Of one thing I’m pretty sure: If this isn’t the most infamous base breaker of MLP, then I don’t want to see the episode that tops it.
Magical Mystery Cure? Equestria Girls? Please!
I think the only other episode that’s equal in terms of badness might be “One Bad Apple”. In fact, they are pretty similar: A touchy subject matter, a lot of unpleasantness and bad characterization of a mean-spirited character, that was bullied before and decides to bully others in return. With the difference that barely anyone tries to defend “One Bad Apple”.
Why is that? I really struggle to see why.
Maybe the defenders think that Fluttershy is a little more justified in her behaviour than Babs – after all, we see her problems throughout the whole episode, while Babs’ bullying in Manehattan is never shown on screen.
And while that is definitively true, it does not fix the main problem: PYHD shows more, yes, but how it develops the story is equally heavy-handed.

One thing before we start:
Most people think the backlash came just because of bias: that Fluttershy fans didn’t like the episode because her favourite looked bad. I ensure you that’s not the case with me – Fluttershy learning to be assertive would be a necessary step in my book, and it’d be only natural that she would maybe go too far.
Most of my problems have to do more with bad writing, bad pacing and general missteps than with the premise.
First scene: We see Fluttershy feed her animal friends and Angel Bunny.
The rabbit has been established as tough and rough before, but mostly to push Fluttershy in the right direction, because he has a little bit more common sense than her.
Here, he’s just a spoilt brat and painted as unreasonably demanding. He demands a salad with cream and cherry, that Fluttershy hasn’t in store right now. So he slaps her in the face (nice!!!) and sends her to the market to buy it.

I really hope his toys survived this episode – if I were a little girl, I would have thrown it in the trash after something like this.

Next, there is the market, with a lot of merchant ponies introduced, selling so common things as carrots and cherries, yet showing business practices as if they traded gold.
Also, a lot of ponies cut in line before Fluttershy or otherwise ignore her, so she can't do her shopping.
Rarity and Pinkie Pie are also there, and they teach Fluttershy how she can speak up ...
… actually not - they just do some underhanded tricks to get Fluttershy what she wants.
Sure, don’t take the moral high ground – it’s not as if anyone on the market will do.

(Who wrote this episode - Ayn Rand?)

Fluttershy tries their tricks, too, but - surprise, surprise - they don’t work out for her.
So then she seeks advice from Applejack, Rainbow and Twilight, does she?
Actually no, because they don’t exist and won’t bother to show up any time soon.
So in the end, Fluttershy skips the cherry, making Angel his bloody salad.
And naturally - he gets so angry that he kicks his caretaker out of her OWN house. And we won’t see him return until the end - he won't get any more than the Stare for this.

But fortunately, we get an even bigger monster: Iron Will, a motivational speaker who teaches assertiveness. He’s loud, obnoxious and cares more for being impressive on stage than about the personal situations of his victims… I mean victims… I mean…
Who am I kidding – he sees them as stupid doormats anyway, so we might as well call them victims.
He believes them all to be weak and useless, but his teachings will help them to man up. 100 % guarantee of satisfaction. Just like any other low-budget self-help guide that’s flooding the market with almost no regards to in-depth quality.

So he gives Fluttershy some motivational wisdoms that basically amount to “If someone’s a jerk to you, be a jerk to him” and… that’s about it.
And what wisdoms that are:

"Never apologize when you can criticize." "When somepony tries to block, show them that you rock!" "Attack the day."

So basically: “Come over to the Dark Side. Channel your anger and strike them down.”
Of course, any psychologist worth their money (as well as anyone socially integrated) might find this advice useless, short-sighted and even dangerous, but don’t we forget: Iron Will is just a benevolent minotaur, he doesn’t have to be professional because he doesn’t charge any money – oh wait, he does.
So yeah, he is an antagonist by all definitions. Of which we already have too much in this episode.
And quite honestly: his presence will actually cause more confusion than simplicity, and that will come back to bite this episode in the ass.

Now it’s the next day, and Fluttershy starts to practice the new methods, mostly on ponies who ignore her: First a gardener who drowns her flowers, than two ponies that block the bridge (don’t mind that Fluttershy probably could fly over them) and finally another queue-jumper.
Angel Bunny doesn’t get his comeuppance at all, nor do the market ponies, and I think that’s another mis-step, because it again amounts to more ass-holes for the sake of conflict. The ponies of Ponyville aren’t perfect little angels, but in this episode it becomes contrived and unjustified really fast. It's almost as if these are townspeople from a whole different series.
Not that Fluttershy’s revenge is anything pleasant to watch – most of these new ass-holes are just ignoring her. And she begins to enjoy the violence far too much.
(Also: Both ponies on the bridge were in Iron Will’s audience front and center – make of that what you want.)

