I started with many (many, many) sketches to get a feel for where I wanted the balloon and family on the page, then opened Illustrator and literally scribbled some gestures of characters and poses.
Once the portraits and poses were done I experimented with some backgrounds. This family is from NYC and wanted to have that represented somehow, but I also gave them a simpler background that would allow the family to pop off the page. This all happened over the course of a few weeks so I sent screen shots for approval along the way. I edited haircolor, added personal details, and experimented with some different treatments of the background. This is going to be an anniversary gift, so it needs to be special, personal, and accurate.
Spoiler: To acknowledge the passing of ten years I added just a few elements in groups of ten. I also added roses from her bridal bouquet into the balloon piece of the image but they are too small to see on here.



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