Books like Deep Purpose

I've been fascinated by a simple question for most of my life: Why do so many of us feel something is missing, even when our lives appear successful from the outside? 

That question led me through recovery, broadcasting, entrepreneurship, spiritual study, financial collapse, heartbreak, and ultimately the writing of Unlearning Myself. The books on this list each helped me see, from a different angle, that what I was searching for wasn't somewhere else waiting for me. It was hidden beneath layers of fear, striving, performance, and identity. I return to these books because they continue helping me remember what was never actually missing.

I love stories about “pilgrimage.” I have always been an admirer of those characters who search, whether in fiction or nonfiction. I respect their steadfast endurance to undertake a calling, meet unforeseen obstacles, and overcome insurmountable circumstances, while never allowing the burning flame that drives them to extinguish. 

My own memoir, Drummer Girl, is the story of my pilgrimage. I have the distinct memory of traveling through a dark tunnel toward a clear light during surgery as a child. This experience of near death has since driven me to seek understanding, to look for words when there were none, and to find solace through life’s many turns.

My search for meaning didn't come when I hit midlife. Ever since I was a kid, I gravitated toward books and movies that offered lessons about living, which I'd try to incorporate into admittedly limited childhood opportunities. As I grew older and gained more agency, I was able to apply what I learned to more significant decisions, which often led me down a very different path than my peers. I suppose, in hindsight, this accounts for why my first three books were released by a publisher in the personal transformation space. I'm happy to share the 5 books that have helped me on my journey toward living a better life...so far.

Since 2014 I have studied, researched, and written about the concepts of meaning and purpose. In 2016, I published a book entitled The Purpose Effect dedicated solely to the topic. In Work-Life Bloom, two of the key work-life factors that make up the accompanying model focus on meaning and purpose. I am known for urging people to declare their purpose, writing it down, and sharing it far and wide. My declaration is as follows: “We’re not here to see through each other; we’re here to see each other through.”

I’ve spent much of my career working with leaders as technology reshapes how decisions are made, authority is exercised, and organizations evolve. What keeps me engaged with this topic is how quickly uncertainty has become the norm rather than the exception. AI and digital systems are no longer abstract forces; they shape everyday choices, incentives, and outcomes. I read these books because they help me think more clearly about leadership in that reality: how judgment, learning, and responsibility need to adapt when systems move faster than intuition. They’ve influenced how I approach real-world leadership challenges in complex, technology-driven environments.

I wasn’t really interested in the Olympics until they came knocking at my door. I lived in Vancouver during the 2010 Winter Olympics Bid. When a plebiscite was called, the Yes side plastered the city with billboards explaining why everyone should want the Olympics. Simultaneously, a much less resourced but vocal opposition argued that hosting would be an environmental, social, and economic disaster. The two sides were so far apart that my curiosity was piqued. When I began a postdoctoral fellowship in the UK, I realized that they, too, were in the midst of similar debates, as hosts of the 2012 Summer Olympics. From here a research project was born.

I have been a ghostwriter for over thirty years, publishing more than a hundred books under other people’s names, as well as those under my own name. It has allowed me to live a hundred different and varied lives and it is a profession I like to encourage all writers to consider. Several of my own novels have featured ghostwriters as central characters, including Secrets of the Italian Gardener and What Lies Around Us.

I have spent most of my adult life using entrepreneurial business practices and principles to redesign and transform nonprofits. From my very first nonprofit organizational acceleration, I was hooked. The wealth one receives from helping other people is so much richer and more satisfying than money–altruism is truly life's greatest pleasure. You know the movie The Sixth Sense where the little kid sees dead people everywhere? I am the same way, except everywhere I look, I see uncaptured opportunities for social impact. I live and breathe social impact strategy, governance, financing, evaluation, and change management. Because by fixing problems in those areas, organizations are able to do more to make the world a better place.  

I build and use emerging technological innovations in business, and I also teach others how they might too! I’m a serial entrepreneur and a Professor at the Wharton School of the University of Pennsylvania. As an entrepreneur, I co-founded and developed the core IP for Yodle Inc, a venture-backed firm that was acquired by Web.com. I’m now the founder of Jumpcut Media – a startup using data and Web3 technologies to democratize opportunities in Film and TV. In all this work, I'm often trying to assess how emerging technologies may affect business and society in the long run and how I can apply them to create new products and services.

I’ve always lived in a small city in Northern Ontario (Canada) that is surrounded by smaller towns and even smaller villages. I’m a first-generation Canadian who grew up without extended family any closer than Scotland. I’ve learned first-hand how wonderful found families can be. Once I started writing, I was drawn to happy endings and small-town settings where everyone knows your business but has your back too. I hope you enjoy these small-town recommendations as much as I do. Here’s to small towns, found families, and happy endings!