You know, there is a general rule that applies to being successful at anything. It is, "Make things look easy."

It's been remarked upon many times, by many great and talented people through history.

Probably the best explanation of sprezzatura I've seen comes from Derek Sivers -

http://sivers.org/sprezzatura

“Sprezzatura” is an Italian word that means “to hide conscious effort and appear to accomplish difficult actions with casual nonchalance.”

I really admire how much work it took to research, write, edit, then practice that speech so that it seemed effortless.

It inspires me twice.

First for its own sake: for being such a great talk.

Second for finding out how much work went into making it.

When you think someone is amazing by DNA or destiny, you can be inspired by their work because it's so unattainably beautiful. You can be amazed and think, “I could never do that!”

But when you find out they're amazing only because of unglamorous persistent sweaty hard work, you can be double-inspired, thinking, “Wow! I could do that!”

Seth Godin has observed and remarked on sprezzatura as well -

This is an archaic Italian word for being able to do your craft without a lot of visible effort. It's a combination of elan and grace and class, sort of the opposite of loud grunts while you play tennis or a lot of whining and fuss when you help out a customer.

Many people are unable to put their finger on it, but this is a magnetic trait for many of us. We want our lawyer, dentist and waiter to demonstrate sprezzatura, but of course, not particularly try to.

Most successful people become aware of sprezzatura sooner or later, because most important works on creativity and accomplishment mention it at some point or other. When you go to give a speech, the people listening don't want to know that you practiced it for 10 hours, tested many different combinations of phrasing and words, and so on.

You want to be light, breezy, casual, as if wisdom just flows naturally from you, and now you're having a casual dialog over coffee or tea with the audience, and it just happens to be amazing...

The problem with this, of course, is that it can mean people seeing your speech (or painting, or writing, or business proposal, or whatever) don't realize that the same thing is doable by them. As Derek writes -

"But when you find out they're amazing only because of unglamorous persistent sweaty hard work, you can be double-inspired, thinking, “Wow! I could do that!”"

So please let the record show that (1) I'm aware of sprezzatura, and (2) I'm about to consciously, knowingly break it.

I don't think anyone starts out writing well. It's combination of tons of practice at writing, and tons of time reading that crafts one into a talented writer.

Additionally, you run into something of a bias when you read works - people are only judged on their best work. Eiji Yoshikawa's "Musashi" is an absolute masterpiece, one of the finest books ever written. Yoshikawa's "Taiko" is also an excellent book, albeit nowhere near the caliber of Musashi. But then most of his other works never got translated into English, because they never excelled to the same levels.

Thus, if you read Mushashi, it would be very easy to say, "I couldn't do that. No way." But you've got to realize, you're reading the top 0.8% of Yoshikawa's work. There's literally 80 volumes of his historical fiction available in Japanese. Musashi is hands-down the best one he did.

So no, if you sat down to write a historical fiction, you almost certainly wouldn't write a Musashi-caliber work. But I think if you wrote 80 volumes of historical fiction, then it's quite likely one of them would be Musashi-caliber. You know, I wrote a while back that I'm a devotee of the equal-odds rule, which says roughly that -

The equal-odds rule says that the average publication of any particular scientist does not have any statistically different chance of having more of an impact than any other scientist’s average publication. In other words, those scientists who create publications with the most impact, also create publications with the least impact, and when great publications that make a huge impact are created, it is just a result of “trying” enough times. This is an indication that chance plays a larger role in scientific creativity than previously theorized.

So, putting out a lot of work does wonders for your chances of putting out good work. But beyond that, you've got to keep refining your craft and trying to improve a bit with every work you put out. Unfortunately, because of this damn sprezzatura thing that most talented people get to sooner or later, it's hard to find guideposts for how to improve your own stuff.

And thus, I decided that even at the expense of the magic, I like to break the sprezzatura rule from time to time. Here is one such occasion - an excerpt from a private correspondance with Jason Shen, which he has very graciously given me permission to publish.

Hey Sebastian,

One thing I've wanted to mention to you for a while is something that I think could really help you with projecting the "strategist" image. It's also an element of your writing style so which is of course such a personal thing when your product here is a blog - but I feel like we're at the point now where we can really share valuable stuff even if it touches on something personal.

