In a system mired by frustrations, complexities, regulations, and shifting priorities, we have no shortage of obstacles to overcome. Leaders across the financial ecosystem are trying to understand and define what the future of finance holds. By tapping into Futures Thinking, a design strategy that prompts practitioners to reveal what could happen in the future due to decisions, actions, and issues occurring in the present, we can begin to unravel possible future horizons. At FXD, we challenged our leaders to imagine their own preferable futures of finance (plural because there is not one single future) by digging deep into the weight of history, push of the present, and pull of the future and the systems, barriers, and opportunities that each carries with it.