So probably the thing you need to start practicing and learning is how to deal with anxiety. Conveniently those sessions can fit right into the time slots you're currently spending procrastinating because of selfsame anxiety. See how long you can sit with it and reassure yourself, before reaching for the phone. Once that's been tamed a bit, I think the ability to enjoy doing something poorly will start to appear naturally as a by-product. Or, you can force the issue a bit by adopting a "punk" ethos: "I suck at this, but fuck you, I'm doing it anyway." And there's your example of doing things in a slacky YOLO way too: listen to early punk rock. They did a pretty good job of channeling their anxiety outward into creativity and energy. And there's a "punk" version of almost anything you can think of. Keep it simple, be a beginner, maybe even mock the experts - some of them need it. Good luck.