The analogy breaks down, though, in that even after his boss went crazy, Cullen still raised his stapler at her and proclaimed for all the office to hear that he still believed in the company. Fast forward four years, and suddenly we get a Cullen who not only resigned, but now spends most of his time trash-talking the company he was supposedly so loyal to that he would turn against his boss to preserve, and very little context for this change.
What happened offscreen throughout these four years to make him hate the Templars so much now? All the reasons he does give in DAI are issues he already had to deal with in DA2, and he had previously worked through them in ways that left him painfully aware of the Order's shortcomings, but never resentful of it. So what changed that his tone is so bitter now? We don't actually know, but we're asked to agree with this change in his character's direction anyway.
I'm in the same place as R2, still trying to process how we went from "Cullen will always be loyal to the ideals of the Templars" to "Cullen doesn't even wanna talk about the Templars" - maybe there was context there, and maybe it would even have been credible, but we never got that context beyond a vague sense of disappointment and bitterness, and that leaves his character development feeling a bit... forced. For people who wanted Cullen to divorce himself from the Templars, that sudden change might be great even if it's not well explained because the end goal of "Cullen also resents the Templars now" is more important than the question of why; but for those who expected him to remain, as R2 perfectly puts, "a templar forever in some ways, whether he was technically employed by them or not," it's still very hard to reconcile DA2 Cullen and DAI Cullen into the same character without feeling like way too much was brushed under the rug, or that the writing asks us to pretend far too much of his previous characterization was never there to force this new perspective onto him.
Basically, too few questions we had about Cullen before were actually answered with this character rebranding of sorts, and too many more have now been left open in their stead. It's a weird place to be if you liked the idea of Cullen as a Templar who represented the better ideals of the Order, since that aspect of him is completely gone now, with almost no context to justify it.
The bigger questions: How can Cullen not be bitter?
Sure, Cullen was a man who believed in the Order, believed they could in fact protect people-he wanted to be a Templar since he was a boy. Then after all the years of training he dons the Templar Order uniform and feels he has gone beyond what his family expect from him-planting fields.
Not long after The Feredlan Circle fell and he was mentally tortured- watching his friends die by the hands of Blood Mages. Cole even says to your Inquisitor, that the questions the demons asked Cullen still hurt him.
Then he was shipped off to Kirkwall. Within a few years Cullen starts to question Meredith and as he says in DA2, “I am not sure if I am serving the order or serving Meredith.” Cullen wants to serve the Order, he wants to do his duty. But how can Cullen do this when his own boss is falling to pieces? Then later The Circle Tower falls, Meradith goes insane. Cullen finally sees his boss for who she is: a zealot twisted by red lyrium and her fear of Mages. While Cullen is fearful of Mages, he however does not agree with how to handle the Mages-kill them all.
For the next three years Cullen spends his time trying to do what he can to keep the order together, to make them stand for what they are supposed to represent-protecting people from magic. No doubt it was during this time Cullen may have thought to himself such things as: “What happens if I continue to serve, would I be subjected to another downfall that damages my mental state and how the Order should be?
It is one thing to endure a single crisis but to have another crisis happen again, sometimes the best thing to do is to change course. And this is what Cullen chose to do. Cassandra recruits him into The Inquisition. By this point Cullen still respects The Order but does not agree with how they are choosing to act. He believes the Order should do what they are meant to do-protect people not seek out their own ambitious goals that are against The Order oath, as it were.
As the story progresses, Cullen becomes more irritated with The Order. They are falling further and further away from their cause. Samson of course does nothing to help with this. It’s hard for Cullen not to be bitter in how the Templars have become.
If he was that little boy again and saw what The Templars are now, I doubt he would have such dreams to join them. Cullen in a way as a child idolize The Order and for someone to come along and shatter that boyhood idolization into a million pieces, makes him furious. It’s a slow climb, a slow death. While Cullen is glad to not be a part of that downward spiral, he sometimes comes across as helpless as if he can do nothing about it. Thus I believe it adds to his anger.
When it comes to Cullen, in my opinion the developers did an amazing job-though I will say I wish the whole lyrium thing was a bit more involved. The fact is, the pace of how Cullen feels towards the Templar Order is fine, nothing wrong with it. You just have to take a step back and understand why Cullen is bitter and there is a reason. A reason I cannot blame him for.
Cullen downward spiral about the Order slowly began in Origins, we just ended up getting tossed into the tailspin in DAI.
In the end though it does make me a little sad to see Cullen’s childhood dream be smashed into a million pieces and there is nothing that can be done to fix it.
Sometimes traumatic events take far more time to let go and start again, it just depends on who you are and when you are ready, if you ever are.
Perhaps Cullen finding love (if it happens) allows him to use that new form of strength to understand, its time to let go and it will be OK.
And I seem to have written an essay, ugh, sorry about that. 
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