"I've made more mistakes than any man, woman and child on this planet, but at this moment, I would not consider your appointment to leader as one of them."

The words felt dry in Ozpin's mouth. Memories, bitter sweet, lingered like an awful aftertaste, always there, reminding him of the deaths that followed in his wake. He had often thought that, 'at the moment,' it wasn't a mistake, only to find himself horribly wrong. He lost himself for a brief moment before remembering the terribly too young child in front of him was listening rapturously, waiting for advice.

"Do you?" He asked not just to make a point, but because the part of him that was still twenty three wanted vindication. It was a small part, but it was there deep in the recesses of his psyche. He didn't think it would ever leave him, and, in truth, he didn't want it to. It served as a good reminder.

"Being a team leader isn't just a title you carry into battle, but a badge you wear constantly. If you aren't always performing at your absolute best, then what reason do you give others to follow you?"

The early days, those first expeditions into the unknown, had become fuel for nightmares. So many dear colleagues and innocent lives were lost, replaced by well hidden scars and the need for a cane. When he first began his supposedly illustrious career, he had ridden on the coattails of his school records and his father's reputation as a great Huntsman, expecting those meaningless things to be his ticket to instant success. He had heard all his father's stories and all the glory of being a team leader and of the successful missions. He had never been told of the horrors and of the failures the man had experienced. Those stories would come at a later time, accompanied by hard liquor and bar peanuts.

"You've been burdened with a daunting responsibility, Ruby. I advise you take some time to think about how you will uphold it." 'Please, listen to somebody who wishes he had done the same,' went left unsaid. He left Ruby to contemplate his thought on the matter. Right now, he needed a stiff drink, a habit picked up from years of contemplation and what others called victories and successful missions. He just called them failures and needless risks.

In the false comfort of his office, he sat with his guest, neither saying a word as they just watched the school below, a bottle of decent alcohol shared between the two. She drank in more moderation than he did, if only just. He thought of when he became a huntsman and all that he had believed it would entail. His Valedictory status at his ultimate school of combat training had left him arrogant and brash, ready to take on the world and all the Grimm that filled it.

He had never been so wrong.

His first few missions had gone well enough, but it was during a simple scouting mission for a new satellite settlement outside of Vale where things had gone horribly wrong. They had been told that there were fairly low amounts of Grimm in the area, that past huntsmen who had gone on expeditions near the same area had encountered and reported nothing more than a few Boarbatusks and Beowolves. It was the reason why that area had been chosen for development. It was believed to be safe and almost untouched by anything malevolent.

Imagine their surprise when they came across an enormous nest of King Taijitu. In hindsight, it made sense. Those snake-like monstrosities were intensely territorial, hostile even to other species of Grimm. They were most likely the reason that reason that the other expeditions had gone so smoothly without much interference. Few other Grimm would dare even leave a scent so close to a full nest of adults.

His team had, in full and plain view, walked right into their lair.

Ozpin, who had been leading the mission, never even thought to be careful or to have contingency plans. It had cost them several days, all of their equipment, and the other three members of his team, but at least one of them survived. He still remembered Derek's look of intense pain as he ultimately succumbed to the burning venom streaming through his veins during one of the few times they were able to rest, relatively safe from the snakes as they rested. Lisa's screams as she was eaten still haunted his nightmares. However, neither of those would ever compare to the look of betrayal on Tom's face as Ozpin was forced to leave him behind, his teammate missing a leg as one of the several King Taijitu descended on their camp.

Afterwards, the area was declared unsafe and that all huntsmen were to avoid it at any cost in the future. He still woke up in a cold sweat some nights, the shouts of fear and fury echoing to him from another time. Other nights, he dreamed of the Siege of Beltham. Others, of the Fallen City of Abbey. During the day, he thought of the Mountain of Forlorn or the March on Lizaro. He took a steady pull of the scotch in his glass and looked down at the children ambling about in the courtyard below. From up here, they looked like small and black, like ants. Or chess pieces. In the distance, he saw James' fleet hovering, like silent sentinels readied for battle.

Silently, he wondered if the past was repeating itself again and what he would do if it was.

"I've made more mistakes than any man, woman and child on this planet, but at this moment, I would not consider your appointment to leader as one of them."

Glynda waited around the corner, waiting for the headmaster to finish his conversation with Miss Rose. At those words, a brief remembrance of days long past and the role that her boss had played in them flashed before her eyes. She quickly pushed it aside. Those times were, for the most part, long over. She was a professor now, deemed too 'experienced' and 'invaluable' to be considered for field duty like she used to. Just another way of saying that she was getting on in years and that she was better suited to teaching school children than she was slaying scores of Grimm.

