There's no rule for this kind of thing. Pick the right moment to play the right card on the right day. In general, you should try to get your raise though, one way or another (especially after what happened with your more junior colleague). However always keep in mind that negotiation is a skill like every other - some people are good at it, and those will be the folks who magically get raises where others aren't. Practice that skill (aka. confidence, persistence, mixed with a healthy dose of realism and resilience) and you'll get to where you want to be in no time. For me, I find that playing hardball only works when you hold all the power, and even then, sometimes they just call your bluff. (aka. Don't threaten a freelance gig unless you actually have one, or believe they value you enough that they won't call your bluff)