As for those types of contracts assigning tech IP to $dayjob, that’s what I was alluding to. If you have one of those, unfortunately you cannot start a business without risking $dayjob wanting a piece (or all of it). Regardless of how often they stand up in court or are even tentatively enforced, I wouldn’t want to risk it.
I know this depends on the company, but, as a general rule, are these clauses really taken so lightly?
I fought the good fight against some silly assertions such as "They could not have built this in so little time without overlapping working hours" but lost the battle when the VCs pointed to the timestamps of some support/feedback comments posted by one of my Engineers on the project's website. He had written those and posted during working hours while sitting in the office of said "day job"
Project squashed, all the IP was rolled up and shelved. It was a bad day.
TL;DR these clauses are typically not enforced because your side project is typically viewed as worthless. If on the other hand your project is seen as a source of value... tread carefully.
In short, by taking these clauses lightly, you are creating failure paths for yourself that begin from the initial light of success. You may not want to kill your big success even before it happens. If your goal is just to create a side income, you would most likely be fine simply because a lawsuit would cost more money than what it may recover, or you may just get some threats/scoldings.
I have heard that if your side project or startup reaches something like $10 million in revenues, your big-company employer actually becomes liable to their shareholders to recover this money from you since it technically belongs to the shareholders.
Some high-profile entrepreneurs have told me that you should not worry about lawsuits as they only come when you succeed and when you do, you have resources to take care of them. But I have also known specific cases of things doing down because of such issues (like the example from etsimm, who also responded to your comment).
By the way, YCombinator submission form includes a question on such IP issues, though I may guess everyone just blindly picks "No issues" for it.
So, if you're actually trying the "ignorance is bliss" strategy for managing $dayjob relation, then consulting a lawyer up front could save you an awful lot of trouble later.