The group went to Ponyville Park, the best place for a race. Drill Bit’s friends got permission from their parents as well to join them, considering it wasn’t every day a princess drops by to hang out with one of your friends.

When they reached a fairly open area they stopped. “Aunt Twilight,” said Flurry. “You go sit down and let me take care of this, okay?”

“Of course,” Twilight replied. “From what Pound said you understand better about his feelings than I do, so you’re the best candidate to get through to him.

“I’ll keep my distance and let you handle things the way you think is best. After all, I’m aware of how prideful that colt is. I know he’s not going to make it easy and I expect he’ll hold back on his true thoughts if I’m too close by.”

She leaned over and kissed Flurry’s forehead. “Don’t push yourself too hard, Flurry. I’ll try not to interfere but if things seem like they’re getting out of control I’ll have to step in to bring things back in order.”

“No problem, but I won’t be needing your help,” she said confidently. “I’ve grown a lot since you’ve last seen me. I’m not the same weak filly I used to be.”

“I never thought you were weak, Flurry. You had to be strong to hold in all those terrible feelings for so long.”

“I guess so, but Crystal has helped me so much to become stronger than I ever thought I could be.”

“Is that right?” she asked warmly. “I guess you chose well.

“Well, everyone’s waiting for you, so I won’t keep you any longer.” She retreated to a safe distance where she could keep an eye on things while still giving them privacy.

Drill called out to her. “Hey, you done stalling over there?”

Flurry turned to him and closed the distance between them. “Are you in that much of a rush to lose?”

Drill chuckled. “Sassy. I know alicorns are skilled with magic, but they’re not really known for their flight capabilities. Do those wings of yours even work?”

She chuckled back. Without hesitation she unfurled her wings, extending them out as far as they could go. “Yeah… I think they do.”

Drill Bit and his friends gaped at her. Her wings were gigantic.

Pound and Pumpkin were shocked too. Even with her wings out she hadn’t lost her smile. She wasn’t blushing or trying to hide them. She looked perfectly at ease.

“Something wrong?” Flurry asked smugly. “Don’t tell me you’re intimidated already?”

It took Drill a moment to refocus. He shook his head, getting his brain back in order. “Those are some wings. You steal those from your mother?”

Flurry gave them a few flaps. “Oh, these old things? They’re nothing special. Sorta like you.” She winked at him.

“Ooooh,” Cumulus said, his eyes twinkling. “I think she just said she’s ready to throw down.”

Drill quietly growled. He knew she was just trash-talking, but for some reason it got him heated up.

“What’s wrong?” asked Flurry. “I thought you were going to send me home crying? Where’s that fire you had just a short while ago?”

He didn’t know himself. For some reason he couldn’t get himself to respond. There was just something about her that was throwing him off, and he didn’t know what. Was it because she was an alicorn, or that she was royalty? Was that making him subconsciously hold back, even though she told him to just treat her like any other kid?

“Oh, I see,” she continued. “You’re intimidated by my inner strength.”

‘No way!’ he tried to yell out, but it was only in his head.

“You see, Drill Bit, Pound’s told me about you. I’ve walked the path you’ve walked.”

“What are you talking about?” he responded, finally finding his voice again.

“I saw it before, when you were talking to your mother. She didn’t approve of you training Pound because I guess she feels you could be spending your time on ponies she feels are more worthy of you.”

Drill let out a huff.

“I used to be the same, holding in my real feelings and hiding who I truly was. Pound and Pumpkin helped me to talk to my parents about the way I really felt, and Crystal helped me to become comfortable with who I was.” She flapped her wings a few times.

She put a hoof over her heart. “Those two things helped me to achieve a sense of inner peace and self-confidence. I’m Flurry Heart, from my head to my tail, and I refuse to be ashamed of something I can’t help.” She pushed her wings out as far as she could again. “I’m proud of who I am, these wings included, and no one can take that away from me.”

“Flurry…” Pumpkin was impressed.

Crystal let out a joyful giggle.

Pound was speechless. She was like a whole different pony. He knew he didn’t have to worry about her being self-conscious anymore.

Drill Bit and his friends couldn’t respond either.

Flurry folded her wings back up. “How about you? Do you have that sort of confidence in yourself?”

