The first one I ever did was by melting a hole through with my iron's tip. It was a sketchy hole, but with the jack installed, you couldn't tell.
Just take your time and make sure to clean your equipment afterward. You have no idea how many tips I went trough over the years becuase I didn't clean off the extra solder.
You are supposed to leave solder on your tips. After cleaning them well with a wet sponge or the metal ball(my preferred method as it doesn't affect the temp of the iron) you are supposed to apply fresh solder to your tips before turning off the iron. It helps keep them fresh and capable of distributing heat.