Performance improvement is thought to occur through engagement in deliberate practice. Deliberate practice is predicted to be challenging, effortful, and not inherently enjoyable. Expert and intermediate level Gaelic football players executed two types of kicks during an acquisition phase and pre-, post-, and retention tests. During acquisition, participants self-selected how they practiced and rated the characteristics of deliberate practice for effort and enjoyment. The expert group predominantly practiced the skill they were weaker at and improved its performance across pre-, post- and retention tests. Participants in the expert group also rated their practice as more effortful and less enjoyable compared to those in the intermediate group. In contrast, participants in the intermediate group predominantly practiced the skill they were stronger at and improved their performance from pretest to posttest but not on the retention test. Findings provide support for deliberate practice theory and give some insight into how experts practice and improve their performance beyond its current level.