What a lot of pilots have to think about is that an operator expects them to get to the other end somehow. The reason you have a CPL is that you are expected have a go and to find any legal avenue to achieve this.
If you cannot do it legally, it is then up to YOU to say to the boss, I cannot do this legally, explain why, and offer a solution. Many pilots confuse the boss's rant of "get out there and give it a go" with "go and break the law".
Now I accept that there might be a couple of bosses that might expect you to break the law, but bear in mind it's their AOC that's at stake.