of passion projects, such as writing, independent research, maker projects, or travel, that probably motivated you to quit in the first place. (Location 2276)
• 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. (Location 2279)
• fun things are only fun when you sneak off from things that feel like work to do them. (Location 2285)
• 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). (Location 2291)
• There are 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. (Location 2296)
• 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. (Location 2311)
• Sneaking off from an under-full to-do list doesn’t work, just as weight-training with no weights doesn’t work. (Location 2314)
• 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. (Location 2321)
• The things you do in your sneak-off time are the things that have a chance of turning into long-term compounding assets. But watch out for a related disease, projectitis: omniscient-bad-boss you will attempt to turn every such activity into a legible project at the first whiff of a possible return, and ruin both the fun and the possibility. (Location 2323)
• 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. (Location 2326)
• 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. (Location 2366)
• it’s only worth fighting when you have effective and sufficiently powerful internal allies who are fighting for what’s worth saving. (Location 2407)
• 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. (Location 2417)
• 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. (Location 2430)
• Hard to hire, hard to retain, easy to fire translates into this structural heuristic: Rely only on inbound leads to get gigs. Within gigs, never do billable work that you’re not explicitly asked to. (Location 2441)
• 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). (Location 2447)
• 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? (Location 2450)
• 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. 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. (Location 2462)
• One of the hardest mental shifts to make as an indie is letting go of this catastrophic failure mental model. You only need a parachute if you think you’re in a crashing airplane. If you don’t believe that exiting paycheck employment is like jumping out of an airplane, parachutes are moot. (Location 2495)
• A parachute is for people who might fall to their deaths. Halos are for angels with wings who can float in the air without an organization beneath their feet. (Location 2499)
• If you’re new to this, one trick is to spot the local star employee halo and then play foil to them in an interesting way. (Location 2544)
• Loosely, ethnomethodology means taking the modes of thought and problem solving of lay people seriously, and in my case, actually making them my own. (Location 2567)
• You’re not a good consultant until you understand the logic and appeal of every popular diagram and learn to use each tastefully. (Location 2570)
• The 2x2 is the barbell squat in the business gym. (Location 2597)
• Hugh MacLeod’s sociopaths-clueless-losers pyramid. (Location 2615)
• Use what works, pay attention to 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. (Location 2713)
• Arthur C. Clarke’s “hazards of prophecy,” from his book Profiles of the Future, (Location 2730)
• 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. (Location 2732)
• Possibly the most basic level of failure in failed gig economy careers is failure of nerve. (Location 2742)
• 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. (Location 2748)
• 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. (Location 2753)
• Failure to trust your gut: When things seem okay on the surface, but there are 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. (Location 2776)

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public: true

title: The Art of Gig, Volume 1 longtitle: The Art of Gig, Volume 1 author: Venkatesh Rao, Grace Witherell, and Jenna Dixon url: , source: kindle last_highlight: 2024-06-02 type: books tags:

The Art of Gig, Volume 1

Metadata

• Author: Venkatesh Rao, Grace Witherell, and Jenna Dixon
• Full Title: The Art of Gig, Volume 1
• Category: #books

Highlights

• Uncritical adoption of career advice is significantly more hazardous in the gig economy than it is in the paycheck economy. (Location 85)
• Solve for industry-level questions, not organization- or world-level answers. (Location 127)
• Never accept a deliverable request from an intermediary who can’t act on it. (Location 128)
• Create choices, not recommendations. (Location 129)
• The work ends when the story ends, not when the last check clears. (Location 133)
• Keep your client-facing identity normie. (Location 134)
• Don’t trust your situation awareness in a gig after six months of inactivity. (Location 137)
• Learn the sector’s paper-napkin math and unique measures of itself. (Location 138)
• Cost-plus accounting over value-based accounting. (Location 142)
• In billing, bundle and unbundle line items for at-a-glance auditability. (Location 143)
• Learn more from every client than they learn from you. (Location 145)
• Never let the truth get in the way of a good story. (Location 147)
• obfuscated chess postman is applying learnings from one gig to another in real-time by creating suitable abstractions to port your new learnings without compromising confidentiality. (Location 161)
• as an indie consultant, you’re very unlikely to be selling happiness (Location 167)
• the problems external consultants solve always fall into two basic buckets: insufficient systematic confidence and insufficient systematic doubt. (Location 170)
• Any consultants present will be seen as parasites to be exterminated rather than utilized more. (Location 172)
• The Explorer is a client who wants to build capacity for systematic doubt at an outer-world locus. They do this by constantly considering possibilities, alternative perspectives, and refactorings of worldviews. They tend to hire a sparring partner type of consultant who can constantly stress test their thinking and actions, and undermine their assumptions from unexpected new directions. (Location 180)
