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Tourism and hospitality employment have long faced widely recognised challenges with regard to employment, its workforce and the workplace environment, issues that have been addressed by generations of policymakers and practitioners without evident success or solution. These wicked problems are frequently characterised by inherent paradoxes and, therefore, accepting the tenets of paradox theory provides the basis for recognising the need to accept contradictions as a reality which a search for solutions will not resolve. This chapter presents six examples of wicked problems in tourism and hospitality employment, which are underpinned by paradoxes as proxies for the much wider range of intractable problems that beset policy-making and practice in this vital area of tourism and hospitality. The chapter concludes by suggesting ways in which wicked problems can be accommodated, and stakeholders can learn to understand and live with paradoxes.