My post on Montaigne is up on Tim Ferriss’s site and it’s called “The Experimental Life: An Introduction to Michel de Montaigne.”

What I tried to do within the limitations of the opportunity was briefly introduce an immensely complex and curious guy and his unusual job. My premise is that Montaigne was Montaigne for a living. Eventually the world came to see this as a worthwhile occupation and rewarded him handsomely for it, both during his lifetime and in the centuries since. I have had a long fascination with people who are able to successfully do this—going back to the article I wrote about Tucker my freshman year of college that opened so many doors for me. In it, I quoted a line from Hunter S. Thompson that applies as much to Tucker as it did to Thompson and as it does to Montaigne. That myths and legends die hard in America (or anywhere) because they let people know that the tyranny of the rat race is not yet final.

The metaphor is something we can apply to our own lives, even if we cannot do it at the scale of the examples above. For instance, Montaigne famously held that his book and himself were one. Well, it extends that a book is a work—a project—just as we are. We ought to have goals such as a start date and an approximate conclusion in mind. But also, like a good author, we should not be afraid to let inspiration bubble up and explore what seems to pour from our fingertips. Follow where the story takes us. My essays and I are one. My [company, job, website etc] and I are one. Either works so long as it is your calling. But never lose sight of these projects that these are endless, ongoing works. Works that can’t be taken too seriously because they can in turn be taken from us at any moment.

The nice thing about Montaigne is that his lessons queue up almost every other philosophical school. For example, the extension of his self-study is the Stoic notion of “learning the backroads of the self.” Yet, he was equally Epicurean in his focus on pleasure and happiness despite the general bleakness of France at the time. Somehow his epistemological humility manages to satisfy both the Skeptics and Christianity. The point is that when you model yourself as a self-funded, self-employed, self-centered project you instantly become platform agnostic. All that matters is what is real and what has practical application to your life.

That is why Montaigne is so special. It also makes him timely and interestingly connected to Tim and Seth Robert’s work on self-experimentation. However, one thing I learned from Peter Burke’s book on Montaigne is to avoid the tendency to remark about “how modern he seems.” The fact of the matter is that many of Montaigne’s most well known practices can be found in his contemporaries, from essaying on the works of other authors to meditating about himself. One great example, which I have read and do recommend is the The Autobiography of Girolamo Cardano.

I think the final (and most overlooked) lesson from Montaigne is that self-study is important, but utterly worthless without tangible results to show for it. Out of Montaigne’s retirement from public life came not only a better understanding of himself, but nearly a thousand pages of it in writing that he could refer back to whenever he needed it. This is why I made keeping a commonplace book a main point of the article. Taking a long walk every now and then might be calming, but cumulatively, what is it building towards? Ourselves is an occupation, not a casual commitment. We must work at it, create insight and wisdom from it and then in turn plow that capital back into more to work at. In other words, philosophy is not just spending a lot of time inside your own head but articulating what you find there, fleshing it out and turning it into something. This is what Montaigne was and continues to be peerless at.

I sent out the most recent installment of my reading newsletter last week. I realized because it has some time since I discussed it here on the site and with the recent redesign a bunch of you probably don’t even know that it exists. More is better so I wanted to explain the concept again:

After getting many requests for reading recommendations, I put together a regular email of book suggestions for anyone that wants them. Each book has a few sentence review, connections to similar or related books and a thought or two on why I feel the book is important. I also try to put a few questions at the bottom to tie all the suggestions together. This all comes from my personal email address so anyone is free to respond directly just by hitting reply and I always try to get back to you. Because of what I do for a living (researching and working for bestselling authors, marketing at an innovative fashion company and advising a handful of successful musicians), I’m always stumbling on unique and interesting books that I never would have otherwise found. This has meant everything from books out of print for 80 years, review galley’s of future bestsellers, the Classics, and so on. My goal with this newsletter is to recommend things that stick with you after you’ve put them down—or better yet, draw you down into the same rabbit hole that I was when I found it. This normally means an email every month or so, with the occasional gap in between. Some recent examples can be seen here, here and here and of course my Reading List here.

If this is something you’re interested in, you can sign up in two ways. You can send me an email at [ryan.holiday (at) gmail.com] with the subject line “Reading Newsletter” or you can submit your email via this link. Either way is fine. If you already get the email and like it, maybe you could do me a big favor and forward the next one you get to a friend. Like I said, more is better.

What I’ve learned most clearly from blogs is that the majority of them write about the problems from the outside for a reason—because they are missing the abilities that allow people to move to the inside. It holds true for so many of the categories, from self-improvement to design to media criticism on down. Of course, there is a lot of value in different angles of perspective but for most of us this kind of analysis (outsiders writing for other outsiders) is disconnected enough from reality that it is essentially meaningless. I think that’s why I was so impressed by this piece on boarding pass redesign by Timoni West.

Like the Dustin Curtis’s post on the American Airline website, the topic was kicked off by a smarmy nerd who laughably failed at what he set out to do [unsoliticted]. Then, thankfully, a better designer weighed in and actually put together something we can learn from. Honestly, I can’t even figure out why the original writer linked to it because it makes him look that bad in comparison.

Doing Analysis Right
What I notice first is that Timoni begins by examining the constraints. This is too rare. If we’re honest, I think we can actually admit that most of her creative insights come out of the discussion of these limitations. It’s how she defines what exactly she’s trying to overcome and then finally that if she’s able to do so, it’d be of use to someone. Alinsky famously said that we must start with where “the world is, as it is, not as we would like it to be” and that this makes no judgment on our desire to change it. In fact, starting where Timoni did—with an inventory on the limiting factors—is how you figure out how to get around them.

Next, she does what she calls “walking through the details.” Another word for this exercise is Empathy. She considers the effectiveness of her design from the perspective of several different actors who are plainly not her. Again, this is rarer than we want to admit. Where is this exercise in the original article or in Curtis’s AA redesign? I think its possible here because Timoni actually knows who she is (a single, childless traveler who self-checks bags) and is aware enough to admit that that sets her apart from fellow travelers.

Finally, she proposes one last addition in case airports are ever convinced to improve their printers: a much more exciting version using Helvetica. I see this as her nod to the latter part of Alinsky’s model for change. This is the seamless ability to move between the insider and outsider perspective—this is what I like as a designer, this is what I like as a designer on this specific project and I have the wisdom to demarcate the difference.

After publishing, comes what Gary Klein would call a Pre Mortem. In a second post, she critically reviews her design and hypothetically examines its failures and successes. Say this design had actually been tested by an airline, any idiot would have been able to incorporate the direct feedback from the users. But that’s not possible here. To hypothetically anticipate where her significant problems would have arisen and consider how to change the plan to avoid them is much more difficult. This is probably why most people don’t do it.

What I like about her is that in one most she shows so clearly what almost every other blog post misses: empathy, self-awareness, and phronesis. In other words, the things that matter in real life—those which get things done. And if we want to illustrate what the online world values, compare the traffic and comments to her page and the one she responded to. We have to ignore these signs because to read the others is a waste. It’s more than masturbatory—it is to pretend you’re learning something when you’re really being entertained like you would be with any other fiction. Not only could nothing ever come of that kind analysis (as in it could never be made), the worst part is that you internalize their logic.