As referenced in my article, 2021 HR Trends and Priorities: A Summarized View of Nine Sources, employee wellbeing (EWB) is a top priority for many organizations. And given that many workers postponed vacation plans in 2020 because of the pandemic, firms are encouraging their workers to use their Paid Time Off (PTO) in 2021 as one way to support EWB. Despite this effort, this article points to one obstacle to driving wellbeing through PTO: a disconnect between vacation policies and culture around using PTO. Said differently, when a firm’s culture does not reinforce time-off policy changes, it further prevents workers from taking time off. A 3-P framework provides a set of actions firms can take to enable workers to get the time off they need within the firm policy. 1) Permission – shift in cultural norms (e.g., being “busy” should not be a sign of pride) to empower workers to take time off. 2) Prioritization – leaders and managers reinforce that PTO is a priority by modeling behaviors (e.g., leaders don’t call into meetings when on PTO), 3) Persistence – maintaining a regular campaign around time off and following up on the actions. Other ideas are discussed, including the benefits and challenges of several time off-policies (e.g., four-day workweek).