Hmm, not the same as my speedo drive!
I'd suggest installing the seal with the bearings fitted in the lower cup, but just gently push in until it is flush. Now push the crown race in. Sandwich the whole lot together, then using two hands push them firmly together (i.e. pre-loading the bearing) and rotate at the same time. Then, repeat, but this time with the seal ring the other way up. Hopefully one direction will rotate smoothly without fouling and the other will be draggy and horrible.
I had a look on Simply Bearings' website, this tech doc:
https://simplybearings.co.uk/shop/files/ina_seals.pdf demonstrates that the seal lip direction is simply that the thin end point towards what you're trying to keep out. In the case of my speedo drive, the main thing was keeping grease away from the brake discs (pretty bad on a motorbike!) hence the seal lip was pointing inwards. On a headset, I'd assume the thin end should point to the outside to keep water and grit out.
^^ this is a long-winded way of saying I don't know which way you're seals go
SP
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