AbstractA fundamental problem in ecology is understanding how to scale discoveries: from patterns we observe in the lab or the plot to the field or the region or bridging between short term observations to long term trends. At the core of these issues is the concept of trajectory—that is, when can we have reasonable assurance that we know where a system is going? In this paper, we describe a non-random resampling method to directly address the temporal aspects of scaling ecological observations by leveraging existing data. Findings from long-term research sites have been hugely influential in ecology because of their unprecedented longitudinal perspective, yet short-term studies more consistent with typical grant cycles and graduate programs are still the norm.We directly address bridging the gap between the short-term and the long-term by developing an automated, systematic resampling approach: in short, we repeatedly ‘sample’ moving windows of data from existing long-term time series, and analyze these sampled data as if they represented the entire dataset. We then compile typical statistics used to describe the relationship in the sampled data, through repeated samplings, and then use these derived data to gain insights to the questions: 1) how often are the trends observed in short-term data misleading, and 2) can we use characteristics of these trends to predict our likelihood of being misled? We develop a systematic resampling approach, the ‘bad-breakup’ algorithm, and illustrate its utility with a case study of firefly observations produced at the Kellogg Biological Station Long-Term Ecological Research Site (KBS LTER). Through a variety of visualizations, summary statistics, and downstream analyses, we provide a standardized approach to evaluating the trajectory of a system, the amount of observation required to find a meaningful trajectory in similar systems, and a means of evaluating our confidence in our conclusions.