• Achiever is a client who wants to build systematic confidence at an outer-world locus. They typically hire consultants who take on roles as teachers or coaches, helping them develop specific functional capabilities and skills, such as public speaking, survey methodology, being more productive, architecting databases, running Kickstarter campaigns, applying for government grants, or sourcing things from China. (Location 183)
• The Explorer Organization tends to be future-oriented and is likely to have people or departments devoted to activities such as scenario planning, futures, and market modeling (often called strategy operations). Explorer organizations hungrily consume forecasts and trend information, as well as historical analyses and industry reports. They believe they are curious organizations. (Location 199)
• The Integrator Organization tends to be employee mental health and culture focused. They love things like employee-engagement programs, well-being initiatives, and diversity and inclusion programs. You will find a strong culture of listening habits inside such organizations: town-halls, manager-employee 1:1s, and effective communication training. They believe they are compassionate organizations. (Location 206)
• depending on how much they are actually winning or losing, the organizational self-images may be more or less deluded in different ways. That’s where people like us come in, and where management jokes are born, but that’s a story for another day. (Location 215)
• I suspect, in terms of sheer population size, Achiever organizations are the most common. I’d guess as high as 70%, followed by Integrator, Explorer, and Tester organizations. (Location 218)
• The tell of the Explorer in Need is a sense of staleness and being in a rut evident in ways of talking, distractibility, and arbitrary pursuit of Next Shiny New Things. (Location 253)
• Achiever in Need is energy being dissipated in random acts of X where they are thrashing and improvising behaviors in an area where skilled and disciplined behavioral precedents exist. (Location 255)
• Integrator in Need is endemic mental health issues across activities. There is too much anxiety. There are communication problems everywhere. Relationships are fraying all over the place. Morale is plummeting. (Location 257)
• Tester in Need is toxic arguments that go nowhere, disagreements over facts and data that get weaponized along lines of control, big ego conflicts, and ideological battles. Behaviors are driven more by the need to feed ongoing beefs than accomplish missions. (Location 259)
• you classify the organization by looking for a locus of futile energy expenditure. That futility is your opportunity. (Location 262)
• both individuals and organizations can have two polar opposite reasons for hiring a consultant: to build on a strength or to mitigate a weakness. (Location 263)
• It usually takes a crisis situation to drive an individual or organization to seek external help for a weakness. (Location 265)
• consultant addresses both the symptoms and root causes is by injecting a much-needed dose of disinterested systematicity in the right place. (Location 268)
• Positioning school takes its intellectual cues from economics and uses formal models and numbers as the ultimate foundation for everything, while the People school takes its intellectual cues from sociology and psychology and uses narrative as the ultimate foundation for everything. (Location 276)
• the opposite of every Great Playbook is also a Great Playbook. (Location 296)
• Take an inventory of actual named players in the situation, sorting them into rings by their level of agency and ability to influence the situation. Make up a story to account for the recent history of the situation, using abductive reasoning3, to uncover what the actual players are up to, and why. Start “nudging” the situation to test your narrative, and start forming live, evolving judgments about the actual players: who matters, who doesn’t, how they align/don’t align, what futures they are working towards. Pick the group of players you think is both right about the future, and capable of winning the future. Help them win. If such a group doesn’t exist, or you’re on the wrong side, exit the situation or switch sides. Keep retelling the story and nudging the action according to the current narrative logic, monitoring the evolving situation for narrative violations and disruptions. (Location 303)
• The Great Truth of the People school is that subjective, internal realities (note the plural) are everything and objective reality is a matter of evolving consensus and dissensus. (Location 318)
• For the People school, formal models and data, if used at all, are like specialized forensic investigative tools to be used when the process of repeatedly retelling the story while nudging it along runs into show-stopping mysteries and puzzles. People school practitioners are essentially storytellers at heart, who believe in truth-by-narrative, but sometimes make what they think of as concessions to empiricist insecurities by including data and graphs. (Location 324)
• Being a consultant is about staying in a state of dynamic balance, evolving your own game with the shifting balance of power between Great Truths and Great Playbooks. (Location 360)
• Knowing which nut to tighten to resolve a mysterious noise is a simple example of a knowledge asymmetry. (Location 385)
• the principal-agent problem is particularly acute in any relationship where the typical principal has a need that is rare enough that there is no incentive for them to get systematically knowledgeable about the domain, while fulfilling the need is so common an activity for the agent that they have incentives to learn to do it very cheaply, systematically, and efficiently. (Location 404)
• Any employee with a very unique, opaque, and illegible skill is a huge risk for an organization. (Location 432)
• Often a uniquely skilled but underutilized employee, despite being compensated enough to make dishonesty uninteresting, will end up leaving and becoming a consultant simply to find more things to do. (Location 434)
• I’ve used the relative phrase reasonable-seeming rather than the absolute reasonable to describe the perception of effort in tasks done by employees. (Location 436)
