When thinking about loss, we frequently consider it in terms of the losses that occur when others die. Yet, non-death losses feature throughout our lives. This arts-based research investigates how we adjust to, and accommodate loss experiences through imaginary dialogue with a dog, along with other creative approaches. As a guidance practitioner, I frequently meet people, whose lives have been altered through illness, disability or unemployment, requiring them to alter their assumptions about their self, others, and the world around them. While many of these losses are apparent, the significance of others are less easily recognised, and indeed, sometimes not acknowledged at all, both by individuals and wider society. There is pressure in a fast moving society to separate ourselves from our experiences and ‘just get on with things’ and those who fail to do so are often considered to be personally lacking. This research demonstrates that by providing safe ‘holding’ environments and opportunities to ‘re-story’ after loss experiences we can make sense of what has happened. However, the emotional impact of our experiences cannot be over-looked and managing internal conflict is essential for a healthier identity to take shape. I explore the emotional impact of loss by providing my own auto-ethnographic account, as well as the narrative of another person, in order to demonstrate how we make meaning. Different sorts of loss are looked at – non-finite loss, ambiguous loss and chronic sorrow – as well as disenfranchised grief and socio- cultural factors, to provide an understanding of how we respond to situations as we do. Narrative inquiry was selected as the most appropriate way to investigate experience with arts-based methods used to creatively explore the research question. I also provide a snap-shot account of my progress in writing this work to convey the emotional evoked in transitions. As loss is such a prevalent feature of our lives, this research offer knowledge not only to the guidance community, but to everyone.