📚 Strategy & a pilot named Boyd (Part I: Big Picture)

A review of Certain to Win by Chet Richards

One of the many things to come out of my business trip to Norway back in April was a discussion with my boss, Tristan, about several nonfiction sources he liked. One was the Founder’s Podcast — the other the book Certain to Win by Chet Richards (here’s an Amazon affiliate link for the book. If you want to check it out, I earn a small commission, yada yada).

When I got home, I hooked my airpods up to my Android phone and listened to a big chunk of Certain to Win while I pushed my daughter’s stroller around town. It was the first time I ever listened to something that long using AI text-to-speech, mostly because I’m not really an audio learner, but it went surprisingly well. One of the nice things about pairing the book with text-to-speech — as opposed to using a proper audiobook — was that I was able to pause and take notes pretty easily and have the actual text in front of me easily whenever I wanted to do some deep thinking.

So even though I first read the book several months ago while walking around, I have pretty good notes. Tristan asked me to share some of my takeaways, and I see no particular reason not to share them with y’all as well. Brace yourself, though — Certain to Win is at the precise confluence of topics that a lot of my friends care about but I’ve heretofore avoided: business and war.

Today I’m going to focus mostly on the broad overview. Part II will focus mostly on the bits I found to be useful advice.

The Fundamentals of Strategy

Richards spends a big chunk of the book focused on foundational concepts that will be familiar to anyone who has ever played a game — numbers advantages, initiative, demoralization, speed, going with your gut, etc. As someone who came of age decades after Boyd’s heyday, who played a lot of strategy games, and whose local economy is in some ways driven by defense contracting, it’s no particular surprise that at no particular point did it feel full of earthshatting insights. I wasn’t tripped up by things like “Blue team” (defense) vs “Red team” (offense) — but it’s hard for me to tell how much context “normal” people would have reading a book like this.

Regardless, I don’t think the point of this book was to blow anybody’s mind. Just like no one expects an analysis of Sun Tzu’s Art of War to be groundbreaking, Richards’ book was in some ways more about compiling well-known concepts, provide useful and relevant anecdotes, and tell the story of how a particular set of priorities made a difference to a particular military force at a particular point in time… in a way that is accessible to business leaders — as opposed to young air force officers — looking for guidance on how to shape their micro- and macro- strategies.

Truthfully, it felt like it was designed to appeal to the grown-up versions of boys I’ve taught over the years, who were squirrely terrors in class until I let them come to my room during lunch and watch old world war documentaries. I know a lot of guys — my father, with his extensive collection of books about planes and tanks and battleships certainly among them — who have never been to battle but are nonetheless fascinated by 20th century military history.

What better way, then, to make the nuts and bolts of running a business interesting than to frame it in the context of clever and bloody battles? What more inspiring hook for “how to win in today’s world” than tying it back to the last glorious war America fought?

At the start of the attack on France, the Germans had no advantage in numbers and lagged in technology. Yet they won and won easily, and they did it through the application of strategy.

How much does size matter?

Since long before the days of David, we’ve loved the underdog. There is a certain psychology to it, I suspect. Advantages are great to have, but sort of definitionally, at the life stage where learning is most common, the obvious advantages rest with the other guy. We seek out learning materials most when we’re young, when we’re small, when we don’t have a lot of experience, when we don’t have a lot of allies, when we don’t have a lot of knowledge. Quite naturally that corresponds to being the underdog, so quite naturally materials geared toward learners are geared toward that dynamic.

And underdogs do, after all, sometimes win. Richards makes it a point to trot out statistics along those lines, for which I was grateful.

How often does the smaller side win? Certainly not all the time, and the historical evidence suggests that numbers do play a role. A recent study of 625 battles from 1600 to 1973, for example, concluded that having a larger force does indeed improve the chances of victory but not by enough to overcome other factors, which they identified as “leadership skills” and “troop morale.” This is the “everything else being equal, size matters” argument. Why in the world, you should ask yourself, would one go into battle with “everything else being equal,” especially concerning the factors known to produce victory?

And yet, as with most statistics, I couldn’t quite bring myself to trust them.

