Going Indie is Going Amateur

Indies should be like Sherlock Holmes

Welcome back.

In October, I hit pause, and took around six weeks off from writing this newsletter. It was a much-needed break for me, and gave me an opportunity to reflect, both on the newsletter, and on my consulting practice. During the break, I also turned 46, landing on the “undeniably” side of “middle-aged.” My 10th anniversary as an indie consultant is also coming up. That will be March 1, 2021. Mark your calendars so you remember to please clap.

In a traditional job, I’d be expecting some sort of cheap plaque marking the anniversary, a “personalized” note from the CEO, and perhaps colleagues taking me out for a beer and roasting me. In the free-agent world, nobody would even know if I didn’t tell them. That’s kinda how I prefer it. Which explains why I’ve already lasted twice as long as a free-agent than I did in my only real job (4.5 years).

During my break (unpaid vacation?), I found myself thinking particularly hard about the next ten years. Do I want to continue doing more of the same sort of thing? Will I still be sparring with executives in 2030? Or will I be up to something different? If so, what?

Whatever I do, one thing I already know: I’m going to maintain my amateur status. No matter how long I play the indie game, I’m never going to turn pro at it, whatever that might mean. If you are thinking of going indie, I recommend you think of it as going amateur.

Nearly ten years into the game, I’ve convinced myself that an amateur posture towards work is central to the idea, appeal, and value of free agency. In fact, going free agent is going amateur, even if you were once a professional in some sense.

For a free-agent, being an amateur, as opposed to a professional, is more important than being paid by the gig rather than with a salary.


Sherlock Holmes, consultant detective, was technically an amateur in the sleuthing business. Doyle’s creation spawned an entire genre of fiction built around the premise of amateurs beating professionals at their own game, despite the handicap of fewer institutional resources.

A hundred years later, the appeal of the amateur sleuth as a literary invention remains strong. My favorite detective shows in the last couple of decades — Psych, Monk, Castle, and of course, the reimagined Sherlock — all feature amateur free-agent (or in the case of Adrian Monk, failed-professional), protagonists.

The conceit of classic detective fiction as a genre is that the amateur sleuth outwits the criminal, while outdoing the professionals, through an unconventional superior intelligence. But I want to offer you a contrarian take: it is the amateur posture that does most of the work, and looks like inscrutable genius to the professionals when it works out. As such, it is available to anyone with the courage to “go amateur.” Which, I like I said, is almost the same as going indie.

To understand why, you have to first understand the amateur in relation to the professional. After all, there would be no amateurs if there were no professionals to define them through negation.


It is easy to construct and tear down a strawman view of professionalism as an artifact of empty credentialism and risk-aversion standing in for credibility, but that would be neither fair nor interesting. Professionalism is a deeper idea, and amateur status only has meaning to the extent professional status has genuine complementary worth.

To be viewed as a professional is enjoy a certain earned dignity in default perceptions; a certain presumption of default value that makes for a great deal of psychological security.

The most subtle part of the security is not the esteem itself, but the certainty of esteem. Within certain institutional contexts, to be a professional is to give yourself permission to suspend your insecurities and let go of imposter syndrome. Nobody will ever wonder why you exist, because under the right conditions, it will be self-evidently obvious why it is good thing that you do. Nobody wonders why Anthony Fauci exists, and most of us in the United States are glad he does.

That’s what it truly means to be a professional. It’s not about credentials, empty or otherwise. Being a professional means you know your worth, and others do too — and not because you brandish your degrees and certifications. To be a professional, in the best sense of the word, is to care genuinely, and try sincerely to do the right thing, and for that to translate automatically into societal value and meaningful validation through the magic of effective institutions.

This is a condition that is worth something both to professionals, and to the society that views them as such. Something that is not to be set aside lightly.

To be an amateur, in the worst sense of the word, is to be an insincere bullshitting dilettante, and for that to result in casual destruction and pain for others.

The last few years have been a battle between professionals in the best sense of the word against both professionals and amateurs in the worst sense of those words.

But what interests me is the missing quadrant: what does it mean to be an amateur in the best sense of the word?


What it does not mean is striving mightily to create an ersatz version of the perception of trust enjoyed by professionals. That road leads to cringe personal brands: campy, failed faux-professionalism for free agents based on anxious, over-wrought perception management.

Thar be personal demons, not trusted brands.

No, being an amateur in the best sense of the word means embracing the lack of guarantees as a feature. Amateur status means you represent no guarantees — but people want to work with you anyway because you bring something else to the party. Something the professionals cannot bring, by virtue of being professionals.

When you are an amateur, there is no no guarantee that caring genuinely, and trying sincerely to do the right thing, will automatically lead to anything good anywhere.

