Courage gets cheaper the more you spend it. The tenth hard conversation costs less than the first.

Part of what the first hard conversation costs you is not knowing what happens afterwards. You are paying for an unknown, and unknowns are expensive. By the tenth you have a record: most of them went better than you expected, a few were rough, none of them ended you. The fear has less room to invent things once you have data to put in front of it.

Keep a short note of the difficult ones you actually had and how they turned out. Read it before the next one. Try not to let long gaps open up, because the price goes back up when you stop practising.