Only a few things are certain in life: death, taxes, and the fact most software projects will go over-budget, underperform, or worse-yet fail altogether. With decades of books, conferences, and materials written on the subject, we continue repeating the same fundamental mistakes that lead to these failures — and we still end-up with massive cost overruns or worse still: complete write-offs with nothing to show. Come take a journey back in time to 1990’s Springfield to get some insights on avoiding these costly mistakes, and to help shed light on why failures like healthgov.org or canada.ca continue happening. We’ll look on how to pragmatically deal with our obsession with shiny objects, our wishful thinking tendencies, our self-interest with Resume-Driven Design, and a slew of other and often non-technical anti-patterns —in order to help mitigate them, and make a more efficient Springfield.