It is this lack of automatic, default positive consequences (and expectations of such consequences by others) that leads to the neutral noun amateur turning into the pejorative adjective amateurish. When something is done amateurishly, the best you can usually hope for is “no harm done.” Amateurishness is not lack of skill necessarily. It is lack of predictability in outcomes.

The presumption is that even sincere, caring amateurs are at best inept bunglers who occasionally get lucky. They do not embody any deterministic causal relationship between effort and outcome.

That’s the downside.

The upside of being an amateur is freedom. Freedom from the confining expectations that accompany perceptions as a professional. Freedom from institutionally rigid notions of value. Freedom from the limiting self-perceptions that inevitably accompany ascriptive professional status. Freedom from the conflation of skills and guarantees. Freedom from standing on ceremony. Freedom to wonder and play without a lurking sense that it is undignified for “someone in my position” to do so. Freedom to take strange risks. Freedom to operate with insufficient gravitas (hehe, bet you didn’t think that link would go where it does).

In this freedom, there is certainly the power to destroy. But there is also the power to see and do things that wouldn’t even occur to professionals.

This freedom does not come for free. Merely declaring yourself to be an amateur does not buy you the freedoms of a consciously held amateur posture.

What does it take to earn the freedom of amateur status? What would a non-pejorative sense of amateurish look like?


In A Study in Scarlet, Dr. Watson describes Sherlock Holmes’ knowledge as follows:

  • Knowledge of Literature: Nil.

  • Knowledge of Philosophy: Nil.

  • Knowledge of Astronomy: Nil.

  • Knowledge of Politics: Feeble.

  • Knowledge of Botany: Variable. Well up in belladonna, opium, and poisons generally. Knows nothing of practical gardening.

  • Knowledge of Geology: Practical but limited. Tells at a glance different soils from each other. After walks has shown me splashes upon his trousers, and told me by their color and consistency in what part of London he had received them.

  • Knowledge of Chemistry: Profound.

  • Knowledge of Anatomy: Accurate but unsystematic.

  • Knowledge of Sensational Literature: Immense. He appears to know every detail of every horror perpetrated in the century.

  • Plays the violin well.

  • Is an expert singlestick player, boxer, and swordsman.

  • Has a good practical knowledge of British law.

What is notable about Holmes’ knowledge is that though he demonstrably possesses a lot of hard-won, high-value knowledge, to Watson’s eyes, it is unsystematic and idiosyncratic, with what seems like glaring gaps and odd lacunae.

Holmes wouldn’t pass a standardized test except as a side-effect of knowing things his own way (in a episode of Psych, the police detectives Juliet and Lassiter engage in a friendly rivalry over who scored higher in the detective exam — until the amateur protagonist Shawn reveals in a casual aside that he got a perfect score on it as a teenager — which could oddly be read as proof of validity of the test).

Watson’s list says as much about his own status as a true professional twice over — a medical doctor, and an army veteran — as it does about Holmes.

Note that he thinks in categories that sound like a combination of a university course catalog, gentlemanly worldly wisdom, and a finishing school designed to teach polite conversation.

Despite his clear esteem for Holmes, Watson is unable to see a pattern in Holmes’ knowledge. Watson is Seeing Like a State personified.

The only area where Watson dimly senses the gestalt of Holmes’ mastery is one that is not an institutionally recognized subject — “sensational literature.”

Today that sort of knowledge might translate, for instance, to being Very Online and having a vast knowledge of every meme that ever went viral on Twitter. Which actually indicates interesting things if you are not fatally wedded to a professional self-image and institutionally validated patterns of knowing.

In most areas in Watson’s catalog, Holmes is “unsystematic” or “limited” or “practical” (as in, vocationally rather than liberally educated on the topic), and somehow comes up short. In one case — chemistry — Watson characterizes Holmes’ knowledge as “profound,” which is an oddly mystical and exoticizing term to apply in an area where he himself, as a doctor, would be expected to have some expertise.

Note that there is nothing natural or necessary about Watson’s map of knowledge; it is as arbitrary as Borges’ encyclopedia, and arguably no more fundamental than Holmes’ own hidden scheme.

The whole list summarizes Watson’s essential puzzlement over the very essence of Holmes, despite being his admiring lifelong companion and biographer. The charm of Watson as a narrator of the Holmes stories is that he never does figure Holmes out. This is something Holmes himself often points out, in noting that Watson’s accounts of cases invariably miss what Holmes sees as essential, while emphasizing sentimental and romantic aspects he himself is indifferent to.


Is Holmes a genius? Or does his amateur status merely present him as such to professionals like Dr. Watson and Inspector Lestrade?

One good definition of genius is: talent hits the target others can’t hit, genius hits the target others can’t see.

Or as Alan Kay once put it, perspective is worth 80 IQ points.

