Newbie indie consultants tend to have a LOT of questions on their mind. Most of these are bad questions because there are no great or terrible answers to them at the newbie stage of the game. The good-enough answers, on the other hand, are obvious and not worth overthinking.

The problem is, newbies pay so much attention to the bad questions, they often forget to look for the good questions that can actually pay huge dividends if asked early enough. So how do you avoid getting sucked into the black hole of bad questions while looking for the good ones?

The key is to think like an actor rather than a model.

Bad Questions

Here are some examples of bad questions.

• LLC or S-corp? (or equivalent question in other countries). The right answer is “probably LLC,” but if you don’t trust me, sure, go with S-corp. It’s not too costly to fix this if you get this wrong.

• Blogging to attract inbound leads, or proactive email pitches? The obvious answer is the right one: try both, see what works, double down. Cheap effort.

• Targeted, researched pitches versus spray-and-pray? Targeted, obviously. But sure, waste your time on spray-and-pray for a while. Maybe you’re one of the exceptions.

The only reason to waste a lot of time on these questions is that you don’t actually feel ready to get going with serious trial-and-error for whatever reason.

Bad newbie questions are not bad because they aren’t worth asking at all. They’re definitely worth say 15 minutes of fairly mediocre mental effort and googling to get to good-enough starter answers. So what makes them bad?

• They’re bad questions because they can trap you into endless analysis-paralysis and hold you back from actually trying things.

• They’re bad questions because you’re trying to fix an information deficit (which calls for trial and error) by over-analyzing information you do have.

• They’re bad questions because they are read-fire-aim or ready-fire-steer questions that you’re posing in ready-aim-fire ways.

• And most importantly: they are bad questions because they distract you from looking for the good questions to ask.

Unfortunately, the few good questions worth asking early on tend to not be asked.

These are not questions mentors or advisors can just formulate for you to ask, because they tend to be highly situation-specific. They are the good questions for you to ask.

So how do you quickly get past the 100 bad questions everybody asks, while making sure you spend serious time on the 4-5 questions that are good for you to ask, that nobody can tell you how to ask?

I have a meta-question that you should ask about every question that occurs to you:

Is this a model question or an actor question?

I need to detour through a discussion of actors vs. models before I can explain how to ask the meta-question.

Models versus Actors

Modeling and acting are both gig-economy professions. Both have a bit more structure than most gig-economy careers. In particular, there exist agents and audition processes for both. Neither is a plug-and-play under-the-API gig economy career like rideshare-driving though. You need talent, aptitude, some training, an element of luck, and a decent amount of mindful strategizing to succeed at either.

But despite their similarity, there is one crucial difference between them.

Modeling is a career based on looking like other models. Acting is a career based on looking different from other actors.

This is not a subtle point. Modeling is a high-end commodity labor market, acting is a differentiated labor market.

The difference is right there on your TV screen.

Actors tend to be recognizable and imitable (their style is unique enough to allow for recognizable impressions and caricatures). They try hard to make a unique impression and create a memorable new idea in the viewers’ head. Benedict Cumberbatch, for instance, changed everybody’s ideas about what Sherlock Holmes could look like.

Models, on the other hand, tend to be interchangeable and unmemorable. They either embody a particular standard of beauty really well (like ramp models), or a particular societal role like “mom” or “office worker” really well (ordinary commercials). They try hard to conform to an idea the viewer already has in their heads. You can’t impersonate or caricature a model, only the broader category that they exemplify well.

Of course there is a fuzzy area of overlap and crossover. Flo, the character in Progressive Insurance ads in the United States, is really more actor than model, and the campaign has been developed more like a television show than an ad campaign.

And of course, there are plenty of B-movies that feature very forgettable model-like actors.

And then there are exceptions like Daniel Craig (James Bond) and Stana Katic (Kate Beckett in Castle) who crossed over from modeling to acting successfully (it’s hard to go the other way, since successful actors by definition are too recognizable to “work” in most ads).

But the basic distinction is a solid one.

The distinction has only a very weak correlation with fame. Actors versus models is a distinction observable both in newbies and famous examples of both.

There’s a game I play with my wife we call “I’ve seen him/her in something else” that is especially fun with obscure actors who have bit roles in lots of shows and movies. Something about them “pops” in a way that transcends the context of a particular story. I’m pretty good at this game, and I usually figure out where I’ve seen an actor before my wife does.

But the game doesn’t work well with models!

This was driven home for me in a very powerful way recently. Walking around downtown LA a few months back, I walked past a photoshoot in progress (a frequent thing around here). The model looked very familiar, but I couldn’t immediately place her.

It took me a couple of minutes before it hit me: it was Cindy Crawford. Only the most famous model of the 80s (as well as star of a few B-movies). Can you imagine that delayed recognition happening with say Meryl Streep, Samuel L. Jackson, or Jack Nicholson?

The takeaway is this: even the most obscure actor tends to pop recognizably from their context, but even the most famous model tends to blend into their context.

Two Kinds of Questions

Now here’s the thing: for almost all of you, the good questions are going to be actor questions, and the bad questions are going to be model questions.

At the same time, 9 out of 10 questions that occur to you to ask are going to be model questions. So your meta-process should be: quickly get to good-enough on the “model” questions, while keeping your eyes open for your unique version of the true “actor” questions.

The reason is simple: even though there are a lot more “modeling” gigs in the gig economy overall, they tend to be staffed by contract agencies rather than true free agents, and mostly offer no financial or life-satisfaction advantages over similar paycheck jobs. They’re basically consolation prizes for jobs.

If you truly want to be an “indie,” then you are going to be fishing for “acting” gigs, not “modeling” gigs. In the short term, model questions help you tread water. In the long term, you sink or swim based on your actor questions. So the sooner you figure out what defines you as an actor, the more quickly you’re likely to break through.

Here are some examples of model vs. actor questions:

Model questions

1. What certifications should I get?

2. LLC or S-Corp? (US-specific)

3. Should I get into the SBIR game? (US-specific)

4. What industry niche should I pick?

5. How do I craft a pitch?

6. How do I describe my services?

Actor questions

1. What is the first thing people notice about me?

2. What are the unique associations that attach to me?

3. What do people typically want to talk to me about?

4. Who do I naturally attract and repel?

5. Why did I get this gig as opposed to someone else?

6. Could anyone else do this gig without rescoping?

To make it crystal clear, let’s cast all these example questions into actual model/actor questions:

Model questions

1. How tall do I need to be?

2. Should I try to break through in LA, Paris or New York?

3. Should I try to get a famous agent?

4. What roles in commercials can I fit into?

5. What kinds of portfolio photos do I need?

6. How should I dress for the audition?

Actor questions

1. What movie/show do people remember me from?

2. What catchphrases do people associate with me?

3. What scripts come my way?

4. Which directors/co-stars do I have good chemistry with?

5. Why did I get this role?

6. Could anyone else play this role without a rewrite?

Notice something? Model questions can be asked and answered before doing anything. Actor questions typically require you to already be in the game before they can be answered.

Another lens. Think about how actors and models are discovered. There’s a chance a model might be noticed by a scout on the street, but most are heavily groomed for the career from a young age, often by parents, and go knocking on the doors of agencies.

Actors on the other hand, are more likely to be noticed by casting agents or scouts in actual performances on stage or in bit roles. While there are famous stars who begin life as child stars, and there’s more of a learning curve to it, acting is much less of a career you can be groomed for. You have to just dive in and strategize your way to success.

It should be obvious that actor questions are all versions of the question, “what makes me pop memorably from context?”

Model questions are all versions of the question, “how can I fit harmoniously into the context?”

Getting to Good Questions

Newbies mostly obsess over the questions they do for one of two reasons: they are procrastinating on actually trying stuff, or they are trying to hold on to the securities of paycheck jobs by asking questions that are analogous to ones you ask while navigating a paycheck career. They usually don’t need the obvious answers pointed out either. Mostly, when they ask more experienced people these questions, they are wishfully hoping for miracle answers that aren’t there.

Of course, knowing how not to overthink the bad questions is not the same as knowing how to ask the good questions.

What’s a good question, beyond being an actor question that you have to ask and answer in a unique way about yourself?

A good question is one to which the answer supplies a ridiculous amount of liberating leverage. A question to which the right answer proves unreasonably effective in moving your career along. A strategic question that’s right for you, even if it looks banal or even ill-posed when asked for other people.

Most importantly, they are very fertile questions that lead to lots of good follow-on questions that generate more energy, via a cascade of self-discovery.

A good place to start looking for your good questions is to think about how people typically mock or typecast you.

In my own case, long before I started writing, a friend used to make fun of me for always “looking for the punchline” in conversations. I decided to own that. It eventually turned into a central skill in both my writing and consulting a decade later.

As an example of typecasting, my first viral blog post, The Gervais Principle, an analysis of The Office, led to an endless stream of requests to do the same kind of analysis for other TV shows. That’s basically typecasting.

Though I refused to let myself be typecast as “blogger who analyzes TV shows,” reflecting on that typecasting led to a series of very good questions and commitments that helped me develop my consulting practice. Some of those good questions, which will make no sense for anyone else, include:

• Am I good or evil? (answer: slightly evil)

• What’s my favorite deliverable medium? (answer: plain email)

• What’s my signature shtick? (answer: 2x2s)

It would take too long to explain how I got to these questions from reflecting on a viral blog post, but trust me, the dots do connect.

Getting to good questions is a process of following a trail of clues, and solving the mystery of who you are as a free-agent. When you’re done, you’ll have a story rather than an answer, one that energizes your career rather than merely removing some uncertainty from it.

And the only way to get to the good questions is to actually get started on your gig-economy career. They cannot be asked or answered a priori.

The gig economy is obviously an economy of mercenaries. The connotation is explicit in the term freelancer, which literally meant a mercenary knight in the European Middle Ages: a “free lance” with no fixed allegiances. The label mercenary is nearly always applied pejoratively (by missionaries of course), in terms of shallow motives like maximizing money. Can we reclaim the term in a positive way, and construct a better understanding of it?

A good place to start trying is with the story of John Hawkwood, a major but obscure figure in the history of 14th century Europe, perhaps the most famous freelancer — of the literal knightly variety — that you’ve never heard of. In a very literal sense, he was the OG indie consultant (the “gangster” part being quite literal).

I’d never heard of him until last month (I learned about him in Barbara Tuchman’s A Distant Mirror, a book about the Black Death and the 14th century), yet he was at least as important in shaping the fate of Europe through the tumultuous decades after the Black Death than many far more famous people I had heard of. Including kings like Edward III of England, Charles V of France, and the popes of the period — Clement VI, Innocent VI, Urban V, and Gregory XI.

His was also arguably a more consequential role than famous mass populist movements like the Jacquerie commoners’ rebellion against the nobility in France.

There is an obvious reason for his obscurity. Hawkwood was a mercenary. A very powerful and important mercenary who often led armies of thousands, but a mercenary nevertheless. And while history is often written by both winners and losers, it is rarely written by the mercenaries who shepherd its less glorious chapters towards resolution.

This is of course a point directly relevant to us. The history of late industrial modernity may be written by/for/about the “kings and popes” of our time — CEOs and Presidents/Prime Ministers — or by/for/about the “commoners” (in the form of say the history of the labor or social justice movements), but it will not be written by/for/about consultants or freelancers. But as in the 1350s-90s, a post-pandemic period that very much resembles today, ours may in fact be the most significant role for a while, even if not recognized as such by the history writers.

Because freelancers today, as in the 14th century, are necessarily, definitionally, mercenaries. In the stories of history as written by winners or losers, it is the fate of mercenaries to be cast in a role that is worse than the good or bad guys in any account: shadowy figures who refuse to pick permanent sides, and subvert, through their very presence in the story, any claims to absolute rightness made by missionaries on all sides.

Then as now, mercenaries were simply outside of the false consciousnesses of the many mutually inconsistent missions they participated in.

The White Company

Admirable as they are in their own ways, missionary leaders like Steve Jobs cannot be role models for indies. We must look in the shadows of history to find the interesting figures we can learn from. John Hawkwood is one such.

Hawkwood’s story is a story of relentless pursuit of greater personal agency through decades where grand missionary campaigns were unraveling in the chaos that was the post-Black-Death world. Details of his life are sketchy, but as best as we can tell, he grew up a commoner, and fought as a longbow archer in early battles in the Hundred Years War leading up the Black Death. He got knighted somewhere along the way, and in the chaos after the Black Death, rose to the leadership of one of the most important free companies of mercenary free lances of his time, known as the White Company (Arthur Conan Doyle apparently wrote a historical novel about them — it’s on my list to read now).

In one sense, especially later in his life, Hawkwood was a corporate CEO — roughly the Erik Prince of his time (but unlike Erik Prince, not born to wealth and privilege). The White Company was superficially rather like the Blackwater of its time: in the thick of the action no matter who was winning or losing.

But in another sense Hawkwood was a true freelancer in the sense we gig economy people use the term. Despite the name, the free companies of mercenaries in the 14th century were nothing like modern private security corporations or even contract-staffing agencies. They were loose networks of at-will, exit-over-voice affiliation closer to open-source projects, or like large networks of individually negotiated subcontracts. This, incidentally, is exactly the kind of structure we’re trying to create with the Yak Collective (which just released its second report, The Old New Home, go check it out).

The “indie” unit of the 14th century military market was the self-provisioned and metonymously named lance (used similarly to “suit” today): an organizational unit consisting of one man-at-arms, one squire, and one page (non-combatant).

Aside: I’m going to start calling my subcontractors on gigs squires and pages going forward.

Lances were free agents themselves, either working by themselves, or signing up for larger campaigns under the leadership of people like John Hawkwood, and bringing on their own subcontractors. But they were not bound to their temporary masters by any grand moral notion of fealty, or to a broader culture of gallantry as the knights of the established nobility were. They were unapologetically just lances for hire, willing to fight for the highest bidder. Which is another way of saying they were skeptical of the grander self-serving justifications driving the missions they fought for.

In his post-Black-Death career as a freelancer and leader of freelancers, Hawkwood featured in almost all the important battles of the late 14th century, often changing sides within a single battle, based on who could pay (or failed to pay).

To a very significant degree, the free companies, rather than the traditional nobility with their vassal troops, shaped the history of conflict in the back half of the 14th century. In fact, a top political objective of kings and popes in starting conflicts between 1350-1400 or so was to try and make the (once useful, but now inconvenient) free lances go somewhere else. Because if they remained unemployed, they simply turned to brigandage wherever they happened to be, preying on nobles and commoners alike (you can see a similar behavior today among a certain class of indies in which I count myself — between gigs they tend to write stuff calling bullshit on the cynically manipulative empty pieties being spouted by missionaries in the paycheck world; a sort of intellectual brigandage).

