Raymond taught me everything there was to know about icon design. Little did I know that he, my humble mentor, was one of the best icon designers in the world. In other words, I sat next to one of the best iconographers, got to pick his brain until I could kick off my training wheels, all the while exchanging stories of our time growing up in South Florida including our trips to ‘Pollo Tropical’ in the search of amazing plantains. Lesson in humility, check.

My first emoji was the engagement ring, and I chose it because it had challenging textures like metal and a faceted gem, tricky to render for a beginner. The metal ring alone took me an entire day. Pretty soon, however, I could do two a day, then three, and so forth. Regardless of how fast I could crank one out, I constantly checked the details: the direction of the woodgrain, how freckles appeared on apples and eggplants, how leaf veins ran on a hibiscus, how leather was stitched on a football, the details were neverending. I tried really hard to capture all this in every pixel, zooming in and zooming out, because every detail mattered. And for three months I stared at hundreds of emoji on my screen. Somewhere in there we also had our first Steve Jobs review, which had created a shared experience of suspense and success when they were approved for launch. And if Steve said it was good to go, I’d say lesson in craftsmanship, check.

Sometimes our emoji turned out more comical than intended and some have a backstory. For example, Raymond reused his happy poop swirl as the top of the ice cream cone. Now that you know, bet you’ll never forget. No one else who discovered this little detail did either.

Another example is the order in which we drew them. We left the tough ones to last, so the dancer with the red dress emerged towards the end of my internship as it was the one that kept getting punted. You can thank her ruffled dress for that and Raymond for the final output. The woman’s turquoise dress with the brown waist band, on the other hand, was one I drew earlier in the process. It was inspired by the color palette and proportions of a dress that my sister had created in real life that same year.

So from funny backstories to realizing he and I attended high schools less than 30 miles apart, our shared past and days drawing together triggered unstoppable laughing spells with watery eyes and all, in other words, with tears of joy. Ten years after my internship, Raymond and I still fill a room with laughter and he continues to provide me with the most flat out honest feedback to keep me in check, and vice versa. All this is what I believe made the emoji successful, our friendship through design.

When I spotted the ever-changing rock found at Bernal Heights Park in San Francisco, both Raymond and I had to pay tribute to the magical pile of poo. Photo taken in 2016.

This year will mark the tenth anniversary of Apple’s original emoji launch. They were first released in Japan on November of 2008, shortly after my internship at Apple concluded. I had no idea that within a few months of completing such project, it would revolutionize our culture’s way of communicating or how the emoji would physically appear everywhere. And I mean everywhere: toys, apparel, stickers, candy, music videos, books, jewelry, landmarks, movies, and whatever else you’ve seen.

It should be noted that although Raymond and I, Angela Guzman, are the original Apple emoji designers responsible for the initial batch of close to 500 characters (and were awarded a US patent for them), there are of course additional Apple designers. Amongst them, Ollie Wagner created around a dozen of the original set after the conclusion of my internship, and many more the following year. The set now totals somewhere in the thousands — some are even animated!

Ten years ago Raymond and I worked on one of my favorite projects to date, one that led me to experience my own ikigai. This Japanese term is defined as the place where one’s passion, mission, vocation, and profession intersect; what some would say the reason to get up in the morning — literally me in 2008. I would eagerly wake up, and on the days I had to bike, I’d carry my bike down three long flights of stairs and head to work with a smile on my face. Now that’s magic!

Gift from Raymond upon the conclusion of my internship, his version of real life emoji. The orange, apple, and eggplant were part of a set that I had created.

On that note, I would suggest to any designer looking for their reason to get up in the morning to find their humble mentor, or be one, and get on the road to friendship. Because magic happens when design leads to friendship, and that friendship leads back to design. For every emoji made, I learned something new. For every emoji made, Raymond and I became better friends. The better friends we became, the better designer I became. In this case, friendship and design happened one emoji at a time. And that’s a story worth sharing.