Drill was feeling frustrated again.

“The thing is, your weak confidence can’t begin to match up to mine. As long as you remain chained to expectations and don’t confront your fears nothing will ever change. So I can already say for certain that it’s impossible for you to beat me.”

He gritted his teeth, quietly growling. He hated the way she talked like she could see right through him.

“When I finally got the courage to confront my parents they showed me that I had had nothing to fear, and they told me I could walk my own path. Now I know that if I’m going to rule the Crystal Empire it’s going to be because I chose to do so of my own free will, not because it was forced on me or because it’s what everyone expects me to do. It was a huge relief, and I couldn’t be happier now.

“How about you? Do you have the guts to face your fears like I did? Not right now you don’t. Even if you win this race it won’t make a difference. You’ll still be scared of losing and letting your parents down. The only thing you can do is win and win, because losing is unacceptable. After all, you don’t want to be a loser.”

Drill was shaking a little, a bead of sweat coming down his face. Why couldn’t he stand up to her? He kept yelling at himself to confront her, but still he just stood there… afraid? No! He wasn’t scared.

Leaning forward a little she continued, “But it goes further than that, doesn’t it, Drill Bit?” She extended a wing, putting it under his chin. “I know you feel like walking a different path than the one you’ve been walking, but you’re terrified that it’s going to be a lonely path. After all, your parents worked so hard to make you into a champion. Maybe you’re scared they wouldn’t care for you anymore if you decided to do something else with your life? How sad would it be if your parents love wasn’t waiting on that other path?”

A cold chill went through Drill Bit, a sharp, shaky breath escaping him as he shuddered. Mindful of the massive display of weakness he just showed in front of his friends he felt his frustration turn to rage. “ENOUGH!” he yelled, swinging his hoof toward her.

Flurry could have stopped him with her magic, but she chose not to. She recoiled a bit as he connected.

“Hey!” Pound called out.

Flurry put a hoof in front of Pound to quiet him down.

Drill was huffing. “Enough of this! Enough! I’m sick of you and your stupid words. You don’t know anything about me! I came here for a race, not a conversation. Now shut up and get ready, or just go home! I’m done listening to this.”

Flurry shrugged. “Very well. But we both know it won’t make a difference. Even if you beat me here you won’t get the victory you’re looking for.”

Drill took to the air, breathing heavily and muttering to himself as he looked around. He returned to the ground a minute later.

With barely contained rage he created a course for the two of them to follow for five laps, then ignored her as he did his warmup exercises far more aggressively than usual.

Pound did a countdown for them when they were ready, and watched as they took off.

Even from the very start Drill did poorly. He was so distracted he took off without flapping his wings, landing heavily on his stomach. Blushing heavily he stood up and set off.

The colt just didn’t have the sharp skills he always did. He wasn’t as fast as he usually was, and messed up tricks that he had done flawlessly hundreds of times. He crashed into a bush as he went to loop around it, then he skimmed his wing on a tree branch and came within a hair of slamming his head into a tree before he corrected.

“What is going on with him?” Cumulus asked with some exasperation.

“I guess Flurry really got under his skin,” said Heavy Downpour.

“I guess so,” said Sandstorm. “He’s never been this pathetic before.”

“I can’t really blame him,” said Nimbus. “Flurry threw me off too. If Drill Bit was an iron wall, she seems more like diamond.

“Her power just seemed to radiate off her. I guess that’s an alicorn for you.”

“Of course!” Sandstorm said strongly. “No pegasus could reduce him to this mess.”

“You think what she was saying is true?” asked Cumulus.

“Who knows?” Nimbus replied. “It doesn’t seem likely, given how the five of us have been competing with each other for so long. I mean, if he doesn’t want to be a racer any more then what else could he possibly want?”

“No idea,” said Heavy Downpour. “He certainly hasn’t mentioned anything to us about wanting something new in his life. The only thing that’s changed is that he spends time training Pound every day before we go at it.”

“I just think the pressure got to him. It’s pretty rare to race a princess. And with his mom expecting him to win it’s no wonder it’s throwing him off.”

Cumulus shook his head. “Well, it’s obvious he’s going to lose with this sorry display he’s putting on. He won’t even be able to tell her it was a close race. It’s just sad.”

