Letter With Me: Snollygoster
I’m starting a new series this week, and I hope you’ll join me: Letter With Me — a weekly practice where we explore one word from the lettering list I shared last week).
Each week we’ll take one word and sketch it out in a few different lettering styles. Nothing polished, nothing final. I’m using my iPad/Apple Pencil since it’s easier for me to record my process that way. But feel free to use the same, a pencil/pen with paper, whatever you have on hand. It’s all about building that creative muscle, trying new things, and building a library of lettering styles you can pull from later for full compositions.
This Week’s Word: Snollygoster
Yep. We’re starting off strong with a long and weird, but fun word. Because it’s so long, it’s a challenge to fit it into a confined space. I should maybe have started off with something easier. Oh well, we can revisit this word at the very end and see how much we’ve improved! (If I remember …)
And just in case you were curious, snollygoster (n.): a shrewd, unprincipled person, especially a politician.
Something to keep in mind as we go through this challenge, we are not worrying about perfecting yet. This is all about exploration and getting ideas out of your head and onto the page.
Step 1: Play with Shapes
I’m going to play with three simple shapes this week: Straight, wavy and arc-shaped.
These are starting points, not rules! Let them guide your thinking as you explore how to fit this long word into different shapes. You don’t have to follow them exactly. In fact, I had a hard time fitting all of snollygoster into any the space I had allotted without some serious stretching, stacking, or shrinking… and that’s okay!
Let your brain and hand play.
Step 2: Monoline It
Once you’ve chosen and sketched out your shapes, try writing the word inside it normally without overthinking. Play with the crossbars and the tails of letters. Try stacking letters and switching between upper and lower case letters. There is no pressure for perfect form here, just seeing how the letters might fit. Pretend your playing Tetris, but with letters!
I tried a few things:
Making the letters thinner
Stacking them when they didn’t fit horizontally
Being mindful not to squeeze so tightly that the word becomes unreadable
There’s no right or wrong here. Experiment, stretch, smoosh, stack. Try, erase, and try again.
Step 3: Add Style & Flair
Once your letters are in place, it’s time to explore styles a bit more!
I took each of the three sketches and gave them different vibes:
First version: a serif-inspired look with added diamonds and thicker ends (like little triangles!).
Second version: thinner bubble letters with rounded edges.
Third version: a more freestyle approach, where I played with funkier letterforms. The "S" was inspired by graffiti I saw on a train once!
Let your surroundings inspire you. Once you start looking for lettering everywhere, you’ll find it: store signs, menus, graffiti, packaging, old buildings, funky fonts. The more you notice, the more they’ll stick in your minds for you to pull out later. Or you can take photos. Build a little inspiration folder on your phone that you can look at when you’re feeling uninspired. But of course, remember: don’t copy directly. Instead, learn by observing and trying to recreate things from memory. That’s how you start developing your own style because you’ll find you’ve tweaked things differently from the original and that’s where your personality and style comes out.
Et Voilà
You just created three different versions of one word.
If you have extra time in your practice session, go ahead and try even more shapes and styles. Each sketch adds to your mental style bank, and later, when you’re working on full compositions, you’ll have so many ideas to draw from.
You're not just practicing lettering. You’re building your muscle memory and your visual vocabulary.
Watch the video below to see my process, sped up obviously.
Let’s Practice Together
So grab your tools and your favorite drink, and let’s letter snollygoster together.
I’ll be sharing mine on Instagram—feel free to tag me (@nolalettering) or DM/e-mail me your versions. I love seeing everyone’s interpretations, and honestly, I learn a ton just from seeing how other artists think.
See you next week for the next word on the list!