Month: June 2020

For the tenth time in ten years, yet again I find myself about to make what is perhaps the most strategic decision for an indie consultant: where should I live? And this time, I think I have to make the decision very differently. This is because the right answer used to depend on one big variable that swamped everything else: the potential for casual coffee meetings. This potential of course, has been destroyed by the pandemic.

The decision is basically this: should you pay a premium to live in an important business hub (typically a major metro), with a major airport? Or should you save on costs by living somewhere cheaper and more remote?

What exactly is the value of being able to take a lot of casual, serendipitous, impromptu meetings with potential clients? And how does this equation change due to the pandemic-related travel freeze, both in the short and long-term?

I won’t bury the lede: I ran the numbers for my own practice over the last 9 years, and 70.3% of my consulting revenue can be attributed to gigs that started out as casual coffee meetings, while 26.2% closed online. Here’s the pie chart (I consolidated 17 small clients with billings under 5k, and amounting to 3.5%, into one small pie slice):

So the headline is crystal clear: at least my kind of consulting practice is hugely dependent on gigs that start out as casual coffee meetings. Here is a more detailed breakdown. Look at the clients tagged A and B in particular.

The clients tagged A began with in-person, casual-coffee-meeting encounters, while the B clients are ones I closed after purely online interactions (including phone/video calls) and negotiations. Some of these, I have never met in person.

The Cs are 8 clients with total billings of 1k-5k each, and Ds are 9 clients with total billings under 1k (typically one-shot spot consults). Almost all of the Cs and Ds are online-only closings, but I haven’t bothered detail-coding them as such, since they’re pretty much a rounding error on the headline: 70% of revenue starts with casual coffees, and four of the top five clients started out that way.

Edge Ambiguity

As you can see, 4 of the top 5 clients started out as casual coffees first. In fact, the picture is even more dramatic than it looks because B1 and B2 are actually edge cases, and if I include them in the A list, the proportion changes to 83% casual-coffee first, and 13% online closings, and 6/6 of top 6 gigs by revenue (81% of the total) being casual-coffee first.

Both these edge cases have interesting anecdotes attached that shed light on how deals close.

With B1, I’d almost closed the deal based on email and phone interactions, and they had even sent their contract for me to review before I met the principal. But then the project got delayed by several months due to client budget issues.

But here’s the thing — by the time I actually closed the deal, I’d had a serendipitous coffee with the principal when we both happened to be in the Bay Area at the same time.

And to add to the edginess of the case, I’d actually met with a secondary person for coffee (not the sign-off person but one of their senior peers in the organization) before we even got to the contracting stage — and that person had been specifically deputized by the principal to meet with me and check me out. So really, B1, which represents 7.63% of my revenue, could be an A.

B2 is interesting in a different way. I’d done a small writing thing for this client (under 1.5k) first, but the bigger gigs only happened after I ran into a bunch of the people from the organization at a conference, after which they sent a series of larger projects my way. So that too could reasonably be called an A gig.

Whether you code revenue type liberally or conservatively, the lesson is inescapable: my kind of indie consulting begins with casual coffees. And there’s a good chance yours does too.

Let’s layer some ethnographic color on the numbers.

What’s a Casual Coffee Meeting?

A casual coffee meeting is a low-planning, low-stakes, opportunistic meeting without a great deal of marginal effort to make it happen. Pre-pandemic, I used to take 3-4 such meetings a month, of whom 1-2 were potential clients, and 1-2 others (like readers with no consulting potential, or young people looking for advice).

Casual coffee meetings happen in one of four ways typically, here’s a breakdown of my top 6 by this logic:

1. They happen to be traveling where you live (A2)

2. You happen to be traveling where they live (A1, A3, B2)

3. You both happen to be living in the same place (A4)

4. You both happen to be traveling to the same place (B1)

This low-effort is important, because it means if nothing comes of it, it’s still an upside meeting: all you did was have an interesting conversation over coffee without any significant investment of marginal effort. My rule of thumb is: a 20-minute Uber-ride away from something you’re already doing.

If you have to go to a great deal of trouble to meet, with marginal effort of say > 1 hour drive for either of you, it is no longer casual. It is a planned, in-person encounter.

Interestingly, this applies even if you’re the one doing the schlepping and the potential client has zero marginal effort. Because the very fact of the schlepping sends a costly signal of how much you want the gig, which could be a good or bad thing. On the receiving end, one time, when I was going to city X, someone emailed me asking to meet — but they were planning to take a 4-hour train ride just to meet me. I said no. That’s way too much pressure to create value.

Of the four modes, types 1 and 2 are typically routine business travel between hubs. Type 3 is all about local meetups and socializing. Type 4 is typically conference travel, often to exotic locations where nobody of business interest actually lives.

Let’s talk about conferences and business trips (types 1, 2, and 4), because they’re pretty much down for the count at this point.

Traveling Exurban Encounters

The good news is: conferences per se don’t matter much. In fact they don’t matter at all, at least for my style of consulting.

You’ve probably encountered a principle of networking along the lines of “most interesting things at conferences happen in the hallways and break areas between sessions.”

This has not been true for me.

Meetings at events, with others who are also attending the event, have not been useful for me. In fact, I’ve never had a gig come out of meeting someone I didn’t know before at an event.

