Before stippling, set your machine up for the performance -
1. make sure the feed dog is down (or put your darning plate on)
2. increase the size of the stitches per inch
3. test the tension with a swatch so you can adjust it
4. use a new needle
5. make sure you use quilting thread and that the needle isn't too small for the thread. If it is the thread will keep breaking
6. be patient, be patient, be patient, practice, practice, practice
7. did I say be patient and practice a lot???????
Put a sample together (top fabric, batting, bottom fabric) and take your time. It's a "hands-on" kind of thing you just have to work at. Be patient. You can't rush this process. You will find that in time your technique will get better.
Use a pencil on a piece of paper and stipple with that first. Just get an idea of what you need to do with the pencil. This seems to help lessen the hesitation. Get comfortable with it. Get ideas from magazines or pictures and continue rolling your pencil all over the paper. No need to lift the pencil. After you have some idea of what to do, you won't hesitate when you work on your quilt. There are pencils and stencils to use as a guide if you want a particular design, but that will come in time.
At first I wasn't sure what type of squiggly line to make. I found loops to be easy and large L's too. Those overlap. The other type is what looks like a puzzle piece. No map on that, its basically freestyle.
Good luck and enjoy the stippling technique. You will find your comfort zone in time.
PS: When I get frustrated with it, I resort to my stash of Jack Daniels above the stove. LOL really!