Some software should be like a powertool, not a butler. It really depends on who you're developing for, I guess, but I can think of lots of software (e.g. Linux CLI tools, IDEs, CAD, etc) that should not treat the user like a pampered idiot.

Link to interesting article that was posted in the comments: http://articles.techrepublic.com.com/5100-10878_11-1045782.h...

I try to take this approach as well. The minute you start thinking of "minor inconveniences" for the user, you already don't care about them. Your tip will be small.

Making your app suck less is easy: go watch real users

This analogy has been explored in "The Inmates Are Running the Asylum" book by Alan Cooper. It's a good book, despite some deserved criticism ( http://sheddingbikes.com/posts/1285436217.html ) it raised.

This makes me think of personal assistants. Has anyone tried Timothy Ferris' "life outsourcing" with a virtual personal assistant? Is it all it's cracked up to be?

I've always looked at what I do as building helper robots for people to make their work life suck a little less.