Two Essential Exercises to Develop Your Hand Lettering

When it comes to learning hand lettering (or anything new), it seems like figuring out how to get started is always the hardest part. The best way to think of lettering is as a combination of typography and drawing: you need to have a solid understanding of typography concepts, but you also need to work on your drawing skills. I’ve come to love these two hand lettering exercises, which have helped me explore new variations and learn how to apply them to any character. They get your creative juices flowing and warm up your drawing muscles, which makes keeping a steady hand for your serious work that much easier!  These exercises complement one another to round out your warm up.

A Quick Type Overview

Before we start, I think it’s important to go over a little introduction to the basic categories of type. Depending on who you talk to, there are a number of ways to categorize type, but I personally group them into 4 major categories when it comes to lettering: serif, sans serif, script, and decorative. This isn’t to say that all typophiles would agree with this (they probably wouldn’t) or that these categories are mutually exclusive - there can be a lot of overlap, but here’s a quick overview of how I define these categories:

  • Serif type includes any type with small lines or extensions added to the ends of a letter’s strokes. There are a TON of serif styles, but here’s a handy image that shows some of the variety out there. Times New Roman, Cambria, or Georgia are good examples.

  • Sans serif typeincludes all non-script fonts without serifs. Fonts like Arial, Helvetica, or Gotham are great examples.

  • Script type includes anything made to mimic handwriting, whether it be calligraphy, plain cursive, or brush lettering. The letters in script type usually connect, but it’s not a hard and fast rule.

  • Decorative type is my mental catch-all for styles that don’t fit nicely into one of these categories, including more ornate letters or those of a more illustrative style (like creating an “O” that looks like a donut, for example). I include blackletter in this category because I haven’t learned those calligraphy techniques, so I approach it as a detailed, decorative drawing style.

Now that that’s over with, let’s move on to the exercises!

Exercise 1: One letter, infinite possibilities.


Pick a single letter of the alphabet (I pick one I haven’t focused on in a while, or a prominent letter from a specific piece), and draw it as many ways as you can. It may sound daunting at first, and you probably think you’ll only come up with a few, but once you get going you’ll start coming up with new styles faster than you can draw them!

There are an infinite number of styles you can create when you’re drawing a letter. To get you started, you can:

  • Add flourishes

  • Try different serif styles

  • Tweak weights of up and down strokes

  • Experiment with the way a letter might extend to interact or connect with another letter.

There are a few different ways I like to approach this exercise, depending on what I’m working on.

Set a numeric goal.

Megan Wells turned me onto this approach in her Introduction to Lettering post on Alisa Burke’s blog. She talks about drawing one letter 100 different ways, but if that seems like too much, start with 25 at first, work your way up to 50 the next time, then 75, and so on.

I like to focus on a numeric goal if I’m just warming up and don’t have a certain style or mood in mind.

Pick a category.

Often I’ll outline a specific piece and know I want to use serif lettering for part of the layout, but beyond that I’m not sure what I want it to look like. I set that as my parameter rather than a number, and draw as many serif iterations of my chosen letter as I can. This is a great way to push beyond the standard looks within a type style, and helps you find your own personal style.

Pick a mood or personality.

Recently I was working on a few pieces for a client where my major art direction was mood/personality-based, rather than specifics about typographic styles. I picked a prominent letter from the piece, and started exploring different styles that might express the mood. One was playful and young, and another was sinister and ominous. I’d never done this exercise with this criteria before, but it was a refreshing way to look at letters and now it’s one of my favorite warm ups!

Exercise 2: One style, every character.  


Pick one of the styles you drew in exercise one, and determine how you will apply it to every single letter of the alphabet. When I started doing the first exercise to explore new styles, I’d often pick a style from my warmup, apply it only across the letters I needed for my piece, and move on. Then, weeks down the road, I’d want to use that style and struggle to figure out how that style would apply to a new letter. Taking a detailed style from an N or an A, and making it work for an S or an O can be extremely difficult (life throws you curves, am I right? I’ll see myself out). I started incorporating this second warm up exercise to nip this problem in the bud.

What characters you include in your final set is up to you. Lowercase and uppercase? Numbers? Punctuation? Some of my styles belong in all caps, and others need both sets of characters. Don’t get discouraged if you have to redraw some letters multiple times before you get it right - that’s the point! The more you do this, the easier it will get.

Once you have every character you need sketched out, create a more polished guide. I may not work in alphabetical order during the exercise, as it’s often easier to knock out similar letters consecutively, but I use my light pad to trace the final sketches of each character in alphabetical order, and file it away for safe keeping. Whenever I think I might want to use that style, I pull out my guide, and it’s much easier to recreate the style consistently!

So there you have it - two of my go-to warm up exercises. Calling them hand lettering exercises seems a little like a bit of an undersell. Iterating like this frequently will help you discover your own unique lettering style. These exercises will also help you improve your drawing skills, your understanding of type, and push your creativity - think of it as mind mapping, but for letters!

Do you have a go-to exercise you use for warming up? I'd love to hear about it in the comments!