“No kidding,” said Heavy Downpour. “I expected so much more out of this.”

Sandstorm and Nimbus nodded in agreement.

It made Pound feel like crying to see Drill fall so far. Flurry had really gotten to him. Although he could be really obnoxious at times Drill was one of the strongest kids he knew. He was naturally gifted and always striving to improve himself.

Maybe it had to be this way for Drill to understand, but it didn’t make it any easier to see. It was like he had lost all confidence in himself. And with every error he only seemed to grow more frustrated and frantic.

It wasn’t hard to see what was on Drill’s mind. His mother expected him to win. He might not have realized it before, but Flurry had illuminated his deepest fears to him, bringing them to the forefront. The more he tried to excel the more the pressure got to him.

Even if it was for Drill’s own good, he couldn’t escape that Drill was so flustered because of him. All of his friends were there, watching him fail. They had heard Flurry reveal what lied in his heart, and they were only there because he had pressured Drill to come by posing the challenge in front of them so he couldn’t turn it down without losing face with them. It was exactly what Twilight had done to him to get him to meet with Tree Leaf.

He didn’t know if Flurry was holding back, but at the speed she was going he didn’t think she was faster than Drill Bit. She finished her fourth lap as Drill finished his third, and he seemed to be on the verge of just bolting or giving up on the race altogether.

He couldn’t take it. He couldn’t bear to see Drill go down like this. “DRILL BIT!” he yelled. “As my teacher you’ve never backed down from a challenge, and you’re not going to start now! GOT THAT?

“You’re better than this, now get it in gear. I know you can win! I believe in you!”

Drill Bit paused for a moment as he turned towards Pound, taking in his words.

He felt a strange warmth in his chest at Pound’s determined expression. What was he doing, getting so worked up over an opponent’s words? He was setting a bad example for his student. Pound had confidence in him, and he couldn’t let that down.

He took in a few deep breaths. Personal issues were for their own time. When he was competing nothing else should matter but him and his opponent.

He silently thanked Pound, feeling renewed confidence. He would come from behind to win for Pound. He was finally feeling that tingling thrill of anticipation that came from an uphill battle. If he was going to win now it would take all his skill.

As Drill took off again Pound saw a markedly different pony. Drill was almost a blur as he flew around now, pulling off precision moves as he zoomed past their group, finishing his fourth lap and rapidly closing in on Flurry.

“Wow,” said Pumpkin. “You really got him fired up, Pound.”

Pound let out a sigh of relief. Even if he lost now he wouldn’t look too bad to his friends.

“About time,” said Cumulus. “I thought we had lost him for a while there.”

“I won’t lose this!” Drill said with gritted teeth, heading between braches as he folded his wings for a moment to avoid clipping them before opening them back up. He did this for the next three trees.

He pushed himself to his utmost. The race was almost over. There was no need to hold back. He didn’t even know if Flurry was aware of how close he had gotten. She hadn’t tried to speed up since Pound had shouted his encouragement, but if she was so assured of her victory she wasn’t paying attention to her opponent that was her own fault.

The finish line rapidly approaching he ignored the stitch in his side and focused all his attention solely on winning. There would be time for breathing later.

Flurry glanced behind her, and saw Drill Bit rapidly gaining on her. She quickly set her face forward, but Drill wasn’t going to let her get away with her lapse of attention.

He pushed himself still harder, to the point even his wings were burning, something he couldn’t remember happening for a long time.

He blew past Flurry just as she started to speed up. With her larger wings they carried her further with less effort, but with the lead he now had it remained to be seen whether it would be enough to let her claim the win.

She was closing the distance on him now as she pushed herself. Drill’s reckless disregard for anything but victory started catching up to him. He began slowing down.

He was starting to feel a little lightheaded, but the finish line was so close. Just a little bit further. He took in one final breath, as much as he could, and used everything he had left for that final push.

Pound had no idea who was going to win. Drill Bit had definitely overexerted himself, and Flurry was quickly catching up to him.

Seconds passed, his heart beating hard, and Drill Bit just barely crossed the finish line first, too tired to stay airborne. He landed hard, his momentum carrying him as he went rolling over and over and he nearly slammed into a tree before a pink aura from Twilight stopped him.