Of course leadership is going to matter, and so is troop morale — but they are hardly orthogonal to troop size! I also found it absolutely bizarre that no mention was made here of which side was defending which is of course going to have implications with regards to the outcome of the battle. They might as well have said “size matters, but so do the logistics lines.” The Roman legions, for example, famously (right? 🙈) did so well at least in part because the legionaires were able to handle all aspects of taking grain from a field and turning it into bread.

Lots of things matter, even leaving aside how overly broad the factors mentioned seemed to me. “Leadership skills” is a huge tent and involves things like “how many guys do you bring to the battle” and troop morale is obviously going to impacted by things like “how many guys do I have on my side.” Sure, yes, there’s going to be stuff like “how well trained are we” and “how good are our guns” and “how much do I trust my friends to come rescue me if I get pinned down” or whatever…. but size not mattering “enough to overcome other factors” is trivially true. You can have an army infinity big and it will still lose if the men are starving so badly they can’t stand, come on that doesn’t mean you shouldn’t give serious attention to making sure you bring enough guys to a fight.

Yes, there is the rare fight where a small, skilled person beats the hell out of some guy who attacks them — but the fact is, pretty often, size matters even when all else isn’t equal. I was reminded of the statistics I’ve seen about high school boys absolutely whupping olympic-level women in most sport categories.

How does the smaller side get away with it and win? He doesn’t always, of course. The Confederacy lost to the Union, Poland lost to Germany, Finland to Russia, and Germany to practically the rest of the world. The research cited in the last chapter indicated that by picking the larger or more technologically advanced side, you can predict victory in just less than 75% of the battles studied. This sounds impressive, until you recall that by flipping a coin, you can predict victory 50% of the time. The fact that the smaller side does win, and not infrequently, is what excites our interest. To start to answer the question of what it takes to win—what it takes to put Boyd’s trinity to useful effect—let’s continue with our initial case study, the Blitzkrieg.

Honestly, I found this section exciting at first. Prediction markets aren’t my thing — neither is gambling in general, and like most women I am more risk-averse than the men in my family — but I do appreciate it when people “put their money where their mouth is” when making claims and predictions.

Nate Silver

would have lost the most recent bet I saw him try to make, but I can appreciate a guy who puts skin in the game a lot more than people who make unfalsifiable claims.

If we had a model — or even a heurstic — that could do a useful job of picking the winner in a conflict, that would be really useful. We don’t, though. Americans can barely predict the outcomes of our own elections. It’s not like any sensible gambler would just put their chips on “bigger side wins” or even “faster decision-makers win” — if it were that easy, hedge funds wouldn’t pay so much for quality quants, and ESG (the “g” stands for “has good governance”) funds would be a complete no-brainer for investors.

Strategy > Tactics

Richards keeps digging into these statistics about whether the smaller/smarter/richer/whatever side tends to win wars, but I frankly don’t understand how the study he cites can possibly have gotten its numbers. I didn’t dig in personally — I doubt I’d understand it all if I tried — but take this example:

What all of this suggests is that individual brilliance alone cannot account for strategies where smaller, less technologically advanced forces win, since, following Deming, such effects should only account for something less than 10% of battles. The study cited above suggested that the true number is over 25%, more than can be ascribed to numbers or technology alone. There must be something else there, some other way of looking at strategy that can enable smaller “weaker” forces to win far more often than conventional thinking would suggest.

Why does it have to be quick, clever strategy? Why can’t it be better knowledge of the terrain, home field advantage, cultural pressures, home front politics, or any of a thousand other factors in play at various times.

If we’re analogizing this to technology, imagine a team that is small but knows a particular tiny niche very well and can hold it against all comers. A passionate bootstrapped company could win out long term against a bigger, more diffuse company with less targeted expertise and less focus when they swing and miss in search of a hockey-stick vroom to keep their source of venture capital happy. Some might call that strategy — but it’s not the “OODA” loops that Richards and Boyd are talking about. He’s explicitly discounting things like “appointed smart lieutenants” on the micro-level, though I would call that part of strategy because I’m just some lady who doesn’t totally understand how military people mean their technical terms.

But I couldn’t help but thinking of when Yahoo offered to buy Facebook and Zuckerburg told them to sod off (metaphorically), or when Musk offered to buy Substack and Chris declined. Is that strategy? Or just mad, glorious passion.

