Mixed Feelings

Today I went out, played the catching game until Woody was really following me well, and haltered him. I brushed him, and took him back to the barn to tack him up and get the 22 foot lead. We went outside, and after we got a nice circle going at the trot with no pulling and slack int he rope, I let him eat for a bit. Then, we went on to try to jump the barrels, but instead he kept plowing through them. I set up two of the barrels, and decided to try the Figure-8 pattern at the trot, which we haven't done much/any. We started with getting a nice walk figure going, then I asked him to pick up his pace. He wouldn't trot consistently but kept throwing himself into the line to try to escape, or trotting past the turn, or, basically, trying to not do the pattern. I didn't really know how to handle it, so we returned to doing the walking pattern, which went fine. After my emotions had come down, I asked for the trot again, and decided to keep trying the trot until something positive happened (I am still not sure if this was a good decision or not). We did the pattern for 20 more minutes about, and he tried everything: pushing against me, running too fast, stopping every five strides, moving the barrels with his nose, but I persevered. Finally I got one, it was at a tralk (trot/walk) but he didn't resist, so I brought him in to me. I let him think on that for a bit, then let him graze some more. I then put on his hackamore and got my helmet, mounted a barrel, and hopped on his back. I let him graze at first, and then I walked around the circle garden to get him focused and with me. He was having a bit of separation anxiety from Charlotte, but he started tuning in and calming down, so we headed back. We practiced the direct and indirect rein positions, and then I turned him toward a row of barrels at a trot. He popped over them nicely, and then kept trotting nicley. I stopped riding in my body and lifted the rein, and he stopped. I was really happy with that, so we headed to the barrel positioned next to the grazing patch, and played point to point with it, and let him graze. After a couple minutes, I turned him and trotted to the other barrel, going over the jump along the way. I was a little apprehensive at first because we were jumping toward the hill he likes to run up, but he did great, keeping a nice even pace. We played point to point for a bit, then headed over to the chicken coop to explore. He was little nervous about them, so I flashed back in my mind to the segment I watched with Linda approaching a summo wrestler on Remmer and her strategy of going zig zag approaching the scary thing, so I applied it to Woody. It worked well, and a coupleof minutes later he was confident enough to want to go up and sniff my dad and the coop. I thought that was nice, so I truned him around and trotted him back to the pasture at a nice, not too fast trot.
I think over all the session was ok, but I feel like I am being to much of a dictator, and not allowing his thought to go into it. I am ordering him around to much I think. Also, I think, looking back, he was LBI today more-so and I was pushing him to trot too much on the figure-8.
Also, I have been very aware of his expression lately, and I have been noticing his ears are back more than I'd like them to be. When we were riding, his ears were up, but on the ground they were back. If anyone has any thoughts or insight or encouragement on this session, I would greatly appreciate it. This was definitely not our best ground session, but a pretty good riding one. Any feedback will be appreciated!
~Eden
P.S. I forgot to add in the post that during the figure-8 session, my dad took Charlotte for a walk away from Woody which caused him to be very anxious and not-focused. I tried to use this opportunity to be a leader to Woody, but I think it came off as not understanding. I kept giving him the aids to go around the barrels, and didn't really acknowledge the fact that he was nervous. Looking back, I don't know if that was the best approach to use at that moment. What are your thoughts?