How to Draw Four Pages of Machiavelli

I’ve been meaning for a while to do a process post about how I go about making a page of comics. I’ll do a separate post about my research process, as that deserves its own section. Let’s assume for this post that research is mostly done (it’s never entirely done) and I’m ready to begin making pages.

I usually work in batches of four pages at a time. This allows me to focus on one task at a time (rough pencils, finished pencils, inks, wash) and keep a certain flow and coherence between pages.Marlowe thumbnail
First, I do a thumbnail outline. Something like a script with little boxes and hieroglyphics, drawn on copy paper and put into plastic sleeves so I can reorder and add pages if necessary. This example is actually from Marlowe, as I don’t think any of the Machiavelli thumbnails remain. Perhaps in my attic somewhere, where my kids will discover them after I’ve passed.

The next step is rough pencils. I typically work on cold press watercolor paper with a hard 3H pencil: light and easy to erase.


I will usually do the pencils in two stages: first, a rough blocking out, then a second pass with more detail added. At this point I scan the page and insert it into an inDesign file, adding text so I know how big to make the text. It would look something like this:

InDesign page

That lets me know how much space I need to allow for text. In this page, I let the text at the top float free and created a large text box between the panels:


When I ink, I use a Hunt 102 nib pen and Higgins Black Magic ink. It needs to be waterproof to survive the wash I’m going to subject it to next.

Finally, the wash; I use watercolor paint (Winsor & Newton ivory black) to finish the page.


I scan the finished page and replace the FPO image in the inDesign file. From start to finish, I can usually produce 2 pages a week if I’m firing on all cylinders (this rate presumes, of course, that the research and thumbnailing is done).

Four History Podcasts You May Enjoy

History podcasts are, in general, far superior to their technology counterparts in that they usually consist of more than a glorified phone call between a couple of dudes about their new phones. I’m sure there are some history podcasts like this, but I haven’t listened to them and won’t be talking about them here. History podcasts tend to be better prepared, better researched, and more tightly focused on topic. If you like history, I highly recommend giving podcasts a try. Here are my top four, with the caveat that this is not an exhaustive list. There are certainly some great history podcasts that I haven’t heard yet because I haven’t had the time. Feel free to reach out to me on Twitter @don_macdonald with your suggestions.


The History of Rome

Mike Duncan’s History of Rome is where you should start. Kind of the gold standard for history podcasts, Duncan’s History of Rome blends rigorous attention to detail with a garrulous and engaging speaking style and a wry sense of humor that doesn’t grate. The first 5-10 episodes are a bit rough around the edges as Duncan finds his voice and upgrades his audio equipment, but he very quickly does so, and by the time of the Latin Wars, the History of Rome is going full speed.

Duncan does a great job of putting historical details into context, making sure the listener doesn’t lose sight of the bigger picture while at the same time not glossing over historical detail and texture. I truly admire his keen editorial sense of which names and dates can be omitted in the name of clarity. He’s a gifted raconteur and this doesn’t hurt his cause either. If there is any criticism I can make, it’s a mild one: I wish he had spent more time on the early history of Rome. But honestly, I can’t fault him too much for this; the historical record is sparse and as I mentioned, he was still just finding his feet.

Duncan keeps his podcasts short, well organized, and information rich. It’s a good sign when you find yourself wishing the episode were longer rather than praying for the sweet release of death that the two-hour phone call format can produce. For this reason, his podcasts are great for binge listening. I listened to all 179 episodes of The History of Rome in a three month period without ever getting sick of it, which is incredibly remarkable when you think about it. Sadly, The History of Rome is completed, but do not despair too much, for next you can move on to



After finishing The History of Rome, Duncan took a break and then dove into a new podcast called Revolutions. Unlike the earlier podcast, Revolutions does not focus on an individual state or era, but as the name suggests covers various revolutions through history. The podcast is divided into chapters, each about 50 episodes long, covering a different historical revolution. He begins with the English Civil War, then moves on to the American Revolution, then the French Revolution. All of my praise of Duncan’s ability to present rigorous research in an engaging style is in full effect here.