Keep On Thinking Straight

Under stress, disoriented people become demoralized, frustrated, and panicked. Once in this condition, they can easily be defeated, regardless of the weapons that remain in their possession. […] Once one side considers abandoning the field, particularly if it loses the initiative, small setbacks can lead to big disasters, and collapse can occur quickly.

A lot of theory — economic, political, social, whatever — likes to pretend that people are perfectly rational actors. Humans are not, however, spherical cows — stress tends to overwhelm our critical thinking skills. Under stress, we generally either freeze up or keep going on our default course. I’ve never fought a war, but I can attest that it is hard to solve problems with a baby screaming, a toddler demanding food, and a spouse getting increasingly frustrated that dinner is burning.

Honestly, I found a surprising amount of Certain to Win applicable not to my professional needs (I thank my lucky stars every day that I am never going to be in charge of setting strategy at Readwise) but rather my personal ones.

Strategy is a mental tapestry of changing intentions for harmonizing and focusing our efforts as a basis for realizing some aim or purpose in an unfolding and often unforeseen world of many bewildering events and many contending interests.

This is useful for more than just companies and war; this is useful for household management and planning.

Emily Oster

has a book called “The Family Firm” and it is a reminder that families count as organizations. In some ways they were the original organization unit by which humans most often accomplished things throughout history. The strategy that you use to achieve your goals as a household manager is pretty key, I think, to happiness and good functioning. And there were related gems too, like:

“This is stupid. Why does the Blue commander just sit there and take it? Nobody would be that dumb.” Unfortunately, however, there have been times in history when the loser’s orientation seized up and he annihilated himself

When my daughter, beloved monster that she is, first started crawling across the floor and biting my four year old, he just sat there and took it with impressive stoicism. He could have gotten up and moved away! He could have avoided her chompers in the first place — she’s not a subtle creature. But he had never experienced anything like it before, he knew instinctively that he wasn’t going to be allowed to hit or shove her, and he didn’t want to hurt himself or her trying to disentangle her by himself. Eventually he got to the point where he would say things like “it’s okay” or “mom! she’s biting me” — then it took a couple more weeks of effort on my part to teach him not to let his sister bite him in the first place.

But that initial freezing up when something unexpected happens is, I think, a fundamental human instinct. Certainly when I saw a snake in my garage I did not calmly think through my options — I shrieked and slammed the door shut, even though there was absolutely no universe that (holy shit, huge) black/garden/garter snake was going to do anything to hurt me. An opposition actor could probably ruin a whole day of productivity on my part by putting a live snake into my office is all I’m saying. Stress makes it hard to think!

People who managed it anyway wrought miracles.

On Trust vs. Numbers

At one point Richards points not to Boyd, but to what I typically think of as Goodhart’s Law:

He that would run his company on visible figures alone will soon have neither company nor visible figures to work with. — W. Edwards

I am someone who understands the value of “key performance indicators” but is often frustrated by them. I spend a fair amount of time fighting the urge to do things that impact visible metrics (e.g. personally answering emails) instead of things that are important but illegible (thorough exploratory testing of new features), for example. There are several metrics I evaluate success by, now and when I was teaching, but relatively few of them capture things like “has good judgment” and “spends time on things that benefit the organization in infrequently tangible ways” (in some ways the most useful thing a developer on the team might do in a particular month is vouch for and refer a really good engineer — which can save a lot of our boss’ very valuable time).

This level of skill can be deceiving when seen by others (again, think of a stage magician), because people who have it often don’t look like they’re working harder or doing things faster.

If the Mr. Beast memo is indeed “a guide to the Gen Z workforce” as

kyla scanlon

recently claimed, my biggest takeway was that more and more people are coming to understand that value is not best measured by “hours spent working.”

There is an idiom I’m fond of; “the map is not the territory.” Farnham Street has a good essay about it here but fundamentally, models are not the world. Richards illustrates this with the following example of how useless computer models are for figuring out what is really going to happen in a war (remember when everyone thought Ukraine would fall quickly?):

the things that these observers found important are impossible to capture in a computer program, since it is difficult to get silicon to panic

As a quality assurance specialist, I like that he says difficult here, and not impossible. I’m a bit disappointed that I don’t have a good “kernal” panic joke to offer. What I can say is that even the fanciest AIs I’m aware of aren’t capable of meaningfully quantifying training, surprise, and fatigue. Despite how much it makes my computer go whrrbrrrr, the “artificial intelligences” in games like Civilization and my beloved Rimworld famously suck.

