So the first question that came to my mind in designing the user interface was: what is the first thing people think about when they are sending the "Hey I'm leaving work." or "I'm almost there." text messages?  At first it seems you think about the person and then message. But that ignores the subtle consideration you make about the location where you decide to send the message.  I asked a lot of people around Madrona's offices and they all had a specific spot that triggered in their mind to send one of those messages.  It's like this: When I am leaving (action) the office (location) after work (time window)  I text my spouse (person) that I am on my way home (message).  So I decided that the setting of the geo-fence trigger naturally should follow that mental model. The settings flow would simply go action>location>time window>person>message.  We will fill in the text before the input to make it sound like a sentence that you are completing: When I <action> this place <location> between these times <time window> tell <person> this <message>.  It flows really nicely.

I posted the above image to Facebook and asked all of my friends to vote on the best icon. I received a lot of great feedback and after that am leaning toward 3rd one on the bottom. The general response has been that it stands out the most. I also like that the negative (white) space makes a trigger like shape, but I am not sure most people pick up on that (at least not consciously).  The wood one (top, 3rd from left) is probably the nicest looking one but is too busy on the actual phone to stand out.  

I was stuck; I looked at hundreds of different apps to see if anyone was doing anything innovative for list views and couldn't find much. Finally had a break through after looking at thousands of images of Dieter Rams work for Braun.  I was actually trying to figure out how the messaging page would look when I realized that it would be cool and perhaps helpful to see where each message a user received was triggered from.  That's when I got the idea that you could choose a message and the map would change based on that choice.  From there was all photoshop heaven. I'm excited to see how users respond to this new UI.  Will they naturally scroll on the round chooser?  Is it clear that the edit button edits the message with the purple line on it?  I'm stoked to find out!