To get this achievement, Lilli needs to get shocked by disobeying commands and trying to do actions that she has a "block" on. At the end of the first chapter, Lilli will be hypnotized by Dr. Marcel and will not be able to perform actions (play with fire, disobey adults, etc).
There are three easy chances to do this right in Chapter 1:
1. When Dr. Marcel asks you to get tea, keep saying no. Each time Lilli says no she will be shocked (for disobeying adults).
2. Try to light the torch to gain access to the secret room. Every time you try to light the torch, Harvey will scold Lilli and she will get shocked (for playing with fire).
3. At the end of the chapter, you'll need to follow Edna. Try to go through the hole in the fence. You will be shocked/scolded for once again disobeying adults every time this is tried.
This can be done at any time (not just in chapter 1) and is cumulative throughout the save file. After being hypnotized by Dr. Marcel for the first time, the blocks will remain until they are systematically removed. Keep getting shocked and eventually this achievement will unlock.