Make no mistake — OG freelancers like Hawkwood were not nice people. They were at least slightly evil. The general historical view of them is as roving gangs of brigands just living off protection rackets in Europe, in the wake of the devastation of the early part of the 100 years war and Black Death. This view is correct.

What is often forgotten though, is that the missionaries they worked for were no better and often far worse. They just had better PR, based on expensively manufactured justifications for engaging in exactly the same behaviors labeled “brigandage” when practiced by the free companies. Often their behaviors were far worse.

Free Companies and free lances also didn’t come out of nowhere. Many members of the free companies were in fact former nobility and even clergy, who had lost everything in either the “normal” missionary battles of the previous decades, or to the devastation of the Black Death. The OG freelancers were also the OG laid-off collateral damage of “missionary” warmongering, as well as those hardest hit by the impact of the Black Death.

Missionary Endgames

As I noted before, the only real difference between people like Hawkwood, and the missionaries they served, was that they didn’t bother to manufacture elaborate and flimsy justifications for their actions.

Manufacturing justifications for “just” wars was a huge preoccupation with the missionary nobility of the time. Justifications were often based on claims to titles, and relied on marriage or ancestry links, and complex rules of inheritance. The role of the church was to make up these rules to its own benefit. The definition of “just cause” usually favored the highest bidder.

Today, “just causes” are often rooted in claims to charismatic leadership, with the literary-industrial complex of the business world playing the role of the church, manufacturing, via TED talks and cover profiles in magazines, fawning justifications for behaviors later revealed to be significantly less noble than claimed.

These justifications that drove 14th century warfare were very much the kool-aid of the time. They operated in much the same way corporate kool-aid does today.

And as with any larger theater of activity — be it 14th century warmaking or 20th century business building — competing kinds of kool-aid didn’t mix well. Which meant that the endgames got really ugly.

Then as now, mercenaries were the products of missionary endgames. The periods when the kool-aid wears off, and the hypocrisies small and large of the various missionary justifications are revealed for what they are, but the battle still needs to be fought through to a natural conclusion.

The end of this period is particularly poignant. Following a struggle over the papacy between two factions after the death of Gregory XI, the Catholic Church went through a period known as the Western Schism, when two candidate “antipopes” — Urban VI and Clement VII, excommunicated each other, leaving the church in an indeterminate state for decades (they should really be called heisenpopes).

Both were awful, violent warmongers, and though both laid claim to the religious mission of the Catholic church, the schism was entirely about political and economic power. Unlike in the reformation a couple of centuries later, there were no significant doctrinal differences, because doctrine wasn’t the central concern. Both sides were simply out for power.

And unsurprisingly, the free companies and people like Hawkwood played a big role in this particular endgame.

I find this both grimly hilarious and highly validating. Missionary endgames reveal the true nature of missionary postures. The idealism that seems so solid, virtuous and noble at the beginning of a mission is often revealed to be thin fictions overlaid on motives far worse than those of unapologetic mercenaries. The endgame violence missionaries unleash in service of their ideologies dwarfs the more pedestrian brigandage mercenary postures can devolve into.

Yet everybody must live through both beginnings and endings.

Missionary beginnings showcase the aspirational best side of humans, but missionary endgames usually reveal the worst they are capable of. When missionaries grapple with each other in an existential struggle for dominance, they can lay waste to everything else.

Mercenaries are not heroes. But they don’t claim to be either.

Mercenaries are not virtuous, noble people. But they don’t claim any particular virtue or nobility either.

But often in history, they end up acting more heroically than people claiming to be heroes, and exhibiting more virtue and nobility in practice than missionaries.

And not because they are better people, but because they have no choice but to do what they must to continue the game to natural and logical conclusions, long after the missionaries have smugly declared victory, or admitted defeat, and gone home. Because unlike the missionaries, mercenaries typically have to live with the consequences of their actions. They have no safe havens to retreat to once missions unravel, but the fighting continues.

So what then is the essence of the true nature of mercenary postures? What makes them not like the caricatures perpetuated by missionaries? Can we define the idea of a mercenary in terms of a consistent definition with an internal logic?

Trick question. Those games of abstract definitions are for missionaries pursing fragile ideals with varying degrees of hypocrisy and cluelessness. If a posture can be defined in terms of a set of abstractions at all, it’s a missionary posture. To be a mercenary is to defy such clean characterizations.

To be a mercenary is to pay attention not to the abstractions, but to the actual story. To be a mercenary is to not just pay attention the scenes historians put into the spotlight, but to what’s happening in the shadows, both in space and time. To be a mercenary is to believe in life rather than abstract conceptions of it in terms of clean-edged missions with clear beginnings and endings. To be a mercenary is to trust revealed preferences, and actual behaviors, over claims to virtue and grand intentions.

The mercenary is not necessarily anti-idealist. Just someone who plays by “trust, but verify.” The mercenary is not merely about the money, but someone who understands that money is a proxy for the reality principles actually driving conflict, whether in business or war; a surer indicator of patterns of ground truth than missionary claims and kool-aid dreams.

To be a mercenary is to be the yang to the yin of missionaries in the infinite game of life. If this means never being either hero or villain in any story, so be it.

I’m going to continue to develop this line of thought, and look for more interesting historical examples of freelancers and freelancer modes of being and working. If you know of any, send me pointers.

I’m going a little out-of-order in writing this series on executive sparring. In The Guru Factor, I teed up a deeper dive into the sorts of appreciative knowledge that prepare you for sparring, but I’ll table that for a future post and tackle something I think needs to come first: the assumptions you must make about yourself, the client, and other people in constructing what I call the problem social graph, which is the foundation of sparring. This is the configuration of other players in the organizational context relevant to the problems the client is trying to solve through sparring.

Here’s a picture.

The Central Dogma of Sparring

Here’s the core idea: in sparring the best starting assumption to adopt is I’m okay, you’re okay, they’re not so hot.

I’m going to call this the Central Dogma of Sparring.

The reference, for those of you unfamiliar with it, is the 1967 transactional analysis pop classic, I’m Ok, You’re Ok, which inspired a parody titled I’m Ok, You’re Not So Hot.

This starting assumption might seem unreasonably gloomy, and in fact goes against some very good management wisdom (Theory X vs. Theory Y for example, which suggests that the best assumption to make about others in an organization is that they’re actually competent and good by default).

The essence of the sparring assumption is that the client is not the problem, and neither are you, the sparring partner. The problem is other people.

This is not in general a good assumption to make about situations or organizations. So why is it a good assumption to make about sparring relationship setups?

1. First, they are seeking out a sparring partner because they have real problems they want to work through. It takes being fairly severely stymied for someone to seek out a sparring partner, so the problem is likely real.

2. Second, they are seeking out a sparring partner rather than a mentor, therapist, or functional/domain expert, which means they are preparing for conflict, which usually means they see specific other people as the problem rather than say a technical challenge or information ambiguity.

3. Third, though humans are of course prone to primary attribution error (blaming individual traits instead of situational factors for others’ behaviors), if you’re sparring with an experienced senior manager or executive, chances are they’re good judges of character, and experienced at sorting out people vs. situational factors. Otherwise they wouldn’t be where they are.

4. Fourth, though people in general tend to adopt lazy habits when it comes to psychology, convincing themselves that others are the problem so they don’t have to change, this is usually not as much of a factor with the sorts of ambitious people who end up as executives.

In my case, there is a fifth factor — as someone whose reputation was initially established on the basis of rather bleak writings about sociopathic office politics (many of my leads come from writings like The Gervais Principle, Be Slightly Evil, and Entrepreneurs are the New Labor) there is a further selection effect, where people seek me out specifically for those kinds of problems.

I suspect this generalizes too. Those who write with more positive frames are likely to attract engagements that are not structured as sparring engagements. So if you get into sparring at all, chances are there is a streak of pragmatic realpolitik in the way you present yourself to potential clients.

Early in my sparring practice, I was reluctant to accept the Central-Dogma-based starting frame that clients came to me with. I felt the urge to challenge them: what if YOU’RE the problem? What if it’s the system and these other people are basically good and competent? What if this isn’t zero-sum but win-win?

I learned the hard way that this is not a good idea for two reasons.

First: it’s a bad idea to challenge a client’s starter frame until there’s serious reason for doubt, or an obviously better frame is apparent. Unless the assumption that other people are the problem leads to bad contradictions and failures, take that initial diagnosis at face value and run with it.

Second: if people with other problems, requiring other approaches, are getting past your first-call filter, you’re not actually ready for sparring, and you’ll fail anyway. So challenging the Central Dogma is a way of second guessing your own gatekeeping gut-feelings.

In general, if the problem is not “other people” chances are you’ll be able to tell very quickly in the first exploratory call. In that case you should politely decline with a suggestion like “sounds like you need a therapist/life coach/executive coach/domain expert in X, not a sparring partner.”

In the first three cases, it is very unlikely that you can serve in those roles (they call for different personality types, as I’ve talked about before), and should therefore refer the person to someone else.

In the last case, domain expertise, you may want to accept, but then it’s not primarily a sparring engagement, it’s a mislabeled sparring engagement lead that just happens to match your domain expertise (such as general engineering, control theory, aerospace industry, or document/web technology in my case, which have all occasionally come in handy for me).

The Problem Social Graph

In any sort of engagement, not just sparring, you’re talking about, and through, problems. These problems involve the following variables:

1. The client

2. You

3. Other people (individually named, or local “types”)

4. The problem (like, “growth is flat” or “the new product is delayed” or “we need to design this new initiative”)

What makes it a sparring engagement is that you simplify the first two variables by assuming that neither you, nor the client, is part of the problem. If that assumption, based on the Central Dogma, turns out to be wrong, then the engagement should end as a sparring engagement, and likely not be handled by you.

This leaves the other two factors. How should you model them?

If you’re talking to younger people new to leadership roles, or middle management in larger companies, there’s a very good chance that the hard part is the problem itself, possibly because they haven’t encountered that kind of problem before, and you have, at least second-hand. These are the easiest sparring engagements: help them solve the problem-problem, and the people problems resolve themselves.

But if you’re talking to an experienced senior executive, the chances are quite low that the nominal problem is in fact the problem. The problem is nearly always other people. This means you have to model the people situation.

Enter the Problem Social Graph or PSG.

In this, you only include people who are relevant to the problem. And though you might find it a hostile starting default, you have to assume that everyone on the graph is part of the problem until proven not to be.

This is one reason in my Yakverse stories, many episodes are cast as detective mysteries involving the fictional Gig Crimes division, featuring Agents Jopp and Lestrode. Everybody is a suspect until proven innocent.

In my case, people sometimes come to me with one my own frames in mind (most often sociopaths, clueless, losers, which I developed in The Gervais Principle, though I have others), but usually they have their own archetypes as well. The cartoon above illustrates 4 common problem-social-graph archetypes — but these are by no means exhaustive:

1. Bozos (as in Steve Jobs’ “flipping the bozobit”) are fundamentally compromised by being clueless or otherwise being too disoriented to either work with or fix, and must be worked around.

2. Sociopaths (as in The Gervais Principle) are ambitious, politically sophisticated, manipulative people looking out for their own interests rather than the organization’s, and might not be interested in seeing the problems solved.

3. Psychopaths are messed-up people for whom work in the organization is just a convenient place to pursue dark impulses like sadism, sexual exploitation, and so forth (careful: often psychopaths present deceptively, as weaklings or passive-aggressive types).

4. Monsters are people explicitly but covertly pursuing agendas that are actively antithetical to the organization’s mission, such as fraud, industrial espionage, pure revenge motives aimed at specific people, and so on.

5. Good ones are people who show signs of being part of the solution. Often this has strong overlap with people the client likes, gets along with, and is allied with, but the actual definition is: people who already believe in whatever you and the client agree is the right answer to the problem.

Yes is a bleak set of archetypes with which to initially populate the problem social graph, but things are not quite as bleak as they might look.

Remember, you’re modeling a specific set of problems, not a healthy situation. You’re not modeling the organization as a whole, or its healthy but irrelevant parts. You’re leaving out people irrelevant to the problem — and quite often this leaves out a lot of the good people because good people usually find ways to do their jobs despite adverse environments. This means the only “good ones” left in the problem graph are ones who are trapped by the problem itself, unable to function effectively.

You’re isolating the problem subgraph of a larger social graph, and you’re starting with the assumption that you actually have a sense of the right answer to the problem.

Problem Graph Analysis is Not Tribal Analysis

That last point is something that is often missed by what I call the “tribal” school of management analysis. This is a school of thought that tends to ignore the content of the problem, and the situational potential for actual right and wrong answers.

The tribal school takes a “bothsides” approach to all tribes vying for control in a situation, and for better or worse, treats the problem as one of reconfiguring tribal boundaries, or using tribal conflict patterns to help their client win. Being right or wrong about actual problems is irrelevant in this frame. What matters is being more skilled at tribal warfare to ensure your solution prevails, regardless of whether it is the right solution or not.

Occasionally, this is the right approach in a sparring engagement, but that’s actually surprisingly rare. Usually, one of the tribes is actually right about the world, and what needs to be done, in a way that will only become apparent later. So a good filter criterion for accepting clients is whether they think they have a right answer to an interesting problem, or are merely trying to score a tribal victory.

So if you are interested in identifying and working with people who are right and helping them win by virtue of being right, you’re in problem-solving mode rather than tribal analysis mode.

This is not idealism, it is laziness. Being actually right about a problem is usually the biggest factor in being able to solve it easily, not power, executive sponsorship, resources, or tribal affiliations. It is odd that this needs to be said explicitly. The only company I know of that does so is Amazon: one of their leadership principles is “Good leaders are right, a lot.”

So while the setup above might look like it’s merely a fancy way of mapping out the in group/out group tribal boundaries relative to your client, and setting up a tribal analysis politics problem, it’s not. It’s about mapping out the problem boundaries on the social graph.

If you’ve picked the right sort of client to work with, their judgment of “good ones” is likely to be good, or at least consistent with your own definition of “good ones.” It is also likely to rest on an opinion about a set of right answers to problems rather than simple personal likes/dislikes. The ones labeled “good ones” on the graph, as I said, are the ones who believe in the right answer you and the client believe in.

