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You asked "Are we teenagers that need mum and dad to monitor our behaviour?"
No. However, we owe a duty to our employers not to take potentially conflicting employment. The best answer is to disclose your intention from the first, together with an acknowledgement that you will accept no potentially conflicting assignments.
Note, please, that "potentially conflicting" may be regarding the subject matter or it may simply be that you become either too exhausted to adequately perform on your primary job or that you become unavailable for any overtime you are responsible for at your primary employer.
If you seek an assignment outside your regular job that will give you skills you can later use with your primary employer, this seems obviously to be worth mentioning.
This is one area where the maxim "it's better to seek forgiveness than permission" may not apply.
As for contract shops, it may also be best to remember that you cannot know in advance who knows whom in your market. Seeking a job shop for getting the sideline assignment can easily get back to your primary employer--and you may find you no longer *have* a primary employer in such a case.
On the other hand, if you have defined objectives for what you seek to do with the sideline work and *sell it* in advance to your primary job supervisor, you may find that they will be fairly enthusiastic about your ambition to further your talents and experience. When this happened to me some years ago, my employer at the time actually picked up a phone on my behalf and spoke with someone he knew in another firm...and I picked up the sideline work from that acquaintance of my supervisor's.
The primary issue, I believe, is to keep people informed so they won't be making assumptions about your actions...and, of course, to be sure that the sideline job does not infringe upon your energy level, your enthusiasm, or your performance in your primary employment.
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