Extending new pilot comfort zone?

Hi everyone, I've been reading "Advanced Soaring Made Easy" by Bernard
Eckey, and this is a fantastic book for a new pilot. It does discuss
learning to get out of the comfort zone of flying safely within glide
range of the airport. This is something I am just venturing into
myself and I was curious how some of you went about this when you were
learning?

When and how did you cut the strings for the first time? Was it with
an instructor? Did you do it in small steps, or did you just plan a
cross country flight? Or did you land out by accident once and get
thrown over that initial fear?

Since I am still renting a glider, it can be a bit of a problem if I
land out, but I would like to start flying a bit further outside my
comfort zone.

I was considering asking a more experienced pilot if I could "ride
along" with them on a cross country flight to help me get over the
butterflies.

Any advice appreciated,
Tom