I especially loved the English Civil War episodes, because it’s an area of history I’m not very familiar with. My areas of expertise are the Renaissance and the History of Art in general, so Duncan’s tour through the 17th century Civil War was new and fresh to me. He also deserves plaudits for making some sense of the French Revolution (well, as much as is possible). I’m eagerly looking forward to the Haitian Revolution, which is next up.


History of English Podcast

Kevin Stroud’s History of English podcast takes the listener from the Eurasian steppes and Proto-Indo-European right up to The Norman Conquest (where we are as of this writing) with attention to detail and gives the listener an excellent sense of larger historical trends. It’s a great companion to The History of Rome because it covers a lot of subject matter that is out of scope for that podcast, like the details of pre-and post-Roman Britain and the prehistoric Indo-European migrations. Stroud’s work on the migrations and his analysis of Proto-Indo-European is spectacular. I cannot overstate how awesome the early episodes of this podcast are. Stroud gets into details of individual words in the language, how they changed in the Latin, Greek, Celtic, and Germanic branches while never losing sight of why this is important for the understanding of English.

Stroud’s podcast is well-researched, concise, and bursting with information. That said, the History of English Podcast is not ideal for binge-listening (this may actually not be a criticism). I find that there’s so much to digest with each episode that I’ll need a break because my brain is full.

britishhistoryThe British History Podcast

Jamie Jeffords covers similar territory in his British History Podcast, although in greater detail. The podcast begins around 50 BCE and the Roman invasions and is (understandably) less concerned with prehistory. The greater detail can sometimes come at the cost of concision and focus, and I often get the sense that the podcast would benefit from stricter editing. Jeffords has an informal, gather-around-the-fire speaking style which is engaging, but his dad jokes and puns frequently elicit audible groans from me as I listen in the car. That said, dad jokes are a matter of taste, and Jeffords’ research is unimpeachable. What I find cringeworthy, might have you laughing.

Jeffords also seeks out subject matter experts to interview in the podcast, which I think is wonderful and I wish more people would do it. When covering Anglo-Saxon history, he interviews the archaeologists and curators of the Staffordshire Hoard and the Sutton Hoo burial. It’s a wealth of information from the very people working on these Anglo-Saxon treasures, and Jeffords does a great job bringing it to us.


I know Dan Carlin’s Hardcore History podcast is hugely popular, but I didn’t include it here because I haven’t had a chance to properly evaluate it. I listened to part of one episode, found it to be bombastic and overdramatized, and didn’t listen further. But that’s not really giving it a fair shake. I may return to it, we’ll see, but I’m hoping this post will elicit some more suggestions from Machiavelli readers that I hadn’t considered yet. Cheers!

Machiavelli: a Graphic Novel on Sale Now

Thank you to everyone who participated in the Kickstarter, it was a huge success and all the rewards have been mailed to backers. Did you miss the Kickstarter? Fear not! I have a limited number (about 100) of signed and numbered books for sale. Or, if ebooks are more your speed, you can pick up the book on Comixology.

So hop on over to the page I’ve set up, where you can see e-commerce in action and buy the book.

Machiavelli Cover

One Week to Go: Once More Unto the Breach, Dear Friends!

With one week to go in the Kickstarter (well, 8 days, but let’s not be pedantic, for all love) we are within striking distance of our goal: just $988 to go. With a concerted push, I know we can blow past this. I’m really eager to get to work and start laying out books and planning the site redesign.

If I could ask a favor. If you could share the link to the Kickstarter through your social media of choice, whether it be Facebook, Twitter, Tumblr, or any other, could you do so? Here’s the link: just copy that bad boy and paste it in. It would mean a lot.

I have an interview and potentially another piece going up soon, and I’ll link them when they’re live.

Now, for your artwork. I believe this is my first character study I did for Machiavelli. It’s pen and ink with an ink wash on paper.