So if there’s a tribal dynamic at work, you’re already part of it ideologically and it’s not a part of the problem per se. For example, I usually end up on the “product driven” tribe within a company rather than the “customer driven” tribe, and allied with technical people rather than sales or finance people. This is because I actually believe they are right more often, and should have more agency in organizations and run the show. This means my sparring practice is an ongoing test of my own beliefs about businesses and management, and a way of being scientific about any appreciative knowledge I bring to the party. As a sparring partner, I’m not neutral. I spar my management ideology, so to speak.

Second, problem graph roles are often already real, simply by virtue of being believed in by your client. The way your client is already dealing with the problem has trusted people they’re deploying as part of their current solution (you’ll almost never walk into a blank slate situation where something isn’t already being tried), and “problem” people they’re trying to fence out in one way or the other. This is a given part of the problem definition. Going against the grain of the problem social graph as it already exists is costly — so work with it unless you figure out that it is wrong.

In other words, the problem social graph is as much descriptive as normative, because it’s already become embodied in the situation by the time you walk in as a sparring partner.

This does not mean tribal analysis is useless. There are times when there is more than one way to be right. There are times when tribal dynamics themselves are the problem and there’s no separate objective problem. Solve the tribal problem and the other problems go away. For those situations, there is plenty of literature out there:

1. Art Kleiner, Who Really Matters

2. Dave Logan, Tribal Leadership

3. Seth Godin, Tribes

4. Bruce Bruno de Mesquita, Alastair Smith, The Dictator’s Handbook

Of these, the only one I actually recommend you read (though you should be familiar with all of them) is the last one, which is both brilliant and very useful when tribal analysis does apply as the proper framework.

But sparring is rarely about tribal conflict. Pure tribal problems tend to be both simple and boring. There is nothing interesting to be right or wrong about. Outcomes merely tell you who is favored by fortune; they don’t teach you something new and true about the world.

Solving pure tribal problems tends to be about simply making the right friends, the right enemies, buying off some people, cutting off other people, firing and hiring. Pure social boundary shaping. There’s surprisingly little to spar about. Either you have enough authority within the problem scope to reshape the tribal structure, or you don’t, and you have to either fall in with somebody else’s tribal agenda or leave the situation. Often, people call me after they’ve already figured out and solved the tribal part of the problem with a reorg or layoffs/hires, and are finally face-to-face with the actual problem.

What if after solving the tribal problem, there’s nothing else left to solve? That’s a pure tribal problem.

I’ll make a stronger assertion that I’m less confident about: if a problem becomes a pure tribal analysis problem, it’s generally not worth solving for intellectual interest, only for material rewards like money.

If the problem is a pure tribal problem, you’re very likely in some sort of Hobbesian endgame of market harvesting and extraction. There is no real vision or wealth-creation activity underway that makes problems interesting and worth solving.

A good sign is that sales or finance people dominate utterly (see my Yakverse story, Maneuvers vs. Melees). If you’re working with clients who are part of what I consider the creative, innovative side of the house — mainly engineering and marketing — chances are there are actual problems to be solved, that are worth solving, with right or wrong answers.

Sparring as Anti-Therapy

Let me close with one more remark on problem social graphs. In transactional analysis, the condition I’m okay, you’re okay is the foundation of healthy, game-free relationships that are rewarding to all parties within them.

This means sparring is a sort of anti-therapy, where you’re helping create broader positive effects from a healthy relationship between you and the client — two healthy people.

But there’s still a problem. It’s just not a therapy problem. And odds are (based on the priors that lead to sparring engagements) it’s a people problem created by some good people being right, and some problem people being wrong, about something real.

There may be tribal dynamics involved, but they’re not the main focus. The focus is figuring out the right answers, finding the people who believe in them, or can be persuaded to, and acting on them to solve problems, thereby learning whether you were actually right.

Helping the truth prevail, in short.

Of course this is an idealization. Of course, both you and your client have your share of psychological problems. Of course people you cast in various roles informally — bozos, sociopaths, psychopaths, monsters, good ones — are more than those reductive analytical labels you attach to them. Of course you might be wrong about your solutions to the problems.

But the starting point is preparing to act, by setting up a problem social graph, based on the belief that you’re right rather than wrong. Sounds tautological but it’s surprising how many people don’t get this.

This is a simple problem setup that will of course change as you think it through. Often, apparent “good ones” will be relabeled part-of-the-problem people. Less often, as you understand a situation, people initially tagged “problem people” might suddenly appear in a new light as part of the solution, or at least not relevant to the problem: red herrings.

These reconfigurations and relabelings are why it is not a tribal analysis problem. The graph changes as your understanding of the problem improves, with new facts becoming apparent. Behaviors presumed to be “bad” turn out to have harmless explanations, while other behaviors presumed to be “good” come to be seen as harmful. Working through this process like a detective solving a murder, gradually getting the right problem social graph converge with the right problem framing and solution, and acting on the answers you discover and learning whether they improve the situation or worsen it — that’s the essence of sparring.

This means success at sparring often amounts to setting up the initial problem social graph approximately correctly early, and refining it well as you progress. If you tend to get your initial setup very wrong very often, you’re not going to be effective as a sparring partner. Badly misreading a situation is not a good look for a sparring partner.

In other words, good sparring partners are right, a lot. Just like leaders at Amazon are expected to be. This is the test of the knowledge you bring to sparring. How do you get to where you’re right a lot? We’ll explore that later in the series.

I’ve mentioned my fellow indie consultant Tom Critchlow in this newsletter a few times before. In this guest newsletter, Tom describes his version of the practice, and explores his mental model of sparring practice as a sort of tenure for consultants. For those who have been following this series (Part 1: Introdution to Executive Sparring , Part 2: The Guru Factor), this post should serve as a helpful second example of the model. — Venkat

I’ve long aspired to be an indie consultant with a default mode of sparring work. From reading about it on Venkatesh’s website to experiencing it in brief flashes on consulting projects (often waking up on the mat, dizzy, wondering what hit me), sparring has been an aspirational end goal; something to quest towards.

I’ve been an indie consultant for ~6 years and have gradually managed to secure sparring consulting engagements. But rather than operate on stand-alone sparring engagements they’ve been embedded (often at the end of) a “more traditional” consulting engagement focused on deliverables and such.

However, I recently participated in the first sparring training dojo as part of the Yak Collective and came to the realization that pure consulting sparring is an odd thing to quest for. For starters, it’s not very lucrative, as Venkatesh outlines:

I estimate that a good sparring partner can support no more than half a dozen active clients in any given month without burning out. And it typically takes half a dozen meetings of 60-90 minutes across six months or so for the sessions to become truly high-value.

Most importantly, though you might be able to bill at a high rate, due to the individualized, automation-resistant, time-intensive nature of it, you’re not going to get mega-rich doing it. Sparring is an artisanal kind of consulting. You can make a decent living from it, but if you’re solving for big money from a 4-hour work week, you should look to a different kind of consulting business model.

Introduction to executive sparring

Contrast this to a more traditional consulting gig that might be 5 figures a month and involve several days of work a week.

So how can it be that sparring is such an aspirational model for indie consultants?

Thinking vs Doing

I believe the answer lies in the aspirational nature of sparring work — in short, it’s thinking for a living.

Maybe the best analogy is: reaching a point as an indie consultant where you can generate enough clients to be sparring as your sole consulting work is like reaching tenure. You’re set.

Let’s illustrate with a dumb graphic:

My theory goes:

When you start out consulting most of your billable hours are spent doing. You get hired for things like writing content, managing ad campaigns, photo shoots, executing campaigns, building websites.

As you get more senior, more experience and as you get access to more senior executives the work starts to include thinking. Your website design project is so good that you’re included in the brand refresh project, your marketing campaign was so good you are invited to restructure the marketing org, your project management was so good you’re invited to help shape OKRs for the company, etc.

Thinking for a living is more fun.

Thinking – the work where you’re looking at client’s organizations as complex systems with access to real decision makers is where the rewarding high value work comes in.

As you get a taste of thinking for a living it becomes tempting to want to spend all your time thinking.

The (wrong!) mental model here is of the indie consultant rising to partner status — a partner at McKinsey or Bain spends all day long thinking, not doing. So we chase the same as an indie consultant — aspiring to get paid handsome sums of money to think all day long.

Except. As an indie typically there’s no one to delegate to.  So you need to roll up your sleeves and blend doing and thinking. (I’ve written about this concept under the label “strategy and stewardship” in this post the strategic independent).

This is where I find myself 6 years into my indie consulting career. Blending executive sparring with executive level capacity building for clients. This might look like:

• A weekly sparring session with the CMO, and:

• 2-3 days a week working with the marketing org on various strategic initiatives

The first feels like getting paid to think, the second feels like getting paid to do.

My hunch however is that this is a local revenue maximum. I often work with clients where I get paid approximately a sparring day rate across all my work — both the thinking and the doing — and this lets me bill well and log a good number of hours per client.

While I’d love to abandon the doing work and focus on the thinking — on the sparring — I think it’s a mistake to prematurely optimize for thinking for a living. Especially while I am young enough to have some doing left in me.

But — 6 years into my indie consulting career — I’m laying the foundation for transitioning to sparring in the next few years. Sounds crazy? There are some good reasons.

The Benefits of Sparring: Owning your Time

So is sparring just an intellectually stimulating but less-well-paid version of consulting?

No — there are some clear benefits of chasing sparring as consulting.

Firstly, I’m a decade younger than Venkatesh and still able to pull stunts like billing 3 days a week to one client and 3 days a week to another client. Dipping into energy reserves and sprinting on work for sustained periods throughout the year. Much like physical fitness I can already feel my capacity for this declining.

Secondly, doing captures a large portion of your head space. When you’re managing a marketing org you can’t “take Thursday and Friday offline to write blog posts”. Operational work requires high availability and an “always-on” mentality. Especially if you’re in doing mode for multiple clients at once. It can be incredibly demanding on your time and any side project / writing / teaching / long-term research gets consistently interrupted, paused or put on hold.

Thirdly, doing is not resilient work. Doing work is much more reliant on the economy, access to local clients and more. Conversely, sparring work thrives in uncertainty as Nicolas Colin wrote in Launching My Executive Sparring Practice:

What do you do as an executive in a world perpetually ridden with uncertainty—because of the nature of computing and networks, because of macroeconomic ups and downs, because of the public constantly threatening to erupt in revolt, because of activists that are all too happy to fuel that perpetual fire to force you to comply with whatever they demand? 

What you do is find a good sparring partner who will help you navigate the uncertainty with clear strategic insights and frequent adjustments to your worldview, helping you to constantly refine your long-term thesis.

Shifting to remote consulting has been a big strain on my consulting practice — not so much on Venkatesh’s.

In a nutshell, sparring work is long-term stable, well-paid work relative to the amount of headspace and energy required.

Tenure-track not Partner-track

Which brings me to the (correct) mental model — not of an indie consultant reaching “partner” but of indie consultant reaching “tenure”. The ability to consistently generate sparring clients is a great way to earn steady money, thinking for a living and with a reinforced OODA loop that connects the value you create for clients to the value you generate personally from sparring. As Venkatesh outlined:

You and the client are each driving complementary OODA loops that intersect in the practice of sparring. You are inside each other’s OODA loops in a way that mutually reinforces both your learning processes. Yours is an appreciative learning process, theirs is an instrumental learning process.

The guru factor

The ability to earn good stable money while keeping a significant amount of time and headspace free is not to be under-estimated. It maps to the idea of a tenured professor in the way that they are free to explore self-directed initiatives and projects.

Let’s update that doing/thinking chart form above to include a third wave of “self-directed” work:

As the doing work gives way to sparring work, so too does sparring work give way to self directed work. I’ve plotted myself and Venkatesh (roughly) on the chart to illustrate roughly where we both land.

Venkatesh, obviously, has been busy: Ribbonfarm, ArtofGig, Breaking Smart, Refactor Camp, Tempo, being a Berggruen Fellow, book #2 etc and is now earning a not insignificant income from self-directed projects.

And this is the end goal — the aspirational nature of yearning for sparring work — it’s that it’s a path, an enablement to get to a place where you can have some model of “tenure” to explore your own self-directed projects without having to force those projects to live on their own immediately. You leverage skill in doing into sparring work and you leverage skill in sparring work to get to self-directed projects and revenue.

Personally, I’ve updated my mental model. I’m no longer chasing sparring as it’s own goal but rather chasing sparring as a means to create leverage to maximize time, energy, and self-directed interests.

The Compound Interest of Networked Writing

The final point I’ll make here is about how to chase sparring. For indie consultants who want to follow this path (and to be clear there are other paths to follow) the evolution and progression across this chart from doing -> thinking -> self-directed is defined by the volume and quality of the thinking in public.

As Venkatesh illustrated in the guru factor:

About 90% of your effectiveness as a sparring partner derives from the depth of your appreciative world view, developed and expressed through critical reading, writing, podcasts, and talks. Only about 10% depends on your in-session sparring skills.

So we might overlay on the graph above a model of thinking in public (writing or podcasting or public speaking or vlogging):

Thinking in public is both a product of spending time sparring with clients and a necessary driver of getting sparring clients. In short, chasing sparring as a consulting model (and ultimately chasing the self-directed “tenure” model) requires investing in thinking in public, creating a self-reinforcing feedback loop of clients hiring you for thinking and higher quality thinking in public.

Last week, I introduced the idea of executive sparring as a practice distinct from coaching. Continuing the series, this week I want to talk about the most crucial aspect of being a sparring partner — developing and embodying a deep, appreciative world view complementary to that of leaders of organizations, which makes you a useful foil to them in their work.

For better or worse, getting into the sparring partner business means coming to terms with a growing perception of a “guru factor” around what you do — even if you are younger and less experienced than your clients. This is a fraught business. It creates serious reputational jeopardy. There is a fine line between “guru” and “laughing stock” (or to use a more appropriate modern term, lolcow).

The jeopardy turns into double jeopardy if you happen to be Indian. And into triple jeopardy if your middle name happens to literally be Guru.

I’m not complaining. Just noting obvious facts.

So a good way to start figuring out the core of the appreciative worldview that can potentially form the core of your sparring practice is to own the guru-jeopardy and ask — what am I a guru of?

Take a stab at answering that question before we unpack the concept. As a hint: contemporary Western usages, such as unix guru, design guru, and of course, management guru, are actually closer to what I think is the correct understanding of gurudom than the literal translation of teacher.

The core of gurudom is not a teacher-student relationship, but a seeker-world relationship.

Nerding out over the innards of Unix, and developing an appreciative worldview through the lens of that nerding out, is closer to the true spirit of gurudom than being good at teaching computing skills. Gurudom is nerddom plus a certain guru factor.

