As demonstrated by Jedi, but it’s surprisingly universal:
1. Start with confidence. “I’m going to play with those kids across the street”, Jedi initially stated with supreme brevity as he went in search of his shoes after watching from the window for a few moments. There were 5 or 6 neighbor kids in various activities, at least one of which he goes to school with.
2. Question the decision. “Should I go play with them? Is it OK? Do you think they have anything to play with that I’d like?”, he wondered. Which is the point where he began talk himself out of it. It’s fine, I assured. I’ll be here watching, just stay within my sight. Go, have fun, I shooed.
3. Need assistance. Like a push. Or a shove. “But you’re going to go with me, aren’t you?”, Jedi asked with a drop in demeanor. “Because I can’t go over by myself.” As a compromise, we all ventured outside to the fresh air where he could make an easier transition. In other words, I got your back.
4. Lose all confidence. As we were now outside, I suggested an easy way to politely ask if he could join in. But he cowered behind me. Instructing instead, in a timid little voice, “Just yell over there and ask for me, please? Please, please, please?”.
5. Blame someone else. Especially when, 5 minutes of back and forth later, you hear the rather loud parent to those children across the street inform them that it’s time to go. “You wasted all that time”, as Jedi’s pout began to quiver. “I could have been playing, but you wasted time.”
6. Repeat steps 1-5. Until one day, maybe, he’ll maintain enough courage to actually walk over and play.