Great thread idea, OP, and very relevant to me at the moment.
I have had low self-worth all my life and was conscious of not wanting to pass this onto my DC (7, 5, 2). I am having counselling related to my low self-esteem and resulting general unhappiness. Something very interesting has come out about where my problems started.
I thought I had had a very lovely, problem-free childhood with no real worries and 2 parents who loved me unconditionally. What has come out is that although I was praised for my achievements, I have completely taken on my Mum's own view of herself (adopted, feelings brushed under the carpet, felt unwanted, etc) and internalised it as MY view of myself. I may have been told to 'do as I say not as I do' but my role model didn't value herself (and still doesn't) and so that's what I learned to do. I was also not encouraged to have strong emotions, or cry, or deal with my feelings in any way, and so am now having to learn to recognise my feelings, express them where I need to and thus let them pass. This is building my self-esteem no end.
I am realising that I need to model good self-worth to my DCs for them to take it on for themselves. I'm in no way there yet but it feels like the right road.
And on the subject of pretty pink princesses - DD1 didn't do this and I congratulated myself for her healthy gender-neutral attitudes. DD2 at 2yo only plays with dolls, pretends to be a hairdresser and wants to wear 'tippytoe shoes' all the time. I am having to go with the pink tide
. I think the problems come when that is all a girl experiences.