I'd be a Elve...
One of the Teleri born pre first age at Cunivien, I'd see middle earth in its infancy during the great journey, and accompany Olwe across the sea to Valinor, after nosing around for a few years, I'd steal a ship and escape back to Middle Earth before the kinslaying (that way I'm safe, and I would have nice unsploit memories of Valinor) then spend the next three ages as one of Cirrdan's following-I could fight with him up the slopes of Mount Doom, accompany him during the ovethrow of Angmar, sneak into meetings of the White Council, sail around Arda at leisure (exploring the other cotinents such as the Burnt Lands of the Sun, and Numenor prior to its destruction) then catch the last ship from the havens back to Valinor.
It would a action packed, very long life, and it could shed some light on Cirdan's backstory and the mysterious Grey Havens.
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