Could it be that Sherlock Holmes is not a genius, but simply a talented amateur whose ways of seeing are inaccessible to the professional eyes of Watson or Lestrade?

Holmes is clearly no insincere dilettante in the stories, so we can eliminate the possibility that he’s the bad kind of amateur. He has accumulated a great deal of knowledge over many years of practice, so his is not a Zen-lucky beginner mind. He is not young, so he cannot be labeled precocious. But his knowledge is not systematic or disciplined, so he’s not a professional.

So having eliminated the impossible, we must conclude, however improbably, that Sherlock Holmes is an amateur, but not amateurish.

He is effective, but his effectiveness comes with no guarantees. He has depths, but his depth-dimensions are invisible to professionals (this is a theme I keep returning to; I first wrote about it almost a decade ago in my ribbonfarm post, The Calculus of Grit).

And it doesn’t matter what kind of professional. Lestrade is a policeman, and in theory should have a better read on Holmes. In practice, he is even more befuddled than Watson.

So it is not the subject matter of expertise that is the problem, it is professionalism as a posture and perspective. Watson and Lestrade both suffer from Seeing Like a Professional syndrome.

The unconventional workings of Holmes’ best-kind-of-amateur mind seem like mysterious but unreliable genius to professional policemen like Lestrade.

For Lestrade, Holmes is something like a magic Deep Learning AI algorithm. Not to be entirely trusted, and full of biases, but someone with unpredictable and sometimes uncanny input-output behaviors. Holmes appears to Lestrade as AlphaGoZero must appear to professional Go players.

So when he gets stuck, despite his confused mix of contempt and awe for Holmes’ methods, Lestrade trudges over to 221B Baker Street, accepts a cup of tea from Mrs. Hudson, sets his professional conceits and insecurities aside, and puts his case to the inscrutable oracle.


So I put it to you — Holmes is no genius. He is something better: an amateur in the best sense of the word. As everybody in the stories notes, his silly acts of abductive reasoning are no more than parlor tricks. His apparent genius is actually a lack of the professional blinders and attachment to institutional systematicity — the book in “by the book” — that limits what Lestrade or Watson can see or do.

And this is something all the characters are aware of. So it is not as though Lestrade or Watson are clueless about their professional blinders. They are aware of them, and aware that Holmes represents a way around their own limitations.

We see this, for instance, in the television adaptation of The Abbey Grange, starring Jeremy Brett (probably the portrayal of Holmes that is most true to the original stories). The episode features the following exchange, after Holmes achieves an unconventional resolution of the case:

Sherlock Holmes : It's almost as though you disapproved of the happiness we have fostered today.

Dr. Watson : Oh, no. I approve of that; of course I do. I am uneasy that you took upon yourself the duties of advocate and judge.

Sherlock Holmes : You are too bound by forms, Watson!

Dr. Watson : Forms are society.

Sherlock Holmes : Hmph.

Dr. Watson : Manners maketh man.

Sherlock Holmes : Hah.

Dr. Watson : It's just as well you are unique.

There is a resignation in the conclusion that Holmes is “unique.” The professionalism that is leveraged capability for Lestrade and Watson in the right institutional contexts turns into a sort of learned helplessness outside those contexts.

Even when Holmes demonstrates that they need not be helpless, and strenuously asserts “you know my methods,” (implying they are learnable), Watson and Lestrade insist on casting Holmes in the role of a sage with access to esoteric methods forever denied them.


It might be a self-congratulatory conceit, but Sherlock Holmes, I would argue, is the model every independent consultant ought to aspire to. Not in the sense of affecting the posture of a genius, but in the sense of ignoring the contours of knowledge held to be self-evidently meaningful and important by professionals, and navigating by your own amateur — but grounded — maps of the territory.

If you keep feeding your insecurities about your lack of a title and clear markers of professional credibility, you’re doing it wrong.

Whether you draw a salary or bill by the hour, the choice to view yourself as a professional is just that. A choice. It just happens to be an easier and more effective choice in more situations.

But it is not the only choice available.

You can always choose to go amateur. The more you know, the more courage it takes.

In a way, you don’t get to experience the essence of independent consulting — consulting as a mercenary calling — unless you go amateur and maintain amateur status.

Amateur status at work, play, and life. There’s just you, the wide-open universe, settling memories of what you have done, animating expectations of what you might do, and no guaranteed expectations for anyone involved.

Going amateur and maintaining amateur status. That’s it. That’s the whole game.

Note to subscribers: Billing, which was paused during my break, will resume starting today.

Heads-up: The annual meeting of the Yak Collective will be held on Thursday December 10th at 8 AM Pacific. It’s a public Zoom event, so do drop by if you’re curious to hear what we’ve been up to and what we are hoping to do next year. Here is the public calendar invite.