This doctoral study is based on extended personal critical reflection (Freire, 1996; Mezirow, 1991; Brookfield, 1990) drawing on evocative autoethnography (Bochner & Ellis, 2016; Denzin, 2014; Fraser, 2018; McCormack et al, 2020; O’Neill, 2015) using a range of writing practices including journalling, stories and poems as well as collage (Formenti & West, 2018; Elbow, 1994; Dirkx, 2006). The purpose of the research is to consider carefully a fundamental aspect of human experience - loss - in diverse forms, such as grief and disappointment, and how this relates to personal meaning making and transformative adult education. Early in the course of my PhD, the death of my dad and sister within six months of each other plunged me into an experience of profound grief which opened a very challenging question, an existential question, of how we can we make sense of things, of our feelings and live with a sense of purpose in the face of profound loss? This disrupted a more habitual sense of who I am, where I belong and with whom I felt safe and loved, I discovered that the navigation of grief, what to do with this sense of loss and how to respond to it, was unpredictable (Butler, 2004; Wyatt, 2010; Kelly, 2003; Sands, 2010). Confronting and working through loss led me into a deep exploration of family experience, family literacy practices, my own values, choices and dispositions and inevitably this led me to reflect upon my working life. I am a passionate and experienced adult educator but with a particular interest in animating values, good practice, and the enabling conditions that foster transformative education (Mezirow, 1991, 2003; Dirkx, 2006; Finnegan, 2019a; Green, 2023; Illeris, 2003) as well as the politics of practice (Greene, 2000; Freire, 1996, 2004; Freire & Macedo, 1987; Fitzsimons & O’Neill, 2024). These familiar and longstanding concerns of my professional life appeared in a new light. Through writing into grief I realised there were other losses, breaks and disappointments in my professional life. I also began to understand how my abiding interest in social justice, autonomy, vitality, belonging and agency in adult education were rooted in personal and familial stories and histories. As such, this thesis troubles easy, tidy boundaries between the public and private and explores how grief and working through grief raises questions about family stories, structures of feeling and social power. Facing and reflecting on grief also brought questions about other forms of loss and disappointment especially in professional life and the conditions that engender a sense of disconnection from practice. It explores the dilemmas and disorientation of grief and loss as biographical and professional matters and as personal and political questions. It also asks how and in what way we can reconnect to values, hopes, loved ones and generative practices through working through loss. These experiences cannot be rendered in a traditional way as tidy and dry research questions but there are several questions that were particularly important to my inquiry that you will encounter in this thesis. They are:  How can I make sense of and work through the experience of grief and loss generatively, to encounter the entanglement of my relational self in the personal, professional, social and political, as a way of reconnecting with loved ones in life affirming ways and revitalise my commitment to being a critical adult educator?  How might this particular experience, allow me to better understand transformative learning processes for myself and others?  How might I open up the inchoate and fragmented nature of my day-to-day experience as an extended critical reflection, while also remaining sensitive to the uncertain, layered and provisional nature of transformational learning? The doing of the research raised a complex methodological question which I seek to answer here - what sort of reflective practices are sensitive and responsive enough to reconnect us with these powerful, even overwhelming, biographical experiences? This involved an experimentation with a range of writing and some arts-based practices that have been a fundamental part of the decades of work I have done in adult education classes. I took inspiration from the “writing as inquiry approach” (Richardson & St. Pierre, 2005, 2008; Cixous, 1997), auto/biographical research on transformative learning as holistic, embodied and psychosocial phenomenon (Bochner & Ellis, 2016; Fraser, 2018; Butterwick & Lawrence, 2023; Elbow, 1994; Dirkx, 2006; Green, 2012; Hoggan et al, 2017; Formenti & West, 2018; Mälkki, 2019) as well as Heron’s (1992) ways of knowing. This has allowed me to create imaginative critical dialogues with the evocative artefacts - journal extracts, poems and stories that offer insight into, and ways of critically reflecting on tangled, layered personal experience with its profoundly relational experiences. These various elements are synthesised into an approach to research that is informed by, and contributes to, adult education. It is perhaps best described as a critical and creative adult education methodology (West, 2016; Brookfield, 1995; Gannon, 2018) which seeks to document and understand embodied transformational shifts of being. The research locates our grief and sense of loss as human beings, as connected to our inability to live whole-heartedly in a culture where our lives are compartmentalised into the domestic, personal, social, professional and political, which separates our adult education practices from our personhood. From a position within the psychosocial world (West, 2016; Fraser, 2018; Steedman, 1986) I go beyond some of the more prevalent concerns within critical pedagogy. I examine how ideas from psychology and transformative learning theory might be relevant in helping us, not only to understand what personal oppression and fragmentation feels like in the private intimacy of our lives and relationship, but also how we might overcome some of these personal contradictions by connecting them with the social and political. Finally, my movement between the family, classroom and my community of adult educators where I feel recognised (West et al, 2013), has allowed me to remember more of myself, and critically examine who and what has shaped me and my relationship with myself, with others and with the world. It illuminates how the work of reclaiming my core values and sense of purpose as a critical adult educator is fundamentally a deeply relational process of trying to reclaim my selfhood (Formenti & West, 2018). I establish transformational learning as a reconfiguration of certain sets of assumptions which cluster around assumptions about the self and shame as oppressor and oppressed (Kaufmann, 1992; Freire, 1997) the dynamic interaction between my past as mediated by the present and shaping the future, as well as my reconnection with my epistemology and lived experience (Lorde, 2017; Cixous, 1997; West, 2016; Mc Cormack, 2013). These communities are explored as dialogical spaces where we feel we belong and our personal and professional dilemmas are rich learning resources (O’ Neill, 2015), which directly or indirectly make us finely attuned to the lives, dreams and struggles of our students, as we encounter our own, within empathetic and emotionally responsive dialogues. From reconfigured and new meanings I have a strong sense of being reconnected to those people and values that I deeply care about, and moving towards a more emotionally freer and reflexively agentic self (Finnegan, 2019a) with new possibilities of living in better alignment with who and what really matters to me.