When a horse says "You want me to what?"

The last time I was out for a ride on Lena, we came across a kind of hole in the ground. It was circular, and there was a way for her to walk into it, and then about a two foot step out. Having developed an interest in doing the extreme trail, I thought I'd see how she'd do with it, thinking she'd face it like a champ.
Oh, boy, was I wrong.
First obstacle: the little paint pony on the other side of the fence.
Second obstacle: said fence was hot, and we had to pass awfully close to it.
Third obstacle: there was a large, round piece of rusted sheet metal in the middle of the hole.
Fourth obstacle: that step out.

That little paint pony has been Lena's friend for a while, or at least, a pal who thinks it's fabulous to see Lena and loves to run around her pasture like a wild horse when we pass by. She was increasingly interested in Lena's adventure into this hole. So, Lena was increasingly distracted by the pony, enough that she zapped herself on that hotwire fence.
That gave us a big step backward, because what horse wants to go back where they believe the shock was? Certainly not Lena.
And Lena has developed a large fear of holes in the ground, which only became apparent to me upon finding this hole. Did I mention she really could walk into it? Yea. Not. Happening.
So, rather than fight with her, I got off and then began to attempt to lead her into the hole. That started successfully, until I decided to pick up that large piece of rusted sheet metal to move it. Sigh. Horse backs out of the hole, to the end of her rein, eyeballing me like I'm crazy.
"Really, Lena? You're 11 years old!" is my mantra whenever we face these challenges. To me, my 11-year-old ought to, by now, have conquered any fear of strange objects. I always think she has, and lo, find a new one that is the scariest thing ever encountered.
So, having moved and set down the offending object, we walk back down. Walk down, snort, back up, repeat, until she's actually all the way in the area. Next challenge: getting out. That was simple enough, I climbed out and Lena jumped up and out, no problem.
So, can we repeat, with me in the saddle? Why, may I ask, is it always different with the rider in the saddle, anyway?
This time, Lena walked into it. She hesitated, but with gentle encouragement, she went all the way and we launched out of it with no problem. Tafra: 1 Lena: 1 Hole: 0
Yes!
The whole situation was definitely one of those, "You want me to what?!" situations. I don't know if it's a Lena thing, or just a horse thing in general, but the look on her face when she looked at that hole was definitely the "You're crazy!" looks.
At this point, after I get those horsey looks of disbelief, I'm just excited to have her through it rather than it ending in failure.