Being a computer science teacher makes you a good person to learn (say) sorting algorithms or good Python style from. But being a Unix guru makes you fun to spar with about the future of computing, and an interesting companion for explorations of that future. People can go as deep as they like with you, knowing that you can keep up, even if you don’t agree with them.

Sparring and Appreciative Knowledge

Appreciative world views, which are at the heart of guru factors, emerge via accumulation of appreciative knowledge, a term due to urbanist John Friedman, who defines it in his book Planning in the Public Domain as follows:

The social validation of knowledge through mastery of the world puts the stress on manipulative knowledge. But knowledge can also serve another purpose, which is the construction of satisfying images of the world. Such knowledge, which is pursued primarily for the world view that it opens up, may be called appreciative knowledge. Contemplation and creation of symbolic forms continue to be pursued as ways of knowing about the world, but because they are not immediately useful, they are not validated socially, and are treated as merely private concerns or entertainment.

Friedman uses the term manipulative knowledge in opposition to appreciative, but he doesn’t mean manipulative in a Machiavellian sense. He simply means knowledge of how to actually do things to drive change in the world, accumulated by actually trying to do those things.

I prefer the term instrumental knowledge for this. I previously wrote about appreciative versus manipulative (or instrumental) knowledge here, if you want to go deeper, but in this post I want to apply the distinction to consulting work, especially sparring.

Here is the big idea to keep in mind:

About 90% of your effectiveness as a sparring partner derives from the depth of your appreciative world view, developed and expressed through critical reading, writing, podcasts, and talks. Only about 10% depends on your in-session sparring skills.

In this, sparring skill is similar to negotiation skill. In negotiations, 90% of success depends on the preparation you do before you sit down at the negotiation table. Only about 10% depends on your negotiation skill.

Gurus versus Pundits

These activities at the core of strengthening appreciative capacity — reading, writing, podcasts, and talks — are not primarily marketing activities, though they do serve a marketing function as a side-effect. They are integral to developing your capacity for sparring, but pursuing them for the sake of getting better at sparring doesn’t work.

I think of these activities as nerdy reflection, something very few people have much time for. It’s a time-wasting, bunny-trail-exploring nerding-out over the significance of things you’re seeing in your life.

So how do you develop appreciative capacity? The linked OODA-loops diagram above should convey the gist. You and the client are each driving complementary OODA loops that intersect in the practice of sparring. You are inside each other’s OODA loops in a way that mutually reinforces both your learning processes. Yours is an appreciative learning process, theirs is an instrumental learning process.

This means you cannot become a “guru” at something by deciding to study all the classics relevant to your interests. That turns you into an erudite scholar, an entirely different thing.

Why?

For much the same reason you cannot become a unix guru by reading scholarly papers and books about operating systems. You have to be at the keyboard, messing around with shell scripts, hacking away.

More generally, you cannot develop appreciative capacities in instrumental ways, anymore than you can develop instrumental capacities in appreciative way.

Here is another way to think about it: you cannot learn how to swim by reading a hydrodynamics textbook on dry land. But equally, you cannot figure out the molecular structure and chemical properties of water simply by swimming around in it.

This is easy to get when we’re talking about swimming versus chemistry, but gets a little tricky and very meta when we are talking about instrumental versus appreciative approaches to book-learning itself.

The thing is, instrumental means develop prowess at instrumental capabilities rather than appreciative capacities, even when the object of the learning activity is appreciative knowledge. You do have to develop your instrumental scholarship capacities to some degree, but they can’t be the primary focus.

That is not to say becoming an erudite scholar with a command over the canonical texts of a tradition is not a worthwhile thing. Go for it if that’s your thing. It just doesn’t develop sparring capacity or a guru factor.

If you are a completist about Sanskrit words for these things, the word for erudite scholarship has been imported into English as well: pundit (in India it is usually spelled Pandit, and is a common last name, as is Acharya, which is roughly synonymous). The differences are worth noting:

1. Pundits engage in scholarly debate with each other within an institutional tradition, and are governed by internal conventions and hierarchies. Gurus spar with all interesting comers, be they beggars or princes, and in any context.

2. Pundits can become institutional stewards of traditions, but rarely create new traditions. Gurus often create new traditions, but usually end up on the margins of even traditions they helped create.

3. Pundits often gain a great deal of worldly fame, wealth, and power, and this is viewed as just reward for their institution-building work. Gurus on the other hand, rarely do, and if they do, are viewed as having sullied their reputations.

4. Pundits represent and embody institutional epistemic authority, and take offense at challenges to that authority. Gurus have no such formal locus standi in relation to the traditions they may draw upon, and are rarely offended by challenges to their authority because they claim none to begin with.

5. Pundits often participate in visible and ceremonial and ritual forms of knowledge performance as the core of their work (traditionally, conducting temple services or sacrificial rites). Gurus typically do not. In consulting, this maps to doing talks or workshops around fully formed theories, versus informal “theorizing” discourses.

6. Pundits often present in highly ceremonial and authoritative ways, with a strong and consciously crafted halo, but often accompanied by ritual protestations of humility. Gurus stereotypically present in self-effacing ways, often being mistaken for beggars, but often present in poorly socialized ways, as irritable curmudgeons, or unpredictable trolls for example.

7. Pundits typically enjoy teaching, usually do it very well, and seek out opportunities to do more of it. Gurus typically don’t enjoy teaching, usually do it poorly, and seek excuses to avoid doing it.

The tension between pundits and gurus is so commonplace, it is practically a trope in Indian history. Similar archetype pairs exist in other traditions. In the Christian tradition, the distinction between regular and secular clergy is somewhat similar, as is the one between research and teaching faculties in universities.

A loosely similar modern one is the Straussian distinction between “great thinkers” and “scholars,” though that one is fraught with additional political-philosophical baggage, and conservative norms of reverence of ancient traditions that makes it not quite analogous.

Why does all this matter?

It matters because appreciative knowledge is not punditry.

Punditry is the result of an instrumental approach to appreciative knowledge. Gurudom by contrast, is the result of an appreciative approach to instrumental knowledge.

(for completeness of the 2×2, an appreciative approach to appreciative knowledge makes you a critic, and an instrumental approach to instrumental knowledge makes you a vocational learner).

In the world of consulting, gurus favor freeform sparring, backroom influence, and proximity to consequential decision-making. Pundits favor developing and delivering workshops and talks, building scaled institutions, and crafting powerful public images. Pundits develop personal brands (not always strong ones). Gurus develop reputations (not always flattering ones).

Both usually do at least a little of the other kind of activity out of necessity, but basically you have to choose, and choose fairly early, which path you want to go down. It’s like figuring out if you’re left-handed or right-handed. I’ve done my share of workshops, public speaking, and teaching. But none of that stuff comes naturally to me, I’m not very good at it, and I don’t enjoy it much. For better or worse, I’ve wandered down the guru path rather than the pundit path.

Peripheral Learning

What do I mean by “appreciative approach to instrumental knowledge”?

A good way to think of it is: Gurudom is weakly codified appreciative knowledge of the sort that develops on the peripheries of instrumental practice. The kind of knowledge that develops when you let attention wander towards the margins of instrumental activity, to metacognitive musings around it. You do have to play, but if playing well becomes the whole point, you’re better suited to playing excellence than coaching excellence.

Here we run into a problem though. Letting your attention wander to the margins of instrumental activity is dangerous. If you do it in mission-critical situations, you can become distracted and make costly errors.

This is one reason the best sports coaches often turn to coaching after mediocre career as players. A weakness for metacognitive distraction that diminishes performance on the field turns into a strength in coaching.

In live-fire situations, letting your mind wander to metacognitive concerns is often a sign of an even deeper weakness. It is a sort of displacement activity triggered by fear or anxiety, rather than actual philosophical curiosity about meta-concerns. This sort of person does not turn into a good coach, because they typically exit the live game with too much insecurity to be effective foils to better players.

There is, however, one activity which allows you to safely let a significant portion of your attention wander to the margins of instrumental activity.

This is of course sparring.

Linked Learning Loops

We are now in a position to appreciate the linked-loops diagram at the top of the page, representing the sparring process.

Sparring is a safe-fail activity immediately adjacent to live-fire activity. It benefits from a little bit of peripheral attention-wandering. It benefits from the kind of experimental trial-and-error attitude, accompanied by mindful critical attention, that is fueled by things you notice out of the corner of your eye.

So appreciative knowledge developed through the work of peripheral attention during sparring is what compounds gurudom, and makes you better able to spar.

This might sound like “the best way to get good at sparring is to do more sparring,” but that’s not quite it. While there is a component of mindful deliberate practice, it is only necessary, not sufficient, and it’s not unique to the sparring partner. The principal too, has to be mindful in that exact same way during sparring sessions, letting attention go to peripheral vision to a far greater extent than they would in the ring during an actual bout.

What makes the sparring partner role different is that you take the fruits of marginal attention around sparring and convert them into nerdy explorations which then turn into fodder for your own private pursuit of things that interest you (via writing, reading, and such), creating a growing store of appreciative knowledge. It is a virtuous cycle that powers growing guru-dom. This is the red loop in the diagram.

The yang to that yin is the loop experienced by the client you are sparring with. In the best case, the same sparring experience is cashed out differently. For the client, the fruits of marginal attention around sparring is converted into superior live-fire application, which leads to a growing store of instrumental knowledge. This is the blue loop in the diagram.

These two loops — both of which are metacognitive OODA loops with the sparring serving as an “Orientation” activity for both parties — are at the heart of sparring.

Where this beautiful symmetry breaks down is in the relative value of the two loops. The client’s loop passes through the real world. The sparring partner’s loop passes through the adjacent possible of the real world. The former, by virtue of having more skin in the game, is worth much more money. This is why the client typically pays the sparring partner rather than the other way around.

If the sparring sessions go well, the client will be forged into a better live-fire decision-maker and leader, while you will inevitably develop tendencies of a guru-like nature, whether or not you want them.

Recognizing Gurudom

The process I’ve described above should make it clear that you cannot actually choose to become a guru. Equally if you’re doing certain things well enough to be paid to continue doing them, you cannot avoid becoming a guru either.

This means gurudom is a tendency in your life that you recognize and come to terms with at some point, based on how people are choosing to relate to you. Including both how they are laughing or sneering at you, and how they are praising and appreciating you.

Again, think unix guru, design guru, or management guru. Not guy with long beard running a commune with sex slaves in the basement and Rolls Royces in the garage.

Some willingly lean into gurudom, some have it thrust at them (and some, like me, have it hang over their entire lives thanks to nominative determinism — I’ve been the butt of “guru” jokes since age 10, thanks to my middle name).

Gurudom is not primarily about a teacher-student relationship. A guru, or equivalent concept in other cultures, is rarely primarily a teacher, though teaching activity usually occurs on the margins of gurudom. The concept of a guru combines four elements that all play a role in sparring:

1. Reluctant teaching that is closer to preceptorship

2. Individual striving for esoteric appreciative knowledge

3. The capacity to keep up with others on their journeys

4. A degree of genuine (and costly) indifference to worldly rewards

Of the four, the teaching element in a conventional sense is the least important. It is the one that can be most easily delegated to others, and often is, at the first opportunity.

In the traditional Indian education model, known as the guru-shishya parampara (literally, “teacher-student tradition”), only the very earliest stages — the first few years — look like conventional teaching, focused on drills, repetition, and homework. And these are often handled by senior students of the guru, much like how graduate students do much of the actual teaching in American universities.

Teaching responsibilities can in fact seriously interfere with the actual responsibilities of gurudom, which are closer to “research” in the academic sense, but not quite the same.

As a result, gurudom finds its best expression via two core activities: sparring with peers in the same intellectual weight class, and through the ongoing development of an appreciative world-view. This latter activity can be understood as being a preceptor, which is closely adjacent to, but not the same as, being a teacher.

The natural fit with sparring and preceptorship is why faculty in American research universities are generally terrible teachers, prefer PhD students to undergraduates, and prefer to treat those PhD students as much as peers as possible, often handling actual advising responsibilities with great reluctance.

As with universities, which evolved in the West from the priesthood, with its vows of poverty and chastity, the guru tradition too has an uncomfortable relationship with worldly wealth. In India, gurus were traditionally expected to live in simplicity and relative poverty in humble ashrams in the forest, outside the civilizational core. They were expected to spar with kings, train princes, groom their own replacements, and produce pundits for the institutions that needed them.

The word is usually translated as hermitage in English, but modern day ashrams run by literal gurus are often relatively luxurious retreat destinations, suitable for entertaining kings and presidents, with great comfort lurking beneath a facade of theatrical simplicity.

Management gurus of course, usually skip the simplicity signaling and go straight for the 5-star leadership retreat experience in lieu of real ashrams.

The spirit of the ashram tradition though, is today best represented by the research laboratory, rather than a luxurious leadership retreat campus.

Emissary of the Adjacent Possible

Past the basic drilling stages, in the traditional Indian model, the student progresses to something that resembles more of a sparring process, focused on debates and disputations around classic texts.

These start out as rehearsals of traditional arguments around age-old questions, heavy with appeals to authority, and progress to increasingly free-form open debates on the “live” questions of the day. By the time the student gets to advanced stages, striving to best the master, in “the student becomes the master” mode, is the expected mode of engagement.

Here a fork in the road appears. The princes of course, go back to their kingdoms, assassinate their fathers, and ascend to their thrones. As adults, they may return to spar with their gurus.

As for the rest, some head towards punditry — stewards of the tradition within institutions embedded in secular life within the civilizational core. Others stay on the margins, and head towards gurudom in their own right — setting up the equivalent of experimental laboratories for their own nerdy reflections as best as they can.

This developmental path is not restricted to intellectual traditions. You can see a similar path in Indian music education, which begins, as in the West, with young students practicing scales and set compositions in ragas, and moves on to learning to render compositions in particular styles, peculiar to specific traditions. But at this point it diverges from the Western music tradition, and heads towards the free-form structured improvisation that is raga performance. These performances often involve a strong element of sparring with accompanying musicians (similar to call-and-response jamming as in jazz) known as jugalbandi.

Some version of this can be found all over the world of course. In Japanese martial arts for instance, we find the idea of kihon (drills), kata (set forms), and kumite (sparring). In the medieval European tradition of gallantry, young noble-born boys were sent off to serve as squires to peer knights, where they learned jousting, horsemanship, and other knightly skills.

