Over the past decade I’ve completed a handful of bucket-list-type challenges that I really enjoyed. This post is about the characteristics of those challenges that I believe made them so engaging. I hope that by documenting them I can continue to find great challenges for myself in the future, and hopefully you can benefit from my experience as well. Across a wide range of challenges, I’ve found that I have the most fun when they hit on most of these attributes: A binary goal that can clearly be marked completed or not Some amount of risk that I will fail, endure physical harm or need to be rescued Unknown unknowns, things I don’t yet know I don’t know about A new location to get to know The need to learn some new skills in order to complete it The need to train and get in some sort of peak shape