Diamond at a Crossroads

by SuperPinkBrony12

Rating: everyone
Tags: Cheerilee, Diamond Tiara, Slice of Life, Sad, My Little Pony: Friendship is Magic
Length: 3027

(Takes place within the universe of "The Sitter with the Diamond Tiara" and its semi-sequel "A Dazzling School Daze".) Plagued by uncertainty about her future, Diamond Tiara visits Cheerilee in hopes the teacher can guide her one last time.

(Takes place within the universe of The Sitter with the Diamond Tiara and its semi-sequel A Dazzling School Daze. Familiarity with both is not required, aside from a little bit of context.)

Diamond Tiara has come to a realization of sorts about what her future should be and what sort of career she wants to pursue. A recent experience has convinced her to become a teacher, rather than take over her father's business.

But the young mare finds herself still plagued by uncertainty over her decision, doubts have crept into her mind about who she is and what her career path should really be. So she decides to have a talk with somepony she believes can help clear things up.

Cheerilee is quite surprised to be visited by one of her former students, but nevertheless agrees to hear Diamond out. And Cheerilee's advice and guidance might be just what Diamond Tiara needs to hear.

Published 2024-04-15 15:30:01 UTC
Last updated 2024-04-15 15:30:01 UTC

Crossroads of Destiny

For Cheerilee, it was just the end of another school day. Her students had been dismissed for the day, leaving it up to the earth pony mare approaching middle age to gather her things and head home. There were no after school activities taking place that required the use of the schoolhouse. And per EEA rules, it was to remain locked up when not in use.

How many years now had she been at this? Thirty years? Thirty five? Maybe even forty? Cheerilee couldn't remember, it seemed like only yesterday she had taken on the job of running the Ponyville schoolhouse. She had seen a few generations of Ponyville ponies in her time, each memorable in their own unique way. You wouldn't be able to tell just by looking at her that she was starting to reach her fifties. There were no gray streaks in her mane and tail, her eyes remained vibrant and full of color, and she carried herself as if she were only half her age.

Cheerilee couldn't help but giggle at the thought that she was older than she looked. She often joked that compared to the teachers in places like Canterlot or Manehattan, she might as well be one of their students.

With that thought brushed aside, the mare approaching middle age was just about to lock up the schoolhouse and call it a day, when the door suddenly swung open! She turned around fast and was greeted by the presence of a young earth pony mare with a lovely magenta coat. Said mare had cornflower blue eyes that sparkled like diamonds, and her light grayish-purple mane and tail were adorned with lovely white streaks. Most telling of all about the mare was the fact that she wore a diamond tiara upon her head, similar to the one depicted on her flanks for a cutie mark.

To say that this earth pony's sudden visit was a surprise would be an understatement. Although Cheerilee recognized this pony at once, she had not seen (let alone spoken) to said pony in years. It was one of her former students: Diamond Tiara, a filly who had started out as an infamous class bully before eventually blossoming into a much nicer pony down the road. And said pony, Cheerilee had proudly boasted, had been among her most promising students of all time.

So what was she doing here of all places? And on such short notice too? Most former students of Cheerilee usually acknowledged her presence only if they happened to cross paths with her while out and about in Ponyville proper. None had ever come back to the schoolhouse for a visit.

A look into Diamond's eyes told Cheerilee all she needed to know. The way they looked around and reflected their surroundings conveyed the look of a pony greatly troubled. No doubt, Diamond had come to Cheerilee for a very important reason. And probably an urgent one at that.

Despite the urgency being shown by the headgear wearing young mare, Cheerilee just flashed a smile as she got up and closed the schoolhouse door. Chances were that her former student didn't want anypony else to be a witness to the conversation that was soon to take place. Once that was taken care of, she turned to face her fellow mare and said with a smile. "What a lovely surprise to see you again, Diamond Tiara. I don't think I've seen you since you graduated from my class years ago. But I've heard so many wonderful things about you from others."

"Really? What do they say?" Tiara asked in a noticeably uncertain tone. It looked almost like she was afraid of something, despite her best efforts not to let it show outwardly.

Cheerilee maintained the smile, hoping to defuse the tensions with her cheerful and calm approach. "What makes you think they'd have anything bad or negative to say about you, Diamond? Everypony I've ever encountered has had nothing but praise for you. It sounds to me like you've grown into a fine young mare. Why I even heard you've gotten married and taken a husband. Pipsqueak, was it?"

The headgear wearing earth pony slowly nodded. "Yeah, that's him, alright. We just celebrated our anniversary last weekend. He took me on a trip to his native Trottingham. It was certainly an enlightening experience to see where he came from. But at the same time, I could see why he'd choose to stay in Ponyville instead of moving back there. Trottingham is..." She paused, putting a hoof to her chin as she seemed to struggle to think of the word she wanted to say next. She ultimately settled on. "Different from Ponyville, and not necessarily for the better," Then she shook her head from side to side. "But that's not what I came here to discuss."

