Riding in the arena isn't as fun but it will help you gain experience. Recreate the issues in the arena where you can work on it over and over. I just took a bomb proof clinic and it helped so much. One of the things is to approach what ever they are balking at. Hold them straight and do not let them walk around or swing their butt around. Keep asking. Biscuit would throw it into reverse plenty of times over a puddle - but will walk through a creek...go figure.
We walked over a flat tarp. Over crinkled up feed bags, over round circles that were painted black. They had to step on them. I was able to get Biscuit to do all of it it. Yeah...we had a back up moment several times. We went over a bunch of plastic bottles in a pile. Crunch crunch crunch. He had a box of wood about 10" high and about 3.5" feet square that they had to step in and out.
Work on these things in the arena - it will help you and the horse and you won't be bored working in the arena. My cousin is my favorite ride buddy too. We have had many miles together so I can relate.
When you can get your horse to go over some little obstacles in the arena without the tiniest bit of a meltdown then get your cousin or someone to go with you while you ride solo around/down the trail. That is how I started riding by myself. I still don't ride far but I am working on it!
I'll have to try some of those things, thanks for the tip :) I was told ladybug will go through creeks too but I haven't tried yet, because the only real water to go through is in the riverbed and that's a long ride which she isn't quite in shape for yet. She really just doesn't like going through puddles in the street but on the trail she doesn't have an issue with it.