Historically, this kind of education has always been something of a luxury, since it cannot be delivered at scale. Around the world, it was largely only available to princes being groomed for imperial leadership roles, or commoner students showing some promise as future pundits and gurus. There is a reason it is generally restricted to business executives today — paying someone in your intellectual weight class to spar 1:1 with you is not cheap.

For those providing this kind of education, the core activity — call it research, call it nerdy reflection, call it saddling senior students with the real teaching duties and sneaking off down bunny trails — became a way of life. Those who adopted this way of life, whether they were called gurus or something else, primarily engaged with the civilizational core by sparring with its leaders — and those being groomed for leadership — at the margins.

That is the essence of the guru factor — your stake in the margins of civilization, as an embodiment and emissary of the adjacent possible, bringing appreciative knowledge to life in the real world.

That’s a rather nebulous thing to try and be. But the core is simple enough — spar, nerd-out, write/speak about, spar some more. Pick people who you can keep up with, and who can keep up with you, as your sparring counter parties, regardless of what they can pay you. Recognize the adjacent activity of punditry and consciously choose one or the other.

The rest is just a matter of doing this steadily, for years, making money as best you can along the way.

Next time, we’ll talk about the actual content of accumulating appreciative knowledge, the content of your guru-factor, but to set it up, consider the opening question: what are you a guru of?

“Nothing!” is a perfectly fine answer.

Gurudom is something that creeps up on you after years of messing around, nerding out over things that interest you, and sparring with people. If you do have an answer, it is probably something that happened when you weren’t really looking.

For me, it happened to be organizational sociopathy and office politics.

The good news is, if you’re a guru of something, it isn’t a box that contains and confines you. That’s a price you pay for the rewards of punditry.

To be a guru of something is to look at the world through that thing rather than being put in a box defined by that thing. There are no restrictions on what you’re allowed to look at. The thing you’re a guru of is merely the appreciative perspective on the world people associate with you.

In other words, if people want to learn about X, they go looking for a pundit of X. If they want to see some aspect of the world through X, they go looking for a guru of X.

You can now ask useful follow up questions.

• Is your relationship to appreciative knowledge closer to punditry or gurudom?

• Is that what you actually want?

• If you somehow ended up on the wrong side of that divide relative to your natural inclinations, how do you cross over?

• How should you relate to those on the other side? As complements? Evil twins? Deadly rivals?

All useful questions, which we’ll get to in the next part.

For a while now, several of my fellow indie consultants have been asking me to share more details about executive sparring, a style of 1:1 consulting that I’ve been developing and practicing for almost a decade now. Before I get into it, I recommend watching this short video of Mike Tyson, at age 53, sparring with his trainer, to get a visceral sense of what I’m going to be talking about.

Yes, at their most intense, executive sparring sessions can feel like the intellectual equivalent of this. Not all sessions are this intense, or this combative, but the most valuable ones — both for me and for the client — are.

Like the sparring partner in this video, an executive sparring partner would not last very long in the ring in an actual competitive bout with a high-functioning executive client. Yet a good sparring partner can provide a great deal of value in a non-bout sparring session.

At this point, I’ve worked as a sparring partner with several dozen senior executive clients (some of them for years) in organizations ranging from startup scale to Fortune 100 corporations, and across half a dozen industries. Sparring work now constitutes almost the entirety of my consulting practice. It’s a fairly demanding and intensive kind of highly personalized 1:1 support work, and is neither cheap, nor very scalable. So unlike things like training workshops, or process/capability consulting, it’s not the kind of thing you can offer at scale. You’re not going to rack up hundreds or thousands of clients in a few years. You’re not going to be sparring with an auditorium-scale audience. Writing a book about your business ideas won’t make it any more efficient. You’re not going to be automating any of it.

I estimate that a good sparring partner can support no more than half a dozen active clients in any given month without burning out. And it typically takes half a dozen meetings of 60-90 minutes across six months or so for the sessions to become truly high-value.

Most importantly, though you might be able to bill at a high rate, due to the individualized, automation-resistant, time-intensive nature of it, you’re not going to get mega-rich doing it. Sparring is an artisanal kind of consulting. You can make a decent living from it, but if you’re solving for big money from a 4-hour work week, you should look to a different kind of consulting business model.

Teaching Sparring

Earlier this week, after conducting a first informal sparring workshop for a few friends, I decided I was finally ready to write about it.

While this series is primarily going to be for consultants who want to do this for money, it should also be of value to executives, since a significant part of being a leader is serving as sparring partner to peer executives and senior reports. In fact, most sparring happens among peers within organizations or industries. Executives hire people like me mostly when they cannot find suitable sparring partners within their own organizations or its immediate institutional neighborhood — which is as it should be.

Sparring is primarily valuable for senior executives who have already risen through the ranks of individual contribution and middle management (though that journey can happen surprisingly fast in startup environments), and is an alternative to the default style of working 1:1 with executives, which is generally called coaching. Unlike in sports, the two are hard to combine for reasons I’ll get to.

A question I’ve wondered about over the years is: can sparring skills be taught, assuming a broadly suitable temperament and an aptitude for it?

I’ve been at it for 9 years, and it probably took me 3 years to get it to consistently good enough that I felt I could do it with almost anybody. Can that learning curve be shortened?

Yes and no.

Some aspects of the skill-acquisition can be speeded up. Some things that took me years to figure out, I can probably teach in a day or two. But other elements of getting ready for the role — like reading widely and deeply about technology and business to develop an appreciative worldview of it (a sparring Weltanschauung if you will) took me decades (I’ve been reading business and technology books since I was a teenager), and I don’t think can be speeded up. I think will take anyone decades.

Fortunately, if you’re interested in developing sparring skills at all, you’ve probably already been doing the right kind of preparation anyway for other reasons, including plain curiosity. So you’re probably more prepared than you realize. It’s a question of recognizing the significance of what you’ve been doing, wax on, wax off style. But you’re probably not as prepared as you need to be.

In the pilot workshop a few days ago, I finally got a chance to try and explain and demonstrate the model to a small group of six willing guinea pigs via a small workshop. The participants were six indie consultants like myself, most of whom already had significant experience working with senior executives in a similar mode, but wanted to refine their practice and understanding of it, and make it more legible to themselves, to be able to continuously improve their practice.

The pilot workshop worked well enough that I decided this idea is actually in a teachable state, so I’m probably going to offer an improved version of it in the future, but before I do that, I decided I need to write up some of the core ideas.

So this is the first in a series of what I expect will be 4-5 newsletters covering the core ideas of sparring (the rest of the series is going to be paywalled though 😈).

In this introductory part, I want to do three things:

1. Define sparring

2. Distinguish it from other 1:1 relational practices like coaching

3. Situate it in the broader context of executive development

In the rest of this series, I will work through how to actually develop sparring partner skills, and a consulting business based on those skills.

Sparring as Live Theorizing

The goal of sparring is simple: to improve the quality of live theorizing executives do around their ongoing work.

The central insight driving the practice of sparring is that busy executives typically do not have time to do more than dip into fully formed theories of management or leadership, delivered through books, or executive education. Even the “case method” MBA students learn, which rests on live conversation/debate in groups, is too far removed from actual live situations to serve the purpose.

If you’ve ever read an HBR case study, you’ve probably had that uncanny sensation of looking at the business problem-solving equivalent of stock photography. A lot of fresh MBAs, who earned their degree perhaps too early, come across that way to me when they talk. They come across as smart, prepared, and with interesting things to say, but fundamentally lacking in serious exposure to live-fire, high-stakes executive decision making.

For strong executives, theorizing happens in a rough-and-ready form in the context of live action, working out how to act in, or respond to, specific situations unfolding now, involving specific people, constraints, and timelines.

Weak executives, by contrast, often come across as eager to avoid, sidestep, or ignore the hardest parts of the situations they are being paid the big bucks to handle. Much of their thinking happens on the sidelines, around situations that might unfold. Often their theorizing is too polished and refined — a dead giveaway that they’re far from the live-fire action.

Consider the analogous situation in boxing. A top boxer might study videos of an opponent for an upcoming title fight with their trainer, form a hypothesis about their weaknesses, and “workshop” bout strategies for that specific upcoming bout with a sparring partner. For example, Muhammad Ali famously did exactly that in preparing for his Rumble in the Jungle bout against George Foreman, abandoning the “float like a butterfly, sting like a bee” style he was famous for, and adopting a “rope-a-dope” style designed to wear out Foreman. Wikipedia describes how that came about:

According to photographer George Kalinsky, Ali had an unusual way of conducting his sparring sessions, where he had his sparring partner hit him, which he felt “was his way of being able to take punishment in the belly”. Kalinsky told him: “Do what you do in a training session: Act like a dope on the ropes.” Ali then replied: “So, you want me to be a rope-a-dope?”

According to Angelo Dundee, Kalinsky told Ali: “Why don’t you try something like that? Sort of a dope on the ropes, letting Foreman swing away but, like in the picture, hit nothing but air.” The publicist John Condon popularized the phrase “rope-a-dope”.

If this anecdote is accurate, than Ali’s intellectual sparring partner, as opposed to the one in the ring, was the photographer Kalinsky. It’s weird how often this is how it ends up working. You might talk for hours, but in the end, it’s one casual phrase or thought that ends up unlocking the critical idea. My very first client said as much to me — that after twenty hours of chatting, the value I delivered all came out of one phrase I happened to drop casually in thinking through a problem: “penny auction.” Two seconds in twenty hours.

That pattern has repeated for nine years. Hours and hours of conversation and emails, punctuated by scattered moments of high-leverage usable insight — a phrase here, a 2×2 there, a particular quote or metaphor that fits the situation. It used to frustrate me a lot initially. Was there no way to cut out all the hours and just formulaically arrive at just those moments of insight? So far I haven’t found one. You have to put in the time — and learn to enjoy it.

Insights like this cannot be found in textbooks, cranked out of fully-formed theories, or by “solving” cartoon case studies in a classroom setting (the equivalent of a punching bag or boxing dummy). They can only emerge through the process of preparing mindfully for specific live-fire challenges with a live sparring partner who can keep up with you.

Like good boxers, good executives instinctively seem to follow a similar, highly situational preparation regimen. They typically study developing situations that require action (many even like the “review the game tape” metaphor), form one or more working hypotheses about how to tackle them, and “workshop” them with trusted partners before actually trying them “in production” so to speak. At any given time, they are shepherding a dozen situations along towards resolution, and workshopping multiple ideas about what to do, often with multiple sparring partners.

This short passage from a classic paper by Karl Weick, What Theory is Not, Theorizing Is, gets at the essence:

Products of the theorizing process seldom emerge as full-blown theories, which means that most of what passes for theory in organizational studies consists of approximations. Although these approximations vary in their generality, few of them take the form of strong theory, and most of them can be read as texts created “in lieu of” strong theories. These substitutes for theory may result from lazy theorizing in which people try to graft theory onto stark sets of data. But they may also represent interim struggles in which people intentionally inch towards stronger theories. The products of laziness and intense struggles may look the same and consist of references, data, lists, diagrams, and hypotheses. To label these five as “not theory” makes sense if the problem is laziness and incompetence. But ruling out those same five may slow inquiry if the problem is theoretical development still in its early stages.

I quote this passage on my own consulting website and describe sparring in relation to it as follows:

The bulk of my practice comprises 1:1 work with senior executives as a conversational sparring partner, to stress test and improve the rigor and quality of their ongoing thinking about their evolving challenges.

Of course, executive work is not boxing. Meeting rooms are not boxing rings (though they can sometimes feel that way). Purposes in organizations are generally more aligned, non-zero-sum, and non-adversarial than in a boxing ring. The preparation is much more of an intellectual process.

But many of the challenges of preparation are very similar.

Who Can Spar?

The executive sparring partner role is a relatively new kind of external consulting role for a simple reason — the kind of immersive shared context required between client and sparring partner could not exist 30 years ago, due to the sheer difficulty of creating the shared knowledge environment in pre-digital environments. This means, historically, the role has almost always been played by trusted insiders and colleagues rather than paid outsiders.

Usually, executives spar with trusted peers who understand the industry well enough to keep up. Common sparring partners include:

1. An executive in another company in an adjacent non-competing business.

2. A board member, key investor, or a retired executive from the same organization.

3. An academic studying the industry or domain (rare).

4. A peer executive in the same company.

That last option is less common than you’d expect. Conflicts of interest often prevent direct peers from serving as sparring partners for each other, despite being the best suited for it in other ways. Peer executives are often competing with each other for power, influence, and control over specific situations, so mutual sparring support is limited to windows of opportunity when they are not striving at cross-purposes.

Despite these problems, peer-to-peer sparring still constitutes the vast bulk of sparring going on in the world, simply because of the numbers involved. It is just a highly unpredictable and unreliable source of sparring support. If an executive relies solely on peers for sparring support, they may find it unavailable just when they most need it.

Basically, it is surprisingly hard for senior executives to find the combination of three key required traits in one reliably available person:

1. Sufficient domain knowledge to allow shared thinking in insider-language

2. Absence of conflicts of interest and misalignments that get in the way of trust

3. Intellectual capacity to process at the typically demanding level

In the past, these three requirements often ended up forming a pick-2-of-3 triangle in a field comprising only insider candidates. But on the other hand, outsiders typically faced far too high a barrier of acquiring enough insider knowledge to play the role.

Until the internet happened.

The Internet as Sparring Arena

Thanks to the internet, it is possible for vast numbers of people who are technically “outsiders” to keep up with an industry or a specific company from the outside, participate in lively discourses around it, and be generally informed and prepared enough to play sparring partner roles.

In 2020, often all it takes to form a surprisingly deep and useful mental model of an organization is a few hours spent on Google, LinkedIn, Glassdoor, Wikipedia, and social media. Throw in a phone call or email or two, and you are probably 80% of the way there even before signing an NDA and being given a peek at internal information.

And you do not need limited, narrow and expensive subscriptions to business intelligence/dossier services to do so. Most of the valuable situation awareness information is free.

Add to that the trend towards increasing openness — many executives openly discussing their challenges on Twitter among other things — and the set of potential sparring partners available to any executive vastly expand. In fact, many seem to show up on Twitter to do exactly that — free sparring sessions with random members of the public!

If you’re an executive at a small, cash-starved startup and cannot afford to pay for a sparring partner, I highly recommend this approach. To the extent you can, just blog or tweet publicly about your work, and you’re very likely to find the sparring you need for free.

And if you’re looking to get into the business of being a sparring partner, there’s no better training ground than Twitter. You can literally try to provoke and engage thousands of executives. You’re very likely to get your first clients that way. I got my first couple of clients via Quora, and almost all the rest through some social media outlet or the other — Twitter, my own blog, contributions to industry blogs, and so on.

