Seemingly impossible endeavors can give us our biggest successes and our most informative failures. Just as importantly, they can be the most energizing to work on. If we can find a way to break down our anxieties and anticipated criticisms, we can be truly bold and wildly successful even when an attempt at the impossible comes up short. This interactive workshop would offer a toolkit for analyzing (and dismantling) the potential points of resistance that keep us from doing amazing, unreasonable, unrealistic things. After briefly discussing the advantages of taking on seemingly impossible projects--it’s actually deceptively sensible!--this session would present an exercise designed to systematically examine barriers to action. The exercise has 7 questions/prompts: 1) Define (and imagine in detail) the worst-case scenario. What doubts and fears spring to mind? 2) Think about potential steps to prevent those “what-ifs.” 3) What could be done to repair the damage if those imagined bad things happen? Who could you call for help? 4) Imagine a partial success. What benefits could be realized by an attempt that comes up short? 5) What bad outcomes are somewhat likely (at least compared to the scariest, worst-case scenario)? What potential benefits might they carry? For example, what would be the value of the lessons learned from these somewhat likely, somewhat bad outcomes? 6) What are you losing or missing by postponing action? 7) For the (necessarily, intentionally) unrealistic goal you have in mind, what are the doable, measurable tasks that would move you toward success? (Based largely on Ferriss, 2017, “Fear-Setting: The Most Valuable Exercise I Do Every Month”) Answering these questions can help deflate fears and doubts that are unwarranted, but it can also provide a clearer view of legitimately problematic factors. Reduced fear and doubt is possible. A clearer picture is almost certain. This workshop session would include a discussion of how these questions helped propel a project completed by the workshop facilitator. Using this type of reflection and planning, the presenter designed and implemented library instruction that uses writing-for-Wikipedia activities to teach information literacy during a one-shot library session, an approach that had not previously been described in the literature. Workshop participants would be asked to complete the fear-dismantling exercise while reflecting on a potential project of their own. After reflecting individually on their own projects, participants would be given the opportunity to work in pairs or small groups to rapidly review each other’s drafts and provide feedback. Lastly, participants would be given the opportunity to offer criticisms and refinements to these questions, and to also offer their own approaches for tackling fears and doubts that impede bold action.