The DoD has a lot more computational power at its command, but I suspect it’s a difference in degree, not kind.

Of course models are useful, and graphs, and KPIs — and big data currently rules the roost for a reason. I also know a lot of mathematicians, electrical engineers and physicists; their models work just fine for what they’re doing. Richards acknowledges this.

There are many situations that call for models and other “hard” analytical techniques. Where the solution to our problem depends on underlying physical processes, as in an engineering simulation, we can extract relationships and build models that make useful predictions and which may provide answers that we can get no other way. But this type of situation—“man against nature”—does not concern strategy.

But fundamentally he doesn’t seem to think that stuff moves the needle — which is, I suspect, eyeroll-inducing to my friends who are fans of the F-16 (and F-18. And F-35)… especially given his criticisms of the F-15:

Blue’s weapons would have to be better than twice as good—we saw that Blue loses and quickly if its weapons are only twice as good—and in fact they would have to be four times more effective just to even the conflict. Since the prospect of an even conflict is not appealing to Blue, they would probably build in some margin of error and launch programs to develop weapons that are perhaps eight or 10 or even 100 times as good. This is not a joke: As the Air force’s new wonder weapon, the F-15 fighter, was nearing production in 1973, Air Force generals produced analyses showing that it would be nearly 1,000 times as effective as current Soviet aircraft. One wag suggested that this was great news for the country’s budget, since now we would only need to buy 100 of them to defeat the entire Soviet Air Force. The Secretary of Defense approved and Congress voted money for production of the full number (749) anyway

I’m not an expert on military procurement, but I get his point. It wasn’t for lack of good enough planes that we pulled out of Aghanistan or haven’t gone after the Houthis. So why exactly are we spending so much on the F-35? But on the other hand, well — deterrence is hard to quantify, and at the end of the day, America did defeat the Soviets, largely on economic grounds.

We have seen in the preceding sections that military models deal in the “hard” factors that can be quantified, things like the sizes of the opposing forces and the levels of technological sophistication of their weapons. We have also seen that except for battles of attrition and military blunders, neither of these has played a dominant role in deciding the outcome of battles down through history.

Other than that, Mrs. Lincoln, how was the play?

Decision-making speed is the number that matters

The innovation that Boyd is famous for, the jargony little acronymn everyone credits him for, is known as the “OODA” loop. I’m not a particular fan of fancy acronymns or jargon — which is how I’ve gone this long without mentioning it — so I preferred when it was explained thusly:

Honda used speed, or more accurately, decision cycle time, to create opportunities in the marketplace and then provide products that customers wanted to buy more than they wanted those of the competition.

The case study of Honda obviously has a lot more going on under the hood than that, as do the examples of Toyota and Southwest (note, incidentally, that these examples are mostly about things related to building and using vehicles — something that naturally aligns well with warfighting infrastructure like, you know, building and flying planes. The usefulness for Boeing executives is clear. Your average software startup? Perhaps less so.)

Still, being able to see an emerging situation, evaluate it, come up with an idea to take advantage of it, implement that idea, and then evaluate its efficacy — quickly — is obviously important.

At this point, the only fact of importance is that in two different fields of human competition, war and business, people found ways to use time to offset and eventually render irrelevant their opponent’s advantages

Back when I was in law school, the class I struggled with most was Civil Procedure, where I was expected to memorize and spout off statute numbers and the precise number of days after filing a piece of paperwork I had to follow up with another piece of paperwork. It took me half a decade to commit my husband’s birthday and phone number (which I use for grocery discounts on a shockingly regular basis) to memory — I am still pretty shaky on my own anniversary. Memorizing numbers is not my thing, calendars exist, ugh I hated that class.

But timeliness is, of course, critical in a lot of fields. Newspapers pursue ‘the scoop’ because recency bias is not always a fallacy. Coming up with a brilliant idea (like Descartes’ vision of contact lenses) ‘too soon’ for the market is in some ways as useless as coming up with it too late. Tortoise and the hare get made much of in school, and ‘slow and steady wins the race’ sometimes — but there are reasons Facebook’s motto was ‘move fast and break things’ instead.

Does technological superiority matter?

One place I was on less sure ground was the question of technological superiority. Richards seems pretty critical of American defense contracting and indeed the American overall strategy of utilizing expensive technology over large, low-cost forces.