Literally never.

Make of that what you will.

I think of encounters within an event, between participants, even outside of sessions in the break areas, as the suburbs of events. When I look at gigs I landed by going to conferences, they happened not at the event itself or its suburbs, but at meetings I pre-arranged on the side, outside of the event proper. Typically with people who happened to live or work in the city, and weren’t actually attending the event.

Usually I did this by adding a day before/after the main event for tourism, to take additional meetings, usually by dropping in at people’s offices, or cafes away from the event venue. I think of these meetings as happening on the exurbs of events. The event is at best your excuse for being in a particular city, not a direct catalyst.

What’s more, as an indie, going to conferences as an attendee, especially as a paying attendee, weakens the exurban casual-coffee potential of going, whether in the suburbs or exurbs. The ideal way to go is as a speaker, with at least your travel costs paid for by the organizers.

Why?

Say you pay $3000 overall to go to a 2-day conference. Travel, accommodation, registration. If you’re a real hustler, and add an extra day, you might be able to fit in a dozen coffee/lunch/dinner/drinks meetings around the event (suburban and exurban).

Assuming the event itself is actually useless, and there’s no value there that you can’t get from the videos later, amortizing your cost over the supposedly “casual” coffee meetings, each meeting has a cost of $250. So the expected outcome value should be at least that to make it worth it. The math works for people in sales or bizdev roles for other organizations, but not for people paying their own way.

And even though nobody explicitly does this kind of math when deciding whether to take meetings, the perception of high marginal cost is there.

Which means it’s not a casual coffee meeting at all.

This is post-hoc analysis for me. For years, I’ve had a policy of basically never paying out of pocket to go to a business conference (social/cultural conferences are different). I only go as a speaker or panelist, with paid-for travel costs, and only to places I actually want to go to as a tourist anyway, preferably with my wife.

Conferences are actually bad for lining up gigs even in an exurban way. What works even better is the exurbs of business trips for existing clients. This puts the cost perception firmly in the positive zone: you’re there making money, not spending it.

Here suburban encounters are meetings with other people in the same large org, which might lead to unrelated parallel gigs (happened once for me) and exurban encounters are with unrelated people at other organizations that just happen to be in the same area (several gigs happened this way).

Of course, all of this is down for the count right now.

What about in-hub encounters?

In-Hub Encounters

What about the value of simply living in a business hub and running into people who also live there?

Again, the direct value is probably near-zero in the median case. Being a scenester and going to a lot of meetups and things is not a great way to get gigs, because the extent of your ongoing effort investment is visible enough that “casual” coffee meetings that come out of these have a high perceived marginal cost.

Though I’ve lived in several hubs (Washington, DC, Seattle, Los Angeles, and at a stretch, Las Vegas back when it had pretensions of becoming a Zappos-driven hub), I’ve basically never gotten into the local meetup or coworking type scene for business purposes. Any meetups I’ve attended or organized have been social, for my blog readers typically. Most local 1:1 coffees have been social, with no expectation or potential for gigs.

Basically, almost nothing big of interest to indies happens as a result of investing in semi-structured “business scene” activity (meetups and such). The yield is simply too low, because these “scenes” are disproportionately full of people looking for gigs and opportunities rather than people with gigs and opportunities to offer. There is an air of I’ll-take-anything desperation and thinly veiled precarity. It is not a good environment to close money deals.

The one significant in-hub gig I landed (A4) was actually mediated by a mutual friend, and the client in that case was only a part-timer in my city (the mutual friend was in the other city). We met up for casual coffees several times before I landed the gig, and these happened during the part-time visits by that client to that city. The slight time-pressure of limited in-person meeting windows made these closer to business-trip exurbs meetings than in-hub meetings.

The Broken Pre-Pandemic Gig Funnel

I think everything I’ve said applies to anybody doing a relatively high-level sort of knowledge work, with weak structure and ambiguous expectations and high 1:1 trust required.

So if you put it together, what can you conclude from this analysis?

1. The bulk of indie revenue can be attributed to casual coffees

2. Casual coffees are encounters with low marginal cost around existing activity

3. These mainly happen in the exurbs of travel business/event travel

4. In-hub encounters are much less important than people imagine

5. Actual participation in “networking” events has little to no effect

6. You need to travel, live where others travel, or both, to catalyze casual coffees

7. If you live in a remote, non-hub, cheap place, you must travel a lot

8. If you live in a high-traffic, high-cost hub, you need to travel much less

This is the pre-pandemic indie-casual-coffee funnel. It is how I — and many like me — used to generate gigflow.

The bad news: this thing has been shot to pieces. Certainly for the next year. Possibly for the long-term.

The good news: if indeed there is an emerging alternative model to doing indie work based on flipping the ratio of casual coffee leads vs. online-closing leads, you should be able to run it from remote hubs where costs of living are much lower.

But we haven’t figured out the how.

And in the meantime, I have to consider a bunch of different apartment choices in the next month, and pick a place to move to before my current lease runs out.

Do I bet on remaining at a hub location — downtown Los Angeles — and betting that normal activities resume fairly quickly? Or do I slouch off to some cheaper location, where costs of living are thousands to tens of thousands of dollars lower, and figure out a whole new playbook?

I’ll let you know what I end up doing after I do it.

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.