The only part that bugs me is: what kind of leader does something like this and then writes about it to brag?
I think Joel's actions, by themselves demonstrate humility and the quality of being down to earth. But the article...I think it would it would have come off a lot better if someone else wrote it about Joel.
Speaking as one of the developers who watched Joel put up the blinds, I know that this one shared instance of "servant leadership" falls in line with plenty of others that go unmentioned.
Just off the top of my head, I remember one Fog Creek get-together when one of my guests (Joel barely knew her) mentioned to me that she was thirsty, and before I could do anything about it Joel rushed off to get her a glass of water. While not a huge deal, fetching water for his developers' guests is not something that Joel really has to do.
...and even if I were to assume the basest of motives (that Joel wants to keep his developers working at Fog Creek so they make him lots of money), it's still a compliment as a developer and the type of attitude that makes me enjoy working hard.
I don't think he's claiming to be a humble person, just humble about his role within his own company. It's not necessarily a contradiction for him to claim that he's really good at being a humble boss.
If you truly believe you're awesome, I'm not sure it's beneficial to sit around and wait for someone else to recognize it. People won't ask you to contribute to the conversation; they'll assume that if you have anything to say, you'll speak up.
I'm not sure Joel wrote about this to brag; at the very least, he wrote about this because it made for an interesting / relevant entry for his monthly Inc.com article.
I agree that it might come off a bit as preening, but to be fair Joel's column hasn't stayed away from mistakes and bad decisions he's made as well. As such I take the tone as being closer to "this is what I've done and why I've done it" than "look at this awesome thing I did".
I think Joel's actions, by themselves demonstrate humility and the quality of being down to earth. But the article...I think it would it would have come off a lot better if someone else wrote it about Joel.