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Any tips for advocating for yourself at work? I'm way overdue for a raise but I am not generally great at standing up for myself, speaking assertively, or inserting myself where I feel I might be impolite or pushy.

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I suggest you look into assertiveness training with a licensed therapist. The change that you want to achieve in yourself will likely require some hard work to deconstruct why you behave the way you do. It's cultural, yes, but getting clear on the root thoughts and feelings is important.

You might ask your manager for feedback on opportunities for you to develop like which areas do you need to work on to get to the next level as you don’t feel like you are progressing .. like asking but not asking where’s my money

The best thing to do is find an offer from the outside. If they ask for salary expectations, just give a number that is 2x your current TC for half the firms, and the other half, say you want market and refuse to give a number

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