So Fluttershy brags in front of Pinkie and Rarity with her new assertiveness, and like Iron Will she starts talking in the third person, because that is totally normal for assertive people.
Suddenly Fluttershy starts to tick out about seemingly little things, like Pinkie Pie laughing, and throws a bowl on her head.
And true to the wisdom “Never apologize when you can criticize” she doesn’t even flicks an eye on Pinkie Pie’s shock. She’s already so much into that state of mind, that we can’t keep track with her. And even afterwards, we are never given an explanation why these things trigger a reaction out of her.
Instead we get another day with Fluttershy going over-the-top, torturing a mail pony and a tourist for mere accidents. These scenes are redundant and they only serve to drive Rarity and Pinkie Pie into action.
They tell Fluttershy to stop, but she already takes it too personal and decides to insult them in the most harmful way possible, particularly about their jobs and passions, calling them shallow and frivolous.

It’s the most infamous moment of season 2 and I can’t get how it is logically sound in any way. Fluttershy never shared an animosity with any of her friends, like Rarity and Applejack did in “Look before you sleep” or even Twilight and Pinkie Pie in “Feeling Pinkie Keen”. All of the other episodes depict her as cartoonishly comfortable with her friends, while the others are enduring her anxiety.
Now she's calling Rarity’s concerns about fashion “petty”, yet in “Green isn’t you Colour” she was complimenting Rarity for her accomplishments.
She's calling fashion something “nopony gives a flying feather about”, yet in “Suited for Success” she was putting just as much an emphasis on her dress as the others (even demanding “haute couture”).
And in “Party of One”, she was enjoying Pinkie Pie’s partys despite some considerable headache.
So that just leaves us with the other explanation: Fluttershy didn’t mean any of this at face value, but just let some pent-up frustration out in a spur of anger. Speaking from the perspective of a person who's actually familiar with spurs of anger: It DOES not work that way.
If you insult someone in anger, close to you or not, you usually begin throwing their own misbehavior back at them; you don’t critic them for something you liked about them before - you just forget that in the heat.
Also, you would do this probably out of desperation – you would not be as happy or gleeful about that.
Fluttershy could easily find other ways to insult her friends; like calling out Rarity for insincere flirting earlier in the episode, or Pinkie for her general tactlessness.
It would be even different if they critiqued the way she handled her animals - than the talk about life pursuits would have a real trigger.
There might be even the possibility that Fluttershy secretly envys her friends and only said these thing that out of jealousy, and I would accept that, if it not were mere speculation.
But as it is, there's no believable reason that she would choose these words out of sudden rage - they're too calculated and far-fetched for this, and Fluttershy is just too gleefully into it.

And that is the core problem of the episode: Fluttershy is active the whole episode, but we don’t get any introspective to why she acts like this – at least nothing that goes beyond “I don’t want to be a pushover".
Yet, after she gleefully insulted her friends, she suddenly sees herself as a monster - not because of the tears of her friends, but she sees herself in a puddle.
I could see that as a legitimate shock moment, but it's actually too down-played. And instead of apologizing to her friends, she just goes home and hides in her cottage, because we haven't dragged out the angst already.

So some days later... in autumn?... Rarity and Pinkie (again with no emotional transition) come back to Fluttershy’s cottage and try to win her back. It's not exactly realistic, but the ponies have always been easy in forgiving. The key factor for the resolution of the plot is now that Fluttershy takes responsibility for her actions and shows regret.
It would actually be challenging to explore her inner demons and the problems she faces in every day life after all of this.
But no - her friends enforce the idea, that Iron Will is responsible for this. However, unless this damn Minotaur had put a spell on her, that doesn’t make any sense either.
After all - Fluttershy did the beating and the insults all by herself, with no further encouragement by him, and she enjoyed it too much to be just a pawn in his game.

