The characteristics of optimal developmental experiences are examined in a group of international Sea Kayaking Guides. This paper considers how these experiences contributed to the development of decision-making. A mixed approach was utilised that included a survey followed by a series of semi-structured interviews that are thematically analysed. An optimal developmental experience is identified as one with authenticity, diversity, transferability, and reflective value. The Guides developed their judgment and decision-making processes as an aspect of their 'seamanship' via experiences they described as 'epics'. The paper concludes that training for Guides must involve individualised, optimal developmental experiences.