Siena is a licensed occupational therapist with care experience from infancy to end of life. She has worked in acute, outpatient, skilled nursing, and step-down settings. Over the past 6 years, prompted by a combination of curiosity, burnout, and inspiration, Siena has been navigating an ongoing career evolution from direct patient care provision to the world of digital healthcare technology development. As a clinical content manager with Rally Healthcare and Optum digital services, Siena is currently participating in the multifaceted development of a provider-led digital therapeutics platform. Forging a non-traditional path has not always been a straight line for the New York transplant to the San Francisco bay area. She is excited, to share her honest reflections on the confusion, self-doubt, and excitement that have cropped up along the way with other caregivers looking to make a transition.