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This study focused on the interaction of demographics and well-being. Diener's subjective well-being (SWB) was successfully validated with Exploratory Graph Analysis and Confirmatory Factor Analysis to track well-being differences of the COVID-19 quarantined individuals. Six tree-based Machine Learning models were trained to classify top 25% SWB scorers during COVID-19 quarantine, after data-splitting (train 70%, test 30%). The model input variables were demographics, to avoid overlapping of inputs-outputs. A 10-fold cross-validation method (70%–30%) was then implemented in the training session to select the optimal Machine Learning model among the six tested. A CART classification was the optimal algorithm (Train-Accuracy = 0.77, Test-Accuracy = 0.75). A clean, three-node tree suggested that if someone spends time on perceived creative activities during the COVID-19 quarantine, under clearly described conditions, he/she had high probabilities to be a top subjective well-being scorer. The key importance of creative activities was subsequently cross-validated with three different model configurations: (1) a different tree-based model (Test-Accuracy =0.75); (2) a different operationalization of subjective well-being (Test-Accuracy =0.75) and (3) a different construct (depression; Test-Accuracy =0.73). This is an integrative approach to study individual differences in subjective well-being, bridging Exploratory Graph Analysis and Machine Learning in a single research cycle with multiples cross-validations. • To combine Machine Learning, Network Psychometrics & CFA is novel research approach. • Offers theory-driven evidence on SWB differences in early COVID-19 quarantine • Adds a newly invented Machine Learning research cycle • Eliminates self-report bias by using demographic inputs in Machine Learning models • Multiple cross-validations with different model configurations strengthen findings. [ABSTRACT FROM AUTHOR]