Purpose: Increasingly, leaders are faced with complex, difficult and demanding situations that challenge their very sense of self, including their workplace wellbeing. It has been suggested that this challenge can be mitigated for leaders by pursuing goals and activities that reflect their beliefs, interests and values. As such, leaders whose motivations reflect intrinsic and self-congruent beliefs and values are likely to experience beneficial wellbeing, yet, reviewing this from a self-determination theory (SDT) lens, the authors find this assertion remains to be fully tested. Concurrently, the work–family enrichment (WFE) literature highlights that potential positive synergies exist between work and home. The authors further argue that this synergy may also provide greater insight and understanding into the quality of leaders’ motivation and wellbeing, and as such also requires attention. As such, the purpose of this paper is to examine the path to wellbeing for leaders and includes leaders’ “whole lives” (including enrichment) and not just their work lives (motivations). Design/methodology/approach: Quantitative research including two studies of 386 junior/senior leaders and 205 CEOs, investigated the role of motivation as defined by SDT and WFE towards leaders’ job satisfaction. Hypotheses were tested using SEM in AMOS to assess the direct and meditational effects of the study variables. Findings: A partial mediation model was found to best fit the data for both studies. In study 1, the effects of self-determined motivation dimensions on job satisfaction were fully mediated by WFE and family–work enrichment (FWE). However, the non-self-determined dimensions of SDT motivations were directly and negatively related to job satisfaction and enrichment. In study 2, self-determined forms of motivation were positively related to WFE and FWE and job satisfaction, while only WFE was positively related to job satisfaction. The non-self-determined dimensions of SDT motivations were directly and negatively related to WFE and job satisfaction. Research limitations/implications: Overall, both studies show that the influence of motivations on job satisfaction of leaders is better understood through enrichment. As such organisations are encouraged to enhance both leader’s motivations, and enrichment, in order to facilitate a path to job satisfaction. Originality/value: This paper is the first to test over two studies and levels of leadership, motivation and enrichment for leaders. As such this paper provides a novel “path” to wellbeing that includes aspects of the leaders’ motivation, as well as the importance of leaders’ enrichment and home domain. Overall the authors suggest that leaders’ “whole” lives play a role in their job satisfaction, and this is important to understand as the authors try to resource leaders, who work in an increasingly demanding workplace environment.