But information availability, while necessary, is not sufficient. Being a sparring partner calls for a particular temperament and personality (not learnable), and a particular mode of being attuned to others (learnable).

Sparring Partner as an Archetype

I’ve previously written about the idea of consultants as a well-defined archetype — shadows. This is particularly true of sparring partners. I also previously wrote about elements of consulting style, and offered this 2×2 of 4 types of 1:1 consulting roles, corresponding to 4 types of clients. While most clients are a mix of the 4 types (achiever, integrator, tester, explorer), most consultants, in my experience, can typically only serve in only one of these roles well.

Let’s get at the elements of the sparring partner archetype (both innate and learnable) via comparisons with the other 3.

1. Unlike a therapist or life coach, a sparring partner does not support inner work except occasionally as a side effect. Psychological insight into human nature is helpful, but not central to effective sparring.

2. Unlike philosophical counselors or mentors, the sparring partner does not occupy the position of a respected elder guiding an executive through inner or outer challenges they themselves have already been through. Your own banked growth experiences are helpful, but not central, to effective sparring.

3. Unlike an executive coach or teacher, the sparring partner does not support general-purpose behavioral development (forming good habits, losing bad ones, developing specific skills), in areas like productivity, emotional self-regulation, or “crucial conversations”. Behavioral insight is helpful, but not central.

What is central to effective sparring partnerships is actual understanding of the business domain and organizational environment itself. Having access to the enabling background knowledge is one half of the problem — largely solved by the internet. But actually being able to think on your feet with that knowledge is a different matter altogether, and the other half of the problem. One most people will fail at.

Often, this is a matter of the sparring partner having enough relevant career experience. People in classic “coaching” roles usually do not — they often have backgrounds in helping professions/fields like psychology, social work, or HR, but rarely in the fields where executives tend to emerge.

Most executives typically have career backgrounds (if not educational) in technology, finance, sales, or marketing, and are facing deep problems in those functional line-management domains. They usually need sparring partners who have at least a passing familiarity with the domains their work touches.

CEOs typically face problems that transcend even those functional domain boundaries and require knowledge going beyond, in that nebulous pile of backstopping activity that is “leadership”. They require sparring partners with domain/function experience and something more — a sort of philosophical fit of sparring styles.

This requirements makes “casting” for sparring roles much harder than for executive coaching roles, and it’s not a problem that can be solved by credentialing.

Executives typically know they’re not looking for traditional executive coaching, but can’t quite put a finger on what they are looking for. But they can recognize it when they see it.

Casting for Sparring

Much of the challenge of being cast in the role of a sparring partner is being visible in the right places when/where executives are looking for sparring support. That will be a topic for a future episode of this series, but let’s talk about how the casting process works.

Executives seeking sparring support often unconsciously look for sparring partners they can talk to in their own language, without having to constantly explain themselves, dumb themselves down, or having to provide quick tutorials on basic working concepts at every conversational turn.

They might provide a few pointers to learning resources, if they really want to work with you, but even that is rare. In general, they will expect you to learn enough to spar with them effectively in the very first hour. As a rule of thumb, if an executive has to spend more than half the time in the first hour of a sparring engagement explaining basic background ideas (especially basic technical concepts or basic business ideas like how to read a balance sheet), it’s not going to work out.

The ideal sparring partner is someone who already has a sense of the history of the industry and its technological foundations, has some functional depth in all the important domains the executive has to deal with, and has already been thinking about the latest fads doing the rounds.

The ideal sparring partner already has an opinionated take on important questions that are at least wrong (rather than not-even-wrong, which is the most common state), based on having kept up with the industry in question.

How do I know this? I know this because my clients have disproportionately been technology leaders, either leading technology/engineering functions, or having risen to CEO-level general roles from the technology leadership side. And this is not an accident. It is because I’m an engineer by training myself, and much of my writing and social media presence is suffused with technology references, metaphors, analogies, and historical anecdotes.

For a technology leader who reads one of my blog posts or a twitter thread, it is immediately obvious that it won’t take me painfully long to get sufficiently up to speed to serve as a useful sparring partner. I’m not going to be asking a machine learning company CEO what an eigenvalue is. I am not going to be terminally befuddled by a chemical industry CEO mentioning the ring structure of Benzene. Or by a CFO talking about gross margins and EBIDTA.

I’ll say more about this knowledge preparedness aspect later in this series, but make no mistake — sparring is a knowledge-intensive role. You have to know a lot, and showcase what you know, just to get in the game. And you have to be willing to learn a lot, very rapidly and efficiently, at short notice, to stay in the game.

If you have the temperament you’ll already know it. You probably read widely outside your field, and fairly deeply. You keep up with industry level trends in one or more large sectors at a play-by-play level. You keep up with science and technology news, at more than a casual level. You can parse at least half of any casual insider conversation you might hear about any industry in a coffee shop, and three quarters if you’re given a few minutes to google stuff (this is a game I used to play with myself a lot in coffee shops, back in the beforetimes when sitting around in coffee shops was a thing).

You don’t get there overnight of course. It takes years of being interested in business and technology and keeping up. But fortunately, it’s not a specialized kind of interest or attention. Whatever your reasons for your past interest and curiosity in business and technology, the fruits are going to be valuable in a sparring role.

Sparring in Executive Development

Let me wrap up this looong first part by placing sparring partners in the context of executive development more broadly. The short version is this: there is no element of sparring anywhere in the typical executive development offering suite, which is why I have an indie career at all.

The traditional executive coaching model does not work for sparring, because most coaches do not have the right background to serve as sparring partners. Other elements of the leadership development world do not address the need either. People in that world do acknowledge the need, but generally leave it alone as an area to be covered by mutual peer-to-peer support. Which also does not work great for reasons I’ve already pointed out.

The slightly longer version.

Back in 2008, when I was still confused enough about my own life priorities to imagine I might want to be on the executive-suite track myself, I was sent off by my employer, Xerox, to a “early high potential” leadership retreat at the Center for Creative Leadership, where I was subjected to a battery of psychological tests (Myers-Briggs, FIRO-B, CPI 260, Skillscope 360… see this pile of material I came home with).

It was a all a lot of fun, but felt like a bit of a LARP. Like I was pretending to be someone I was not — and doing it fairly well. Clearly, in some way I fit into this world, but not the way I was present in it during that program.

The capstone piece of the retreat was a couple of sessions with an executive coach. It was the first time I had done anything like it, and my expectations were low.

The exposure to executive coaching was particularly valuable because the coach assigned to me was pretty good at it, and it was a valuable session as a coaching session. I came away impressed by how well the coach had been able to get under my skin, and help me see some things about my behaviors. But I also came away with the impression that useful though it was, it somehow wasn’t even remotely helpful with the actual challenges I was facing at the time, in leading my project teams.

Perhaps that was just a matter of finding the right coach? Unfortunately, that’s not the case. I learned that my experience of coaching was in fact typical, from a book I read around that time: What Got You Here, Won’t Get You There, by Marshall Goldsmith, a pioneering executive coach, who in some ways invented the field (you can read my 2008 review here),

Goldsmith is known for pioneering the modern style of executive coaching, focused on behavioral rough edges. It begins with the assumption that anyone headed for the executive suite already has high competence and capability in their core leadership/managerial areas, but might require help addressing one or more seemingly innocuous blindspots and behavioral rough spots that end up being a huge liability.

Goldsmith’s model is the mainstay of 1:1 consulting models. As far as I can tell, all executive coaches practice some version of it, even if they’re not aware of it.

Unfortunately, the Goldsmith model has its limitations, and it became clear to me that coaching was not going to be the source of the kind of support I could actually use. Though I didn’t know it then, and didn’t call it that, what I needed — and never got — was sparring support. The few people around capable of serving in a sparring partner role with me were far too busy to spare more than the occasional hour, and usually available only when they wanted to talk to me, not when I wanted to talk to them.

Cut to three years later, in 2011, with my first couple of clients, it immediately became clear that what I was doing was in fact sparring — filling the gap I had myself perceived from the other side in 2008.

The idea that sparring is a distinct kind of 1:1 relational work has since been repeatedly validated by my experiences in the nine years since.

In fact, several of my wealthier clients have hired me for sparring while already working with both a coach and a therapist. These have been some of my best sparring relationships, because the client already recognizes that these are different roles, that call for different sorts of people to be cast in them. The sparring work does not accidentally slide into these adjacent kinds of work that I have neither the temperament, nor the taste for.

So that’s it for my introduction to sparring. In the coming weeks, I’ll cover several other topics: how to prepare for a sparring role, how to conduct yourself in a sparring session and in the follow through, assessing fit with a potential client, what kinds of potential clients to seek out or avoid, scoping engagements and setting expectations correctly, and how to find interesting sparring roles.

For now, I won’t be offering any in-person workshops outside of informal ones for people contributing to the Yak Collective, but if there’s enough interest, I might make an online course or something.

If you’re an executive looking for a sparring partner now, or might be looking in the future, drop me an email. One of my intentions in writing this series is to go beyond merely offering my own sparring services, to teaching the model and playing matchmaker to some extent, connecting executives with suitable sparring partners. We’ll see how that goes.

You’ve probably heard of the halo effect, where a generally positive gestalt is created around things or people with specific positive traits. For example, charismatic and articulate people who project confidence are viewed as more trustworthy and intelligent.

Take a second to think about this question: what color is your halo?

Or less figuratively, what do you think is the gestalt effect of how you are perceived in a client organization.

I got the idea for the question from a 1970s job-hunting classic called What Color is Your Parachute? According to author Richard Nelson Bolles, the title came about as a joke:

Years later, Bolles explained the book’s memorable title as his response at a business meeting in 1968 when someone told him that he and several co-workers were “bailing out” of a failing organization, prompting Bolles to joke, “What color is your parachute?”. “The question was just a joke,” he said, “I had no idea that it would take on all this additional meaning.”

It is interesting that a precipitate exit from a job in the industrial world is, by default, perceived as a catastrophic failure event that requires a parachute to survive. Even senior executives think in terms of “golden parachutes.”

One of the hardest mental shifts to make as an indie is letting go off 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.

As it happens, I’m in that situation right now. Next week, my 9-month fellowship at the Berggruen Institute will end. I’ll be back to full-time indie consulting starting May 15. Yet, though it’s a fraught time out there in the open economy, it doesn’t feel like I’m stepping out of a flying airplane without a parachute. To my pleasant surprise, I have enough confidence (and savings, and live cash flows, and active clients) that it feels like just stepping outdoors again, after a sabbatical indoors. The weather outside is bad, and things are probably going to get rough, but I’m not about to plummet to my death.

Certainly, there is risk involved in leaping out of paycheck employment, but in 2020, it is hardly leaping-out-of-a-plane level of risk. Or if it is, indies leap out not with parachutes, but with wings. Pandemic or no pandemic.

Halos over Parachutes

A parachute is for people who might fall to their deaths. Halos are for angels with wings who can sort of float in the air without an organization beneath their feet. Your future depends not on the color of your parachute but the color of your halo.

So a better question for the gig economy is this: what color is your halo?

Halos are very important in indie consulting, because they shape how you are perceived when you enter a client organization as an outsider, which is very different from entering it as an employee, as you’ll have learned if you’ve been at it for more than a few months.

In consulting work, it is important to be able to recognize a few important types of halos, including your own. Here is a picture of a handful:

Non-Indie Halos

Let’s take a quick inventory of the five non-indie halo types in the picture above:

1. Star Employee halo: This is the most basic kind of halo. The star employee harmonizes with the organizational background without blending in, is generally viewed positively, and sets the internal standard by which the halos of external parties are judged. The star employee is the hero of the organization. The halo color is gold, as in Golden Boy. I enjoyed a Golden Boy halo for a couple of years a decade ago. It was fun, and came with many privileges, but it is frankly an over-rated experience, since it tends to create limiting perceptions.

2. Big Consulting Firm halo: Employees of big consulting firms are the main external parties with recognized internal status (contractors and below-the-API staff are generally not “seen” at all). They tend to have somewhat robotic, one-size-fits-all, terminator-type halos. They project a mix of effective professionalism and intimidation (through borrowed authority of the CEO, and perception of involvement in things like layoffs). Their halo color is blue, as in blue chip. Big consulting firms are often seen as emissaries of the broader industry or market. There is a hint of benchmarking and judgment in the very presence of one of them in your workgroup.

3. Specialist Consultant halo: Specialist consultant types, such as lawyers or CPAs, tend to be put in well-defined boxes (hence the square halo). Their halos too are blue, and they too are seen as emissaries of the broader industry or market, but less threatening. They are sometimes indies, but more often part of partnership firms, receiving both paychecks and a share of profits. The often represent a particular sort of risk management, but crucially, they don’t own the risk, and don’t participate in it. They just help clients manage it.

4. Auditor/Inquisitor halo: Some sorts of outsiders have unambiguous threatening halos: auditors, compliance consultants for health regulations, pollution, sustainability, or diversity, trainers offering sexual harassment seminars, and so on. Their halo color is green, as in green-lighting (as in signing off on your compliance/conformity to some sort of external standard), but also as in green-washing (accepting complicity in a theater of compliance, particularly common in sustainability, hence the term).

5. Charismatic halo: Charismatic outsiders — famous authors, celebrity professors, ex-Presidents — tend to be brought in for largely ceremonial purposes such as keynotes during marquee meetings. They are not there to provoke, rock the boat, or actually make any difference. They are there to lend star power and charisma to the status quo. Their halo is therefore the same color as star employees — golden. Except their halo is actually star-shaped, since they are stars in the broader world outside. Often, they model, in exaggerated form, one or more desirable characteristics the organization wants to encourage in employees. They also afford senior leaders a chance to BIRG — bask in reflected glory.

That’s just a sampling of the halos you might see in a typical organization. There are many more, but that should give you an idea of how to think about perceptual gestalts of people against organizational backdrops.

Let’s talk about the sixth cartoon, the indie halo.

The Indie Halo

The indie halo…

Now here we run into a problem. Indies come in many varieties. In fact each indie is technically a distinct variety or they wouldn’t be called indies. There may be a certain amount of imitation in methods and postures, but we aren’t cookie-cutter types.

In one of my earliest newsletters, I argued that indies are shadows. In another, I argued that a fixed self-image is a dangerous thing for indies and that the right self-image is that of a trickster.

My opening question was a trick question. There is a correct answer: as an indie, your halo should not have a fixed color. The whole point of indie status is a certain amount of adaptability.