• In either case though, one of the tells of an organization working very hard to stabilize a dissonance between internal and external realities is resistance to consultants: When the internal reality is deluded, consultants might inject an entirely unwelcome reality check. When external reality is deluded, consultants might contaminate a fragile island of deeper truth by injecting bad external thinking. In either case, we consultants represent informational risks and threats to the organizations we try to help and it’s generally up to us to manage the risk. (Location 446)
• Crisis-only consulting policies: Organizations will simply resist retaining consulting services unless there is a crisis, and the costs of not bringing in outside expertise to help become unacceptable. These organizations simply leave certain knowledge-gap risks unmanaged. Ecosystem competency: Organizations will consciously develop competency in managing an ecosystem of consultants via specialized monitoring mechanisms—think certification programs. Externalize the risk explicitly: Many organizations will require consultants and contractors to carry specialized insurance policies, as some of you will know. I’ve never yet taken such a gig. Relying on exceptions: Many organizations will have default no-consultant policies, but allow senior executives to make exceptions based on special needs, and the existence of trusted relationships. This of course, is an entry point for a lot of cronyism. (Location 456)
• Build relationships that allow you to be an exception to anti-consultant rules/barriers. So long as you keep yourself honest by resisting the lure of cronyism, and only taking gigs where it is clear that you’re bringing genuine external knowledge or relationships to the party, it is the best way to address the legitimate principal-agent concerns of clients, without bearing too heavy a burden of externalized risk-management costs yourself. 1 en.wikipedia.org/wiki/Principal%E2%80%93agent_problem 2 en.wikipedia.org/wiki/Transaction_cost (Location 469)
• Indie consultants need to be aware of their operating epistemology, in order to avoid buying their own bullshit, and turning into unconscious grifters. (Location 483)
• If you’re an entrepreneur or an indie consultant, whatever else you might be, you are not a scientist. (Location 492)
• There is no such thing as an evidence-based startup or gigup. In the world of gigups and startups, only failures can be evidence-based. (Location 494)
• how do you know the important things you think you know?Through fiction, through simulation, and through thick description (a fancy word for anthropology). (Location 500)
• Indie consulting is speculative and/or story-driven. (Location 502)
• Calculating how the ball bounces is valuable for Great Yak Enterprises because x. . . . you inevitably, and inexorably, go from science to something else. Whatever that is, to call it science is a distortion of it, and a disservice to it. But in that X lies the core of how you do know things and add value. (Location 511)
• When you try to “science” a system, you don’t carve out pieces that are important, interesting, or useful. Those are merely nice-to-have features you can hope for in a carved-out piece, but essentially unrelated to whether or not you can science it well. The chances that you can “carve reality at the joints” in ways that conform to the contours of practical concerns are low. You carve out a part that offers potential for systematic ambiguity reduction, and hope that when you go back (if you can go back) and integrate it into an understanding of the whole, some of that lowered ambiguity will pay dividends in some unpredictable way. (Location 521)
• Simulation, storytelling, and thick descriptions are integrative modes of knowing. When you’ve taken something apart and scienced what you can science (and that subset might be “nothing”), the real work of a startup or gigup begins. (Location 527)
• I concluded that what I deal with poorly is the combination of high risk and high time pressure. (Location 534)
• Indie consultants naturally fit in where the capability gap is either small enough and oddly-shaped enough to be filled by a few individually contracted people, or where the gap is large, but can be filled by a fairly generic type of labor without the help of a labor-aggregating counterparty. (Location 542)
• I offer Strategy for Explorers. You might be in Preventive Care for Integrators or Surge Capacity for Testers. Here’s a handy 4x4 table for you to think about. (Location 549)
• What is perhaps less obvious is that the lack of systematized capability (either in-house or outsourced) is generally rational. (Location 556)
• many struggling consultants seem to believe that the lack of in-house capacity for the services they offer is irrational. That their work ought to be a job and that they ought to be hired as an employee to do it. This belief leads to weird and potentially crippling mental blocks that put you in the worst of both worlds. (Location 558)
• preventative care, surge capacity, strategy, and first response. (Location 561)
• This is the kind of consulting offering (often made up by laid-off mid-career middle managers who have succumbed to up-or-out pressures) that best fits the accusation that consultants are people who help solve problems that wouldn’t exist in the first place without them. (Location 564)
• If you’re in this quadrant, chances are you’ll struggle to brand and position yourself uniquely. You’ll also struggle to set your own price or differentiate yourself from contract labor supplied by contracting companies. One test: you have a blog, portfolio site, or other marketing asset, but most of your work still comes through gig sites like Upwork. You’re unable to actually attract any work at your preferred bill rate, and are forced to work at prevailing market rates. (Location 575)
• High risk and low time pressure is generally the combination of conditions that makes anything strategic. (Location 583)
• Strategy-centric offerings are usually based on a track record that induces trust, and idiosyncratic personal mind-melds of taste and intellectual style between client and consultant. (Location 585)
  • Note: Who do i have this with
