Book recommendations can come from the most surprising places. No, not “can”; they DO come from the most surprising places. Our awesome developer Nico mentioned in passing how he was influenced by the book Why Greatness Cannot Be Planned: The Myth of the Objective by Stanley and Lehman. His summary of the thesis–on the power of serendipity, on the importance of surprises on the path towards doing anything seriously high quality, and serious focus on an objective largely prevents you from even seeing these essential surprises–sounded intriguing, and I purchased the book the same day, and a few days later organized the SpotlessMind Book Club with this book as the first one.
So, before I criticize the book, I need to qualify my criticisms. I enjoyed the book. It had some good quotes and insights. Clearly, the writers and smart and on point. If you were to read my (still unwritten) biography, you’ll see that, in a way, I’ve optimized my entire life for serendipity and surprises, so there’s a basic level on which I liked it, it’s a good point, and I live by it. And not only do I live by their core concept and have for decades, but the converse is also true: the people I know who are obsessively obsessed with some goal in my experience 99% of the time is is pure narcissistic greed (often but not necessarily financial greed) in the worst sense, and I can’t stand those people, so culturally I am totally on the author’s side. It’s therefore hard for me to criticize the book.
And it also passes one of the tests of a good book: is there anything I read in the book that I’m likely to quote in the future? The answer is, yes (so it does pass the Morgan Book Filter!). As one example, the joke they mention about the biologist, physicist, and mathematician watching people go in and out of a house is awesome, made me laugh outloud, I had never heard it before, and there’s a 100% chance I quote it multiple times in the next six months.
As a result, all the criticisms I’m about to share are half me just being an asshole, half me trying to sound smart, and half me trying to outsmart the smartest people out there–and while I may succeed or I may fail in that last goal, it’s one of my favorite pastimes to try to make my own brain smarter! Yes, that’s three halves, and you’re really smart for having caught that. So read the following criticisms with huge grains of salt and the criticisms are more about me being an asshole and my own worldview than any real criticism.
Oh! There’s one other reason to discount all my criticisms that follow: books can influence you in different ways at different points in your life. Had I read this book when I was 15, before I had realized the power of serendipity and wandering, it might have had a profound impact on me. So this is yet another reason why you should ignore my criticisms: it’s not necessarily a not-great book; but it might just not be the right time in my intellectual and development over the course of my life to read it.
I’m emphasizing all these qualifications because I know what I’m about to say, and I will sound like a dick, and I really don’t mean it. Had I read this book at another moment, I think I would have loved it!
So. My hesitations about the book are basically on three levels.
The first level is that, while the book makes an important point (see above: a point I actually live by!) that that point can basically be summarized in the same sentence I used in the first paragraph of this essay without losing much nuance nor subtlety, and that’s basically it. The book could have been a paragraph. The rest of the book does add a touch of additional insights, but not too much.
This speaks to a fundamental challenge of the publishing industry: no one would spend $25 buying one paragraph of text. You need to expand it to a book to sell it and for the publisher (and, ideally, the author) to make money. The first chapter is largely quotes from famous people supporting the one-sentence summary. The second chapter is about some software they wrote that led them to the core one-sentence idea.
This leads in to my second hesitation: the subject is actually indeed a rich and subtle subject and they could have attacked it in much more depth from many different angles. It’s a great starting insight; I just wish they took it deeper.
Let me give you an example of an unexplored angle: as they argue, there’s a bit of a trade-off between a focus on your objective, and the power of surprise (because when you’re so focused on an objective, you don’t wander enough to allow yourself to discover surprises, which are actually essential to creating true, high-quality work). The more objective-focused, the fewer surprises. Okay. But where and how should one draw the balance between those two? (They don’t explore that topic at all, other than arguing against objectives, except for the nuance for when the objectives are small, which they support.) I wish they explored that tension — in fact, tension is what makes a great narrative and great analysis, and they just left the tension off to the side, just arguing against having objectives (with their exception for the case when they like objectives.)
