Innovative web work requires good ideas and risk-tolerance, but how do you create a culture in your institutions where a) innovative ideas happen frequently; and b) your institution is willing to take the risk and try it? In this presentation, I share my strategies (i.e. "Five Things You Should Do Even if They Make You Uncomfortable") for creating a culture of risk-taking, innovation and change at my institution in the hopes that others might be inspired and empowered to do the same. This was originally presentated at the ILEAD-U Cohort in Springfield, IL.