If you look at a lot of strategy writing (and I'm sure you've ready about 10 - 100x more of this than I have) I think part of what makes it powerful is the density of the writing, and the avoidance of the use personal.

I think your writing is already very idea-rich, maybe at like 70% where 200% is like the art of war (where every idea can be interpreted in all sorts of ways and is really intense and meant to be mulled over for months). I think if you made a conscious effort to really pack in your articles, they would just hit with such a great intensity.

Also, I think by inserting yourself too often into the article, you continue to remind the reader that this is simply your perspective and your "opinion" rather than as significant insight that should be taken "as is". Even using "we" or "one" or "a warrior" or "solider" allows you to generalize more your advice and helps people take it in with a broader perspective.

For example, in the first post you wrote, you've said here:

Yet, as time passes, I start to see some value in defeat. Oh, not in the defeat itself. No, no, no. A hatred of losing and love of winning is healthy and good. The opposite is disastrously bad.

But on the occasions when defeat has its way, there is probably some value to be had in it.
...
And thinking just like that, the defeated feeling gives way to reflectiveness, which is infinitely healthier and more positive than despair. Yes, perhaps these are lessons here. Ah, now I can scale my arrogance back, and not be defeated in larger measures at a later time. It’s not good that this error was made, but I am still at a point where I can recover from it – much better now than when an entire empire would crumble later.

If I were to take a crack at this as me writing as the best strategist of our generation, I might phrase it more like:

Yet, as time passes, we can begin to see value in defeat. Not necessarily in the defeat itself - as a hatred of losing and a love of winning is healthy and good - but in the reflectiveness that follows the feelings of defeat. Reflectiveness, infinitely healthier than despair, allows us to scale back our arrogance. Reflectiveness helps us avoid defeat in larger measures at a later time.

Errors are never good, but better to make a mistake now when we can still recover and rebuild than later when we may cause the entire empire to crumble.

I think partly you are understanding your thoughts as you write and its your choice to show that thought process for what it is, but you may want to try re-writing some future post and making it 50% shorter but 100% more dense to see what it does for you and your readers.

I mean for this advice to apply specifically to your "strategy" posts, different from your "personal story" posts or your "advice" and "reader comment" type posts (like the 2nd post you have here).

Anyway, would love to know what you think. Pleasure again for our chat.

Cheers,
Jason

First, Jason - thanks. Honest, straightforward feedback is an incredibly rare thing on the world, especially when you're reflecting on a person's craft. I've learned from experience that it's kind of dangerous in a way to give feedback to someone about a topic they base their identity around - much of the time people react poorly. So, to Jason - thank you for the honest, straightforward, practical feedback.

Now, in conscious defiance of sprezzatura, I'm going to walk you through what I'm considering and how I'm working on improving my craft.

On the one hand, Jason is completely and totally right. He's suggesting I write in more of an authoritative tone. And indeed, if I wish to project the image of the knowledgeable and wise strategist that I look to be, that would be a good decision. There are a number of pieces of feedback in his letter to me which are excellent and much-appreciated. Perhaps I'll write a pure strategy article at some point, and keep writing completely in "expert tone" (or "strategist tone") and see how that goes. Yes, in fact, I think that's a good idea. I'll do that sometime in the next month or so.

On the other hand, I was just discussing the craft of writing with two other friends of mine. Phaedrus and I had a lovely chat recently where he gave mentioned that he likes the conversational tone on here.

So I think - hmm, I have two pieces of feedback that are largely at odds with each other. Phaedrus says go conversational. On the one hand, this helps keep me accessible and friendly and ideally encourages people to reach out to me, as I frequently encourage. (By the way, feel free to drop a line if you've got questions, comments, feedback, or I can be of service in some way)

On the other hand, by inserting yourself into a discussion on a topic like strategy, you kind of display an anti-expertise. You make it known that yes, indeed, you are someone with an opinion, not The Authoritative Expert. Now, I think a lot of those authoritative experts are bollocks, but most people buy into the myth that The Authoritative Expert = Quality.

So, this is the behind the scenes considerations of improving writing, this is the scratching and clawing type thing.

