Well, first of all, let us assume that you want to continue living, because not wanting to die would be a great reason to avoid losing your head.

You need your brain attached to your body to perform even the simplest of tasks. As far as I know, there haven't been any successful "brain in a jar" experiments.

For however long it happened to take before you were completely dead, it would be excruciatingly painful.

It would raise issues such as:

"Do we need a casket for the head and the body, or should we try to glue it back on first?"

Also, if that did happen, and you were immortal, it could still kill you! I saw this on Highlander. Not to mention, your body would get very confused for a few moments, and you'd probably try to scream and grab at your missing noggin, etc., etc.

As an end note, I'd like to say that this is the most disturbing node I've ever written and probably ever will write. God bless insomnia and the hole in the universe. I apologize to those with exceedingly weak stomachs, in advance.
I swabbed my brain with a sponge and some more reasons got caught in the holey bits:
It would be a terrible waste if you really liked hats.
Many people find themselves less attracted to the headless.
You might be too short to go on rides, or join the military.
Watching your body flash past you upside down causes motion sickness.
Naturally, each of these points has an entirely valid pro counterpoint.
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