Building a Sparring Business

Only 2 more newsletter issues to go before Art of Gig wraps up on April 30th!

Last year, I wrote a 3-part series1 on executive sparring, but never quite wrapped it up neatly. So that’s been on my to-do list before I wrap this newsletter.

1. In Part 1, Introduction to Executive Sparring (May 14, 2020), I set up the basic idea, and explained how it is different from things like coaching, how and where you can learn the skill, and what traits it takes to be good at it.

2. In Part 2, The Guru Factor (May 21, 2020), I explored what kind of epistemic posture is appropriate for sparring (you bring an appreciative view on instrumental knowledge as an emissary of the adjacent possible) and how to manage perceptions (including self-perceptions) around labels like “Guru” and “Pundit” so you can be effective.

3. In Part 3 I’m Okay, You’re Not So Hot (June 3, 2020) I explored how to set up what I call the “problem social graph,” as the context for the sparring, based on the operating assumption that your client is not the problem; other people in their organization are.

In the first three parts, I circled, but never quite got to what I consider to be the solid knowledge foundation on which to build a sparring business. So let’s wrap up the series by addressing that question.

What Are You a Guru Of?

For better or worse, having a guru factor going is kinda necessary for sustaining a sparring practice as your core indie consulting activity, as opposed to just occasionally doing sparring on the side of other activities.

The big question I set up in Part 2, as a way to understand the knowledge foundations that your sparring practice is based on, was:

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.

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.

To be clear, as I’ve repeatedly emphasized in this series, I don’t recommend you self-consciously set out to “become a guru.”

But if the behaviors that lead to one eventually crystallizing come naturally to you, then you have a choice about whether to be open to that outcome or not.

One of the reasons to be open to gurudom is that it opens up the option of sparring-partner type consulting work.

Which is worthwhile because it is fun, stimulating, relatively undemanding in terms of time, and to be frank, relatively easy compared to many other ways of making similar amounts of money, and a great career option for lazy people.

My intent with this series has been to set you up to recognize and deal with what’s happening if gurudom descends on you (or if it already has), whether or not you asked for it. Gurudom is a bit like becoming randomly internet famous for a silly viral video. Depending on who’s looking, gurudom can look like a halo, or a stink around you. Some people will look up to you, others will see you as a lolcow. You don’t get one without the other.

It’s not quite a career outcome you can plan, study, and train for, but certain behaviors make it more likely to happen than others, and of course, you have to be open to it happening to you.

It’s also not a career outcome that obviously leads somewhere, the way landing a VP role leads naturally to being in contention for a CEO role. A guru-factor descending on you kinda just sits there. It doesn’t propel you anywhere necessarily. You have to make up a place to go once it descends… if you choose to be. Doing nothing with a guru factor, once you have the option, is actually a fairly common response. It is a commonly un-exercised option.

But if you choose to do something with it, “sparring partner” is one of those made-up places you can go.

As I explained in Part 2, navigating labels like “guru” is basically a cost of doing business as a consultant, and doubly so if you want to offer sparring services as the core of your consulting. There is no point fighting the perception. All you can do is own the label instead of letting it own you.

So, with that preamble out of the way, what are you a guru of?

Guru Factors vs. Brands

This is one of those questions where if you know the answer, you know it immediately and unambiguously. If you have any doubts at all, you haven’t figured out the answer.

You’ll know it’s the right answer because you’ll feel an odd sort of sense of being trapped by it, but detached from it. It will be something you’re neither proud of, nor ashamed of. It’s something like blood type rather than height or looks. It’s just a fact about you that is overwhelmingly salient to your indie consulting business.

In my case, if you’ve been following my writing/blogging career, the answer is obvious, I’m viewed as a “guru” of pragmatic organizational politicking.

The perception kicked in with the Gervais Principle series that launched both my writing and consulting careers, and I’ve never been able to either get away from it, or significantly recenter around something else.

There’s a bunch of side dishes I offer alongside the main course:

1. “Fat” thinking over lean

2. OODA loop stuff

3. Software eating the world

4. Working with the Silicon Valley management playbook

5. Self-aware mediocrity as an executive/managerial ethos

There’s also a number of “guru brand attributes” like a strong bias for history, phenomenology, and anecdotal knowledge over abstract theories and process models/frameworks, a cartoonish association with 2x2s (which is something like a signature “tell” of my style), and so on.