In the military, the function of obtaining and understanding information from the outside is called “intelligence.” Today, despite a stream of intelligence failures, intelligence is not highly prized in the United States military establishment. The highest-ranking uniformed officer in charge of a Defense Department intelligence organization wears three stars, one less than the general who runs purchasing and weapons development for the Air Force. This is certainly not the way an organization operating according to Boyd would do things.

For as much as we complain about the the US government spying on people, this surprised me. Apparently the American military is very doctrinally oriented around air superiority? This is definitely not my area of expertise — I’m from Maryland, where the big swinging dicks tend to be spooks and seamen. But I suppose it makes sense — it is very easy to point to a plane, and very hard to point to a dossier. We tend to glorify soldiers, not spies — Bond notwithstanding.

But procurement and logistics are really important, actually! And if Boyd and Tzu think that’s less important than intelligence, okay sure fine. Richards certainly very little time addressing it; I searched “logistics” and literally returned 0 hits. The string “logist” returned 2, so I know search was working. There’s a bit of attention given to “just in time” type stuff being key to Toyota’s success, because their engineering excellence means they don’t tolerate mistakes, they’re able to build exactly as many widgets as they need exactly when they need them… but logistics is more than that, as Amazon’s vast network of delivery trucks demonstrates.

And the Roman armies certainly seemed to do just fine with what seems to me as a focus on supply lines and ensuring their gear is in shape over knowing exactly where the enemy forces were. Certainly the Romans had imperial spies (and a critically important road network) and scouts but it certainly seems to me that they may have played second fiddle to the guys who handled the legion weapon stocks and military treasury during the Imperial period.

Once the option of a large, low-cost force is ruled out, the only course open to Blue strategists and politicians is to keep trying for higher and higher levels of high-tech effectiveness. In the real world of defense contracting, this always means higher and higher costs as engineers turn to exotic materials and advanced electronics in their attempts to deliver the desired effectiveness.

I think there are a lot of criticisms to be made of American defense contracting — Naval Gazing has a great write-up on the problem of defense economics that I trust more than Richards for a variety of reasons — but my own instinct here is “but the Brits won the Battle of Rourke’s Drift.” Cortes, love him or hate him, managed to achieve an awful lot of his strategic goals with some guns, some horses, and a relative handful of not terribly motivated men. Oh, it wasn’t just because of advanced technology — but I found the dismissive attitude toward a small, competent, wealthy, highly technologically innovative military pretty jarring given my (admitedly laymen’s) understanding of how much success Israel has been having with things like the Iron Dome and a system that seems to really work hard to identify brilliant young minds and put them in charge of things.

He does touch on Israel, of course:

So perhaps it is ironic that today, some Israelis credit trust for whatever success was achieved by the first intifada, the largely unarmed Palestinian uprising that caused Israel far more problems than the Arab armies ever did. Intifada leaders, it turns out, built mutual trust through years of organizing within Israeli prison camps. This trust on a person-to-person level had proven stronger than the factional rivalries that divided these leaders before they were jailed.

It reminded me of American gangs, too. History doesn’t repeat, but it rhymes. To wit:

By 1969, North Vietnam had worn down US political will, causing our withdrawal and leading to their conquest of the South in 1975. Three years later Vietnam became bogged down in a quagmire of its own in Cambodia with ultimately the same result—withdrawal. The Soviet Union gloated over the US debacle in Vietnam, then marched into Afghanistan. Tiny Israel took on the entire Arab world between 1948 and 1973 and won. Yet the Israelis were forced to retreat from their 1982 preemptive war against Lebanon, and their mighty army has yet to deal with civilian uprisings—the Palestinian intifadas—or provide much security against suicide bombers. So whatever is producing these counter-intuitive results does not seem to be the special property of any particular country or society.

I suspect Richards would have other things to say about the current Israel v. Palestine war, things that point out that technology isn’t carrying the day, or that giving those brilliant minds the freedom to act despite their young age and their relative lack of empire-building is indeed precisely the sort of thing America isn’t doing that does make for an effective strategic emphasis, but it put my back up… as did this:

Anytime a military commander gets into a “battle of attrition,” as these Lanchester engagements are called, and gets his people ground into the dust, he deserves the “blunder” label, even if he wins.

