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[Year 3] [Week 1] *January 4th - 10th, 2016*

In my headcanon, Twilight's dad is the director of an Equestrian Intelligence Agency. There's plenty of headcanon's about Twilight's mom, Velvet, but next to nothing about her dad, Night Light.
And, it can still work with agency that was established in the 100th episode. Actually, when I saw that episode, I adjusted my headcanon a bit:

He was part of the Equestrian military as part of a family tradition, later found a much better use for his talents in information gathering by joining up with the Monster-Hunting Agency (though, to his brothers and the rest of his family, he was just an average pencil pusher). Basically, in his younger years, I imagine him as something of a Witcher with a bit of Shadow of Mordor thrown into the mix, since he'd routinely get sent on operations in hostile territory.
I imagine that the monster-hunting part of the agency started to phase out when he started moving up in the ranks until he became the Director. He went on less field-ops when he got married and had a family. The agency still exists, but they're mostly information gatherers, not black op soldiers or hit squads anymore. Not to say they can't, they just find more use knowing when and how a Griffin warlord plans to attack rather than breaching his fort's gates, killing his guards, and possibly spending a couple good lives stabbing that warlord in the throat, only to later have someone worse take over.
His main role now is organizing ops and deploying assets on missions, as well whatever else the head of a massive, clandestine intelligence agency does. He does, on rare occassions, join on dangerous missions if he feels that failure is not an option or if he's worried about his agents making it home alive.

....Another piece of fun head canon. I imagine that he and Velvet are both fiercely intelligent ponies, to the point where the two of them routinely have games of deduction. Surprisingly, he's managed to keep his secret life away from Velvet and the rest of his family.

Description
[Year 3] [Week 1] *January 4th - 10th, 2016*

In my headcanon, Twilight's dad is the director of an Equestrian Intelligence Agency. There's plenty of headcanon's about Twilight's mom, Velvet, but next to nothing about her dad, Night Light.
And, it can still work with agency that was established in the 100th episode. Actually, when I saw that episode, I adjusted my headcanon a bit:

He was part of the Equestrian military as part of a family tradition, later found a much better use for his talents in information gathering by joining up with the Monster-Hunting Agency (though, to his brothers and the rest of his family, he was just an average pencil pusher). Basically, in his younger years, I imagine him as something of a Witcher with a bit of Shadow of Mordor thrown into the mix, since he'd routinely get sent on operations in hostile territory.
I imagine that the monster-hunting part of the agency started to phase out when he started moving up in the ranks until he became the Director. He went on less field-ops when he got married and had a family. The agency still exists, but they're mostly information gatherers, not black op soldiers or hit squads anymore. Not to say they can't, they just find more use knowing when and how a Griffin warlord plans to attack rather than breaching his fort's gates, killing his guards, and possibly spending a couple good lives stabbing that warlord in the throat, only to later have someone worse take over.
His main role now is organizing ops and deploying assets on missions, as well whatever else the head of a massive, clandestine intelligence agency does. He does, on rare occassions, join on dangerous missions if he feels that failure is not an option or if he's worried about his agents making it home alive.

....Another piece of fun head canon. I imagine that he and Velvet are both fiercely intelligent ponies, to the point where the two of them routinely have games of deduction. Surprisingly, he's managed to keep his secret life away from Velvet and the rest of his family.