This career reflection illustrates that pathways to the field of psychology and, later, to an academic career are not always linear. Wise and supportive mentors play important roles at critical junctions. Luck has a hand, too, in both successes and setbacks encountered along the way. Acknowledging the role of luck suggests that professional successes should be regarded with a measure of modesty and professional failures weathered with a measure of self-acceptance. Making peace with one’s limitations (e.g., not being a dazzling public speaker) can also come from recognizing that psychology is a huge field that has relevance to a multitude of societal problems – many ways exist to make a contribution. Unexpected roles, from forays into administrative work to caring for an elderly parent, can create significant challenges but can also spur growth and deeper connections to others. Allies and sources of inspiration can be found to help to guide each of our unique journeys.