Is it awkward to bring up the possibility of annual merit raise (usually done at end of year) with my boss now? It seems the job market is cooling a bit and I might lose some leverage if I wait longer to bring this up, in case the economy turns for the worse. But it being June now just makes timing a bit awkward and worried it might come off negatively/too self serving

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Depends on when the company sets budget for the next year. If they are setting the budget for headcount/merit increases now, it could be appropriate to raise it even if it wouldn’t go into effect until next year. If not, you could mention it but it’s unlikely that your manager would be able to commit to a raise now if it’s off-cycle.

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