Tom MacWright

How and why I illustrate

Since 2011 when I started this version of my website, I’ve illustrated nearly every post. Creating art alongside these posts is one of my favorite things: here’s how and why I do it.

The process

draft/matic mechancial pencil

Almost every illustration starts with a pencil-sketched outline. I almost always do a single draft, without any concept sketches or practice runs. I know I should, just like I should write outlines before writing posts, but sticking to one shot feels more natural to me and, as you can tell, I’m not going for photorealistic results.

micron pen

Once the sketch looks decent, I draw over it with Micron pens. They’re lovely - waterproof for later paint stages, precise, long-lasting, and nice to hold. Then I’ll erase the pencil with a good eraser, like the HI POLYMER Pentel erasers. Good erasers are key: the old-fashioned yellow, dry ones tear up paper, making scanning and painting much harder.


Then, depending on the subject, I’ll scan that and digitally color it in Photoshop, or do a round of watercolors or color pencils. I use a Canon LIDE 120 scanner, which is about $60 on Amazon. Like a good eraser, a scanner will save you so much time and trouble, and isn’t very expensive. A camera will do in a pinch, but you’ll need to do a lot more futzing around in Photoshop with a photo than with a scan.


If I’m going to do watercolors, I’ll always scan the inked sketch, so if the watercolor stage doesn’t work out I can digitally color it instead. I use a basic Sakura watercolor set with some higher-quality brushes at the local art supply store.

There are some other things involved that I didn’t draw for this past:

  • An adorably short little ruler I got at Muji
  • Paper! Watercolor paper is nice, but I often just use whatever I have around.

The digital flow

I use Image Capture to scan everything at 600 dpi, and the immediately save the resulting JPEG files to my network-attached-storage device. This thing - a Synology 218+ - saves me from either filling my MacBook’s limited storage space or relying on some cloud provider.

Then, I use Photoshop to clean up the images and sometimes color them. The workflow varies, but one typical example would be:

  • Use the Curves tool to get rid of the paper’s texture and color
  • Use either Magic Wand, clone, or the paintbrush tool to get rid of remaining specks
  • If I’m going to digitally color the sketch, close some loops that would prevent the paint bucket tool from filling a particular area

Once I’m happy with the image in Photoshop, I save the PSD file with all layers and effects intact to the network-attached-storage drive, and export a JPEG file for sharing. For a while I used Pixelmator for this step, but it just doesn’t match Photoshop for complicated workflows.

I push that JPEG file to Flickr, and also import it into, so I can load it on my phone and optionally share it to Instagram.

Then - and this part is very new to the workflow - I reference the files from Flickr in a post, but run an image-localizer task before publishing, that downloads, resamples, optimizes, and rewrites those images to work locally, without Flickr’s involvement. I avoided using images in git repos for a long time, but now that Git LFS is available and supported by both GitHub and Netlify, keeping everything in one place is practical and efficient.

My drawing setup is probably pretty typical and I’d recommend similar equipment to other people who want to start drawing again: my digital setup is the opposite. Using a NAS for long-term storage, carefully keeping image resources local to this domain - these are nitpicky, personal workflows that grow out of ideas and opinions that I hold but can’t get into in this post.


A lot of the people I admire have mixed mediums - _why, the mysterious, disappeared, fantastic creator of software and prose, always did excellent sketches. substack’s art has always complemented his creations in a lovely, integrated way. Rasmus Andersson, another inspiration, has always blended visual, prose, and functional elements.

In other fields, John Baizley, leader of the band Baroness, also does the band’s incredible album art.

Creating multiple levels of a work seems like a way to multiply and deepen the experience of creating, and a way that doesn’t have an end. Rasmus, for example, not only writes his blog and does the illustrations, but also created the font in which it is typeset.

And then there’s the challenge of staying vulnerable and creative as we grow older. It’s so easy and so common to lose not only the ability, but the willingness to share one’s creations. We fear that they aren’t good enough or they’re childish. I felt that hesitation a lot when I was initially adding drawings to posts, but the more I shared drawings, the less weird it became. I always keep my favorite quote in mind:

when you don’t create things, you become defined by your tastes rather than ability. your tastes only narrow & exclude people. so create. - why the lucky stiff