Oswin: Regrets, so many, omg - she never really had a 'dream job', but more a dream life where she got to see all the wonderful things out in the universe. She was very much a 'can't wait to get out of this town' kid, and saw serving on board the Alaska as a way to do that. It went so well.
Clara: ... In her 'real life', the one that everyone else knows about? Regrets, but... not? She answered the question of 'what do you want to be when you grow up' as 'an adventurer' rather than with a job, mostly thanks to her mum. She didn't really have a super-clear plan on how to accomplish these adventures, just that she was going to go. She did graduate college (no really, there's a picture in canon, true facts) though there's never any real clue as to what her major might have been (it certainly wasn't culinary school or computer science). Maybe something with a literary bent - the library is one of the rooms she actually bothered to stop and check out while being chased around by a monster in the TARDIS. ANYWAY. No real regrets now that she's met the Doctor, for lo, ADVENTURES. Weird adventures. But still. She's having them, and it's grand.
Ace: Had absolutely no plans whatsoever on getting older. Live fast, die young, probably get nicked a few times for something or other along the way. She has no regrets, but getting older is weird. Getting older in a stable family relationship is weirder.
Balthazar: If you'd asked itty!bitty!lordling!B what he wanted, before he figured out what was expected of third sons when your eldest brother had already married and produced an heir to the title, he would have said dragon slayer. But that was before he figured out that sort of thing and before he met Merlin, which pretty much sealed his fate. No regrets (except maybe about being in Spain when the Inquisition started), but he certainly never expected to be in the 21st century whilst dragon slaying.
Katya: ... it's a regret, kinda? She has natural talents towards being a healer, and she probably could have been a good one. But that's not what Moscow needed at the time, so. She didn't become one. But Skellig's chronic injuries bother her quite a lot, and she helps as best she can, but she knows that an Other trained as a healer could have repaired it all ages ago.
Haymitch: ...................... LET'S NOT ASK HAYMITCH HE HAS A KNIFE.
Glorfindel: No, this isn't what he planned on doing while growing up - sorta. He did plan to be in a 'not in command but commanding' position, because there were houses with higher rank than his. He didn't expect the kinslaying. Or to be following his chosen king across the ice. Or to lose said king after a betrayal. Or to come back to the land that killed him so he could continue to serve the family of his king. But he certainly isn't unhappy about his place in life.
Bones: Is doing exactly what he wanted to do as a kid. He comes from a family of doctors, and has been idolizing them his whole life. He just... does it in space. Which some days he regrets deeply. He's looking at you, Kirk. Just. Really. Really</>.
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Clara: ... In her 'real life', the one that everyone else knows about? Regrets, but... not? She answered the question of 'what do you want to be when you grow up' as 'an adventurer' rather than with a job, mostly thanks to her mum. She didn't really have a super-clear plan on how to accomplish these adventures, just that she was going to go. She did graduate college (no really, there's a picture in canon, true facts) though there's never any real clue as to what her major might have been (it certainly wasn't culinary school or computer science). Maybe something with a literary bent - the library is one of the rooms she actually bothered to stop and check out while being chased around by a monster in the TARDIS. ANYWAY. No real regrets now that she's met the Doctor, for lo, ADVENTURES. Weird adventures. But still. She's having them, and it's grand.
Ace: Had absolutely no plans whatsoever on getting older. Live fast, die young, probably get nicked a few times for something or other along the way. She has no regrets, but getting older is weird. Getting older in a stable family relationship is weirder.
Balthazar: If you'd asked itty!bitty!lordling!B what he wanted, before he figured out what was expected of third sons when your eldest brother had already married and produced an heir to the title, he would have said dragon slayer. But that was before he figured out that sort of thing and before he met Merlin, which pretty much sealed his fate. No regrets (except maybe about being in Spain when the Inquisition started), but he certainly never expected to be in the 21st century whilst dragon slaying.
Katya: ... it's a regret, kinda? She has natural talents towards being a healer, and she probably could have been a good one. But that's not what Moscow needed at the time, so. She didn't become one. But Skellig's chronic injuries bother her quite a lot, and she helps as best she can, but she knows that an Other trained as a healer could have repaired it all ages ago.
Haymitch: ...................... LET'S NOT ASK HAYMITCH HE HAS A KNIFE.
Glorfindel: No, this isn't what he planned on doing while growing up - sorta. He did plan to be in a 'not in command but commanding' position, because there were houses with higher rank than his. He didn't expect the kinslaying. Or to be following his chosen king across the ice. Or to lose said king after a betrayal. Or to come back to the land that killed him so he could continue to serve the family of his king. But he certainly isn't unhappy about his place in life.
Bones: Is doing exactly what he wanted to do as a kid. He comes from a family of doctors, and has been idolizing them his whole life. He just... does it in space. Which some days he regrets deeply. He's looking at you, Kirk. Just. Really. Really</>.