This presentation will recount my own personal journey as someone who is tasked with library programming but is also susceptible to "doomerism" thought. But more so, it will focus on what there is to learn and gain from what I at first considered “failed” programs. This presentation will recount a few specific events, what I consider to be their shortcomings, but also important lessons I took away from them including ways to measure success beyond numbers, the importance of gathering data and how to use it, and how partnering with other departments and organizations expands our audience and lightens our workload. While it is easy to focus on what goes wrong, it is important to focus on our serendipitous successes.