• A good strategy consultant is often simply someone who is good at just being present in a situation without becoming yet another part of the problem. This can be surprisingly hard to do. (Location 589)
• You have to be able to pattern-match and generate appropriate responses much faster. Not just that, you have to be good at dealing with clients in abnormal states, like patients in ICUs. (Location 596)
• If you think of organizations as cars, a good mental model of the politics (not economics) of work is that capital is the accelerator, labor is the brake, and middle-management is the gearbox. And we gigworkers? We are the clutch. We help disengage/re-engage the drivetrain during gear-shifting, as operating regimes change and organizations need to adapt behaviors. (Location 624)
• The defining characteristic of a scab is striking a self-interested independent bargain with the capital-owning/managing/leading class that breaks from any larger collectively bargained deal. (Location 633)
• A graphic designer or independent strategy consultant is fundamentally a more mobile type of economic actor than a welder or an auto-assembly specialist. We work with our own cheap tools: laptops and notebooks for the most part, rather than with million-dollar machine tools or billion-dollar factories owned by investors seeking returns. We serve broad rather than narrow patterns of demand. (Location 651)
• Because the gig economy, especially the indie consulting corner of it, relies on production capabilities that are 5% based on owned capital equipment and 95% based on affordances of the free internet. (Location 661)
• But from the perspective of a 2020s digital economy, we are members of the clutch class who largely own our means of production, have too high a degree of agency in shaping our own lives to be part of labor, and too little wealth to be part of capital. (Location 664)
• The rare corners of the gig economy where organizing like traditional labor is meaningful—actors are a good example—typically exist where the demand is concentrated enough that it can be targeted by collective action. (Location 674)
• Mechanisms do matter, but the ones that we actually employ towards political ends are adapted to our political ends, not those of either capital or labor. (Location 701)
• We swap notes, we share leads, we pitch in to help each other out on specific gigs, we put ourselves in crucible groups to rapidly learn skills far faster than labor or capital, we serve as market makers in an economy of referrals, we do what needs to be done. And we do an end run around the stale battles of the 20th century. (Location 706)
• Push come to shove, where we stand depends on where we sit. And in almost all cases, we sit right next to management and capital, serving as clutch players, helping shift gears where necessary, helping with surge actions, helping break out of stalemates. (Location 716)
• Clutch Time is evenings and weekends. With apologies to Chris Dixon,4 what the clutch class does on evenings and weekends, everybody will be doing in ten years. (Location 726)
• Clutch time is when capital and labor both try to rest and relax and gigworkers get going. That’s the time when those of us in the clutch class really come into our own. We go to meetups, we get coffee with each other. We scan the social streams for openings, seek out room to maneuver, ways to deploy high-leverage cheap assets, learn breakout skills, and dream up hacks and arbitrages. (Location 729)
• And we sneak one-at-a-time into the future, through gaps on the economic frontier, rather than marching rank-and-file in slogan-chanting cohorts. (Location 732)
• First-principles analysis would suggest that in general, the smaller a business, the more fragile it is likely to be. And nothing is more fragile than a one-person business operating in the gig economy. (Location 772)
• Many lines of business that indies like getting into do not allow for easy scheduling of breaks, interruptions of service, or service-level degradations. Passive income is mostly a myth. (Location 788)
• If the opportunity spike coincides with an emergency spike, you get hit with a double jeopardy: you lose the income opportunity and you have to deal with the emergency-related expenses. It’s what Charles Perrow labeled a normal accident—a condition in a complex system (like nuclear reactors or the modern gig economy tech stack) where two unrelated and ordinary risk events coincide to create extraordinary risk conditions. (Location 796)
• This finding jibes with the observation, in Bill Janeway’s book on the startup economy, Doing Capitalism in the Innovation Economy, that what gets startups through turbulent times is simply cash and control. (Location 816)
• being a Lindy Indie really just boils down to building up reserves. (Location 837)
• The brute force answer is to simply cut down expenses till they are half the after-tax income, saving the other half in conservative reserve form (cash). (Location 844)
• Just focus on making money any way you can, and acquiring your own idiosyncratic understanding of how the game is played. (Location 877)
• At this level, you’re basically learning to run your indie consulting life as a business, and acquire and refine basic instincts around pricing, supply and demand for your services, and negotiations, all driven by an understanding of your own needs, lifestyle costs, and operating margins. (Location 885)
• To last longer, you have to discover who you are, by doubling down on things you like to learn, while working on gigs. (Location 889)
• It’s a bad mistake to separate your learning interests from your working interests. (Location 890)
• At the learning flywheel level, you should strive to say yes to gigs where you’ll learn more of what you want to learn, and no to gigs where you won’t. It’s as simple as that. (Location 895)
• it’s the opposite of passive income. This is as active as income gets. You’re not looking for shortcuts. You’re looking to make the long way the fun way. (Location 897)
• This is effectively indistinguishable from what you’re learning the fastest, which in turn is almost entirely a function of what behaviors you are repeating most frequently and enjoying in your gigs. In other words, the iteration rate of mindful deliberate practice. (Location 898)
