With my first I had no idea how long you were ment to BFed for so I figured if you give a baby formula till 12 months I will bfed for 12 months. The I learn there was toddler formula, so I figured I will bf him as a toddler as well. By the time he was 7 months I was involved with ABA & was happy to just follow Evan flow. He self weaned at 18 months. I think if I wasn't pg it may have been longer but I dunno. But it was the same story, sore nipples & probably funny tasting milk that encouraged him to wean with out me realising.
With Glenn I have always said once we get to 2 I would probably encourage weaning, but once again I am pg & he is 2 next month. I could put a stop to feeds now if I wanted too. I am sure there is no milk but Glenn is happy to suckle to sleep. Its the only time the breast is offered. He is asleep with in minutes. But I have also just layed him inbed next to me & he eventually goes to sleep with just a cuddle. No crying etc, just lots of chatting!
If he is really tired I will just cuddle to sleep but if he wants to keep getting up & running around I offer the breast & bang he is asleep.