Among those who didn't know him well, friends and foes alike, there was no doubt that a piercing intellect and a deviously creative imagination were the core attributes which drove him to succeed despite the efforts of his opponents and most importantly, despite himself.
While his tactical and strategic imaginations were both alive and well, anyone who knew Shikamaru properly knew that his creative imagination was an unmitigated failure compared to even the paltriest of dreamers. After all, his ambitions were pathetic, and his choice of career stemmed from a desire to seek more excitement in a world that by and large bored him -- and even then, he was too dispassionately lazy to find that excitement when it was handed to him on a platter. Early in his life, he remembers that someone, and he was fairly certain it was his mother, had said that he would probably grow up with a tatami pattern printed on his face because he'd rather sleep on the floor than play.
And really, when he bothered to think about them in the context of the lives of his friends, and family, and acquaintances, and enemies, and people he didn't even know, his ambitions really were pathetic.
In his own words, he wanted to be a so-so ninja drawing an average salary, marry an average looking wife, and have two children, first a girl, and then a boy. He wanted to retire once his daughter was married and his son was independent and eventually die before his spouse did.
What he hadn't ever counted on was life going right ahead and screwing everything up.
For example: when he'd said he wanted to be a so-so ninja, he hadn't realized that life would interpret this as being a so-so ninja on paper. His entry in the bingo book wasn't particular astonishing, really. His name and vital statistics filled the space under a picture taken -- in his opinion -- way too damn early in the morning. A list of the Nara family techniques passed on more as a matter of course than anything else, and a few others he'd picked up along the way. And then, of course, a record of his completed missions in all categories. Not particularly many, although he supposed that maybe the four completed S-ranked missions stuck out just a little. Failed missions weren't listed, thankfully.
The annoying part was that they only ever trotted him out for the express purpose of leading those incredibly dangerous S-ranked missions in the first place. He'd actually been asked to take twelve total, and his success rate was still higher than anyone else currently in Konoha.
It always started the same way. The Hokage would send of the fastest, and more importantly more persistently annoying ninja around as a messenger. Maybe Lee or Kiba, and they'd badger him into leading the team. Notwithstanding that once he got back to Konoha from his pleasant, out-of-the-way cottage, Rokudaime Uzumaki Naruto was even worse than Lee or Kiba at harassing him enough to make an S-class mission smell like roses by comparison.
Another example: he'd said he wanted to marry an average wife, but on his wedding night he'd admitted to himself that the sinuously lascivious way his princess of Sunakagure and ambassador to Konohagakure in one had seduced him away from any vestige of self-control was anything but average. This was a regular occurrence, more so when she was wearing that black thing. Even though he'd left behind his sexual peak quite some time ago, Temari didn't ever seem to be even approaching hers.
Not to mention that she was even worse at domestic matters than he was initially, having lived her entire life with a crew of servants to prepare meals and clean up after her. The manner in which unpleasant household chores were distributed -- ninety-nine to one in his favor -- was definitely not average, especially considering the percentage of women who'd filled out 'homemaker' as an occupation in the last census.
Things got steadily worse after that. When he'd said he wanted two children, first a girl and then a boy, he certainly hadn't meant one and then another sort of at more or less the same time. Less than two months before Temari had borne him a strong, healthy daughter, Kankouro's pregnant widow was poisoned by Grass ninja hoping to wipe out his legacy. An emergency c-section saved the boy if not his mother. Temari had given Shikamaru one look and he'd acquired a second child, this time a son. Technically his son is older than his daughter by two months.
He definitely hadn't meant twins, because that's what they grew up as, an aggressive girl with jet black hair tied back in twin pony-tails, and a tow-headed blonde with his biological father's irredeemable snarkiness. Neither resembled him in the slightest, and neither had the patience for the plodding games he loved.
He suspected he'd never get to retire under his original premises. At the age of six his daughter had declared one morning that she wouldn't marry anyone except for her white-bearded grandfather, but he was still married to Nara Yoshino, and offered to teach her kagemane instead. Shikamaru still hasn't forgiven him, because his traitorous wife showed up right when his daughter's shadow caught his while he was engrossed in a game of go with Asuma and promptly taught the girl how to dance before Shikaku had taught the girl how to release the spell. He personally took over training her in that arena afterward, just so he wouldn't get caught again. Temari still taught her how to dance with a fan. She still wasn't married, and neither was Shikamaru retired.
His adopted son, on the other hand, was very independent. He didn't have Nara blood, so couldn't learn any of their trademark shadow techniques. As a substitute he ended up immersing himself in Kankouro's scrolls and journals, and ended up becoming scarier than Shikamaru had ever imagined any of his offspring might ever be. Not enough independence, though, because he still comes home to annoy his adopted father and wheedle him for money, just because he can.
Shikamaru might still have a shot at dying before his spouse, though. There's not much either of them might do about that, although he suspects that Temari will die right when he does just to spite him.
After all, life has taken to laughing at him and messing with his ambitions. And she's become his life.
He doesn't care, though. It's close enough.