Death and taxes may be unavoidable, but the confusion, conflict, and complexity they leave behind do not have to be. In this episode, Gary sits down with Joe Donahue, Attorney at Law with Donohue, O’Connell & Riley PLLC, to unpack the often-overlooked world of wills, trusts, taxes, and legacy planning. Joe shares how estate planning has changed over the past two decades, why simplicity is often the greatest gift you can leave your family, and how trusts, life insurance, jurisdiction, and tax laws can shape the legacy we leave behind. From common misconceptions like the dramatic “reading of the will” to the real delays families face when settling an estate, this conversation turns an uncomfortable topic into a practical reminder: planning ahead is not just about money, it is about clarity, confidence, and leaving less of a mess for the people you love.