I agree that grinding your people into dust needlessly is a blunder, but it’s hard for me to believe that it is never the case that a slugfest is the only option.

I understand the impuslve to be contrarian, but I think Richards takes it a bit too far.

Instead of something useful, conventional thinking produced strategies that led to some of the worst disasters in military history.

I strongly suspect that there’s a bit of a survivorship bias thing going on here, along with a certain amount of “man bites dog” style novelty effect — when some tries something crazy and it goes badly, that doesn’t really get written down for the ages, it get chalked up as “dumb kid does dumb thing he shouldn’t have done, remove him from leadership and let’s move on with our lives.” When following conventional wisdom ends badly, on the other hand, the experts and experienced leaders who, until then, were relying on conventional wisdom, are actually forced to confront the implications of that failure, evaluate and debate whether habits and norms should change, etc.

Sure, sometimes following conventional wisdom is the wrong call — Elon Musk is out there breaking rules and shooting for the moon and it’s clearly working out for him. Kids who dream big and have a growth mindset and stay convinced they can do anything are, in the end, not all going to become astronauts. I’ve personally seen a lot of pain come from people trying to break out of the conventional mold in ways that wouldn’t even occur to upper middle class guys hanging out with Air Force officers and writing business books, and I think there’s something to be said for following time-tested paths for things like “get an education, get a job, get married, have some kids.”

Imagine if he’d said “following conventional thinking has resulted in some of the worst marriages in history.” It is trivially true! But I leave it as an exercise to the reader whether I think that means that all conventional thinking about what makes a stable marriage and functioning family should be thrown out with the bathwater.

In my experience, conventional wisdom becomes conventional because sometimes it works. I’m reminded of the cycles of teaching pedagogy schools have been fighting over for decades. The phonics vs whole language debates inspired Dr. Suess but they’re still being fought. Now it’s all about classically liberal educations, play-based childhoods, early literacy and whether drill-and-kill has any merits.

You’ll forgive me, but I’ve seen a lot more harm come from implementing any teaching method that managed to get good reviews in a non-replicable study that didn’t scale than from following conventional wisdom in a classroom — I instinctively distrust statements like the above.

How Old Is All This, Really?

Everything old is new again. Phonics is one example, but I remember being really shocked when Richards talked about the late 19th century as the time when “soldiers being free to act on iniative” was “created.” Lest you think I’m being unfair, here’s the direct quote:

Armies that engage in Blitzkrieg and maneuver warfare in general differ in fundamental ways from armies designed to conduct attrition warfare. Blitzkrieg strategies do not aim to execute the same maneuvers as other forms of warfare, such as charging across no man’s land, only more quickly. In a typical operation, blitzing units don’t expose themselves to direct enemy fire any more than absolutely necessary. They seem to loom up from out of nowhere to overwhelm a section of the enemy’s line, then penetrate to create surprise and confusion in the rear. It is this abrupt, unexpected, and disorienting pattern of action that forms the basis of his strategy.

…

The people who created this style of warfare in the late 19th and first part of the 20th centuries realized early on that it required a type of discipline different from the mindless obedience to orders that characterized the Prussian armies of Frederick the Great in the mid-1700s. Modern weapons are extremely lethal and opportunities to surprise and shock an intelligent enemy are fleeting. Soldiers at all levels must be free to—must be required to—use their creativity, intelligence, and initiatives to work around the enemy’s weapons and generate and exploit opportunities.

I must certainly grant that there are elements of the Blitzkreig that were new — I know almost nothing about war in the late 19th century, and certainly the trenches of WWI led to shocking amounts of bloodshed. But manuever warfare as described sounded an awful lot like the “waves of arrows” that the horse nomads of the Eurasian plains used against infantry, to me.

And every American schoolchild learns about how American revolutionaries in the 1700s used the habit of allowing great initiative to their low-level militiamen to defeat the redcoats. I’m sure the version I got thirty years ago was vastly oversimplified but I distinctly recall learning that one of the great strengths of the revolutionary army was that if we shot enough redcoat officers the British army ended up useless, whereas when we lost our leaders, every man was ready to step up and take over.

