People’s success in achieving their goals can have profound consequences for their subjective and objective well-being. Hundreds of research studies identify factors associated with success in goal pursuit, but little is known about the occurrence and influence of these factors in daily life. This dissertation aims to complement and build on extant, mostly laboratory, research by characterizing ordinary goal pursuit and identifying factors that meaningfully affect it in the context of daily life. The first chapter offers background: a review of prior research, a discussion of potential limitations on the replicability and generalizability of prior research, and an argument for more robust, naturalistic, and descriptive work. The chapters that follow present prospective observational studies focused on pursuit of New Year’s resolutions and used to address eight research questions pertaining to the content and framing of goals people pursue, the outcomes of goal pursuit, and the potentially mutable factors associated with goal achievement. The second chapter presents Study 1, a descriptive study focused on understanding what goals people set as resolutions and the typical process and outcome of pursuit. The third chapter presents Study 2, a study focused on assessing the predictive value of goal-varying factors. Goals varied greatly in their content, properties, and outcomes. Contrary to theory, many resolutions were neither successful nor unsuccessful, but instead were still being pursued or were on hold at the end of the year. Across both studies, the three most common resolution outcomes at the end of the year were achievement (estimates ranged from 20% to 40%), continued pursuit (32% to 60%) and pursuit put on hold (15% to 21%). Other outcomes (e.g., deliberate disengagement) were rare (<1% to 3%). Motivation and habit formation were associated with subjective success consistently, over and above trait self-control, but no other goal-varying properties showed robust associations with goal outcomes. Predictive models suggest that relatively little variance in goal outcomes can be meaningfully predicted by goal-varying properties, and that linear regression models are particularly bad at predicting goal outcomes. This dissertation demonstrates the value of naturalistic, descriptive, and prediction-focused work for advancing understanding of self-regulation.