I was really nervous of letting Goldie off leash when we got her....I didnt have much experience then. Luckily I met a lady who encouraged me to try it and it worked...Goldie stuck close by.
This time around I felt much more at ease about letting Lottie off leash and did it the first walk out, once we were on safe area away from the road.
I always have treats in my pocket and give them one when they come back and sit to have their leads back on, that way they learn it's not a bad experience to give up their freedom.