Thank you for starting this thread. I think it’s fundamental that you’ve recognised the core cause, that’s the first step in catching future self-doubts early so you can analyse and move through them, hopefully wiser. You've eloquently and boldly described a lot of my own inner processes. Thank you for giving the name to what’s been bothering me too, I never boiled it down to self-doubt.
I can relate very much to style journey not being about clothes only. The same thought struck me a while back and ever since my posts have been a sort of self-discoveries (some I share explicitly, some I don't) through which I was trying to cement one fact in my own mind: I actually knew all along what's true me style-wise (or, who I truly AM) , yet I needed someone else to confirm to me that. Why was this outside voice needed to 'allow' me to be me if I felt all along it was right, I was ok just the way I was? Does it make sense?
I figured out one thing though - style journey is fantastic, harmless, easy way to do a lot of soul searching. MaryK (I think) called YLF a laboratory of personal growth. I agree with that. I also think because dressing myself is one thing in my life -- probably the only thing -- over which I have sole and 100% control, I can really use it to grow. I don't wreck my brain over what I'll wear. But, I get in tune with myself over 'why's behind some choices and give names to certain feelings and thoughts, which minimises unnecessary self-doubts. I often mentioned how learnings from YLF spill over to my whole life. It's like strengthening the muscles with some exercises, only to figure out IRL that the muscle is there when you need it.
And I understand - you want to know WHY the self-doubt is there in the first place? I don't know, I'm working on it too. It can be tiring, but I can't not search any more once I asked myself the question about the foundation. I also think it’s a bit harder when you become a parent and watch your child make sense of the world, for me at least. I often wonder how we go from these little, fearless people to grownups which seem to spend too much time getting over various issues instead of just - being, here and now. Nothing will bring this moment back, yet it can be ruined by unnecessary thoughts.
Btw, here is great TED Talk that I’ve been returning to often lately, it had reshaped my way of thinking a lot
http://www.youtube.com/watch?v=IvtZBUSplr4
ETA: I've been thinking about this a lot this morning after my initial response. it struck me that similar to finding a lot of joy in exploring, defining and expressing myself through what I wear, I also grew immensely as a person through my parenting experience. Unlike what I said about style being 100% under my control, parenting is a shared task and as such requires common approach - but, I'm doing it differently to many 'norms' I was brought up with or saw around me when I became mum. I am happy with our path so far. There are challenges and frustrations, yes, but there never was self-doubt. I know I am a good mum doing my best to raise caring, confident and independent individual.
So, I started drawing parallels with going through a new experience in a new way (which in itself creates no doubts) with going through very common, shared experiences such as those you mentioned above (which can lead to self-doubts). What is different between the two? Why I feel undoubtedly on the right track, as much as I don't know what future brings and how things may turn out, in something so crucial, yet in something I have so many examples and models and guidelines for I can find myself self-doubting?