Executor Guidance with Heart: A Conversation with Shelley Essery

Linda Mackie
Aug 17
3 min read

Some topics we naturally lean into—family, work, travel. Others, we avoid. For many, end-of-life planning and the role of an executor fall into that second category. But today’s guest, Shelley Essery, is showing us it doesn’t have to.

Shelley is a multi-passionate entrepreneur, educator, workshop facilitator, and founder of The Empowered Estate alongside her partner, Carla Kerr. Based on Vancouver Island, together, they help families have the conversations most people would rather put off—about death, legacy, and what we leave behind. And they do it with compassion, clarity, and a surprising amount of warmth.

I’ve known Shelley for years, both as a friend and a client. She’s the author of The Empowered Executor, The Executor’s Survival Guide, and Life Revived: The Business of Living. Through workshops, community talks, and one-on-one sessions, she’s creating a movement around proactive, values-based planning—with one goal at its core: keeping families connected, even through life’s hardest transitions.

Shelley Essery sits down with Linda Mackie about Estate Planning and more.

Why Shelley Started This Work in Estates & Executor Guidance

Shelley’s background is in legal administration. She’s seen, up close, the confusion and heartbreak that can follow a death when families haven’t planned ahead.

“I’ve seen so many families fall apart at this time,” she told me. “It’s usually because of the lack of communication.”

That lack of communication can turn grief into conflict. Shelley’s mission is to change that—helping people take small, doable steps to ease the burden on the loved ones they leave behind. And she knows it works because she’s seen it in her own life. When my dad passed away, his planning binder made all the difference for my brother and me. Everything we needed was there, right down to the smallest details.

The Binder—and How It Supports the Executor

Shelley and Carla’s binder is more than a checklist. Yes, it covers the practicals—financial accounts, legal documents, property details—but it also includes a legacy section, a place for personal stories and messages that keep a loved one’s memory alive.

The transformation for clients is real. Shelley shared one story about a woman who came to their workshop unsure where to start. She kept showing up to their monthly “Accountability Parties” (yes, they really call them that) and, step by step, finished her binder. “The elation and the excitement in her… she was just glowing,” Shelley said.

Another favourite moment? Working with a family where the mother wanted to talk about her plans, but her kids resisted. Shelley and Carla brought everyone together, gently guiding the conversation until it became less about death and more about values, traditions, and love.

Accountability Parties and Executor Support

These monthly check-ins are Shelley’s favourite part of the work. Anyone who’s attended a workshop with a binder can join for free. They’re a mix of Q&A, deeper dives on specific topics, and shared celebration when someone hits a milestone.

Right now, they’re online, with clients joining from multiple provinces, but Shelley’s hoping to host them in person soon. “We called it a party for a reason,” she said with a smile. “We like to have a little fun.”

The Executor’s Survival Guide by Shelley Essery

Shelley’s most recent book grew from her years in the legal world. While it’s written for executors, it’s also a must-read for willmakers and family members. It covers duties, responsibilities, and insider tips that can save time, stress, and conflict.

She also weaves in the human side—reminding executors to care for themselves, take breaks, and have a support plan. “It’s a very paperwork-heavy role, but it’s also very emotional,” she said. “You’re managing your own grief while navigating family dynamics and government processes.”

Shelley Essery’s Vision for the Future

When I asked Shelley about her five-year dream, her answer was immediate: take this work across Canada. Larger events. More families. More conversations that bring people closer, not farther apart.

Part of that vision is The Empowered Family, a natural offshoot of The Empowered Estate, focused solely on helping families open the door to values-based conversations. “Once we start with traditions and stories, it makes room for the bigger talks,” she said.

Why Executor Planning Matters

Every time I talk to Shelley, I can see how much this lights her up. She’s proof that making a difference doesn’t have to be loud—it can be steady, intentional, and deeply human.

If you’ve been putting off planning for the inevitable, maybe this is your nudge to start. As Shelley says, “Somebody needs what you’re already offering. Start there.”

📚 Learn more:

Visit www.theempoweredestate.ca for workshops and resources.
Find The Executor’s Survival Guide on Amazon, Chapters Indigo, or directly from Shelley.
Follow Shelley on social media for tips and upcoming events.