The main reason why I started saddle hunting is that as I was getting older, ( I'll be 61 this year,) I noticed I was developing a fear of heights-heck, I'd watch a movie with a "high rise" scene like the 1st "new" james bond movie where he's chasing a guy across a construction crane, and my palms would start to sweat!!
That irritated me, as earlier in my career (I'm now retired) I had to work in high locations alot, & it didn't bother me, so I decided to do something about that. I'll be honest-the first time I went up in a saddle, I DID NOT feel safer than I did in my climbing treestand, even though I KNEW that I was!
So, how did I "make peace" with it? The answer for me "was simple, but not easy-" PRACTICE!
I'm lucky enough to live on 1 little wooded acre, with PLENTY of different sized trees to climb-What do I want today- a straight one with no limbs down low-got a bunch...how about a huge black oak twin that tests the length of the ropes on my sticks or steps, and forces me to decide which "twin" I'll go up on-got one...what about a skinny leaner... got a few, as well as trees with branches sticking out all over the place! It's raining? Time to see how I do this in the rain. (My wife thinks I'm crazy on those days!)
The more you practice with your gear, the more confident you will become! If it sits in a tub all year long, then you'll be nervous when you use it-it's that simple.
I also get plenty of exercise doing this, so it's a "double benefit." I see my Dr every 6 mos because I have high blood pressure, & when I saw her after about a year of playing with saddles, she asked me what I do for exercise, & I told her that I climb trees! She gave me a perplexed look until I explained, then she said, "keep doing that!"
I also enjoy the challenge of proper equipment use-carabiners, knots, sticks, steps, you name it. I feel that it helps me keep my aging mind sharp. In fact, I feel comfortable enough with my original gear (took about 3 yrs) that this year I've decided to try an aider on the way up, to reduce the number of steps I take in, and a rappel line to come down.
Another benefit for me is I have become my own "tree arborer." I can climb trees and take care of small problems that may otherwise turn into big ones!
Plus, I also always set up some of my 3D targets around the tree I climb-then I get to practice pulling up my bow, hanging it, & shooting it-no sense going thru all of that effort to climb & not get to shoot!
Bottom line- confidence comes with good, regular practice! Hope this helps!