Personally, I have appeared in client organizations with a whole range of halos. I’ve had opportunities to do the charismatic star halo (even if only at D-list level) thing, the nerdy specialist halo thing, and the ersatz Big 3 thing. The only kind I haven’t done is the green audit/compliance thing.

But these fixed halos, even in imitation, are the exception. The default mode of indie consulting is to adapt to a very specific situation. Sometimes this means projecting confidence and charisma. Other times, it means projecting a narrow kind of competence. And sometimes it means projecting an annoying Jiminy Cricket type of conscience-on-the-shoulder personality.

You can never tell until you’re in the situation what the right way to play it is.

This is in part because indie consulting, no matter what you do, nearly always has a strongly improvisational component to it. You have to go yes, and… in response to the opening overtures of the client. And the nature of that improv response depends on the nature of the situation, and the posture the client is adopting within it. Your task is often to provide a response that is surprising without being disruptive.

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. You don’t want to be seen as competing with the local hero, nor as the natural villain opposed to them. You want to be seen as someone whose presence makes the local hero’s journey more interesting. If you’re lucky, that local hero is in fact your client. If not, it’s a trickier improv challenge.

It takes time and practice across many situations and with many clients to develop a broad “halo range,” but once you’ve expanded beyond a couple of basic postures, you’ll find that it gets easier and easier. It’s a sort of method acting practice.

So take another stab at answering the question: what color is the halo?

But this time, think of the range you might develop around it, and how you might expand it.

You’ve probably noticed that in the past month or two, this newsletter has been increasingly hijacked by not one, but two kinda off-topic threads. The first is of course the Covid19 pandemic which is hijacking every conversation in sight. The second is the indie community bootstrapping effort that I, along with a few other indies like Tom Critchlow, Paul Millerd, and Pamela Hobart, have been working on.

I’m happy to report that the later persistent hijacking has now evolved and matured into Its Own Thing.™

Introducing the Yak Collective, and its first collaborative project, a report titled Don’t Waste the Reboot, with contributions from 21 independent consultants, and additional support from nearly half a dozen others.

Paul Millerd led the effort, and the process of pulling it together was as enlightening as thinking through the content itself.

Take a browse, explore the deck, and share/signal boost as you think it deserves to be. If you have the ability to do so, take it out fishing in executive-suite land, and bring us back a gig on the strength of the deck.

A big thank you to all who contributed, not just to the content, but to the process of pulling it together, and building out the just-in-time infrastructure required to get it out there. “Open-source” style output often lacks the finish and polish of commercial stuff, and that applies to open-network emergent indie collaborations as well, but in this case, we solved that problem — people volunteered for everything from proof-reading to sizing images correctly.

I’m particularly proud of the sheer speed with which we managed to pull this together. From inception to delivery, this deck, and the website/distribution infrastructure to put it out there, took about 2 weeks.

It’s one thing to claim that indies operate on a faster, more responsive OODA loop than big organizations, but another thing to actually demonstrate this.

Can indies turn into the special forces of sense-making and rapid action in the post-Covid world? I think we can. That’s what I want to talk about tomorrow morning, so let me tee up that discussion.

Town Hall

Tomorrow morning, at 9 AM Pacific, the usual time I host a Discord chat, I will host a special edition, longer, one-hour chat open to all who care to join in — a town hall to talk about this first project launch, and where we go from here. So make sure to join in.

To tease what I have on my mind to talk about tomorrow, here’s the thought-starter: If we can keep up the kind of tempo that drove our first project, while increasing the complexity and ambition of our collaborative efforts, indies can easily turn into the special forces of consulting — able to get off the ground faster, do our sense-making faster, analyze and synthesize faster, and deliver serious intelligence and output to the world while larger organizations are still holding endless meetings, lost in the FUD.

How can indie teams competing with traditional orgs deliver output that’s twice as good in half the time?

That, I think, is the challenge we face, and the reason I personally have been investing time in getting this thing going.

To that end, for those of you want to join this effort, here’s your chance to get in on the ground floor — a call for proposals, which I’ll talk more about on the chat tomorrow.

6 Reports in 6 Months: Call For Proposals

In the next 6 months, we hope to do a Yak Wisdom series of Covid19 themed collaborative projects like Don’t Waste the Reboot, using the pooled resources of the Yak Collective. The idea is to grow a network of indies who are connected not just through casual social network links, but through a shared history of working together on meaningful things.

We’re already underway — 21 of us are linked via co-authorship links on this first report, and have developed a certain amount of trust in each other.

So to get that going in a bigger way, we’re issuing a call for proposals. Check out the Yak Collective Collaborations page on our Roam database.

There’s a link to a proposal form there where you can submit a proposal, as well as a list of thought-starter ideas if you need inspiration. Join the Discord, chat with me or one of the other partners (Paul, Tom, Pamela), sound out potential contributors via informal conversations, and submit a proposal.

The deadline for proposals is Friday, May 8th.

Our goal is to put out a report a month for the next 5 months, all broadly on the Covid19 theme, to build up a solid repository of reboot intelligence for organizations of all kinds. We’ll figure out some collective way to prioritize the ideas to work on — maybe something as simple as green-lighting the ones that attract the most contributors.

I’d like to particularly encourage those who contributed to the first project to consider proposing and leading one. Compound interest is a powerful thing, and I’d like to get that particular learning loop iterating as quickly as possible in our little fledgling network. The more of these efforts a single contributor participates in, the smarter the network gets about such efforts.

Right now, only Paul Millerd has learned how to pull one of these indie collaborations together. I’d like a dozen of us to have acquired that know-how in 6 months.

We have to initially limit output to a report a month simply because our shared ability to market and disseminate work like this is still pretty limited (it’s a bunch of us with newsletters and social media followings/existing clients). To be honest, even one a month seems like an ambitious stretch goal to me at this point.

So we want to build up momentum slowly. If we can put out 6 reports in 6 months, each better than the last, people will sit up and take notice, and good things will start to happen for all who participate.

Slow is smooth, smooth is fast, as the special forces saying goes.

If we want the indie world to turn into the special forces of sense-making, we’re going to have to actually operate that way.

Why Do This?

It might not be clear to some of you, especially if you haven’t been in the indie game very long, why it is a good idea to attempt this marathon of 6 reports in 6 months.

Building up a track of internally generated collaborative activity like this will, I suspect, address the single biggest thing that prevents independents from going after larger gigs and projects — a proven ability to assemble larger teams with varied capabilities.

This is an area that I myself have significant learning ahead of me. The most collaboration I’ve ever done on gig work is with 1-2 other subcontractors, and for a few months at most. By contrast, back when I had a paycheck job at Xerox 10 years ago, I was leading a great team of 10-12 people for nearly 3 years straight.

I honestly have no idea how I’d pull together a 12-person/3 year team for a larger project out of a loose network like the Yak Collective, while still operating by a model that is still essentially indie in spirit, with its ethos of people working on their own time with very low mutual-dependency levels. It will be hard to do that without defaulting to the old ways developed by paycheck organizations and reproducing their well-known failure modes. If we’re going to fail at this sort of thing, I’d at least like to fail in new ways.

It’s not going to be easy to have our cake and eat it too — retain that sense of individual freedom that attracted us to indie work in the first place, while realizing the benefits of working in larger free-agent teams on larger projects.

But I’d like to learn this game, and give the paycheck consulting crowd a run for its money. As I’m sure many of you would too.

And once we address that weakness around building larger teams, our natural strengths — diversity, speed of sense-making, loose synchronization, true variety of capability, improvisation ability — will kick in.

But there’s a larger principle here. Not only can we attempt this, in a sense we must attempt this. Here’s why.

How Can Indies Not Waste the Reboot?

Our first deck has launched with the title Don’t Waste the Reboot. If you’ve been participating in the community, or contributed, think about that for a second.

That advice applies, first and foremost to us, the ones presuming to give it to others. How can we make sure that we don’t waste the opportunities being created by this crisis to advance the interests and capabilities of the indie sector?

It’s not a cynical disaster-capitalism type question. It’s not about profiteering.

I think most of us genuinely believe that the indie sector is a force for good in the world, bringing speed, variety, diversity, dissent, unique capabilities, alternative value orientations, and other good things, to a monocultural institutional world that sorely needs all of those things in spades.

So yes, we have to ask ourselves first, how do we not waste the reboot?

The tagline of our first report is “Making the next normal better than the last one” and again, by the dog-food principle, if we aren’t able to take that advice ourselves, what exactly are we doing peddling it to others?

So the next normal for the indie consulting sector should not be the same as the old normal. What does that mean?

1. It shouldn’t be limited to small 1-2 person table-scraps projects on the margins of bigger, more consequential projects.

2. It shouldn’t have to struggle for the attention of leaders in organizations driving the most interesting work around the world.

3. Bringing on teams of indies shouldn’t fail for stupid reasons like not having the ability to set up the necessary webs of subcontracts, insurance policies, and NDAs, or managing the payment distribution logistics. Those transaction costs need to go down.

4. Bringing on a team of indies should be the first thing an executive thinks of when faced with a new kind of challenge, not the last resort. New problem, new people. Why isn’t the calculus as simple as that? It should be.

How do we make these sorts of things happen? Let’s figure it out, one collaborative effort at a time, one conversation at a time, one attempt to pitch a team project at a time.

That’s what I hope the Yak Collective will be about, at least to the extent I have had a hand in shaping it.

A New Praxis for Indie Work

Not wasting the reboot as indies means thinking harder about every aspect of how we operate, from philosophy to low-level tools and tactics.

I talk about both a lot in this newsletter — as do my fellow instigators of the Yak Collective in their writings — but for the next-level thing we’re attempting here, those ideas have to evolve from talk and “advice porn” to a larger praxis — an attempt at situated, philosophical practice.

We’ve already put some effort into laying out our philosophy on the About page. It’s not the usual yada-yada-contact-us boilerplate. So check it out.

But that’s just starter thoughts that occurred to us in the process of pulling this first project together. The real work of figuring out a reimagined praxis of indie work for the post-Covid world is going to be done in the conversations around actually trying to do different kinds of work.

And doing it in different ways, through open-network modes, like the Yak Collective is trying to do.

Eating our own dog food as indies is not about doing philosophy, but about doing philosophically. It’s not about debating manifesto points, but about mindful reflection on work being done and shipped. Rough consensus and running code, applied to gig work collaboration.

So let’s not the waste the reboot. Let’s make sure the next normal is better than the last one — for indies. By starting to work differently now and learning from it.

What might happen if we succeed?

Back in the 1950s they used to say, what’s good for GM is good for America. It was a positive sentiment about the worth of big paternalistic companies that eventually turned into a satirical line.

I’d like people to start saying: what’s good for indies is good for the world — but intend it sincerely rather than satirically.

That’s my personal success metric here.

And I hope the Yak Collective is not the only effort of its kind to emerge in the post-Covid world.

I for one would like to see dozens of such experimental efforts sprouting up around the world, trying out new ways of working within the free-agent economy, and new patterns of relating to the paycheck economy.

Most such efforts will fail. Most, but not all.

New entrants to the indie economy in 2025 will enter a different, better indie economy than I did in 2011. Because at least a few experiments starting right now will work out, and then the next normal won’t be like the last one.

Where to Now?

You can follow the progress of the Yak Collective on Twitter, Facebook, or LinkedIn. I’ll continue to highlight interesting developments selectively here, as will the others involved, on their newsletters/blogs etc.

As most of you know from the last few newsletters, there’s a knowledge base built on a Roam database, and a Discord community with several hundred people. We’re slowly building out more infrastructure, as people step up to build out bits and pieces of what we need to be effective.

A fledgling community building effort like this will of course continue to require significant TLC and stewardship from all involved, especially from those of us who instigated it, so I expect to continue talking about the Yak Collective and its work from time to time on this newsletter.

We’re past the hijacking stage, since the project is now starting to take its first wobbly steps on its own, but it will be a while before it becomes sentient, turns into the Indie Skynet, and takes over the world.

I haven’t yet decided how I will be weaving in the community stuff with my own writing, but I’ll figure something out.

Those of you who are primarily here for my writing, you’ll be able to tune out the Yak Collective stuff if you want.

Those of you who are interested in the Yak Collective, and my piece of that activity stream, you’ll have ways to tune in to that too.

Even at the level of this email newsletter, I’m trying not to waste the reboot myself. So yes, there’s a small pivot going on here, but I hope most of you will decide to stay with me through it.

We’ll be back to regular Art of Gig programming next week. No doubt my participation in the Yak Collective will shape some of the topics I cover here. For example, I already have a LOT of thoughts on how to make larger indie collaborations on gigs happen, so I’ll be writing about that. And of course, this whole effort has inspired a lot more ideas for me for Yakverse stories, so there will be that too.

Strap in. Interesting times dead ahead.

And don’t forget — browse and signal-boost Don’t Waste the Reboot, follow us on Twitter, Facebook, or LinkedIn, join in for the Discord chat tomorrow morning, and consider submitting a proposal for our Yak Wisdom series.

I can’t believe it’s been a year already, and time for the first Art of Gig annual review issue 😦.

I started this email newsletter on April 30, 2019, and here we are now, 54 issues later, in the middle of a pandemic, trying to run an already difficult playbook in perhaps the toughest environment ever. If we get through this, we should award each other medals.

More on that, and on where we go from here, at the end. But let’s do a review of all the Year One articles first, grouped in hopefully helpful ways. If you’ve been meaning to introduce any friends to this newsletter, this would be the issue to forward (or even give them a gift subscription perhaps?).

First Leap Series

Though most of the content in this newsletter is aimed at people who are already in the gig economy, particularly as indie consultants or freelancers, I did write some material explicitly with potential new entrants in mind, in the form of a five-part series covering the basics of preparing to leap into the gig economy.

1. The First Leap: Employees hunt, entrepreneurs launch, gigworkers leap. Understanding how to enter the gig economy.

2. Leap Risk: The financial math and risks of leaping into the gig economy, and what you can do to mitigate it.

3. Minimum Viable Cunning: How to inject enough strategy into your first leap to manage the risk.

4. The Inner Game of Gigwork: Managing your inner life by becoming more of a robot to express more of your humanity.

5. The Road to Agency: Concluding the five-part series, mapping out the path to gaining control over your own life, which is what typically drives those who manage to last in the gig economy.

This series was partly paywalled, but I’ve made the whole series public now, in case it is helpful to people suddenly thrown into the gig economy due to the crisis.

