What if the most important plan you will ever make is the one you keep putting off?

In this first episode of Are You Ready?, host Neil Cockburn,Director of Family Enterprise Advisory Services at Kingston Ross Pasnak, explores one of the most overlooked but critical areas of readiness planning: wills, estate planning, and end-of-life preparation. Drawing on decades of experience advising business owners and families, Neil introduces two guiding principles that shape effective planning. Be proactive and begin with the end in mind. These ideas set the foundation for thoughtful decisions that can significantly impact the people you care about most.

Neil is joined by Greg Barnsdale, a Certified Financial Planner and licensed funeral director, who brings a rare and powerful perspective to the conversation. Greg shares why so many Canadians delay estate planning, despite the reality that more than half do not have an up-to-date will. He also reflects on his own experience with a life-altering brain tumour diagnosis,which deepened his belief in the importance of preparing early. Together, they discuss the emotional challenges of these conversations, the need for professional guidance, and the role communication plays in ensuring a plan actually works when it is needed.

This episode is a reminder that readiness is not about fear. It is about clarity, preparation, and care for those you leave behind. When planning is done well, it reduces stress, supports better outcomes, and allows families the space to focus on what matters most during difficult times.

About Neil Cockburn

Neil Cockburn is a Chartered Professional Accountant (CPA),Trust and Estate Practitioner (TEP) and Family Enterprise Advisor (FEA). He serves as Director of Family Enterprise Advisory Services at Kingston Ross Pasnak LLP. With decades of experience advising business owners and family enterprises, Neil focuses on succession planning, estate strategy, and helping clients navigate complex transitions with confidence. His work centers on one key question: Are you ready for what comes next?