Niccolo Sketch

TEDxBoston: How I Learned to Stop Worrying and Love Machiavelli

Last month I gave a talk about my graphic novel, Machiavelli, and my reasons for writing about him. Thanks to everyone who attended TEDxBoston, who tweeted about it, and were otherwise supportive on your social media of choice. You guys are the best. I had a wonderful time, and the talk was the result of a couple of months of drafts, rehearsals, and helpful feedback from the excellent TEDxBoston curators.

So, without further ado, here’s the talk: (I’ve included my prepared remarks after the video. It’s mostly the same, but some parts vary where through the vagaries of speaking in the moment.)


What do you think about when you hear the name Machiavelli?

Do you think of the Borgias, Assassin’s Creed, or Tupac Shakur? Maybe more likely, you think about a figure of base cunning and malevolence. The ends justifying the means. That’s what it is isn’t it? The definition of the word. We call our most amoral politicians Machiavellian, especially if they are particularly plotting or cunning. But how has this notion endured the five hundred years since Machiavelli was alive? Where did it come from? Mostly from the line in the his landmark political treatise the Prince: “it is better to be feared than loved”. This is Machiavelli’s most infamous quote. Maybe the thing he’s best known for. Even if you don’t know who Machiavelli is, you’ve probably heard this line.

But when we hear that we’re not getting it in the full context of his work, we’re not even getting the quote in its own context. Because what he says there is if one cannot be both, that is, the ideal leader is feared and loved. In other words, he is respected. Machiavelli cautions time and time again, both in the Prince and the Discourses that the worst thing any ruler can be is hated. There is nothing more dangerous to a regime than the hatred of its people, because you will never be at peace. Enemies of any regime will always be looking for weaknesses to exploit, and a hated regime will have the most enemies.

And so I wanted to write about Machiavelli. I have just completed a graphic novel which I researched, wrote, drew, and published online, in which I hope to go beyond this caricature. Something about the injustice of it struck me, that this thinker had such a malign and undeserved reputation. I felt I needed to right a wrong that Machiavelli was not history’s greatest monster. That the idea we have in the popular culture of Machiavelli as a kind of devil was something I wanted to fix.

This image of him as exalting the despot is exactly backward; Machiavelli was actually a big fan of the republic. He preferred the republic to the principality because he believed the citizens of the republic in the aggregate were wiser than a prince, and made better decisions. He also believed that the republic was better at adapting to changing times than a prince, due to the diversity of opinions and backgrounds of the citizens that are in it, and was thus more stable in the long run.

In the academic setting, this view of Machiavelli is uncontroversial. But in popular depictions of Machiavelli, like The Borgias on TV, the old caricature persists. Machiavelli is portrayed as a paragon of his own adjective, always in the shadows, ready to whisper the some sort of dark advice into the ear of power. But Machiavelli was not particularly Machiavellian, actually. He wasn’t really great at advancing his own career or navigating the internal politics of Florence for his own benefit. But most importantly, he never stabbed anyone in the back.

He was loyal to his government. He worked as an envoy and a diplomat and advisor to Florence’s republican government (the government in the early 16th century) and he was loyal to that government to his own detriment. When the Republican government was overthrown by the Medici when they returned to power in a coup, he lost everything. He was picked up as an enemy of the state, tortured, and banished to the countryside where he wrote his political works because he could no longer work in government. But he never betrayed his state. He probably could have, when the Medici were marching on Florence and things were in the balance and at their most desperate, but he did not.

So I set out to make a comic book about it. I like drawing on paper, working in inks and watercolors. So I based the look of MACHIAVELLI (the comic) on the kind of artwork that got me fired up: the pen and ink works of 16th and 17th century artists. Except for the lettering, everything is done by hand (and in the future, I promise to do even the lettering by hand.) I wanted to make art that evoked his time, that was suited to the time and place of Machiavelli, but also was suited to me. I like working with paper, working with paints, inks, low tech. And so, I’ve been a bit of an outsider as well. My choices of materials and subject matter place me outside the mainstream in the age of Photoshopped comics. But I have chosen to distribute the work electronically, to publish on the web and publicize through Twitter and Facebook. So the more low tech my artwork becomes, the more I’ve relied on technological solutions for getting it in front of people. The more I look into ebook and tablet formats—it’s very exciting!—I think to myself “You know what’s going to look awesome on this? Hand drawn and lettered artwork”

