Previous research demonstrates that thinking counterfactually about life experiences facilitates meaning making about those events. Two studies extend this work into the well-being domain by examining the effects of writing factually or counterfactually about one’s birth on well-being. In Study 1 participants (N = 252) were randomly assigned to write factually or counterfactually about their births or the election of Barack Obama and then completed measures of meaning in life and life satisfaction. Writing counterfactually about one’s birth led to higher evaluations of life relative to all other groups. In Study 2 (N = 98) participants wrote factually or counterfactually about their births and again completed well-being measures. Fate attributions probability estimates and feelings of luck were explored as potential mediators. The effect on well-being from Study 1 replicated but was not driven by any of the measured variables. Implications for existential psychology and well-being research are discussed.