But the core has always been pragmatic organizational politicking.

If you are an executive and you know I exist, I’m probably on a fairly short list of people you might call if you’re trying to get something ambitious done while dealing with organizational politics along the way.

People often want to talk to me about lots of other topics, such as TV shows, storytelling, memes, tech trends, and so on, where I can be generally stimulating company. But they only tend to hire me when they run into a challenges that require modeling and sorting out organizational politics, and understanding what peer executives are doing/trying to do, and why. And how to work for, against, with, or around them as necessary, to do what you want to do.

The thing about being subject to this sort of perception is that:

1. You have to have one to have a sustainable sparring career

2. You will hate it for a while once you find it, and feel pigeonholed by it

3. You must come to terms with it and kinda ironically own it to enjoy it

You’ll know you’ve found your guru factor when you see people referring to you as “that _____ guy” and you react with a slight cringe, but then shrug.

When it’s easier for people to remember your shtick than your name, you’ve found your guru factor. For a lot of people, I am “that guy who wrote that thing about The Office.” Even if your name is easier to remember than mine, your shtick will overwhelm it.

Note though, that your guru factor is not your personal brand, though the two are closely related.

Your brand is how people remember who you are. Your guru factor is the perspective people come to you for.

By way of analogy, consider something like the Hubble Space Telescope. It has a brand as a high-tech, complex, expensive gee-whiz space mission that is a showcase of American technological prowess. Science nerds of all ages love it, and share its photos.

But what people, specifically astronomers, come to it for is a specific set of observational capabilities — visible spectrum from LEO, requiring the aperture size Hubble offers.

If you wanted a different part of the spectrum, like radio, you’d go sign up for time on a different telescope, even if Hubble is your favorite telescope. If you needed observations that were less sensitive to atmospheric distortions or doable with smaller telescopes, you’d go elsewhere (Hubble doesn’t accept observation proposals that can be done by ground-based telescopes).

The “unique telescope” analogy also provides a clue as to how to go about developing a guru factor, the thing you’re a guru of.

Don’t try to be “smart.”

This is the most important thing.

Nobody ever goes to anybody else for the “smart” perspective to complement their “stupid” one. If you think you’re stupid, you look for a therapist or life coach and work on self-esteem issues, not a consultant to help you take on the world.

Being smart may or may not be relevant in becoming known for specific perspectives (obviously, if you are known for surprising neuroscience metaphors, you have to be smart enough to do neuroscience), but people don’t come to you for sparring for the smarts.

Well sometimes, misguided potential clients do, but the first call goes so awkwardly, they realize it’s not actually what they want.

This can be very confusing, because many people will say they came to because you’re “smart,” or “sharp,” but a little digging will reveal that did not. There’s just a lot of general-purpose flattery that goes on in the game of introductions that should not be taken seriously. Even if they genuinely believe you’re smart, or very smart, that’s not why they’re there.

Pro tip: the more extreme their adjectives for you, the less they understand their own motives for reaching out to you. Someone who merely says “I wanted to chat with you because you seem like a smart guy” understands their own motives much better than somebody who says, “I wanted to talk to you because you seem like a super-sharp whip smart, amazing and unique mind.”

Bottomline, “smart” is never part of a guru-factor past a basic minimum. You can’t be a moron, but you don’t need to be a genius either. Mediocre smarts is the sweet spot.

Consume different inputs.

This is the second most important thing.

You learn to see differently — differently enough to sustain a guru-factor shtick — if you’re fundamentally consuming different inputs than most people who talk about the things you talk about.

How you see is a function of what you’ve seen. If you’ve seen the same things as everybody else, it’s hard to see differently from everybody else.

But it only has to different in the target context. Watching lots of mainstream TV isn’t a particularly rare behavior. That was basically my “seeing training.” But it’s an unusual perspective in the context of executive business lives. Executives are rarely big TV watchers because it is a time-consuming pastime for lazy people, not one for people putting in 100 hour weeks. So an eye trained by hundreds of hours on the couch consuming sitcoms is different for them.

Of course, you still have to have enough literacy in their domain to make the connections and talk on common ground about the actual problems. I don’t spend sparring sessions talking to my clients about my favorite episodes of The Office. We talk about whatever they’re actually working on or dealing with. For that, I have to do my homework like any other kind of consultant.

