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The Secret to Finding Your Checkmate in Life's Purpose

Insights From Corporate Executive to Professor Greg Davis

By Matt Mueller

As leaders navigate the complexities of their professional journeys, the importance of finding clarity becomes paramount. In a conversation with the award-winning University of Illinois professor of accounting and seasoned finance executive, Greg Davis, we explore valuable insights from his book, Checkmate: Tips & Lessons to Help You Make the Right Moves to Achieve Happiness!, that can guide leaders towards a path of fulfillment and purpose. Davis, with his extensive experience in the corporate world and academia, offers a unique perspective that resonates with those seeking to balance personal and professional success.

The Intersection of Passion and Profession

Greg Davis, a retired University of Illinois professor with numerous certifications, began his journey with a keen interest in teaching. His accolades include a successful 23-year tenure at Hershey Entertainment & Resorts, a globally recognized entertainment company based in Hershey, PA. Davis attributes much of his success to a pivotal moment where his passion for teaching intersected with his corporate role.

“I thank Hershey for giving me the opportunity to teach within the company and acknowledging that I had that skillset,” Davis says. This intersection opened doors for Davis to create courses on financial literacy within the company, an initiative that empowered employees to understand how their roles contributed to the overall financial health of the organization.

From Corporate to Academia: Making the Leap

One of the significant shifts in Davis’s career was transitioning from a thriving corporate role to academia. When asked about the challenges associated with this transition, he shares candidly about the financial aspects. “Sometimes the money’s not there when you make that career change,” Davis says, acknowledging the common dilemma faced by leaders exploring new paths.

Davis emphasizes the importance of creating a budget, even for those in their 50s, to navigate a potential pay cut. His personal experience highlights the need for individuals to reassess their lifestyle and spending habits when embarking on a new career trajectory.

CHECKMATE: A Strategic Solution for Leaders

Introducing CHECKMATE, a strategic solution for leaders seeking clarity and direction in their journey. Inspired by Davis’s experiences and insights, CHECKMATE offers a structured approach to help leaders assess their professional and personal goals.

CHECKMATE encourages leaders to consider the intersection of their passions and professions, providing a framework for identifying key areas of alignment. It guides individuals through career transitions, offering practical advice on managing financial challenges and making informed decisions about their future. I challenge you to assess each point of CHECKMATE as your checklist to a happy career and life.

C – Career changes are hard work but worth the effort.

H – Happiness is only achieved when you find something you love.

E – Ensure you are spending quality time with your family.

C – Cancer and other medical issues are hard, but overcoming obstacles is part of life.

K – Knowing that age is just a number & new experiences lead to an enriched life.

M – Money is hard for many of us to discuss but Failing to Plan is Planning to Fail.

A – A job that has special meaning is worth the time it takes to obtain.

T – Take the time to find a good life partner.

E – Enjoy retirement as you work hard to purposely achieve it.

The Power of Money Dates: Planning for the Future

Davis introduces a unique concept called “money dates.” These monthly sessions, often accompanied by a nice dinner and wine, create a dedicated space for couples to discuss financial goals and assess their budget. While Davis humorously notes that his wife dislikes these dates, he underscores their importance in fostering open conversations about finances and life decisions.

The discussion expands beyond immediate financial concerns to retirement planning. Davis outlines a three-legged stool concept involving savings, pensions, and social security. He cautions against the common misconception that retirement will magically fall into place and stresses the need for proactive planning.

Mindfulness in Planning: The Key to Success

The conversation circles back to the importance of mindfulness in planning. Davis encourages individuals to set aside time for reflection, whether it’s a five-minute break or a more structured meditation session. “The mindfulness part is something you can’t say enough about. It’s not going to happen magically; you have to mindfully set time aside for that,” he says.


In conclusion, Davis’s insights, combined with the strategic guidance provided by CHECKMATE, offer leaders a comprehensive roadmap to navigate their leadership journeys successfully. Whether it’s finding the intersection of passion and profession, making career leaps, or planning for the future, CHECKMATE serves as a valuable tool for leaders seeking clarity and purpose.


As Greg Davis aptly puts it, “You have to think about where you want to be down the road, and for a lot of people, that’s 20, 30, 40 years down the road. It’s something you have to sit down and do constructively, and CHECKMATE can be your partner in this constructive journey.”

Innovator Matt Mueller

Matt Mueller

Thanks for reading! My goal is to provide an insightful, simplified, point of view on innovation, CX and insights to help you create positive change in everything you do. 

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