Learn To Use The Pen tool – Basic Point Placement Exercises For Lettering Freebie

Learn to use the pen tool title

You tried using the pen tool to vectorize your lettering but you got frustrated with it? I’ve been there! I’ve cursed it so many times I’ve lost count! But I didn’t give up because I’m stubborn and I hate when I can’t figure something out. That resulted in me going on an internet craze, trying to find information and figuring out how on earth other people do it. As much as I don’t like being stubborn, in these cases, it pays off because I did eventually figure it out. It took a long while and I honestly believe it should not be that hard so I want to help you figure it out faster. The pen tool is an amazing resource (love-hate relationship here) and there is so much you can do with it, it certainly pays off to take the time to learn it. 

For lettering especially, there are rules that you need to follow but are unfortunately not common knowledge. When you get yourself familiarised with those rules, working with the pen tool becomes much easier and your vectorized letters start to look better and better. Even if you know all these rules there is still a bit of a learning curve to the pen tool, but if you start the right way, you will be a master in no time!

I’m going to explain the pen tool a little bit before diving in to the rules, and I’m going to assume that you are familiar with working in illustrator in general, but if this is the first time you encountering it I would suggest watching a couple of instructional videos, just to get familiarised with the software. 

What are vectors and why are they important for lettering?

Unlike raster graphics or images that are a collection of millions of colored pixels, vector graphics are created by drawing paths, each one with a mathematical formula that describes their shape and color. Since math is working here, no matter what size you make your artwork, it will stay the same. 

There is a good chance your lettering will end up in print one day. Whether it’s t-shirt print or a billboard, it’s a good idea to have a vector version of your lettering so it can be scaled to any size and that the print is crisp. Also, there is a possibility someone will ask you to create a logo for them, in which case you should definitely make a vector version so you can deliver them the files that are versatile enough to be used in any medium or situation their brand requires.  

What is the pen tool and what does it do? 

By using the pen tool we draw the paths that describe our letters. Those paths are stored in the program and reproduced in a graphical interface that enables us to see what we are doing. With the pen tool we create points, handles paths and curves. 

Points, Handles and curves

Points are just coordinates and they describe a start and end of a path or curve. Each point can have one, two or none of the handles that we use to manipulate the path or curve. 

Type of Points

Depending on a number and position of the handles there are a variety of points we can create. They are all used in vectorizing letters. 

How to use the pen tool? 

In the video below you can see instructions on how to draw with the pen tool. The keyboard shortcuts are shown below so you can better understand what tool is used and when. NOTE: I’ve changed my keyboard shortcut for the pen tool from P to S because it’s closer to other tools I need the most and easier to reach. 

The Rules

There are many rules for working with vectors, but these are the ones I found to be most useful for lettering. Rules are there to gives us guidance but can also be broken, depending on the situation. If your curve looks wonky, it’s a good chance you are breaking one of these rules. 

Extrema points

If you drew a rectangle around each letter, the intersect points are called extrema points and this is where you should place your vector points with the pen tool. 

Horizontal and vertical point handles

All of your handles should mostly be either horizontal or vertical (not on an angle) and to make sure they are, hold shift while you draw or move the handles. There are cases where that is impossible but in general, you can apply this to most points. 

Never intersect the handles or make on considerably longer than the other one

Handles from different points should never touch each other. If you run into a situation where that is happening check to see if you placed the point in the correct place and if nothing else helps to add one more point. 

Change handle direction

Each time you draw a point with two handles change their direction, so one horizontal and one vertical and so on. If you can’t change the direction, add an intersect point in-between that is at an angle. 

Additional tips

Fill vs Outline

Once you make a rough outline of your lettering it’s a good idea to fill it and make adjustments that way. You will see the weights much better and will be able to correct.

The circle is your friend

Using a circle to measure your width is a great way to quickly go through your piece and make sure everything looks the same. This doesn’t mean that everything needs to be exact, you can use the circle to spot the very big differences in your weight. 

Keep the letters separate shapes

You will have to move stuff around. I promise you that so do yourself a favor and keep all the letters in separate shapes so you can do that more easily. 

Overlap the corners 

To make your life easier try putting an overlap on the corners rather than just adding one point. It will make it much easier to make adjustments later


Now that we know a little bit more about the pen tool we can go ahead and practice it. Download the free worksheet to get some practice under your belt. Once you finish with the worksheet try to use the pen tool with your own sketch and let me know if you have any questions in the comment section below. 

Take me to the free worksheet!

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