• Finding and staying in the maximal iteration/learning rate zone of what you enjoy is a pretty subtle challenge. It took me nearly three years to figure out that it was “conversational sparring” for me. (Location 901)
• Believe it or not—and this is heresy to doerists—a life of pure learning and new personal records is not satisfying. If you get stuck at the learning level, you will burn out in about three years. To survive longer, you have to explore how you create value for others. (Location 903)
  • Note: This was me
• When you’ve bootstrapped this level of mindful ongoing interrogation of your working life, you will be able to more readily see the world from the point of view of your clients, critically interrogate your own evolving identity, and become aware of your blindspots, rationalizations, and limiting self-perceptions. (Location 908)
• you can get sucked in from there into perennial agonizing and fine-tuning of your work, in an attempt to find a Grand Unified Theory of Guaranteed Value Addition. This is a utopian trap. You’re actually doing far better than average if you can claim that you are adding value in one out of two gigs. A more typical rate I suspect is one in five (below that, you’ll likely feel like you’re participating in a bullshit-work economy). The corresponding dystopian trap is coming to believe that nothing can ever get better, and slowly succumbing to the temptations of fraud, bad faith, and corruption. (Location 914)
• One of the reasons many indie consultants fail to do this, and get trapped at the value theory level is that they fail to distinguish learning (one level below) from growth (one level above). They think the value-theory level is the top of the pyramid. (Location 920)
• You can learn without really growing, and many people do exactly that. (Location 923)
• A fad is basically an uncritical, fixed, widely shared value theory that only dies when it starts to fail miserably, triggering utopian or dystopian yearnings and behaviors. (Location 925)
• Growth is the result of integrating your experiences, figuring out what they mean, healing any scars, and evolving beyond them. (Location 927)
• How do you know when the lessons are the right ones? When they point the way to continuing the game in the most interesting way possible, instead of adding more details to the map of whatever value-addition rut you are in. (Location 929)
• You will compensate for cognitive decline by seeking out skilled hobbies and interests and narrow paths of personal accomplishment with feedback loops of strengthening high-integrity behaviors. (Location 961)
• You will compensate for chronic social anxiety by investing increasing energy into premium mediocrity1 (looking more successful than you actually are). (Location 963)
• You will compensate for overwork and exhaustion with hedonistic excess. (Location 966)
• you have to pick two of three, but you don’t have to make the same choices in all situations and at all times. (Location 985)
• Make your choices. Accept the consequences in the short term, but resist them in the long term. Make new choices when and where you can, in order to avoid degenerating. (Location 997)
• Freedom is for what Samo Burja calls live players.3 If you act dead, you will eventually die for real in an unpleasant way. (Location 1000)
• Up until the Great Recession, the perception of the Big-Three 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. (Location 1053)
• A good part of the consulting market is a corporate assisted-living facility for geriatric companies. (Location 1067)
• That’s the most important thing you have to understand about the Big-Three consulting world: it selects for intelligent, high-energy grinders, not snowflake philosophers driven by foundational curiosities. (Location 1076)
• 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. (Location 1079)
• 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 manageable grinds. (Location 1100)
• They are the organizational equivalent of expensive medical imaging equipment. (Location 1103)
• 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 (Location 1110)
• 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. (Location 1118)
• 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. (Location 1122)
• The DEI and ESG theaters are the latest examples of such boutique sectors, where you are more likely to find grifters or power-tripping political opportunists than people sincerely engaging with the actual ethics issues supposedly in question. (Location 1138)
• Hanlon’s razor: never attribute to malice what can be adequately explained by unexamined philosophical commitments. (Location 1155)
• ethics in consulting is simple: it’s a matter of saying no to things. Which usually means lowering some topline or bottomline expectations, and being content with less. Ethics are a form of self-imposed taxation. (Location 1167)
• TINA assumptions—There is No Alternative. (Location 1174)
• indie consultants, indie contractors, and under-the-API gigworkers, (Location 1204)
• You’re an indie consultant if you don’t have to deal with gatekeeper organizations, such as purchasing or HR. You may still need to do paperwork with them, but they have little control over whether or not to hire you because sufficiently senior managers or executives are making that call. (Location 1207)
• For the contractor to consultant move, a good stunt is to write a book. (Location 1244)
• 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. (Location 1251)
• 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. (Location 1269)
• If we wallow in nostalgia for creaky, century-old constructs, all we’ll do is reproduce old models with cosmetic tweaks, and undermine the gig economy rather than strengthen it. (Location 1278)
• people have lately been talking about the passion economy3 as the evolutionary descendant of the gig economy. (Location 1294)
• Gigworkers? We leap into opportunity spaces. Not just once, but repeatedly. In the most extreme case, every new gig is a leap, and since you ideally have many gigs going in parallel, you are always leaping on some track. (Location 1319)
• there’s no such obvious ceremonial starting point for scripting a leap into the gig economy. Only a joke one—getting business cards. (Location 1332)
