The Power of Difficult Conversations

Recently, a conversation with my neighbor stuck with me and reminded me just how challenging it can be to have meaningful end-of-life (EOL) discussions with our loved ones. The story she shared about her family’s experience—especially the loss of her mother—felt like a wake-up call about how often we delay these uncomfortable conversations.

My neighbor, her brother, and her dad faced an unimaginable tragedy years ago when their mom passed away suddenly from a grand mal seizure. There was no time for a “goodbye.” No opportunity to say the things left unsaid, and no time for preparing for what comes next. The shock and grief of losing her so suddenly left deep scars on the family, and in many ways, it created a wall between them and the difficult topic of future planning.

Imagine being in their shoes: how could they possibly talk about their dad’s burial or any other end-of-life matters when they had never truly processed the loss of their mom? It was as though every conversation about what would come next would re-open the raw wounds from her sudden death.

I think most of us can understand that—how tough it is to bring up something as heavy as end-of-life planning, especially after losing someone in such a traumatic way. After all, these are the people who we love the most, and it feels almost impossible to talk about their passing without it seeming too real. It's easier to ignore it and hope that it won’t be a conversation we need to have anytime soon.

But then, something surprising happened.

In the midst of preparing for the inevitable loss of her dog, who has been by her side for 16 years, my neighbor’s dad finally shared something unexpected. As she was working through the painful process of preparing for her dog’s eventual passing, her father quietly said, “The pinstripe suit in the closet… that’s what I want to be buried in.”

This was the first time he had ever acknowledged that his time would eventually come. And for my neighbor, it was the first time he had shared anything tangible about his own end-of-life wishes.

This simple statement—so small, yet so meaningful—marked a huge shift. It was the first step toward opening the door for more conversation about his burial plans, his wishes for his final moments, and the future of his estate. Finally, he had offered a starting point.

It’s a breakthrough that many of us can relate to. Conversations about death, burial, and funeral plans are often avoided because they feel too overwhelming. But the moment someone finally speaks up and shares just a little bit of their desires—like that suit in the closet—it opens the door for much-needed planning and preparation.

It also reminded me that sometimes the most difficult conversations we can have are with the people we love the most. There is something inherently vulnerable about talking about the end of life. We want to protect the ones we love from pain and suffering, and discussing these matters can make it feel too real, too soon.

This is where I believe organizations like PHL can play a vital role. There is an immense need for resources that can guide families and individuals through these challenging conversations. By offering tools, support, and guidance for end-of-life planning, PHL can help make these talks feel more manageable, more open, and ultimately more meaningful. That is our goal.

I hope that PHL continues to grow and offers even more resources to help families navigate these difficult moments. I want that simple moment—like the mention of a pinstripe suit in the closet—to evolve into a full, purposeful conversation where all parties can feel peace, knowing that their wishes are understood and honored.

As PHL builds its roadmap for 2025-2030, I want to hear from you. What resources or support would help you or your loved ones with end-of-life planning? If there’s something specific that could make these difficult conversations easier to navigate, please drop us a note in the postbox below (we promise we won’t spam you!).

Together, let’s make it easier for families to honor one another's wishes and experience the peace that comes with planning ahead.