It is relatively easy to take good care of oneself in times when things are going well. But what about managing your wellbeing in challenging moments? The author of this chapter is a Zen monk and serial social entrepreneur. As one of the co-leads of The Wellbeing Project, an initiative that aims at catalyzing a culture of inner wellbeing for changemakers, he has been investigating the relevance of inner work for personal wellbeing in the light of his rich experience. In this chapter he tackles the potential threats behind the motivation to become a social entrepreneur, outlines why the emergence of The Wellbeing Project has been relevant for the changemaker sector, and shares a personal story of stress, anxiety, and despair to illustrate how Zen practice qualifies to overcome even the most challenging moments in our lives.