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One year later, and he knew he'd avoided it. The devil wasn't ever going to get out of his box. Sam was dead. Dean wasn't hunting. The Croatoan Virus had not become the next bubonic plague.
Sure, Dean was miserable, but the world had dodged the bullet. He'd saved the world, if not necessarily himself.
Two years later, and Dean was too busy with other things to ever think about things that had happened in the past. As a hunter, you lived in the moment. Never in the past. He had to worry about Sam now, because he was alive but not alright.
Three years later, and the Apocolypse was a bad dream, hardly a passing thought. Three years later and they spent all their free time fighting Cas and helping Sam with controlling his own mind.
Cas doesn't go down without a fight, but at least he redeems himself in the end. He comes down from his soul-high, admits he was a cocky, arrogant sonuvabitch.
Which would have been a lot ore liberating to here him say, if he hadn't also admitted he was a cocky, arrogant sonuvabitch who really, no matter what he'd thought at the time, had no idea how to open a cage without letting the devil out.
Four years later, and they're fighting Lucifer again. Except this time it's almost hopeless. No angel to help them out, nobody at all to help them out, really. And Sam is hardly in his best fighting condition. Neither is Dean, for that matter.
Five years later, and Dean realized Lucifer never did lie. Five years later, and Dean realized, while the circumstances were different, here he is, standing outside the building, waiting for the decoys to run in. Five years later, and Dean realizes he'd become what he thought he'd avoided.
Five years later, and Dean realized there's no escaping the fate given to you. You can only delay it for a little while.