The Pen is Mightier
posted by Liz
The Pen Tool. It's one of the hardest tools you will learn in either Photoshop or Illustrator. An important one to know, but hard to explain.
Let's start with a simple exercise.
The images below were created in Illustrator for easier viewing. All of the techniques I'm going to go over work exactly the same in Photoshop, so if you're using Photoshop, I recommend setting the Pen tool to Paths before starting.
Making a line (As far as I know, you can only do this in Illustrator; you have to use the line tool or a brush in Photoshop.)
Click somewhere in the document and then click somewhere else. Ta-da! If you want to make a line that's perfectly vertical or horizontal, hold down Shift while clicking the second anchor point.
Now let's try tracing a basic Bezier curve to get the hang of things.
Making a curve
Save this image to your desktop and use it as a template if you'd like.
Drag a horizontal guide down from the ruler to form the base of your curve. With the Pen tool selected, choose a starting point somewhere on the guide, click and drag upward. Hold Shift to maintain a precise vertical line. Release the mouse just above the top of the curve if you're tracing my template. Otherwise, just drag the handle up a little ways and let go. This handle will tell your line to start by going up.
Now click on the guide somewhere a little to the right or left and drag downwards. This second handle tells the line to end by going down. It should now match the original template. Again, holding Shift helps. 
If you didn't get it exactly right on the first try (and don't worry, nobody does), take the Direct Selection Tool, or white arrow, and click on your curve. (Click and hold the Path Selection Tool button to reveal the white arrow underneath.) It will show your two anchor points and the handles that extend out from them. You can grab and move either of the anchor points if you didn't place them correctly or grab the tips of the handles and fine tune the curve.
Now, let's add on.
Adding more line segments
Method #1: Draw a new curve identical to the first one for practice. Now imagine that the anchor point you just finished your first curve with is also the starting point for your next curve. Choose a spot a little farther along your guide (I'm going to the right), click again and drag upward. Curve number 2 completed! 
So this is all I need to know, right?
Well, it works great if you're tracing an image from a photo or a sketch because it's fast and it ensures that your line segments flow together smoothly. I would recommend this method for certain projects. But a lot of times, you'll run into problems if you do it this way. Why is that? Think about it like this:
What if you wanted to attach a second upward curve to the first one instead of the downward one we just did? Start with your original curve again, but this time click to the right of it and drag downward instead of up. Did you get something like this?
That's because this new curve doesn't have two anchor points of its own. It's using the second anchor point from your first curve and the one you just added. Let's break it down. You told your first curve to start by going UP and end by going DOWN. But your didn't give your second curve a new starting direction. You just added onto the last DOWN handle with another DOWN handle. Of course the results were different.
The other problem with this method is that when you finish drawing your path and try to go back with the Direct Selection Tool to fine tune it, you'll realize that you can't adjust specific areas because all the line segments are sharing the same handles. If you try to adjust one line segment, the one next to it changes too, whether you like it or not.
Method #2: To set fresh handles for each new line segment, hold down Option (Alt) and click on your most recent anchor point (the one you ended the first curve with). Now you can drag your mouse in whatever direction you want your next segment to flow because you're giving it a new starting handle.
Create a new curve to practice with. This time when you make the second curve, hold Option, click on the bottom right anchor point of your original curve and drag UP. Release Option, click a little farther down the guide and drag DOWN to create a second, downward-facing curve.
You'll notice that now you can take the Direct Selection tool and adjust the handles on the each curve separately. Click on the segment you want to adjust and it'll pop up the two handles controlling that line.
I will say that the extra control this second method gives you means more work. Now you're responsible for making sure all the line segments blend smoothly together because they won't do it automatically anymore. The key to getting this right is to draw the first handle of each new segment in approximately the same direction as the second handle of the one before it.
It's important to practice so you can figure out how close together or far apart you need your anchor points to be in order to get a precise outline. Farther apart means getting it done faster, but usually, closer together means a more exact tracing.
The Pen tool has more complex features, but this is a start.
One important thing to note if you're using the Pen tool in Photoshop is the toolbar at the top. If you want to draw a shape, stick with the default setting Shape Layers. But if you're trying to outline something in a photo to cut it out, use the Paths setting. Then go to the Paths palette and click on the Load Path as a Selection button at the bottom. (I recommend feathering your selection by 1 or 2 px, depending on your image size, before cutting it out to avoid hard edges.)
Pen tool using Paths in Photoshop. Notice the two handles on this line segment and how they guide the curve around the neck of the swan.
The Shape Layers setting is not good for outlining because it fills in as you draw and covers your image. Still, look again at the handles and see how they guide my line segment.
Hopefully that was in-depth enough to get you started. My final tip is to always zoom in. I think I traced this swan image at about 300%.
Thank you to Markus for requesting this tutorial! If anyone has further questions about this or about anything else, let me know in the comments.
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