Hell, even limiting ourselves to Germany, Arminius of the Cherusci certainly did not limit his military forces to “mindless obedience to orders” — he stopped the Roman expansion basically cold at the Rhine, by luring three legions into a boggy ground by dint of what amounts to exceptional intelligence work and clever ambushes. Rome’s greatest defeat? Perhaps not. But certainly by my lights the most interesting one.

I suppose it’s too much to ask for a business guy to care about obscure ancient history but it was really jarring — in a Gell-Mann sort of way — to see it implied that soldiers being “required to use their creativity, intelligence, and initiative” to work around an enemy was something new and never seen before, particularly given the other references to ancient history. For example:

For the attack on France, the panzer thrust in the southern sector of the campaign provided focus and direction for the whole operation. All the activity at the north was intended to set up the allies, mentally and physically, for the armored penetration in the south. Similarly in the First Gulf War (Desert Storm), the Marines offshore, and a visible massing of forces next to Kuwait, set up Saddam Hussein for Schwarzkopf’s famous left hook (Map 5 in chapter I.) This notion of “setting-up” activities followed by a knockout punch is as old a concept as mutual trust. Its known roots go back thousands of years, and the ancient Chinese even had expressions for this type of strategy, calling the setting-up, “cheng maneuvers,” to be followed at the decisive moment by the “ch’i” knockout punch.

But it’s not just the Chinese, he also talks about the Greeks:

Even our notion of strategy today is tepid compared to what the ancients used. The Homeric Greeks, for example, had the concept of metis, which meant “strategy,” and also had the connotation of cunning, deception, concealment, ambush and surprise. The complement to metis is bie, which essentially means “violent force.” Both were necessary in battle, but it was Odysseus’s metis that finally defeated Troy where Achilles’s bie had failed.

At one point he comments:

other armies, notably the Israelis, use these principles today, and a study of guerilla warfare—or “fourth generation warfare,” as it is becoming known—reveals the same characteristics

which I similarly found bizarre. Guerilla warfare is not particularly new. To give one example, the people of the Pyranees mountains remained functionally independent from the Romans and later the Holy Roman Empire precisely because it was so hard for a conventional lowland army to take and hold the mountains against what amounts to guerilla warfare. But there are similar mountain ranges (and probably deserts, and large grassy plains) the world over that have been doing geurilla war since I would bet the beginning of civilization.

It’s not Richards’ fault. The concept of “generations of warfare” comes from a team of US analysts led by William S Lind in 1989. They pointed out that the changing nature of warfare resulted in dramatic changes in military doctrine, operational and organizational concepts, and the character and conduct of military operations. And on the micro scale of things of concern tomodern western militaries this is true.

But I find it a bit “off” as a random layman to treat “second generation warfare” (a linear style of combat that uses firepower, movement, and indirect fire to gain an advantage over the enemy) as fundamentally preceeding third generation aka maneuver warfare — a style of combat that uses speed, stealth, and surprise to bypass enemy lines and defeat their forces… which, sure, Google informs me mostly refers to “armored units, military aircraft, and airborne forces” but sure seems an awful lot like… cavalry screens.

The idea that there has been some sort of “march of progress” evolution of warfare in the last couple of hundred years is… look, I get that email is fundamentally different from telegrams is fundamentally different from hand-written letters is fundamentally different from cuneiform tablets. And it all makes sense as a framing device for teaching modern-day military officers how modern-day warfighting works with regards to tanks, missiles, marines, infantry, drones, helicopters, urban warfare, etc… but taken in the context of the history of war it is really weird to me to act like the entire class of (1) bow and arrow, either mass fire or as used by cavalry forces or outright massed nomads and (2) phalanx fighting (as though it didn’t go in and out of vogue in Greek history alone!) … is fundamentally all the same class of thing, strategically speaking.

I digress, I’m sorry, it just bothered me.

Overall Reaction

That said, I did find Certain to Win (affiliate link) to be an excellent book. It was well written, with relatable anecdotes, and more importantly with anecdotes that did not assume knowledge I did not have. For all my nitpicks above, it did not shy away from getting deep into the details.

I really liked it, and I learned a lot from it. More importantly, I learned a lot about why businesses (particularly the one I work for) do the things they do. It also finally gave me something to talk about with the guys in my life who are interested in stuff like battleships, fighter jets, and war — although the two I talk to most were distinctly unenthusiastic about Boyd.

Next edition, I’ll go into more detail about the bits I really liked, and the useful advice I took from it.