This is the reason people should read and re-read Carnegie’s How to Win Friends and Influence People; not because of the advise on how to sidle up to people and start a conversation, or how to promote your latest scheme, but Carnegie’s central theme that he hammers in again and again: See the situation from the other fellow’s point of view. It doesn’t matter if he’s spending himself in a hole, or justifying his behavior on some tenuous rationale, or even if he is intentionally yanking your chain just to keep you from confronting him about a raise. What matters (if you want to get what you want) is convincing him that it is in his best interest to offer this to you. You’ll never be right by convincing someone else they are wrong; that way likes conflict, argumentation, and defensive rationalization. Instead, you convince him that he’s more right by doing what you suggest, because it benefits him as much as it benefits you; if not fiscally, because it makes him a better employer and person, and keeps a qualified person in an important role.
In this case you might start by approaching him and saying that this is a really great place to work, you appreciate his leniency on schedules, treatment of staff, whatever (something at least vaguely sincere and appreciative, even if he is a complete raging asshole); and then follow that up with while you enjoy working there and the experience that has provided you, you’re concerned that your compensation is not keeping up with cost of living, increase in experience, et cetera. If you want to be slightly more aggressive, present him with a list of things you’ve done to improve administration of the practice (organizational improvements, cost reduction, et cetera) and how you think this has added value. He may not agree with your assessment and may turn you down, but if you are polite, respectful, but firm, it is going to be hard for him to get openly angry with you, especially if he is the passive-aggressive jerkwad you making him out to be. And then you’ll know: he’s not willing to treat you fairly regardless of circumstances, and that you need to search for another employer.
The one thing you absolutely do not want to do is confront him about his personal spending. Not only is it not any of your business, any more than your spending habits are his, but even if he’s the nicest guy in the world and just forgetful about promised raises and perqs, you’ve just suddenly and without warning thrown him on the defensive. Now he has to justify himself to you, and who the fuck are you to be accounting for how he spends his money, and why are you tracking how many vacations he goes on, why do you think you have some ethical high ground, et cetera. Putting yourself in this position, you can see how this is not only confrontational but actually offensive and personally insulting. This approach is practically guaranteed to result in hurt feelings.
Stranger