Oh wow. That sounds kind of awful - I'm sorry!
First, it seems weird to me that they expect you to take the boxes out to the dumpster, especially - as you mentioned - given it's such a trek, in crappy conditions, AND requires a special key. What the heck?
I can almost understand how, in a small company, they might need people to pitch in with taking out the trash, but this sounds kind of crazy. (And ironic, the point of leaving the boxes, I assume, was so the recycling company would pick them up! If you're tossing them in the dumpster, they're not getting recycled?)
And, I 100% agree with you that it's obnoxious to communicate by leaving notes by the recycling bin that are targeted at you. Frankly, I'd be tempted to just ignore the notes and assume that, given the colorful and misspelled words, they were not posted by anyone with any authority. I'd want to take a stance of, "until my manager tells me to do it this way, I'm going to continue leaving the boxes by the recycling." Heck, I might even be tempted to ask if the company really thinks it's a good use of your time (and their money) to be getting dressed back up for the outside weather (I'm assuming you need to suit up for the cold!), trekking through the parking lot, risking injury out in the snow banks and ice, to dump boxes that are *supposed* to be picked up by the recycling company!
Argh. I'm upset for you! What makes it worse, to me, is that some of this stuff doesn't *need* to be an issue if people would learn to communicate in a somewhat normal fashion. Instead of leaving notes, if someone had simply approached you and nicely said, "oh, we can't get the recycling folks out here any more frequently, and the boxes are creating a bit of a hazard for us. I know it's a bit weird, but would you mind taking the extra boxes that you've got and bringing them out to the dumpster?" - you probably would react differently. (It's still a sucky thing to have to do! But it's a bit more respectful of a way to approach it!)
Sigh, I'm so sorry Hvert!
Your boss sounds kind of nuts. I don't know how to deal with people like that either. It always strikes me as crazy when a company hires someone who is good at what they do, but then won't let them do it! You could be so GREAT for this guy - take all this IT stuff off his plate so he can deal with whatever his expertise is in, reduce his stress and worry, free up his time, make sure he's getting good IT solutions... that, I would think, would make his life so much easier... if he'd get out of the way.
*ugh people!!!*
And, I have no clue why companies are so ineffective. I think it's not the company, it's certain *people* within the company that do a bad job, but maybe have other redeeming factors (or friends in high places) that allow them to stay in jobs for too long, without realizing the consequences.
For example, with my boss... it IS crazy that there are people like me on the team who are not only bored, but also not engaged and having their skills just wither away. And nobody above him manages to see it... the reality is, he's good at some of the things he does, he is just a *TERRIBLE* manager. He doesn't like details. He doesn't like administrative stuff. He doesn't read emails that are longer than 3 sentences!!! He should NOT be managing a team - he's great working with clients, selling ideas, brainstorming, and even strategizing. He's just not good at actually managing multiple work streams, or god forbid, developing people under him (I could laugh at this, if it didn't make me cry).
But, he does what his boss wants, and his boss doesn't ask/care about how my boss' direct reports are feeling... that's not part of how he gets reviewed.
I really wish more companies would review managers by talking to their direct reports.
Anyway, sorry for all the ranting. It's just crazy to me too, and frustrating, and I have a sense that it's not really better anywhere else. Or that, more accurately, it's not company-dependent, it's manager-dependent, so you really need to find a good manager to work for, and stick with them!