Does it look bad to ask for a raise with the economy being the way it is right now? On the one hand, I know I should just be grateful to have a job in the first place, but on the other hand, I haven't had a raise in over 18 months. I'm drowning over here. But I don't want my manager to think I'm greedy or put myself in a position to be laid off if the worst should happen.

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Timing can be everything. Put together your reasoning for why they should give you a raise and deliver it at the right time. If budget cuts and hiring freezes are happening, not the best time, for example.

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Personally, I think it’s realistic. However, you have to temper it like everything else. Talk to your supervisor and ask them for clear answers, but they may not have any control over your compensation, so you don’t want to beat a dead horse either.

I typically would suggest asking yearly, with a check-in mid year

That's a long time to go without a raise. We get them yearly during annual reviews. You're well within your rights to ask for one and shouldn't worry about being laid off over it. Wanting to earn enough to pay your bills is perfectly fair, not greedy. Just focus the conversation more on your contributions than your personal struggles. The unfortunate reality is that your manager doesn't care to hear them and will only be willing to grant the raise if you give them a good reason to.

It’s never bad to advocate for yourself

No.

Make the ask, have a few points prepared why it makes sense, and do it at least 4-6 months ahead of compensation cycles.

Focus on your contribution and the impact you make. As for me, I negotiated for 150K in bonus if I meet the goals. I learn we get paid for what we negotiate not what we deserve.

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