• Well, actually, there is one real starting point: getting and staying married to someone with a job, who is willing to support your risk-taking and backstop your first leap with their own stability. (Location 1333)
• The first mistake you can make in launching a gig economy career is to think it is pure improvisation. (Location 1344)
• The second mistake you can make is thinking the kind of scripting that works for job-searching will also leave you prepared for the gig economy as a bonus. (Location 1347)
• The third mistake you can make is to treat the gig economy as a natural and predefined Plan B you automatically land in if you fail at the other two. (Location 1349)
• computing your unmanaged leap risk, as illustrated in the diagram on the next page. Our goal with this exercise is to first estimate your income replacement horizon (in months) and from that, your unmanaged leap risk (in dollars). Let’s make up acronyms for these, why not: IRH and ULR. (Location 1379)
• A good way to think of this is in terms of a time advantage. You’re hoping to make up for this 10-year-long, dumb, no-risk preparation time with sheer strategic cleverness. You’re trying to leap ten years into your own financial future somehow. You’re trying to disrupt yourself. (Location 1417)
• favorable exit conditions, a parental factor, a spousal factor, and a transient lifestyle cost-down (Location 1425)
• Figuring out how to close risk gaps with cunning rather than money is essential early training in gig economy resourcefulness. Because remember: the gig economy is not a single leap, but repeated leaping. (Location 1454)
• every cycle of brain time you spend playing defense you’re not playing offense, so it is hugely valuable to have somebody else take care of that, allowing you to focus on the top line rather than the bottom line. (Location 1481)
• Don’t be snobby about parental support. Your parents’ generation probably didn’t have to try making it en masse in the gig economy, so give yourself a break, courtesy of your parents (or in-laws), if you can. Intergenerational wealth transfer is a major dynamic in civilized life and most parents are more than willing to help as much as they are able. (Location 1501)
• It’s not actually a strategic cheat if you have to pay for material support with your mental health. (Location 1508)
• here at the Art of Gig, we are solving for a non-minimalist, non-spartan lifestyle: just on your own terms rather than those of a paycheck employer. (Location 1524)
• The best high-cunning exit condition is one in which you’ve created a live asset, out in the open, that can be turned into a viable foundation for a gig-economy business with the flip of a switch. (Location 1552)
• Marketing assets like a blog or newsletter where you can start to look for and create opportunities. I had both. Product assets that can be turned into a money-making thing on Day 1. I had a nearly complete book that I was able to finish and put up for sale within a month of quitting. Instant spike of cash flow right when it was most useful. Live, hot leads that can be converted to starter gigs before you quit. I had two consulting gigs and a writing gig lined up a month before I quit. They didn’t amount to much, but having any cash flow going was a big deal. (Location 1556)
• All you win is the opportunity to leap yet again. And again. And again. (Location 1574)
• Lifestyle design is robot design. (Location 1592)
• Timothy Gallway’s Inner Game of Tennis (Location 1608)
• The inner game is hard enough that you could argue the best way to tackle it is to not even realize how hard it is before diving in, and then working it all out under live-fire conditions. Then you can look back and marvel at your own survival. (Location 1624)
• When you are in a job, you are unaware of the extent to which you rely on other people to manage you. (Location 1646)
• Most people need a certain amount of structure in their lives.1 When the structure falls apart, they don’t do well. As a gigworker, you have to build structure for yourself. (Location 1658)
• Think of self-structuring as creating an operating system around yourself. (Location 1665)
• I like A. G. Lafley’s definition of leadership as “interpreting external reality for the organization.” This is not an objective, dispassionate description, but an opinionated, emotional understanding that makes a particular direction of movement seem inevitable and aesthetically necessary, rather than merely logical. (Location 1672)
• The mere existence of any default interpretation of reality and direction of movement is enough to fill the need to be led. (Location 1676)
• Charlie Munger for instance, is the de facto CEO of thousands of free agents. (Location 1680)
• Think of self-directing as making and maintaining your own maps, location awareness, and movement. Don’t underestimate how hard it is. The easy part is drawing a map and picking a logically coherent direction to go. The hard part is doing it in a way that you’ll actually care about going in that direction enough to take step after step, indefinitely. (Location 1685)
• The point of self-ceremonialization is to close a sensory-cues feedback loop to manage your psyche. (Location 1706)
• Think of self-ceremonializing as creating an effective UI for your new life. (Location 1715)
• The difference between armchair strategy and non-armchair live action often boils down to a ticking clock. The clock is the bridge between strategy and execution. (Location 1727)
• If your clock is no more than the sum of billing clocks in your gigs, you’ve come temporally undone. Don’t come temporally undone. Build an inner clock. Set your own pace with reference to the state of your own inner game. (Location 1731)
• The hard part of self-socializing is understanding how you depend on other people, who they are, and the extent to which they recognize the role they play in your new life, and then rearranging things if they seem to be unhealthy and limiting rather than healthy and enabling. (Location 1741)
• Self-Management: Learning to program yourself Self-Structuring: Creating an operating environment Self-Direction: Sense-making external reality by making your own maps Self-Defining: Architecting a permissions identity for yourself Self-Ceremonializing: Creating a UI and packaging for your new life Self-Pacing: Sense-making time by making an internal clock for yourself Self-Socializing: Architecting a network identity for your social environment (Location 1750)