Drill Pant was gasping for oxygen, turning over onto his back. The pain of the crash felt like nothing with adrenaline running so high.

Pound ran over to him. “Are you alright?”

Drill didn’t answer at first, too focused on getting oxygen back in his body. When he could finally speak a few words the first thing that came out of his mouth was a slurred, “D-did I… win?”

“It was a photo finish, but you won by a hair.”

Drill Bit let out a delirious laugh, feeling slightly lightheaded as he kept taking in big gulps of air. He hadn’t pushed himself like that in ages. There was nothing like a hard fought conquest, snatching victory from the grasp of defeat.

Drill’s friends trotted over, congratulating him on his win. He didn’t have the energy to respond. He felt too dizzy at the moment, closing his eyes as he recovered.

It took a few minutes, but Drill Bit finally rose to a sitting position, and then a short while later he stood up, his breathing steady. His heart was still hammering, but it was also slowing down to a more natural rhythm.

Flurry walked over now, putting a hoof out to him. “Well, it looks like you won. Good job.”

Drill Bit stared at her outstretched hoof, and for some reason he started to get irritated again. He met it regardless. “Good race.”

“Oh, well. I wasn’t really expecting to win. You have a lot of experience with this sort of thing. I’ve always spent most of my time focusing on magic rather than flying.”

“You weren’t expecting to win?” Drill dropped his hoof, his eyes narrowing. “What kind of attitude is that? Don’t you realize that victory is the only thing that matters?”

“Back on that, huh? Maybe in a life or death situation like Equestria being in danger, sure, but you can learn as much from your failures as your victories. Do you feel satisfied now?”

“No! As a matter of fact I don’t. The only reason I struggled with you is that I let you get into my head and let it interfere with my performance. It’s obvious you don’t have what it takes to compete with me. If I had flown at my best from the start I would have creamed you without breaking a sweat.”

Flurry shrugged. “Probably.”

Drill Bit growled. Her nonchalance over the whole thing just annoyed him more and more. “Don’t you even care that you lost?”

“Why should I? I had fun. And after all it’s not like I have someone back home expecting me to prevail.”

Drill tensed. “Well, good for you. And honestly this was all just a big waste of time. I got my victory, so we’re done here.”

“Hold on!” Pound called out.

“Save it, loser! In my world the winner is the one who wins, obviously. Flurry lost the race, so whatever junk she said before is meaningless.” He lifted his hoof, laughing. “No one cares about the words of a loser.

“Later!” He took off without another word, a little wobbly as he flew from pushing himself so hard earlier.

“Eh, tough luck there, kid,” said Cumulus. “But our boy can’t be beat.”

“See you around,” said Sandstorm, the four of them going on their way.

Pound felt a sense of gloom as Drill Bit vanished into the distance. He had failed again. And worse, it was all his fault. “I’m sorry, Flurry,” he said sadly, tears coming down his eyes.

“Why’s that?”

“I ruined everything! If I had only kept my big mouth shut this wouldn’t have happened. He would have lost, and then he would have had to accept what you were saying.”

Flurry smiled, unfurling her wings. “I told this to Crystal before, but you know what these wings are great for?”

He didn’t know why she was asking, but he shrugged. “No.”

She extended them towards him, pulling him close as she wrapped them around him. “They’re great for giving hugs.”

She lifted her hooves, hugging him with them too. “Don’t feel down, Pound. Just like I told him, winning or losing didn’t matter. I’ve already succeeded in what I came here to do.”

“But if he had lost-”

“Then he would have felt humiliated and embarrassed in front of all his friends, and terrified of the reaction of his mother. In fact, it’s better that he won. Now he can’t use that as an excuse to turn away from his true feelings.

“Now no more tears. You did what you felt was right in your heart, and you can’t do any better than that.”

Pound settled into her hold. “How did you do it, Flurry?” he asked. “You’re calm and relaxed and confident. I don’t feel any of those things.”

“It wasn’t easy, I assure you. Every day Crystal made me go for a walk with her with my wings out for as long as I could stand it.”

