I have a friend who has created a unique way to develop leaders.He brings groups of eight to twelve persons from diverse careers to work on a challenge. He has found that the key to ongoing success is for the group to achieve some almost immediate success. It is not vital that the result be earth shattering ,but it builds success and the ability to think wider and take risks. The same holds true for your bucket list. Rarely does anyone bolt totally out of their comfort zone but small steps that work build confidence and fortify the courage to continue.