An auto-ethnographic perspective on using technology-based devices to boost motivation when lettering by hand. To learn or to improve skills surrounding cursive handwriting, one needs to practice the letterforms. To produce these letterforms we need to build muscle memory, and the best way to do this is using repetition. The standard method of repetition is to repeat the same letterform over and over again—for example repeating a page of A’s and B’s and so on. This method of learning, although useful, has the potential to lose the interest of the learner. By using multiple sensory activities and project-based learning, one can be motivated to complete, the otherwise mundane act of repetition. Practice and repetition are necessary if one is seeking to improve skills when writing by hand. There are many areas, both digital and non-digital, that can be explored to improve the process of handwriting practice. No matter what the activity, if the focus is on learning the movement and the strokes of the letterforms, we can start to play and experiment with a range of different techniques. Emerging technologies using creative apps in virtual reality are an exciting development. There is something engaging about writing with ink- filled nibs across paper fibres, then switching over to virtual reality and writing the same letters on a much larger scale.