“Difficult” is not “Different.”

This is the third most important thing.

If you learn to think well about difficult topics, that makes you an expert. A pundit. People will come to you for definitive, authoritative expertise, not sparring. They’ll come to you for advice, and then generally take it, because they are not competent enough to spar with you. Conversely, while you need a basic literacy in difficult topics they are experts in, you can’t actually spar with them on that topic. You’re not competent.

So strangely enough, to uncover a guru factor, it’s actually better to immerse yourself in topics that are demanding (in terms of being time consuming) but not actually difficult. Mastering difficult subjects puts you on the pundit track, not the guru track. Other doors open, not the sparring door.

For example, I’ve read a lot of history, and classic, older business literature. It’s not difficult material, it’s just unusual to consume it, since the pop-business literature market is driven by fads, and focused on the most recently published books and ideas. So while many people may have heard of the “Peter Principle” from 1969, surprisingly few working-age people have actually read it or even known to look it up on Wikipedia. For many people much older than me, my 2009 Gervais Principle was actually their first introduction to the idea!

So you just have to have put in the time. In my case, since I started consuming this material in the 80s, I know a lot of “old” stuff that most people my age, or even much older, aren’t usually familiar with. Most people only get into management literature as adults, and more commonly, when they are actually within striking distance of executive roles. It’s not a common teenage nerd interest, so I accidentally started building an advantageous appreciative knowledge perspective in the 1980s.

The Guru-Pundit Divide

Once you’ve answered the basic question, what are you a guru of? or at least figured out what to watch out for and what behaviors to practice, you can ask whether you actually want to be one.

If it seems rather late in the game to be asking that question, it’s because you don’t really understand the question until you have the live option, ready for the exercising, in front of you.

As I’ve said earlier, I believe having a guru factor going is necessary, but not sufficient, for being a good sparring partner. I’ve never met a good sparring partner who was not a guru of something. To spar, you cannot have a “view from nowhere” of the world.

But if you have a live option, and you’re asking the question at all, chances are, there is an unspoken “do I want to be a pundit instead?” secondary question.

You can ask several follow-up questions that clarify this, which I listed in Part 2:

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

Here’s a test to tell apart gurus and pundits. In their relationship to appreciative knowledge, pundits prioritize taste, while gurus prioritize insight.

Recall that I defined pundits as people with an instrumental view of appreciative knowledge, as opposed to gurus who have an appreciative view of instrumental knowledge.

If your relationship to appreciative knowledge is grounded in taste and aesthetics, and you appreciate the beauty in a knowledge domain, you’re better suited to being a pundit. You will automatically gravitate towards difficult domains that demand smarts. You will automatically consume the same things others do, but develop a reputation for being a tastemaker, who declares which subset of commonly consumed information is good or bad. You will naturally want to cast what you know in the form of polished workshops and glossy printed artifacts.

A guru on the other, prioritizes discovery of “aha!” insights, and doesn’t much care who discovers them, gets credit for them, or what the discovery says about their smarts.

This is an ideal posture for sparring, since usually insights pop up as part of the process, and don’t say anything much in particular (whether flattering or unflattering) about who uncovered it. It’s like going on a hike together, and one of you points out an eagle in a tree.

It is something of an accident who gets to spot the eagle. The point is going on a hike where interesting things can be spotted.

Is gurudom what you actually want?

Though the popular modern image of a guru is a cult leader who mesmerizes a flock of brainwashed morons, the term actually refers to someone people argue with, and this is the connotation that has carried over to business guru. Where the guru is a teacher of young novices, the aim is to get good enough to argue with the teacher.

This is not actually a pleasant thing for everybody. Many people prefer and expect to be deferred to.

A pundit is someone people defer to. If that’s really what what you want, that’s what you should cop to, and aim to be.

Master a difficult domain that takes smarts.

Start a newsletter to bestow wisdom unto the world.

Make declarations that follow the rough template: This thing is good, that thing is bad. Do this, don’t do that.

It’s a good hustle, and I admire people who do it well. It’s just not something I can do.

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

To quote Part 2 again:

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).

Statistically speaking, I’d say about 60% of the population is vocational learners with little to no interest in appreciative knowledge of any sort. Another 30% is critics, focused almost exclusively on consumption tastes, whether or not they are connoisseurs. Of the remaining 10%, I’d say 9% are pundit types, and only 1% are guru types.

