VR and AR hold enormous promises as paradigm-shifting ubiquitous technologies. The investment in these technologies by leading IT companies, as well as the buy-in and general excitement from outside investors, technologists, and content producers has never been more palpable. There are good reasons to be excited about the field. The real question will be if the technologies can add sufficient value to people’s lives to establish themselves as more than just niche products. My path in this presentation will lead from a personal estimation of what matters for adoption of new technologies to important innovations we have witnessed on the road to anywhere/anytime use of immersive technologies. In recent years, one track of research in my lab has been concerned with the simulation of possible future capabilities in AR. With the goal to conduct controlled user studies evaluating technologies that are just not possible yet (such as a truly wide-field-of-view augmented reality display), we turn to high-end VR to simulate, predict, and assess these possible futures. In the far future, when technological hurdles, such as real-time reconstruction of photorealistic environment models, are removed, VR and AR naturally converge. Until then, we have a very interesting playing field full of technological constraints to have fun with.