The currently off-duty teacher still smiled. Her years of experience in working with and shaping young minds had trained her well in picking up subtle signs about things that ponies were hesitant to discuss. And as the many parent-teacher conferences she had been part of could attest, she was highly skilled at keeping her true feelings close to her chest until the time was right to use them. She would not pry if Diamond didn't want to tell her outright. She instead gently coaxed her fellow earth pony. "Well, what did you come here to talk about, then? Is it something you don't want anypony else to know about?"

Tiara gulped and swallowed hard. The anxiety within her was slowly but surely rising to the surface. "Y-yeah, something like that. I only just started thinking about it a little while ago because of an experience. It made me start questioning things that I thought I already knew."

"Perhaps you'd like to talk about it?" Cheerilee offered, motioning for her former student to walk around and stand in front of her desk. "I could even 'Pinkie Promise' not to tell anypony else about this if that'll make you feel better."

Diamond protested with a shake of her head. "No, I don't want you to make any sort of promises, Miss. Cheerilee."

The off-duty teacher sweetly replied. "Diamond, I'm not your teacher anymore. You don't have to call me Miss. Cheerilee. You can just call me Cheerilee like all my former students do."

"But it just feels right to call you by what I was always used to calling you," The headgear wearing filly replied as she slowly trotted around. "There's just so many thoughts and feelings swirling around inside of me. You're really the only pony I could think of on short notice that I trust to be honest with me."

"More than your friends, or your husband, or even your family?" Cheerilee inquired.

Diamond slowly nodded. "Yes, more than them. You saw the best and the worst in me firsthoof for years."

Cheerilee's smile slowly faded. "Well, what is it that's got you feeling so conflicted, Diamond? You always seemed to be so confident when I was teaching you. But I shouldn't be surprised, you did get your cutie mark in leadership, after all."

Tiara glumly replied. "Yeah. And I thought that was steering me towards taking over the family business from Father, like he did with his father before him. It's certainly what Mother expected, which is probably the only reason she didn't disown me on the spot when I stood up to her," She shuddered and whimpered. "We haven't spoken to each other since I started dating Pipsqueak. To say she didn't approve of my choice of a suitor would be an understatement. If not for Father, I probably would've been forced out onto the streets right then and there. Seems Mother's just as skilled at getting her way as I am."

"Oh Diamond, you mustn't worry about her," Cheerilee tried to reassure her fellow mare. "You're all grown up now. She can't tell you how to live your life any more than I can. Whatever it is you decide to do with your life, I would gladly support you. And I'm sure your father, your friends, and your husband all would too."

But Diamond could only respond with. "Can you be so sure? Because what I'm thinking of doing means I'll probably have to move away from them for a time. I don't see any of them ever leaving Ponyville, not even the Cutie Mark Crusaders, and they're teachers at Princess Twilight's School of Friendship."

The off-duty teacher opted to carefully press that last statement. "What do you mean by 'leaving Ponyville', Diamond?"

The earth pony mare with a magenta coat finally opted to confess. "Well, because of that... experience," She paused in hesitation, before eventually resuming. "I decided that I want to be like you. To be a teacher."

If Cheerilee was at all surprised or taken aback by the confession, she didn't show it outwardly. She simply sat there, letting the news sink in. Then her smile returned to her face as she happily and sincerely stated. "Why, I think that's wonderful, Diamond Tiara! I'm certain you'll make an excellent teacher! May I ask what the particular experience was that inspired you to follow my career path?"

"Well, you know how I used to foalsit the Cake Twins to get extra allowance money as a filly?" Diamond explained.

"I was not aware the twins still needed a foalsitter," Cheerilee blinked. "They seem to have everything well in hoof running Sugarcube Corner. Besides, they have Pinkie Pie to help them out."

Tiara went on explaining. "Yeah, and she's the one who needed a foalsitter. I agreed to look after her son, Lil' Cheese. Figured it was a good way to pass the time when I had nothing better to do," A smile slowly crept onto her face as she recalled. "I enjoyed it far more than I thought I would. Guess it helped that he was potty trained and had his cutie mark, so I didn't have to worry about diaper changes, that's the one aspect of foalsitting the twins that I don't miss," She was quick to get back on subject before she could allow herself to get distracted and ramble on. "Anyway, foalsitting that colt made me realize something I hadn't realized before. I liked being around little kids, especially kids Lil' Cheese's age. I wanted to be part of their lives, to help shape their futures and guide them."

Cheerilee's smile grew brighter. "That sounds like the same sort of realization I had when I got my cutie mark as a filly. And it sounds to me like you'll make an excellent teacher. You've already got plenty of experience working with children, which is always a positive in the education field," With a wink she added. "It may not look like it, but it can be a very competitive job market. The EEA doesn't settle for second best."

But Diamond's mood soured. "And that's what worries me. If I'm going to be a teacher, if I'm going to dedicate myself to helping kids learn and grow, there's a lot I'm going to have to do. I'm going to have to go away to attend school where the EEA can more easily take notice of my talents. I'll have to prove myself to ponies who don't know a thing about me. And given the troubles Princess Twilight had with the EEA back when she was establishing her friendship school," She gulped anew. "How do I know I'll be able to live up to their high standards? How do I know they won't already think badly of me or look down on me because of my past?"