While this First Leap playbook is obviously much harder to run in the Corona era, it is still the minimum-viable playbook you have to run. If you’re new to the gig economy (voluntarily or involuntarily), or still in the paycheck economy and eyeing it as a future option, this series should be helpful.

Core Articles

The heart of Art of Gig is a track of essays where I try to pick out and discuss themes that are important, but not always obvious if you’re new to the game. The bulk of these essays are intermediate level, and assume some work experience, if not indie experience. I wrote 20 essays on this track in Year One.

1. Elements of Consulting Style: The 4 types of clients and how to serve them: achiever, integrator, explorer, tester.

2. A Tale of Two Schools: An introduction to the structuralist versus people school philosophies of consulting, and why indie consultants tend to fall on the people school side. 🔒

3. Knowing Which Nut to Tighten: How do you price your knowledge? Consulting and the principal-agent problem. 🔒

4. You Are Not a Scientist: Gigups and startups share an important attribute: neither is science-based. A “scientific” self-image of what you do/know is a liability. 🔒

5. Response Regimes in Indie Consulting: What mix of risk and time pressure do you help your clients respond to? A typology of 4 kinds of needs met by indies: strategy, first response, preventative care, and surge capacity.

6. When is a Gig an Engagement?: The importance of not haggling to positioning yourself as a consultant, rather than a contractor.

7. The Clutch Class: Gig workers are neither part of capital, nor part of labor; we are the clutch class. An examination of our role in the politics of work. 🔒

8. The Gigwork Hierarchy of Needs: A combo mid-year review and a diagram organizing indie learning/maturation on a Maslow-like hierarchy.

9. The Price of Freedom: The fundamental choices and consequences of gigwork, in the form of a helpful pick-2-of-3 triangle diagram. 🔒

10. A Self-Image is a Dangerous Thing: A self-image is a dangerous thing for indies to have, because it’s likely to end up an ersatz knockoff of a paycheck role. Instead, you have to be a trickster of sorts, crafting a persona to suit the gig. 🔒

11. Sneaking Away From Yourself: You’re a bad boss, and you should sneak away from yourself. There’s no point taking the gigworker out of the paycheck organization if you can’t take the paycheck organization out of the gigworker. 🔒

12. Training Your Nerves: As a free agent, your nerves matter more than your skills. How do you systematically train them?

13. The McKinsey Affair: Lessons for the indie consultant from contemporary events in the Big 3 world, particularly the gradual tarnishing of McKinsey’s brand. 🔒

14. You Are Not a Parasite: Consultants are often accused of being parasites. Weak organizations always harbor parasites. The question is, are you one? 🔒

15. The Importance of Being Surprisable: The superpower of indie consultants is openness to being surprised. 🔒

16. Basic Consultant Diagrams: I diagram therefore I am. An introduction to the basic diagrams that come up in consulting work.

17. Ten Dimensions of Gigwork: It is important to understand the class hierarchy of the gig economy. Are you a consultant, contractor, or platformer? Ten ways you can tell. 🔒

18. Bootstrapping with Beefs: To find clients, start beefs, a tribute post to Clay Christensen. 🔒

19. Indie Fragility: Indie businesses are fragile. It is important to come to terms with that fact (this was written just before the Covid19 crisis hit). 🔒

20. Your Passion Mission: Arranging your money-making around your soul-feeding. If you don’t do this, your career in the gig economy will likely not be sustainable psychologically.

The Yakverse

If the core articles are the heart of this newsletter, the soul, at least for me, is the Yakverse series. Currently, the series stands at 13 parts, with 2 ancillary special posts.

The series has its own series home page.

The Yakverse is a fictional universe within which I set a series of somewhat absurdist stories inspired by my consulting work/experiences. I will be the first to admit that these are not exactly Dickensian masterpieces of fiction. This series is the most experimental part of this project for me. I’m trying to do several things with it. There’s an element of teaching consulting through stories, and an element of teaching myself world-building and fiction writing at your expense.

But the biggest goal of the Yakverse series, frankly, is just having some fun. The gig economy can be a grim, even depressing place, a place that can turn into All Soulless Hustle All The Time if you’re not careful. I have fun writing the series, even if not all episodes work. I hope Season 2 improves. Maybe I’ll even get a Netflix deal to make an animated series out of it. One can dream 😎

I know from your feedback that for some of you, this is the most fun part of the newsletter, and for others, it feels like hit-or-miss rambling and a distraction from the more “practical” track of core articles. Thanks for either coming along for the ride, or putting up with it, as the case may be 😆.

Tips and Tricks

I am a huge believer in aphoristic, fortune-cookie level wisdom, which I put out on the @artofgig twitter account. Here are compilations of all those tweets, plus the very first proper newsletter, which was also a collection of fortune-cookie sized thoughts.

1. 42 Great Imperatives

2. Consulting Tips Compilation: 1

3. Consulting Tips Compilation #2

4. Consulting Tips Compilation #3

5. Consulting Tips Compilation #4

6. Consulting Tips Compilation #5

7. Consulting Tips Compilation #6

8. Consulting Tips Compilation #7

9. Gig Economy Trivia Compilation #1.

Pandemic Specials

The crisis is a very special condition for the gig economy, and I’ve been writing a series of posts on that, all are public.

1. Gigging in the Time of Corona

2. Getting to the Reset

3. Murder on the History Express

4. Get Fat

Community Stuff

I haven’t written much about the community side, but I laid out my basic philosophy in Towards Gigwork as a Folkway. About a month ago, I took the first steps towards putting that philosophy to work. There is now a nascent community brewing, which we’ve tentatively named the Yak Collective. The basic community infrastructure is free and open to all, not just paying subscribers.

Right now there is a growing resource database with resources like case studies, a gig exchange page, and a directory. There is a Discord with over 300 members, and a track of experimental voice chat sessions. There is a first significant collaboration ongoing — on a Covid19 reboot strategy deck.

Not all of this will work, but hopefully enough of it will to get a mutually useful and interesting community going. For those of us who have been in the indie economy for a while, this Covid19 period feels like a highly stressful coming-of-age period. The kinds of experiments we try through this period, and the resourcefulness and imagination we bring to the party, will determine whether the pandemic destroys the nascent gig economy, or boosts it to a whole new level.

Thanks to all who have been helping with this early experimental phase, and figuring stuff out: Paul Millerd, Tom Critchlow, and Pam Hobart in particular. Thanks also to all those hosting voice chat sessions and figuring out how best we can be of value to each other, one conversation at a time: Scott Garlinger, Jordan Peacock, Drew Schorno, Sachin Benny in particular. Apologies if I missed anyone.

We will get this stuff much better organized in the coming months hopefully, as we slowly figure out what works by trial and error, double down on things that work, and put better scaffolding around it.

I will also be reinvesting some of the subscription income from this newsletter into the community component, once we figure out good ways to do that.

Year Two Prospects

As of today, this newsletter goes out to 2124 people (thank you!), of whom 380, or around 17%, are paying subscribers (double thank you!).

For Year Two, I had planned out a few big themes to explore, but like all of the best-laid plans, the pandemic has trashed them. So for the time being, I’ll be on an improvisational track, watching and writing about the gig economy and indie consulting as it responds to, and evolves, in response to the crisis.

Many fundamentals of the indie world have changed, some perhaps permanently. But many more fundamentals haven’t changed. The basic game is still drumming up leads, closing the deals, hustling through them, chasing down invoices and getting paid — all while having fun, learning, and growing with each pass through that process.

So I will be continuing to write about those fundamentals too, at all levels from beginner to whatever level I’m at. The pandemic will eventually recede, but most of us will still be here I hope, going on going on, hustling and scheming the same as ever.

So once again, thank you for your support and participation through Year One. Onwards to Year Two.

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It had been two weeks since that very odd meeting at Khan’s borrowed mansion. Two weeks in which decades had happened. Both Guanxi Gao and Arnie Anscombe looked tired and careworn in their little video windows.

I said, “Well, I guess I’d better kick us off since we’re using my Zoom account. Did everybody get a chance to open those manilla envelopes Khan gave us? I assume we all got the same thing?

“A photograph of an antique 2×2? I assume Khan has the original,” said Gao

“Yeah, a dumb 2×2,” said Anscombe, “I don’t know why we’re even talking about a stupid project to resurrect some sort of medieval Yak-themed consultant guild. In case anyone hasn’t noticed, there’s more important stuff going on in the world.”

I said, “Well, let’s spend a few minutes on it at least. The pandemic isn’t going anywhere soon. Here, let me share my screen, I scanned the photograph.”

“Well, Rao, you’re the 2×2 expert, what’s your take?” asked Anscombe.

“Hmm… interesting that the right side of the x-axis is labeled future, but the left side is is labeled here and now rather than Present. The y-axis makes sense. Clearly some sort of creative-destruction theme there. The bottom half is preservation behaviors, the top half is growth behaviors. I’d guess it dates to the 19th century.”

“How do you get that?” asked Gao.

“Labeling each quadrant became common in the 20th century. Here we have just blocks of text. It’s an early 19th century style. I’d guess late Edwardian or early Victorian England, since it is in English. English ones are rare from that period. It was more of a German thing then.”

Gao said, “Soldiers, physicians, nurses… clearly from some sort of wartime period. Maybe the Napoleonic wars? Crimean war?”

“WHO CARES!” Anscombe said. “Why are we talking about this? Why aren’t we talking about, I don’t know, THE PANDEMIC?”

“Hmm… maybe this IS from a 19th century pandemic period. There were a few cholera outbreaks then, right? Some smallpox? And there was a plague in China too.” said Gao.

I looked at Anscombe, “So what do you want to do? Rush out and investigate the N95 black market? Tweet an offer to donate one hour of pro bono consulting to a nonprofit for every hour a client buys? Our skills are not, you know, particularly useful right now. It’s not like we are holding up anything important by focusing on something else.”

“Speak for yourself. I’ve been scraping data, running my own analyses on flattening the curve, and my own simulations of test-and-trace protocols. I’m also reading virology papers.”

“And you think that is the best use of your time and energy right now?”

Anscombe sighed. “I don’t know. I just feel like, you know, I should be doing something productive to contribute. It’s not like I have anything better to do right now.”

Gao asked, “Didn’t you say you had a bunch of new leads for contingency planning modeling work when we met at Khan’s? You were even offering to hook me up.”

“It’s a total bust. All those leads dried up. I guess the situation evolved and escalated too quickly. Half of them went into radio silence, the other half said they had sudden cost control measures kicking in and had to back out.”

“No business continuity plan survives first contact with the coronovirus, old Chinese saying,” said Gao philosophically.

“I guess we could talk about the 2×2 a bit,” said Anscombe grudgingly. “It’s not like everybody and their uncle isn’t building curve flattening and test-and-trace simulations. The marginal value of anything I could do is probably zero. I guess I was clutching at it because it’s at least something I could do. I’m feeling pretty useless right about now.”

“Never let that bother you. The trick to consulting is to own your default uselessness. You’re always useless until suddenly you aren’t. It is nobody’s Plan A to rely on consultants as an essential resource. Our role begins where Plan A ends.” I said.

“And it’s not like we’re not all in the same boat here. I started some community stuff for the gig newsletter I write, because it was something I could do, not because it’s a huge game-changer that will magically solve coronavirus.”

“I’ve been trying to get better data from my contacts in Wuhan,” said Gao. “It’s not working very well.”

“So to summarize our collective status: when there is a hammer in your hand, everything looks like a nail. Great. Maybe I should just go volunteer at a food bank or something. Or offer statistics tutoring to kids stuck at home,” said Anscombe.

“The second best use of a book is as a doorstop, old Chinese saying,” said Gao.

“Well,” I said, “maybe this 2×2 will spark some better ideas. If we’ve guessed right that it’s from some sort of 19th century wartime or pandemic period, then I guess the top right with the yak is where the old Order of the Yak thought consultants should operate in a crisis?”

“Renew and Grow and Future. A bit banal isn’t it?” said Gao.

“The interesting thing, for me, is that there is no text there. The other three quadrants have text. Future and serve-and-protect is basically opportunistic, cynical politicians. Here-and-now and serve-and-protect is what they’re calling ‘essential services’ just now. And I guess, the top left is the escapist corner of the response. Renew and grow in the here-and-now. Baking sourdough and playing Animal Crossing basically.”

“Gotta protect those precious, fragile middle-class psyches,” said Arnie sourly.

Gao asked, “Was the top right quadrant the best quadrant int he 19th century? Like it is now?”

“I think that default emerged after World War I. The 19th century 2x2s usually positioned the bottom left as the most valued quadrant. They usually had a pretty moralistic tone like this one. The bottom left tended to be the devout, god-fearing, virtuous quadrant. The top right was viewed as the profane quadrant. So makes sense that the old Order of the Yak would cast themselves there. They had a subversive view of their role in the world.”

“Makes sense. The bottom left is doctors, nurses, soldiers. Not very different from today. Anybody you’d label a hero in a crisis.” said Gao.

“That’s a good idea, why don’t we update the 2×2 to a more… modern idiom, and add some quadrant labels. Here… lemme take a stab at it.”

I pulled up my Keynote scratch deck, duplicated my 2×2 template slide, shared my screen, and sketched one out.

“How’s this?”

Gao and Anscombe leaned forward to peer at it, and then leaned back.

“An improvement in clarity I guess. Still doesn’t tell us what should be in the Yak quadrant, and whether we should be operating there,” said Anscombe.

Gao said, “That original is more concrete. So I guess the yak question is: what does future-oriented renewal work look like inside a crisis?”

“There’s a definitional problem there,” I said. “A crisis is pretty much defined as a condition in which all positive futures seems foreclosed. When the only futures you can see clearly are the doomsday ones. When serendipity has shut down.”

“Zemblanity for the win!” said Anscombe, with perhaps a little too much dark glee.

We pondered the new 2×2 silently for a bit.

“It is obscene to work on anything other than immediate, pressing concerns and pain alleviation in a situation like this. You shouldn’t talk of growth and renewal until the crisis has passed. That is all,” Anscombe declared, a touch piously.

“And if growth is the only way out?” Gao asked, in an uncharacteristically quiet voice.

To my surprise, Anscombe seemed to find the thought calming. He said, “That’s a nice paradox. You can’t work on growth until the crisis has passed. The crisis won’t pass until growth returns. You can’t reopen the economy without stopping the virus, you can’t stop the virus without reopening the economy.”

“Out of paradoxes arise the right questions. One must stay with the questions, until they are ready to seek answers.”

“Old Chinese saying?” asked Anscombe sardonically.

“And that,” I said, “is a good paradoxical note on which to adjourn the first meeting of the new Order of the Yak.”