Edit: if it fits perfectly while tinned, just heat the cup, and the tin will probably goo it onto the side, then just bridge it onto the topside of the connector too.
Yeah, just make sure what's holding your connector isn't pointy so it doesn't leave marks. There's really nothing too it, I quite enjoy soldering Cardas connectors, done a bunch of them and it's only really scary the first time. Having a pretty fine solder tip is handy, and certainly the left side is easier as you don't have to hold your right hand at an awkward angle. Just get some pretty fine solder, tin your wire slightly. Then stick the solder end into the cup, and touch the iron to the side, rhodium is insanely conductive which can be a curse as it dispels heat fast onto the plastic, but the plastic is fairly resilient. 6 seconds max then take a break, you could probably shoot it with upside down cans of compressed air to quick-chill it. The solder will easily melt into the cup at least where you have the iron, and you can move the iron tip around to guide the solder - it naturally goes where there's heat. After you take a cooling break, pretty easy to add some extra solder to bridge the side edge of the wire before it enters the cup to the side of the cup for good measure. Then, the wire isn't going anywhere. Then, my personal favorite part - filling that person with hot glue. I'll say this, you'd need some he man strength to rip a cardas connector off once it's really on. If you are using 18g cable that's really uber thick, and probably not suitable for interconnects. Lawton audio has the same impression with Jena 18g, saying it was unrefined in its sound for Senn cables and that they prefer 22g. I personally like 22-24awg wire best - decently pliable but not spaghetti like 26awg tends to be. 26awg is fine though, although it's my limit on size. I was kinda hopeful that the Cardas connector would be open on the top rather than being a cup (like an RCA plug's center pin solder point) but it is a smart design in that it holds the wire captive, I somewhat hate soldering 1/4" jacks just because holding the wire in place is tricky, getting a good joint in there.