MummyBerryJuice
I have four children who have all been breastfed until they weaned naturally, bedshared until between 3-5.5yo, all been carried whenever they've needed to be transported etc. etc.
After having DD1, I realised that trying to stick to 'attachment parenting' ideals isn't helpful. What is helpful is to do what works, so long as it hurts no one.
So, for our principles, for example:
If a baby cries, it's harmful so we try to avoid that as much as possible
If a baby wakes alone, it can be frightened so it sleeps with us until it's brave enough to sleep alone
If a baby sleeps in it's own room, I get harmed by having to wake up properly to feed them
But:
It doesn't work for me to carry a baby 100% of the time when I am also playing with older siblings so, unless they are crying, they play on the floor or get cuddled by a sibling or one of my friends or family.
I have had one very, very high need baby (the oldest) and three much more independant ones. The oldest was very, very hard work, and I often got to told to just make her leave me alone at toddler groups, or to leave her in creches and just let her cry - "she'll get used to it" - etc. etc. I am so, so glad I stuck to my guns now.
She was very clingy for years and I got very frustrated and despairing, and I was lucky I had so many friends who supported me in letting her let go in her own time, or I would have done all the things that would have harmed her - forcing her to do things before she was ready. Then, about 18m ago, when she was nearly 6 (she's home educated so we've never had to do the having her pulled off me crying by teachers, but I know that's what sending her to school would have needed!), she wanted to go to a street dancing class with her friends. She got up the courage to stay without me, although she wouldn't join in. Then she started joining in on the second session, and then something clicked in her. The time was right for her.
Fastfoward to now. She does Badgers since January, and stayed for hte first session just her and her 5yo sister. She waltzed into a new, more local street dancing class where she knew no one at Easter time, and insisted that I leave as she wanted what she learned to be a surprise. And last week she ran off supremely confidently into her first ever swimming lesson.
She is a completely different child and I am totally confident that her confidence and independence is totally genuine and profound - it's not based on knowing there's no point in clinging or crying because no one will bother listening to you or taking you seriously. Seeing her like this makes all the cuddles and enduring the clinginess worthwhile.
If you try to get a child to separate before they're ready, you just invite even harder work - e.g. the emotions of leaving a child crying at a scout group; or the bedwetting that often starts when a child is stressed by something that they are not ready for; or the having to get up in the middle of the night because you are putting baby to sleep in another room. It's far easier, if you can manage it, to go with the flow and work on surviving, not on 'training'.
Please trust in your son and his instincts. He knows better than anyone, including you, when he will be ready to separate, and how that separation will happen, just like he knows how much milk he needs and when he needs it. Trust him. Do what works and is helpful for you and your family, not what a book says or what your friends say.