Here squirm can mean many things. Usually, I would tend to think of this sentence simply as "I don't make things easy for myself". The word squirm is used fairly often in speach and in writing. In literature it does bring quite strong images to mind. In summary, it is quite a powerful word that is in common usage.
Thank you for your illustrative example. I give my consent to your preference for this powerful word. The truth is that many words of English language are very weird in the beginning, but after the convincing explanation, which I receive from the respected teachers and the experienced NSEL's I become the feeling that this mysterious and enigmatic words, lose their mysteriousness and turn in precious stones and gems, that I try to use later in my daily grind.
As proof of this I will repeat the mention above quote:
I like to make myself squirm. That's when I'm good.