So I know Something that is True and Important (STI). Those who were born to Software know it in their bones, but they don't know to speak it. Only we between worlds can tell these terrible secrets.
Gather close dear reader; I would have done well to understand this some years ago.
The STI is that that the Software World is kin to the Badlands of South Dakota.
When you Walk in Software you walk among mazes and valleys and cliffs. Promising paths end in sharp drops and hard walls.
Developers build things that seem right, until you walk off the end of the metaphor. The problem is more than bugs and complexity, it is something innate to imagination made digital.
In the physical world, we don't use spend months using a drill, then discover that everything we've build with it must be abandoned. In the world of Software tools, that can happen. We can use software to store knowledge and meaning, then lose all the knowledge when the software stops working without replacement.
In the physical world it may be impossible to find a good toaster, but it's easy to figure out that a new toaster is no good. In the Software world you can invest months in learning a new tool before you find the fatal flaw. Five years ago I though Apple would enable merging of iPhoto Libraries (sorry, six years ago), but their marketing team decided that was an Aperture feature, not an iPhoto feature. 
In the physical world, it doesn't take five years to realize that your car isn't very good.
Perhaps, to a creature of Software, the physical world would seem tricksy. For a creature that's evolved to dirt and blood, however, the Software World is more treacherous -- even if it doesn't rip limbs off as well as a chainsaw might.
In the world of Software, explorers pay a high price. We Pioneers need to be far more careful about what tools and solutions we use, and we need find new ways to navigate this space.
We must train Scouts and Pioneers who will return from the badlands to warn all of the horrors of Sharepoint and Microsoft Word ...
 Yes, I know about the heroic 3rd party merge efforts of iPhoto Library Manager.