• If your robot suit is visible (in the form of formulaic behaviors that mark you as an easily identified “type” for instance, or as a “personal brand” robot that is put together with preternatural poise), it is a badly designed robot suit. (Location 1761)
• On the other hand, if you seem painfully all-too-human, but your behaviors seem whiny, overly vulnerable, and low-agency, you haven’t in-sourced enough of your psychological support environment yet. Like a starving artist who produces no art, but is very loudly human about it, playing the part of a sensitive soul being tossed about by a cruel world. (Location 1766)
• That is performative learned helplessness. (Location 1768)
• Illogical though it might sound, you have to pick a date or leap event (such as a certain critical meeting going a certain way), and then do the best job of preparation you can before that. The rest will have to be done under live-fire conditions after the leap. (Location 1784)
• preparedness, risk appetite, opportunity, and depressors. (Location 1788)
• There is a tide in the affairs of men. Which, taken at the flood, leads on to fortune; Omitted, all the voyage of their life Is bound in shallows and in miseries. On such a full sea are we now afloat, And we must take the current when it serves, Or lose our ventures. (Location 1819)
• 0<N<1: You’re in launch ramp zone. Count the number of friends outside your work you interact with regularly outside of work and increase that. They will be more valuable in the short term than shallow “networking” contacts or current at-work colleagues (who may feel betrayed and not inclined to help when you leave). Double or triple your investment in outside high-frequency friendships. If you’re in a line of work that allows for creating outside-of-work artifacts, identify a small warm-up pre-gig like a pro bono project for a nonprofit or a contribution to an open-source project. And most importantly, ramp up your performance at work. Exiting on a high note creates a lot of positive externalities. And of course, start saving aggressively, on a war footing. (Location 1872)
• The correct answer is that they each pick a beef worth picking, but not too strongly. The Gervais Principle picked a beef against feel-good “nice” management thinking that dominated the pop-business literature at the time.5 Entrepreneurs are the New Labor picked a beef against people in the tech sector shilling what has come to be known as “hustle porn” and flattering founders with a hero self-image that blinds them to industry dynamics and debilitating behaviors. Fat Thinking picked a beef with the lean six-sigma crowd in big corporations, and the lean startup crowd in the startup scene. (Location 1963)
• In both cases, I stand by my criticism and believe they are bad books. But the point is, the reviews were 100% beef. I didn’t reject selected premises and build something else better on an alternative foundation. In both cases, it would have been possible; I just didn’t bother to do it. (Location 1983)
• spotting a widespread pattern of disillusionment in the margins identifying the prevailing orthodoxy driving the disillusionment analyzing its foundations rejecting one or more flawed premises fueling the disillusionment adding imaginative alternative premises running with it to see where the whole thing can take you becoming conscious of what and who you’re for and against articulating it out there in public and standing behind it. (Location 2002)
• The work is hard because it takes a certain amount of courage and a good deal of taste. (Location 2009)
• Differentiation is the right amount of beef in your positioning; notionally about 20%. (Location 2018)
• You’re offering an irreversible path of political action. You’re making your support for that action mean something by association. You are meaning. (Location 2025)
• I recommend Arendt’s The Human Condition as philosophical background reading (Location 2027)
• Executives typically got where they are not by being exceptional performers, but by being bold and opinionated decision-makers who took interesting risks with a broad but mediocre set of abilities. (Location 2036)
• I learned this when one of my early clients literally introduced me to someone as his “secret weapon.” (Location 2039)
• Add three or four novel elements for every one rejected orthodoxy element. Use the Warren Buffett rule: praise by name, criticize by category. Offer an exit to a better way, rather than a voice in a fight. Bring out the funny side, which is not the same as being haha funny. Reject what you reject with force and clarity, don’t pull your punches. Embrace what you embrace with doubt and qualifications. Follow your truth where it leads you, not your adversaries where they draw you. Openly acknowledge any motivating resentments and set them aside. You don’t have to pick every battle, but you do have to pick a few. Disengage from the rejected way, do not seek to destroy it. Firmly reject resentment-driven supporters who want to fight for you. Be kind. If you forget every other rule, don’t forget this one. (Location 2049)
• The situation is that a high-profile member of the Guild of Assassins is talking to a bunch of contract-muscle types for a job, and one of the contractors uses the word employed to refer to the team’s relationship to the client. He bridled at this. Assassins were never employed. They were engaged or retained or commissioned, but never employed. Only servants were employed. (Location 2096)
• As an indie consultant, you too are always engaged, never employed. A mark of this is that you almost never haggle over your price. (Location 2100)
• Consultants have quasi-social relationships with clients, with nonfinancial aspects you may or may not value. (Location 2107)
• If you’ve successfully positioned yourself as a consultant, you’re in the quasi-social zone and people will either say yes or no to the price you quote. If nobody ever says no, you’ve priced your services too low. (Location 2116)
• Why this dynamic? Because consulting is an intellectual partnership that is too bespoke to easily compare to substitutes, and only works if both parties see each other as fully human. (Location 2125)
