This may sound silly but it's what I do. Every time I get a new piece of gear I try it out in the backyard. My first time in a bivy, my first time using a tarp, and my first time in a hammock were all backyard trips. My first time under a tarp in the rain was also in my backyard. I want to fuss with my gear in a controlled environment so that when I go out on a real trip I have some confidence in myself and my gear.
Heck, I still do this, and get odd stares from the neighbors. If I make my own stuff, and or decide on
some new idea on how I'm gonna use something, I wanna make sure It works for me before I end up
20 km in somewhere and depending on it. Recent examples - new hammock bottom insulation meant a snooze outside in the snow, Garage sale aquired svea meant leaving it out overnight in -20 then cooking
dinner over it outside in the snow, etc. etc.
Now I'll also do it one "bailout" trips when I decide to walk in a few clicks and know I can walk right
out again and give up if something goes wrong - or just car camping. but you should continue to do this, even if not a beginner.