This study examines the complexities of community planning and the significant role of human emotion in the process. Using a practice-based approach, the study explored an innovative codesign strategy as implemented in the Local Area Planning Program (LAP) of The City of Calgary to address these challenges. The LAPs embody a community-led approach to policy and growth planning in established areas, prioritizing emotional co-authorship and the integration of community-specific knowledge in planning. Using a series of semi-structured interviews, six distinguished practitioners provided their diverse perspectives and approaches, with the goal of generating new considerations, tools, and recommendations to integrate into my practice. Applying the LAPs as working models of community connection, this study employed a design science methodology to collect information, reflect, and obtain expert feedback on both practice and design. The aim was to curate a contemporary collection of practice-based tools, strategies, and insights that contribute to The Handbook for Community Connection, a practitioner's guide for fostering emotional connections between communities and the redevelopment process. The Handbook offers a range of practical tools that can fit into a variety of contexts, scales, and available resources, enabling a redefinition of planning processes. The study concludes that by prioritizing empathy and building relationships, redefining planning processes becomes more habitual in practice. Furthermore, continually reflecting on your practice is key to facilitating meaningful connections within community. Relying solely on policy to address societal issues yields limited results; the profession needs a more nuanced and holistic approach. Ultimately, with the study in mind, community planning can be an act of of caring, one that helps to build stronger, more connected, and loving communities.