People frequently encounter situations when they must choose between two pathways. Pathways in this context are a route, or series of decisions, that represent the things individuals’ value in pursuit of their happiness. As a result, the trade-off decisions an individual makes and believes to be worthwhile should, therefore, reflect the personal importance of that pathway. Those trade-offs might also be judged worthy by observers depending on the relative importance of the chosen versus unchosen pathway to the observer in question. The studies included in this paper examine the relationship between several distinct pathways to happiness (Security, Outlook, Autonomy, Relationships, Skilled and Meaningful Activity, and Contact with Nature) and their relative value to individuals (Haybron, 2013). I am interested in understanding individual differences in how these pathways are valued relative to one another. The first Study develops the Pathways to Happiness measure, while the second and third studies examine its validity. Results from the first study confirmed 5 out of 6 of Haybron’s Pathways to Happiness. These factors were utilized in the subsequent studies outlined in this paper. Results from Studies 2 and 3 confirmed the discriminant validity of the measure developed in Study 1 for all subscales; and the convergent validity for most subscales (the Autonomy subscale did not converge enough with other similar measures). A future study is introduced in the discussion section that proposes an examination of the relative valuation of pathways as measured by this scale and whether those scores predict how an individual perceives choices between two pathways