Like back on the Mountain of Forlorn.

She blinked as Ozpin rounded the corner, who surprised to find her leaning against the wall with glossy eyes. She knew he recognized that look. When he asked her to join him in his office to discuss the academic reports she was carrying, she accepted his coded inquiry as to whether or not she wanted to join him for something else. They had long since created a secret code of sorts, their reputation at the school too prestigious to smear with the association of hard drinking.

It was a popular rumor amongst some of the children that they were secret lovers and that their long hours into the night were, in fact, furtive trysts. It was anything but. The closest they had ever even come to such was decades past in that one night, with their emotions and anxiety running high. Neither spoke of that night in that cold, snowy mountain cave, not out of embarrassment or regret, but out of respect for one another.

She sat next to him as they watched the lamps in the courtyard lit up, almost mirroring the night sky. She didn't remember much besides that one night, but what she did, she would never forget. He was shouting at her, his face set in a deep grimace as it hovered directly over hers. Surreptitiously, she stole a glance at him. His face had aged much over the years, his youthful vigor now replaced by weary caution. She supposed that there was some sort of irony in that he needed a cane every so often and she didn't.

The scar, covered by silky nylon, burned. The one on her back, crossing from hip to shoulder, joined in, smoldering like venom scorching in her veins.

She rubbed at her thigh where the twisted flesh sat. She remembered waking up that night, only to be greeted by the other two members of their team, their gaze utterly still and unwavering. She had known Kendra since her first year at combat school, and while she had only just met Philip, the stories he told of his family were heartwarming. She cried for hours inconsolably, knowing that Philip's children would never see him again and that she would have to tell Kendra's brother what had happened. Ozpin merely sat next to her, his hand rubbing at her back as if he could softly beat away the pain.

In a way, he had. In her grief and want to feel something else, Glynda had kissed him. Kissing had quickly escalated into desperate grasping and fondling, which turned into the sloughing off of clothes that felt too warm and heavy. Ozpin later admitted that he had felt uncomfortable throughout the whole experience, like Kendra and Philip were watching them, judging them; he did not like her like that and thought it was a mistake. Glynda agreed, that she didn't really think of him that way either and that she would like to remain as friends. That was the last they ever talked about it, and they were comfortable with it staying in the past.

A hand, rough and littered with small scars, gently closed over hers. She gently squeezed it, taking comfort in its warmth and assurance. Her leg cooled slightly. The two of them kept watching the grounds below, both occasionally emptying their glass, only for the other to fill it back up.

Glynda thought of all the other missions she went on afterwards. She had always requested that she be teamed with the man beside her and that he be their leader. Many times, their assignments went without much problem, but things spiraled often quickly out of control. He had been forced to make a judgment call and those few times where he had made the wrong choice, the situation had descended to chaos. He tried his best to salvage what he could of the situation, but he couldn't save everybody. When he had been questioned in investigations following their field reports, she was always the first to defend him as a huntress under his command or as a character witness or as whatever she could be for him. Usually, it was as his closest friend.

When she had been forced into retirement, he had followed her. She didn't bother trying to convince him otherwise. She knew it was futile to even try to do so. Ozpin was the sort of man that was intensely loyal to his friends. Glynda believed it was the reason why he had remained close to James despite everything. When he applied for a position at beacon, she had followed. She couldn't prove it, but she suspected that he had threatened to reject his immediate acceptance if she couldn't join him. It wasn't necessary; both of their outstanding field records had more than met the expectations of the board.

The moon had long since risen into the sky. A small clink of sounded amidst the churning of gears as the two old friends raised a final toast before knocking back what was left of the now empty bottle. They toasted to their good health, to a good future, to friends and colleagues, and to everything else between. Silently, of course.

After all, the two of them had long since passed the need for words.

Author's notes:

This is my submission for the /r/rwby MonCon (or Fanfiction and Fanart Contest) for March 2015. This month's theme was a piece featuring Ozpin and Goodwitch with the theme of Life Lessons. I encourage everybody who's even slightly interested in it to go and check out the other entries. If you liked my entry, the please vote for it. If not and you liked somebody's else more or are just not interested, then feel free to do otherwise. Still, contest or not, I hope you liked this piece. I was happy to write this bit as I was a bit burned out on Fate Recondite. Don't worry, I'm still working on it and Chapter 5 is in the works as I type this, but this was a nice distraction while I got my Muse to speak to me again. See you guys soon (hopefully. I'm not exactly the most coordinated person in the world).