Empathic design strategies focus on engaging with the user on more intimate levels to ensure that appropriate and intuitive products are developed. Empathy needs developing and nurturing, and may not come easy to all designers. Taking students outside their comfort zone can be an uncomfortable, disconcerting, and unfamiliar experience. Current design students are less likely than any previous generation of designers to be designing for people just like themselves. With the increase in life expectancy, disability no longer being a barrier to quality of life and a shift towards personal responsible health maintenance, this current generation of designers is likely to be designing for older users with multiple disabilities. The authors took themselves outside their own comfort zones to experience visual impairment in order to appreciate how design students may respond when they experience a range of visual impairments. Three approaches to empathic modeling are explored; (i) unsupervised walking with cane; (ii) trained and supervised walking with a cane; and (iii) the students conducting empathic modeling. As we prepare our future designers for their careers, we need to equip them with appropriate skill sets, so that they can respond to the dynamic and evolving experiences of the user.