She released him, standing there with her wings unfurled. “It was so embarrassing and humiliating at first, and all I wanted to do was hide. But she kept pushing me and pushing me, and eventually I stopped paying attention to the stares.

“As our bond grew I knew that I had a friend I could trust to the end, so what did their hurtful words mean to the love that we shared? I became determined to make myself a better pony, so that when the time comes I’ll be able to protect my friends.

“Not all villains are mindless and destructive. Feeling humiliated by my wings left a large weakness that could be exploited. I had to ask myself a hard question: would I be willing to let harm come to my friends because of my shame toward my wings? The answer, of course, was a big NO!

“So, as difficult as it was, I knew I had to overcome that weakness, and learn to accept myself for everything that I am. I chose to keep my wings this size when Mayhem offered to shrink them, and I want to stay true to the reason I did so.

“Good day or bad day, success or failure, I want to love myself through it all.”

“Wow, Flurry,” said Pumpkin, beaming. “I think that’s really inspirational.”

Flurry chuckled. “I still don’t know whether I’m going to be the ruler of the Crystal Empire or not, but I am an alicorn princess. I might not have all the feats that the other princesses do, but I feel that the main role of a princess is to inspire others to do better and feel confident, and I can’t teach others to feel that way if I don’t feel it myself.”

Off to the side Flurry heard clapping. She turned and saw Twilight sitting nearby, a dreamy expression on her face. “Oh, Flurry, you’ve matured so much since I last saw you.” She let out a little sigh, her smile fading a bit. “I remember how much you were suffering just a few months ago. Just look at you now.” A tear came down her cheek.

“Well, Aunt Twilight, I couldn’t have done it without the support of all my friends.

“As for you, Pound, I stand by what I said before: I think you did the right thing. If you hadn’t shouted out when you did he would have felt all alone, humiliated and ashamed.

“Sooner or later Drill Bit is going to have to face his heart, but it’s nearly impossible to do that all alone. You showed Drill that you were on his side regardless of whether he was behind or ahead. I think that will be crucial in the days ahead.

“I can’t promise any particular result, but we’ve done all we can. The rest is up to him. He has to be the one to make the choice, just like I did.”

She looked towards the sky. “You haven’t failed to help him change. You just haven’t succeeded yet. You told me that in the past he was just a bully, but then you stood up to him, and he started to train you. Then he told you that the time you spent together didn’t mean much, but you said that he’s been spending more and more time focusing on you. Whatever his mouth is saying, it just doesn’t line up with his actions. He definitely is changing, whether he wants to admit it or not.

“I’m sure that today is no different. You can’t force him to change, but you can be supportive of him as he does. So long as you do that you have something to be proud of.”

Pound slowly smiled. “I was feeling pretty bad before when he took off, but you really did help me to feel hopeful that Drill Bit can still be saved.

“Your words… they kinda remind me of Twilight’s. When Drill told me that our time together didn’t help him understand why his brother changed I felt like a failure for letting Twilight down. She told me that the only thing I could do was to give it my all, because I couldn’t force his mind or his actions to change. So she told me that as long as I did everything I could she’d be proud of me.”

“And I still am,” said Twilight. “I also told you that with more time Drill Bit might come around. He still hasn’t reached that place yet, but he seems a lot closer to it than the last time you spoke about it with me.

“We’ll just have to see what the next few weeks hold.”

Pound was feeling calm. Flurry was right. Drill Bit had gone through a lot of changes since he first started school. He just had to be patient, and hope that Drill Bit got something out of their race.

***

Drill Bit landed in front of his house, his wings dully aching. He let out a sigh as he folded his wings up. His mind had been curiously blank as he had took off for home, but now he felt a weight in his stomach.

He just stood there, unable to bring himself to open the door. Why was he acting like this? He had won the race and his mother wasn’t even home.

Where was the sweet thrill of victory? Where was his sense of accomplishment? If he had won, then why did he feel like he lost?

He let out a sigh, his head drooping.

Author's Notes:

As we can see Flurry has gotten comfortable with herself.

It seems most people were expecting Drill Bit to lose, but as Flurry said winning the race wouldn't give him the victory he actually wanted.

With a prideful pony like Drill Bit I never intended for his issue to be wrapped up so easily.