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A Thanksgiving Tradition: Sharing Pumpkin Pies with My Clients

Every November, as the air turns a little cooler, and the holidays begin to sparkle on the island, I start one of my favorite traditions: delivering pumpkin pies to my clients. It’s a simple gesture, but one that has grown to mean a lot more over the years. I love supporting a favorite local restaurant, Zippy's, and placing my pie order of 100 pumpkin pies for the week of Thanksigiving. I deliver the pies throughout the week leading up to the holiday, rain or shine. Normally I load up and bring either my assistant or my husband, Alan, with me. It's a great way to spread holiday cheer, and I've never missed a year since I started (not even during Covid)!

When I started in real estate, I quickly realized that buying or selling a home is more than a transaction: it’s a milestone, a memory, a big life moment. Over the years, I’ve had the privilege of helping clients achieve everything from first-time home purchases to investment properties to downsizing after decades in a family home. Each client has a story, and every story matters.

The pumpkin pie tradition began as a way to say thank you. Thank you for trusting me with your home, for allowing me to be part of such an important chapter in your life, and for welcoming me into your community. What started as a handful of pies delivered to a few clients (10 in my first year) has blossomed into a tradition I look forward to every year. Now, I drive all over the island delivering pies. I choose a neighborhood and send a friendly text - "Are you home? Pumpkin pie delivery!". I don't always make it to every past clients' house, but that's part of the fun - seeing who's home for a quick drop off, a smile, and a hug for the holiday.

I love visiting my clients’ homes, seeing how their spaces have changed, meeting new additions to the family, or hearing how their life has evolved since we first worked together. Each pie I deliver is more than a dessert. It’s a small token of gratitude, a chance to reconnect, and a reminder that the relationships we build in real estate last far beyond closing day. It warms my heart to see how my clients' lives have changed in the time I've known them, and how they're enjoying their home.

Over the years, I’ve seen families laugh together as they receive their pies, friends gather around the table, and children excited to help “sample” a slice. Those moments make every early morning, every late night, and every delivery worth it. My clients often tell me it’s one of their favorite parts of the holiday season, and I can’t tell you how much joy that brings me.

Real estate is my passion, but client appreciation is at the heart of what I do. Every pumpkin pie I deliver is a small way to say thank you: to honor the trust my clients place in me, to celebrate their milestones, and to remind them that I’m always here, not just as a realtor, but as someone who cares about their journey.

As Thanksgiving approaches each year, I’m reminded that success isn’t just about the deals we close, it’s about the relationships we nurture, the memories we help create, and the gratitude we share. And for me, delivering pumpkin pies has become one of the sweetest ways to do just that.

Work With Diane

Specializing in mid-century, modern Hawaii homes, her desire to broaden the scope of the service has been successfully achieved as a 5-time award winner of the Top 100 agents in Hawaii by Hawaii Business Magazine.