My book begins when he enters public service and brings us to the point at which he begins to write the Prince. Although the dialogue is invented—although based whenever possible on actual period accounts—most of the captions are based on his writing. I draw extensively from his letters to his friends, his coworkers, and his family—and their replies to him—to illustrate the great relationships that they had together. They show Machiavelli as a decent man who did his best for his country and stood by his friends and his patrons. Machiavelli as a friend, colleague, husband, and father. *That* was the story I wanted to tell. That was the historical record I wanted to correct.

Machiavelli was more statesman than schemer, more philosopher than plotter. He was loyal, he didn’t backstab anyone. It is a great irony that Machiavelli’s great misfortune—his banishment—became a stroke of luck for world literature. Had Machiavelli been more Machiavellian in his own career, had he betrayed his government and gone over to the Medici early he might have kept his position in government and the Prince and the Discourses would likely never had been written. That historical irony drew me to Machiavelli’s story, not to mention that his rise and fall and eventual redemption in literature makes for a great narrative.

He never told us that cruelty and duplicity are virtues, or even the best means to our ends. He tells us not to be cruel, so that we are not hated. He tells us above all we should inspire a sense of greatness and goodness with our actions, and that working together we as a people are wiser and make better decisions than any monarch. Demand respect, do not be over-cautious: go and do what needs doing because fortune will favor you for it, even though it may not be in the way you anticipated.

Machiavelli is criticized for describing the harsh realities of ruler ship, but you will make better decisions if you see things as they are and not as you wish they were.

I commend myself to you. Be happy.

TEDx Boston

I am very excited to announce that I’ll be speaking at TEDx Boston next month. My presentation will be about how I’ve tried to address misconceptions about Machiavelli through my graphic novel. And how popular culture gets him wrong. So a TED talk about Machiavelli, graphic novels, and webcomics. What’s not to love? I really hope to see you there. TEDx Boston takes place Friday, June 22nd at the Boston World Trade Center and you can apply for tickets until May 23rd. The curators have assembled a great, inspirational group of speakers, and I have no doubt it’s going to be awesome. So get right on that!

2011: the Year in Review

I decided to take a moment in between Chapters 7 and 8 to look back on the things I’ve posted this year, it being the holidays and all. I’d kind of like Chapter 8 not to fall into the black hole of the holidays, so I’ll be starting it next week. Then again, maybe I should post, as no-one else will be posting anything and people will be starved for stuff to look at on their new iPads. Decisions! Anyway. Unsurprisingly, the cover to Machiavelli (the first page of the comic) is the most visited page overall (not counting the index page obviously). Keep Calm and Carry Machiavelli continues to be the most popular non-comics thing I’ve posted on the site (although it is technically from late 2010 and is thus disqualified.)

So here’s the top five from 2011:

1. Machiavelli and Anthony Weiner: Traffic to this post is largely search driven (as opposed to referrals or readers browsing the site) this was an attempt to apply some lessons from The Prince to a current political scandal.

2. Machiavelli is Not Interested in Overthrowing the Status Quo: One of my favorite posts from this year, as I was able to use detective work to set the record straight and debunk a fake Machiavelli quote. Real author: Newt Gingrich!

3. The Typography of Machiavelli: Some notes on the typefaces I use in Machiavelli (P22 Operina Pro and P22 Morris Golden).

4. Machiavelli and the Economy of Violence: The most recent post on the list, from November. It’s always gratifying when something that involved a bit of research is popular. Here I argue that Machiavelli did not view violence as an end unto itself, but as a necessary evil to be used sparingly and with deliberation.

5. Let’s Not Talk about Content or Its Consumption: I don’t like the worlds “content” or “consumption” w/r/t art. Here I explain why.

So stay tuned for Chapter 8. Things are about to get really rough.

Palazzo Medici