Flexible Learning (FL) is a pedagogical approach allowing for flexibility of time, place, and audience, including but not solely focused on the use of technologies. We describe Flexible Learning as a pedagogical approach in four courses framed by three key themes: 1) objectives and aspects of course design, 2) evaluation and assessment, and 3) challenges and improvements. Examples of strategies include: digital media-based assignments; iClicker and on-line quizzes; a librarian-created tutorial and links to copyright-cleared readings; use of Calibrated Peer Review as formative feedback; TurnItIn for self-review; wiki sites, group blogs and community work through Community-based Action Research (CBAR) conducted through the pedagogy of Community-Based Experiential-Learning (CBEL). We believe that the transferability of our experiences and findings is most relevant to educators seeking to create learning experiences that increase student engagement with complexity and uncertainty. FL approaches can help educators create learning environments that more closely resemble the contexts that students find upon graduation.