But speaking of our “professional” – Iron Will shows up to get his *husthust* well-deserved payment.
(Which begs the question, why doesn’t he collect right after the show?)
Rarity and Pinkie try to distract him (which is amusing, but not amusing enough), and then suddenly Fluttershy comes out of her cottage – totally in control and able to deliver this conclusion:

“As I recall, during your workshop you promised one hundred percent satisfaction guaranteed, or you pay nothing. Well, I'm not satisfied.“

Hey, that reminds me of an episode of “Dinosaurs”, where Earl Sinclair made a deal with the devil to get what he wanted, therefore turning into a jerk.
I wonder if Merriweather Williams knew that episode... and noticed that it was a dream scenario.
Iron Will doesn’t have satanic powers, so – again - he can’t be made responsible for the side effects of his teachings and should be paid anyway.
Maybe some people were right to consider him the scammed victim... However – there is one little distraction: I don’t believe his “one hundred percent satisfaction”-and-"All of my customers were satisfied always"-bullshit.

Let's ask some questions about Iron Will: Does he have any place of residence? Does he have some form of official registration? Will he even take complaints after the pay roll is already done?

After all: If all of his customers were satisfied, it would only mean that they never complained. But with being this blindly aggressive, it’s just a matter of time before they face the limits of his teachings, in a very unpleasant, probably even traumatizing way.
And honestly – why do I have to ask questions like this in a kid’s show? Shouldn't it be a little more easy to follow?

Why do we even need this whole business talk and contracts and all that? I took this was supposed to be a character episode for Fluttershy. But now Iron Will is here, and his presence creates conflict that distracts from the main conflict. In the time he spent fighting with Pinkie Pie, we could have dealt with Fluttershy and how she comes to term with her faults – a reasonable transition from her being angsty to her being in-control would have made this episode much more relatable.
Hell, Iron Will doesn’t even has to be in the story – there are other ways to bring Fluttershy in the wrong direction. She could have gotten bad advice from any other source – a book, a sound tape, maybe even some of her friends.
Rainbow Dash for example could have been a very believable candidate for that – she doesn’t think things through to the end, she showed impatience with Fluttershy, but would also have helped her out of good will.
Then again: Both writers, Charlotte Fullerton and Merriweather Williams had already written episodes about RD this season… both weren’t very good.

But okay – let’s pretend, that Iron Will is merely a business man. Let’s put aside my bias for unprofessional self-help advice.
What really makes me angry above and beyond, is this reaction of Iron Will:

“No means no, huh? Nopony's ever said that to me before.”

… may I use another quote:

“But I pity the fool who doubts Iron Will's methods! You don't doubt me, do you?”

… so… maybe... just maybe he should have accepted the value of a doubt.
But hey, that’s only part of the show! I mean, it’s not like ponies come to him because they really need help . For an honorable business man, he doesn't care a lot about professional quality control, doesn't he? He can't even think of something as simple as “No means no”.

I’ll just wrap this up now, before I start to think about his love life.
(Yes, apparently this asshole has family... go figure!)

The moral of the episode is presented as “Standing up for yourself isn't the same as changing who you are. Now I know how to put my hoof down without being unpleasant or mean.” And that’s absolutely true I’ll say. Thousands of people out there are able to get through everyday life without reaching to violence and aggression. And I don’t speak of extreme situations – I mean in civil day life.
I get that this episode wanted to handle a mature issue in a dark and cruel world, and wanted to encourage people to face it. But it went over-board with the darkness: Too many scenes spent their time on unpleasant bickering, mean-spirited humor or conflicts that did not need to be there. They brought the unpleasantness and suffering to high extremes – even to realistic extremes - , yet spared the audience from any insight beyond dramatic platitudes. All of the main characters are cartoonishly one-note, and we don't get the favor of different perspectives. The villain is too simple-minded to be taken seriously and too unlikable to find him funny.

I’ll give the episode that it tried to throw in some slapstick humour to lighten the mood. But if it had not gone so over-the-top with the gritty darkness, it would't have needed that. It’s still jarring as it is, and the humour itself doesn't do anything for me.
As I said at some points, this premise called for a much simpler script: Just cut out Iron Will, let some of Fluttershy's friends give bad advice to her and leave out the insults – the moral dilemma and most of the episode would be still there. Now add a heart-felt talk and maybe a confession of Fluttershy in the mix, and you'll be fine.

In fact, I’ll just leave you with a link toPutting Your Hoof Down – rewritten and let you decide. It might not be that intense, but it sure is more relatable.

ultimate verdict : 1/5 Personal verdict : Too over-the-top