Kyle Baxter:

Sometimes, obstacles we run into while designing something are because we have our eyes so close to the ground, the detail blinds us to a larger truth. It’s useful all of the time, but especially when you can’t seem to figure out a design issue, to consider the greater intent of what you’re designing. What is it meant to do for the user? What is it ultimately doing for them? Answering that question, and thinking through the design problem within that context, often will make the answer immediately obvious.

The best question to step back and ask when you get stuck is “what problem are we really trying to solve?” Too often, we get caught in the form (design) or technology that we forget what we’re really trying to solve.