But let me share how I, personally, resolve that tension–and it’s basically the opposite of their argument. They support small objectives, but for big things, they support wandering. My approach is: I set for myself big goals–but to get there, I allow myself to wander, take my time, explore, go in a round-about way, always be on the look out for surprises, I allow for changes in the path–and even possibly for changing the big goal. My personal strategy here is an awesome way to get the best of all worlds–or so I think. That’s why it’s my strategy.
My third hesitation about the book is, for me, the mark of intellectual honesty is to articulate the smartest—deeply smart—version of the other side of the argument (against your case), in such a compelling way that those who disagree with you would agree wholeheartedly with your characterization of their side, as if you were one of them. (I will only ever listen to an Israeli defend Israel if he can first articulate the Palestinian argument with such intelligence and subtlety that the smartest nicest Palestinians would agree with him; and vice versa, of course! Note that this is also why, in personal conversation and my management style, I often start out criticisms by articulating the other person’s arguments from their eyes, before I explain the situation from my eyes.)
But this book doesn’t do that. Yes, they do mention multiple times that objectives are useful on the tiny scale; it’s not bad for a bureaucracy to try to improve the quality of its product by 1% this year. But on the bigger, deeper level, there are smart arguments for why objectives could be great, and (like in my personal way to reconcile the opposites of objectives and surprises) there are, or (if you don’t like my personal method I just summarized) there could likely be, ways to get the best of both worlds. More broadly, the authors could have had a fun time really diving into groups and teams who take objectives very seriously and listening to the best of their arguments, or the corresponding literature. One example that comes to mind most obviously are serious military operations, intelligence teams, and perhaps even the not-so-secret societies who arguably have built their existence around achieving serious-long term objectives. And even a review of classic literature on the subject would have been a fascinating starting point; just offhand, I still quote Von Clausewitz on military strategy, which I read in college, and he over-the-top emphasizes having an objective as a starting point. But there’s none of that in this book, not even a hint (beyond quoting semi-famous quotes, always quoted in support of their anti-objective argument.)
What are the strong arguments for objectives that they don’t articulate? That could be a book onto itself, and this is just a lowly little blog post by a founder of SpotlessMind who has committed to write one relevant article per week. But here’s one: it keeps us individually in touch with, and focused on, our mission in life. The first question in setting an objective is, “If you are to have an objective, what should it be?” and that question, once you start unraveling the various levels of “why-s” behind it, is hard to separate from “why do you exist?” and “what is your mission in life?”. I’m of the viewpoint that there is little or nothing more important in life for an individual to have a clear sense of his mission–and then seize it.
Or viewed differently: maybe the key quote attributed to McArthur, “plans are useless but planning is essential” applies to defining objectives: maybe objectives are useless but forcing yourself to go through the rigorous intellectual process of defining non-arbitrary objectives is essential, for merely trying to figure them out will unlock surprising (I chose that word on purpose) and important insights and help you figure out what is your mission that you need to seize.
But of course, in seizing your mission–you might have to wander around intellectually and be open to surprises to accomplish it. Or–step back–you might have to wander around intellectually and be open to surprises merely to discover what your mission is. Indeed, half of the trick of of defining objectives is making sure you have the right objective. That is substantially harder than it seems, and nearly all human beings I’ve met who have stumbled in life, come across (in their public appearance to me) as having chosen an objective that’s orders of magnitude away from what it seems like would have been a better objective for that particular person or team with their particular idiosyncrasies in that particular moment in that universe. As my favorite Saturday morning cartoon when I was a little kid used to say–did I just seriously age myself or what?–“knowing is half the battle,” and that applies here as in everything in life: actually knowing what the right objective to choose for yourself or your team is gets you halfway towards your goal. Now how do you do you choose your right objective? And how do you know when it’s time to change your objective? Now those would have been subjects worthy of a book that I would have enjoyed reading even more.
