Asking for more money from a client you have worked with for a long time feels uncomfortable for many freelancers, even when the rate increase is clearly deserved. You do not want to seem greedy, but staying at the same rate for years does not make sense either. The way you bring it up can make a big difference in how the client responds. Some people do it gradually, others wait for the right moment. What approach has worked best for you when having this conversation?