After everything that happened in the previous episode, it's no surprise that the writers wanted to step back a moment. It's odd to think that Sera Gamble wrote this episode, while Ben Edlund wrote the previous angst-fest. Tonally speaking, one would have expected the opposite, given the material. Edlund is usually the go-to writer for darkly comedic episodes, but Gamble did a capable job.
Anyone stuck in the corporate world, even under the current economic crisis, understands the soul-crushing culture that dominates. It's so antithetical to everything about the Brothers Winchester that it almost seems to be an incorrect test of Dean's true nature. I don't think you need to be a hunter by instinct to feel like the mind-numbing power politics of corporate hell are something to escape!
That said, a more subtle shift in their lives might have been harder to render effectively. The amusement that comes with Sam and Dean in the white collar world is necessary to give the episode enough scope. The further the brothers begin from their normal lives, the longer the journey back. Structurally, it definitely makes sense, and there are some cute moments.
The entire episode hinges on the very end, because while it's amusing to see Sam and Dean out of their element and living alternate lives, there had to be a reason for it. I like how they tied this into the end of the previous episode and gave Dean a reason to keep fighting. It's definitely better than watching him deny his nature for several episodes, and better than having Castiel or Sam talk him into it. In essence, Dean makes the choice to return to his old life, and though some persuasion is involved, he makes that choice for himself.
In practical terms, Sam has to be inserted into this alternate life along with Dean, because otherwise, Sam would immediately try to do everything possible to intervene. But it also seems as if Zachariah knew that Sam would be a catalyst for Dean's realization that he should be a hunter. It feels like Sam's role was also important for some reason, but despite his overwhelming sense of destiny, that doesn't quite gel.
It could have something to do with the impression that he's already on his destined path, and Dean is the one that needs to get his head back in the game. Zachariah's explanation to Dean seems to indicate that all those hints about Dean dealing with Sam will, in fact, come to fruition before all is said and done.
If there is one flaw to the episode, it's the pacing. The story takes its time, and some scenes feel like they take forever to unfold. It's a lot slower than the previous episode, for instance. That's not necessarily a bad thing, but I found myself wanting them to get on with it more than once. The end helped to mitigate much of that annoyance, but on the whole, the pace took a little away from the impact of the episode.