Here's the thing: starting from the outside of your lips in, the way you're "supposed" to, actually doesn't work if you're trying to get even, daylong wear. It's one of those pieces of advice that's a lot better backstage than it is on the street. Instead, start from the very center of your lips and brush the color outward.
Don't even worry about getting all the way to the edges. Just rub your lips together well when you're finished, and the color will distribute itself. Since your lips are darker in the middle anyway, this also looks more natural, and since the center is also the part of your mouth that gets used most, you're better off having the majority of your product there. Unconventional, sure, but beauty rules were made to be broken.