The off-duty teacher's smile slowly faded. "Diamond, that's absurd. You really think the EEA wouldn't also know that you're not that pony anymore? If not, I know I'm not the only one who can vouch for your change of heart. You've got so many ponies here in Ponyville who've seen the best of you over the years. Any one of them would gladly testify about your qualifications if asked."

"No!" Tiara stubbornly protested! "I can't have other ponies fight my battles for me, even if I want them to! If I'm going to be a teacher and be like you, Miss. Cheerilee, I have to be able to prove that I can do it on my own," She sighed and let her shoulders slump downward as her overall mood again became pessimistic. "But what if I'm not good enough? What if I haven't changed as much as I think I have? How do I know that I won't break under the pressure to perform to expectations?" Looking her fellow earth pony firmly in the eyes, she questioned. "What if I end up being asked to replace you? I don't know if I could ever be good enough to be even half the teacher you've always been!"

Having finished her abrupt chain of confessions, the headgear wearing young mare unhappily sighed. "Well, at least talking with you helped me get all of that off of my back. Sorry if it's a lot to take in," She eyed the door. "I guess I should probably get going and give you some time to think. No sense in taking up any more of your time than I already have."

Yet just as Tiara had trotted to the door and prepared to open it, Cheerilee spoke up. "Diamond Dazzle Tiara."

Diamond spun around very slowly, Cheerilee hadn't addressed her by her full name since... well, the headgear wearing earth pony couldn't remember when. That's how long ago it had been.

Cheerilee's tone of voice and overall expression was hard to read. It looked and sounded equal parts sympathetic yet also disapproving. "Why do you doubt yourself? Do you really believe that after everything you've been through, that you won't be up to the challenge of being a teacher?"

"But what if I'm wrong?!" Tiara protested with a whimper, shrinking from Cheerilee's gaze. "What if it turns out I don't like being a teacher after all?!"

"Everypony has doubts like that from time to time," Cheerilee reassured the troubled headgear wearing filly. "Even I was uncertain about whether I was truly qualified to be a teacher back when I started out. I know I told you and many other students the story about how I got my cutie mark, about what it represented. But that was only half true. I could just as easily have applied those beliefs to at least a dozen or so other professions. I couldn't be sure being a teacher was the right call for me, despite how strongly I felt that I wanted to be one."

At that, Diamond questioned. "So, what made you decide to go through with it? Why is it that you haven't given it up by now? Surely, you've been thinking about retiring, haven't you?"

The off-duty teacher shrugged off the concern with trained ease. "I won't lie and say it was all sunshine and rainbows. You're old enough to know the truth. Like everypony, I've had my share of good days and bad days. And before you ask, no, not all of my bad days involved dealing with you back when you were a bully. Sometimes, my good and bad days were entirely unrelated to anything my students said or did. But what kept me coming back and what has kept me from calling it quits are the smiles on my students' faces. It always warms my heart to know that I'm getting through to them, forging a bond with them. It's a bond that cannot be undone no matter what."

"And you think I could inspire a similar bond in any students I might have?" Tiara hesitantly inquired, her attitude appearing to improve ever so slightly.

Cheerilee brushed her mane with a hoof and firmly nodded. "Given everything I've seen in you, Diamond Tiara, I'm more than convinced you can. You can do anything you set your mind to. After all, you've stood up for yourself and proven everypony wrong before. Regardless of whether other ponies approve of your decision or not, I know you have what it takes to be a fine teacher in your own right. And if someday you do end up taking my place here at this schoolhouse," She sweetly added. "Well, I can't think of any higher honor than being succeeded by one of my own former students."

For a moment, Diamond remained silent, letting Cheerilee's words slowly sink in. Then, a smile slowly returned to her face as she said to the off-duty teacher. "Thanks for believing in me, Cheerilee. I mean it. You must've known there was good in me even before anypony else could see it. It's no wonder you haven't been replaced here. A teacher like you comes only once in a lifetime!"

Cheerilee nodded back. "So I've heard. And I'm thoroughly convinced you could be just as good if you try. If it doesn't work out, at least you'll know. But I have every confidence and every faith that you will succeed, that you'll make for an excellent teacher no matter where you end up." And with that, she watched as her former student departed, now brimming with confidence and ready to take on whatever life might throw at her.

Author's Note

Apparently, the Gameloft mobile game has suggested that Diamond Tiara's future profession is related to philantrophy, which mostly involves donating money to good causes. But given her confessed talent in leadership, I feel like she could just as easily become a leader or get a career that is directly involved in leading others. I had planned to do a story of her taking over from Mayor Mare, but then a really good fanfic was written about that concept before I could do anything with it.

So instead, I decided to build on my stories involving grown up Diamond Tiara and Lil' Cheese, and have her become a teacher. And yes, I'm going on the belief that Lil' Cheese is male, not female.