I wish to improve as a writer, so I ask - how can I get the best of Jason's wisdom (authoritative expert tone, coming across as a wise and professional strategist) while still maintaining the friendly conversational tone that makes people feel welcome to reach out, and ideally not feel the intimidation that The Authoritative Expert Tone frequently generates. The Authoritative Expert Tone seems to say - "I'm above this whole fray. Don't bother contacting me."

So this is when I sit, and think, and muse. This is how I try to improve my craft. I look at good historical works - and yes, Jason's right. Carl von Clauswitz, Sun-tzu, and Miyamoto Musashi all get that 200% density of content, that clear expertise and precision and wisdom.

On the other hand, you can see people excelling by breaking free from the standard expertise-tone by inserting themselves into the discussion and analysis to some extent.

Take the field of history. Most historians write in standard, objective, expertise tone.

But Edward Gibbon broke free from it just a bit when writing his histories of the Roman Empire. He mostly maintains objective historical expert tone, but he slips in a little dry English humor and personality which is what makes his work still shine and entertain to this day. Thomas Carlyle takes that to a whole other level, which made him one of the most popular historians of his day.

Gibbon and Carlyle, both excellent historians, had a way to step down from the soapbox and mingle with the crowd they're teaching. You feel like you're part of a conversational series in the den of the historian's home, with a few other smart people, a cup of tea, and the fireplace burning a faint warm heat into the room.

So I meditate on this. While it's another post for another time, I'm also working on striking value judgments from my writing, or at least being very aware of when I do them. So I'm trying to replace "good/bad" with "effective/ineffective," replace "better" with "yields higher output," etc.

And this is the working on the craft that goes on behind the scenes.

I'll probably shift naturally to expert tone over time. One of the biggest downsides of casual tone is that it empowers jerks to feel like they're welcome to give criticisms along the lines of, "I'm the emperor of the god damn internet and this guy's opinion is not what I like! How dare he write an opinion I don't like!"

For a variety of reasons, that reaction never happens to someone writing for the Harvard Business Review. But interestingly, it also doesn't happen to people writing for their personal blogs in the same tone you'd use for the Harvard Business Review. While perhaps it's not conscious, people aren't inclined to attack someone who positions themselves as The Authoritative Expert. If you write friendlier, accessible, and in a way that firmly acknowledges that this is your opinion, that empowers some otherwise cowardly people to make it known that they don't like your opinion, and furthermore, how dare you have an opinion they don't like! Authoritative Expert Tone manages to generate less of that, which is a plus.

I'm still a sucker for praise, and I still take nastiness far too personally. I'm working on transcending that. But in the meantime, I did want to break from sprezzatura, and show you some of the considerations I've been studying as I've been trying to improve my craft at writing. And indeed, a friendly acquaintance of mine who is an editor at a major publishing house just wrote to me, "You've done a remarkable job on your blog, following a steady line of improvement since [we first met]. You don't see that kind of deliberate effort to get better from many folks, in their online or offline effforts, so you can count me impressed."

Gosh, I am a sucker for praise. That made me giddy to read. But, alas! I am violating sprezzatura here again, coming across as all too human, and not enough Authoritative Expert. Soon hordes of emperors-of-the-internet will be making it known that my opinion is unwelcome and offensive to them, and I'll have to work on my patience and not taking the nonsense personally.

In any event, I hope raising the curtains on how I actively develop my craft, the considerations I make, and how I try to hone my writing has been valuable to you - as always, please feel very free to drop me a line. Oftentimes, it's not so straightforward, and you have to balance competing objectives - in this case, striking the balance between the benefits of expert-tone and striking a welcoming conversational tone. Perhaps someday, always effortless, but for now I scratch, claw, consider, think, and keep moving forwards... yeah, that's the way. That's the only way.

Further reading on the topic -

Derek Sivers on Sprezzatura
Seth Godin on Sprezzatura
Elizabeth Gilbert's TED talk on creativity
Jason Shen's blog
Phaedrus's "Letters to a Friend" blog
Yoshikawa's Musashi - my favorite book - Amazon page
Eiji Yoshikawa, writer - Wikipedia
Edward Gibbon, historian - Wikipedia
Thomas Carlyle, historian - Wikipedia
A couple of my posts on the topic:
"How do I write so much, you ask? Well, glad you asked -"
"Studying Patience"

I'd really like to hear how you're trying to develop your own craft in the comments.