That is the piece that I stumble on for sure.
Some people are able to look at a menu and see lots of good options. If I find something I like, I stick with it and don't really look around for other options because the menu seems overwhelming (and why risk getting something I won't like as much as the tried and true.)
I have no idea where this self-limiting behavior comes from...maybe it's time to hire a life coach to help me through this part.
Well it's pretty obviously fear based, but what's underpinning that fear?
Humans tend to put an ENORMOUS premium on what they know, even if they aren't optimally happy with that option.
I mean, if you are optimally happy with the tried and true menu option, then stick with it. But if you aren't optimally happy, then you do actually have the power to change this pattern of behaviour and seek out better options.
When you have the kind of freedom you do, fear of the unknown is completely useless. It doesn't serve you in any way, shape or form.
I also get totally overwhelmed by menus at restaurants, I don't like all of the options, but I have the opposite reaction to you. Instead of playing it safe, I roll the dice every time. I just ask to be surprised.
People think it's batshit insane when I do it, I get really strong reactions from people, but FFS, it's just food. A bad meal here and there isn't nearly as deleterious to my emotional experience of life as being rigid and fearful is.
I find it telling that people are so shocked when I don't even look at menus and just say "surprise me" to wait staff. Like, this is about the lowest stakes risk a human being could possible take in their life, but it goes to show just how powerful the fear of the unknown is in people.
Perhaps you need some professional support to work on this, like a coach or therapist, but you can also just push yourself out of your comfort zone and see what happens.
Getting a crappy meal, or finding out you don't enjoy amateur live wrestling, or that learning guitar sucks and hurts your hands, or that geocaching really isn't your thing, or that Tai Chi in the park is boring, and Shakespeare in the park is even more boring, or learning Spanish takes way more practice than you expected and you just can't roll your fucking R's, or martial arts is just too high risk for injury, etc, etc
All of these kinds of realizations are low stakes costs to trying new things.
FTR, amateur live wrestling is absolutely fantastic entertainment and after being dragged to it pretty much against my will, it's now one of my very, very favourite activities. Actually I love almost all of the activities listed above except for geocaching, never actually done that.
You just never know what unknown things are going to resonate for you. And the cost of trying new things is pretty low, like 99% of the time.
So you could just, y'know, try stuff. Not necessarily even to find new things that you like, but just to get accustomed to expanding your comfort zone.