• all parties are contributing to the outcome in highly entangled ways that make it hard to break out and accurately value a given individual’s contribution. (Location 2128)
• Their choice is between doing it one way with you in the picture and doing it a different way without you. (Location 2131)
• read my old blog posts The Economics of Pricelessness3 and Bargaining With Your Right Brain. (Location 2138)
• So why do we gravitate to these self-images? Because uncritical imitation is easier than thinking about your own situation. That, plus easy availability of real people to imitate. And the fact that they are familiar images to project to clients, making for easy (if not particularly effective) marketing and sales strategies. (Location 2191)
• Upton Sinclair once observed, “It is difficult to get a man to understand something when his salary depends upon his not understanding it.” (Location 2202)
• rank-and-file workers, served by martial-artist trainer types staff management, served by pattern-language maven types executive leadership, served by storyteller/bard types line management, served by no-bullshit grinder types (Location 2214)
• The pattern-language maven self-image was pioneered by design consulting firms, many drawing inspiration from the work of architectural thinkers like Christopher Alexander, that pandered to the vanities of aesthetes and wannabe autocrats seeking comprehensive “systems” for running little empires. (Location 2224)
• As an indie consultant, your situation is opposite that of salaried consultants. Your livelihood depends on understanding what the traditional consulting industry, in the form of larger firms, actually does. That’s the only way you’ll find a guerrilla niche for yourself in the landscape they’ve carved out. salaried consultant self-images are liabilities for independent consulting. (Location 2250)
• Believing in any kind of kool-aid is an existential risk for you, even though it is a crucial enabler for some breed of salaried consultant. (Location 2256)
• You’re not Christopher Alexander, you’re a dumpster diver. (Location 2260)
• Sometimes that’s a 100-hour work week, sometimes it’s a 4-hour work week, and it’s never a straight line from interviews to spreadsheets to powerpoints. (Location 2264)
• You’ll find that you have periods with plenty of nominally free time, but mysteriously, no time for the kinds of passion projects, such as writing, independent research, maker projects, or travel, that probably motivated you to quit in the first place. (Location 2276)
• 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. (Location 2279)
• fun things are only fun when you sneak off from things that feel like work to do them. (Location 2285)
• 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). (Location 2291)
• There are 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. (Location 2296)
• 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. (Location 2311)
• Sneaking off from an under-full to-do list doesn’t work, just as weight-training with no weights doesn’t work. (Location 2314)
• 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. (Location 2321)
• The things you do in your sneak-off time are the things that have a chance of turning into long-term compounding assets. But watch out for a related disease, projectitis: omniscient-bad-boss you will attempt to turn every such activity into a legible project at the first whiff of a possible return, and ruin both the fun and the possibility. (Location 2323)
• 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. (Location 2326)
• 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. (Location 2366)
• it’s only worth fighting when you have effective and sufficiently powerful internal allies who are fighting for what’s worth saving. (Location 2407)
• 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. (Location 2417)
• 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. (Location 2430)
• Hard to hire, hard to retain, easy to fire translates into this structural heuristic: Rely only on inbound leads to get gigs. Within gigs, never do billable work that you’re not explicitly asked to. (Location 2441)
• 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). (Location 2447)
• 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? (Location 2450)
• 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. 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. (Location 2462)
• One of the hardest mental shifts to make as an indie is letting go of this catastrophic failure mental model. You only need a parachute if you think you’re in a crashing airplane. If you don’t believe that exiting paycheck employment is like jumping out of an airplane, parachutes are moot. (Location 2495)
• A parachute is for people who might fall to their deaths. Halos are for angels with wings who can float in the air without an organization beneath their feet. (Location 2499)
• If you’re new to this, one trick is to spot the local star employee halo and then play foil to them in an interesting way. (Location 2544)
• Loosely, ethnomethodology means taking the modes of thought and problem solving of lay people seriously, and in my case, actually making them my own. (Location 2567)
• You’re not a good consultant until you understand the logic and appeal of every popular diagram and learn to use each tastefully. (Location 2570)
• The 2x2 is the barbell squat in the business gym. (Location 2597)
• Hugh MacLeod’s sociopaths-clueless-losers pyramid. (Location 2615)
• Use what works, pay attention to 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. (Location 2713)
• Arthur C. Clarke’s “hazards of prophecy,” from his book Profiles of the Future, (Location 2730)
• 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. (Location 2732)
• Possibly the most basic level of failure in failed gig economy careers is failure of nerve. (Location 2742)
• 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. (Location 2748)
• 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. (Location 2753)
• Failure to trust your gut: When things seem okay on the surface, but there are 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. (Location 2776)