People tend to think of planning as laying out a (singular) path ahead. Odyssey planning gets us out of this mode of thinking, leading us to consider several paths forward. We work with clients to scope out three radically different futures — including one that might seem totally infeasible in the moment. An international financial institution came to us wondering what the future of learning would look like. The pandemic and its disruption transformed how things work, and they wanted to define this ‘new normal’ and explore how to best shape the learning and development department based on a range of possible outcomes. We started by doing some research and used the trends we saw as a springboard. Then we coupled them with odyssey planning to envision three possible directions. By opening the landscape of possibilities and helping the team see new opportunities, they were able to stretch their thinking. The process forces participants to think deeply and critically about key alternatives, propelled by these wildly divergent paths. The contrast between these possibilities forces important conversations and tradeoffs, and engages healthy creative tension.