This has nothing to do with being unique or special. Gurus are rare because few people are lazy and unambitious enough to hang out on the sidelines, appreciating interesting doings without moving to participate consequentially in them.

Most people have an agency itch. They want to energetically do stuff. Even the critics are way more energetic than the gurus. They energetically consume and analyze what they consume in excruciating detail. All the wine nerds I know are extremely energetic people. All the pundits I know are voracious and hard-working readers and judges of difficult, demanding material.

If you’re reading this at all, you’re unlikely to be a purely vocational learner or a critic. Chances are, you’re either a natural pundit or a natural guru.

9:1 you’re a pundit.

Not that there’s anything wrong with that 🤣.

If so, you’ll probably be miserable sparring. You’ll experience the persistent impulse to speak with careful authority rather than in spitballing mode. You’ll feel more comfortable when you can occupy a “professional” role in a situation (“Alice here is our machine learning consultant”) rather than am amateur hobo type role (“Bob here is this guy I met on Twitter who I thought would be interesting to have in this conversation”). When you have to ask a question, you’ll feel a slight twinge of reluctance at having to “admit” to not knowing the answer already. You’ll get a little dopamine hit whenever people defer to, or validate your sense of expertise, by accepting your recommendations without question.

This is a pundit trapped in a guru role.

I mean, seriously, this is fine. If this is you, go there. Be the pundit. Don’t try to occupy sparring roles. Find a box you feel valued and comfortable in, claim it as your own, and live in it. Exercise the influence that will accrue to you if you’re good at things you claim to be good at. Get yourself out of sparring conversations, and simply reserve the right to distance yourself from decisions you don’t agree with, but don’t want to get into arguments about.

On the other hand, if it’s being the “professional” anything that makes you uncomfortable, if being asked to make a decision for others makes you wary, if having your expertise on some matter validated makes you naturally say self-deprecatory things to mitigate the perception of expertise, if you get a genuine kick out of being the hobo in the room… you might be a guru trapped in a pundit role.

Putting it All Together

I realize this four-part series hasn’t exactly been a cookbook recipe for building a sparring practice. It’s been more of a field guide to recognizing it happening to you, and some hints on what to do more or less of to increase or decrease the chances of it happening to you.

But to put it all together, the way to build a sparring practice is… to spar.

Spar at every opportunity, in every available context, with any and all comers. Whether you’re being paid or not.

Don’t stand on ceremony. Don’t assume arguing with randos on Twitter is a waste of your time. Don’t set uppity conditions and criteria around who is/is not “worth” arguing with. Standards of competence are for pundits.

Don’t let your sense of your own expertise stop you from sparring with anyone unless it’s down to not even having a shared vocabulary. And the funny thing is, if you let lack of shared language stop you, you probably don’t want to spar anyway. People who want to spar generally find different language if necessary. If you have a PhD in a jargon-heavy field, but someone random who lacks the jargon says something insightful about it, you’ll find a way to engage and spar.

Sparring is like writing. You can’t set out to “be a writer.” All you can do is write. And more importantly, rewrite. For sparring, the equivalent of rewriting is simply taking notes and reviewing them periodically, maintaining threads of continuity through extended conversations across many sparring sessions.

So log the hours and the notes, and enjoy it. Do it long enough, and people start coming to you to spar about particular things. At some point a guru factor pops and you have to get over hating it and coming to terms with it. Then at some point you find people want to pay you to spar with you.

Don’t make it too complicated. Keep it caveman simple. Taking a cue from Dan Harmon’s “story circle,” here’s my attempt to reduce it to just 8 words.

1. Spar as much as you can.

2. Take notes.

3. Enjoy it.

4. Find a guru factor.

5. Choose to be a guru rather than a pundit.

6. Accept that you’ll hate it for a while.

7. Come to terms with it.

8. Charge money for it.

Spar. Notes. Enjoy. Guru. Choose. Hate. Terms. Charge.

That’s all there is to it. That’s how you build a sparring practice. You just have to do it for long enough.

Note: This newsletter will be shutting down on April 30th, 2021, and the archives published as an eBook.

To simplify the shut down, new subscriptions have now been turned off and existing subscriptions have been paused. Existing subscribers will still be able to access the paywalled archives until the list shuts down in May. The rest of you will have to wait for the ebook.