As we accelerate headlong into the 2020s, digital security grows ever more ubiquitous, sophisticated, and necessary. With an increased reliance on "The Internet of Things," a proliferation of hardware and software attacks on businesses and the ripple effect of GDPR are still a concern for those who do business in or with Europe we all face a challenging road ahead. With this in mind, we have compiled a checklist of concerns for the mindful CIO. This list will give you peace of mind in the aspects where you are doing well while also helping to expose areas for development.