This article gives us a little bit of hints how people some times act contradictory behavior. http://www.theatlanticcities.com/design/2013/08/people-are-less-likely-recycle-stuff-s-crumpled-cut-apart-or-deformed/6628/
In my community, government has granted special treatment to public junior/junior high schools in the city I live. Students learn in special class to bring up leaders of the next generation. Skills they learn are: Problem Solving, Self-Management, Innovation, Interaction, Information/Communication Technology and Community. How they learn is similar in some points to Small Failure, they define a Challenge, Research, Ideate and Transmit. However they only spend 115 hours in junior and 80 hours in junior high. Again, this is special treatment so most of the schools in Japan do not have such kind of program.
This is a great idea to spread to the world! In Japan, because of cultural reason, people tend to hold back their feeling, which is considered as virtue. If this idea comes out as a toolkit easy to adopt, it could be very strong tool for young people all over the world.
>HELP NEEDED: how might we develop the Smart Failure brand to communicate this idea to young people?
I think it would be difficult to teach every individuals so small number of skilled influencer could help to spread the idea. The trained influencers demo for some schools and they would provide training the trainer lessons to teachers so the teachers can teach Small Failure anytime.