Everything is changing for web professionals: our websites are global, our audience is aging, and people with disabilities are accessing the web more every day. If that wasn't challenging enough, we wrestle with so many devices, screen resolutions, and environments, it's not surprising that we feel a bit lost. How will we design for all these different user needs? Exploring our assumptions about web accessibility and design as it relates to user experience, I will review common user mental models within the context of aging populations, disabilities, and non-Western cultures. I will present compelling research that illustrates vastly different user expectations based on age, culture, language, and disability, and how these factors impact the UX design patterns and solutions we create for mobile and desktop interactions on the modern web. Illustrating key concepts within Universal Design, I will provide compass points to help attendees embrace the uncertainties and create a more beautiful and usable design.