Book Review: Day One by Drew Dudley

I first met Drew Dudley in 2011 at a TEDx event in Toronto, where we were both speakers. I was drawn to his story telling, and his conception of leadership, and this book does not disappoint. It shows that his understanding of leadership has been consistent over the years, and has allowed him to really deepen his mission, to make all of us recognize the leadership skills within.  There is also an incredibly personal message about committing to Day One each and every day.

Also, this past month, myself, Tracy Faucher – Deputy Head at Holy Trinity School in Aurora, and Graham Vogt, Deputy Head at Saint Margaret’s on Vancouver Island, wrapped up the inaugural year of the CIS Ontario Leadership Lab. While Cohort 21 Design Stream has been around for 13 years, this was the Leadership Lab’s inaugural year. Our vision of the Leadership Lab, and Drew’s book Day One  is highly resonant – and so for all of those who were in this first Cohort, this is a strong recommendation.

Drew’s book is a compelling exploration of purposeful leadership that resonates deeply with the mission of the CIS Ontario Leadership Lab. Dudley argues that genuine leadership is accessible to everyone and emerges clearly when we identify and embrace our unique leadership purpose – a call to action that would be familiar to Leadership Lab participants as their Leadership Purpose Statement. For educators and early-stage leaders, particularly those involved in shaping young people’s leadership journeys, this book is a vital resource.

You’d be interested in this book, One Day,  if:

1. You believe deeply in the transformative power of purposeful leadership. Dudley emphasizes that leadership isn’t defined by achieving traditional markers of success but by daily actions aligned with a clear, articulated purpose. This directly connects to the foundational ethos of the CIS Ontario Leadership Lab, which supports leaders in discovering and expressing their personal and professional purpose. Dudley’s approach complements the Lab’s mission, advocating for leadership that is intentional, authentic, and consistently visible through one’s actions and interactions.
2. You’re committed to broadening the perception of leadership beyond conventional standards. Society often underestimates leadership potential, focusing exclusively on high-profile success stories—typically male and traditionally recognized. Dudley challenges this narrative, emphasizing the countless unnoticed acts of leadership occurring daily. He argues, convincingly, that every individual possesses untapped leadership capabilities. This message aligns powerfully with the Leadership Lab’s dedication to recognizing and nurturing leadership in all forms, irrespective of role or status.
3. You’re passionate about advancing female leadership and addressing systemic inequities. As Dudley starkly highlights, women remain significantly underrepresented in leadership roles across sectors, confronting persistent societal biases and structural barriers. His book provides sobering statistics underscoring these disparities and offers a compelling call to action. For educators and leaders, like me, at girls’ schools, Dudley’s insights reinforce the critical importance of empowering young women, helping them recognize their inherent leadership potential and equipping them to challenge prevailing inequities.
4. You resonate with the profound simplicity of impactful leadership moments. Dudley’s widely celebrated TEDx talk, “The Lollipop Moment,” underscores the profound impact of small, intentional acts of leadership. This aligns beautifully with the CIS Ontario Leadership Lab’s commitment to cultivating everyday leadership moments that shape organizational cultures positively. Dudley urges readers to acknowledge and celebrate these seemingly minor acts, which collectively transform communities and organizations.

Ultimately, Day One is more than a leadership book—it’s a call to redefine leadership with inclusivity, intentionality, and purpose at its core. Dudley’s engaging narrative, practical insights, and passionate advocacy for diverse leadership make this a must-read, especially for educators shaping the next generation of women leaders. The CIS Ontario Leadership Lab community will find this book not only affirming but inspiring, reinforcing the Lab’s foundational belief: leadership begins with clarity of purpose and is cultivated through everyday actions.