What Matters to Randy Gregory II

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Debbie Millman has an ongoing project at PRINT titled “What Matters.” This is an effort to understand the interior life of artists, designers, and creative thinkers. This facet of the project is a request of each invited respondent to answer ten identical questions and submit a nonprofessional photograph.

Randy Gregory II is a problem solver in Austin, TX, where he’s worked for IBM, PayPal, and soon, Meta. He likes to paint, cook, and force his friends to watch low-budget films.

What is the thing you like doing most in the world?

This is difficult to answer, as I am a bit of a hobbyist, and I do lots of things that bring me joy. Rather, if I focus on a particular moment, it’s the first time I come to a new city, and I experience a wave of anxiety and excitement, and despite how tired I might be, I need to get out there. Every time I visit New York City, I have this moment where I close my eyes and let the sounds of the city overwhelm me. It’s a very personal and exhilarating moment.

What is the first memory you have of being creative?

When I was a child, I would take old issues of GamePro Magazine, Nintendo Power, and Electronic Gaming Monthly and trace the various characters and logos into lined notebook paper. Sonic the Hedgehog, the Phantasy Star logo, Street Fighter characters, and the Zelda Triforce all became iconic in my head.

What is your biggest regret?

Not responding to a Disney recruiter in 2015 out of fear that I wouldn’t be a good fit for them. I didn’t even give it a shot, and while the project has been mired in usability challenges and business problems, it would have still be an intriguing part of my career journey.

How have you gotten over heartbreak?

I recently experienced the death of a family member, which was a different kind of heartbreak than I had experienced before, as I was always shielded from death as a child. In processing it, I reflected on what my uncle meant to me, and how he affected my childhood. I realized that some of my love languages and mannerisms were very much his, and I was overcome with another wave of sorrow when I realized that I should have spent more time with my family members. As a result, I’ve made it a point to reconnect with my family.

What makes you cry?

Shared experiences. When I went back to the movie theater for the first time since COVID shut everything down in Austin, I cried.

How long does the pride and joy of accomplishing something last for you?

It used to pass quickly. I think it was because I felt shame around accomplishment. Nowadays, I celebrate it. I like to reflect on my victories, whether it’s work that I’ve shipped, a miniature model that I feel exceptionally successful at painting, or a meal that really came together. And I look back at my body of work with pride and consider what it taught me.

Do you believe in an afterlife, and if so, what does that look like to you?

No. When I die, I hope that my body can be used to help others. iOrgan donations, or for a body farm where they train forensic scientists and cadaver dogs!

What do you hate most about yourself?

I tend to be overly critical of myself. Everyone will tell me a meal I made is great, but I can’t not criticize the outcome. I’m working on that.

What do you love most about yourself?

Over the last few years, I’ve realized that my experiences and stories inspire and help others. I love that I can be the person that I wish I had in my formative years.

What is your absolute favorite meal?

Uni, especially if I can get it from different oceans. It’s decadent and wonderfully oceanic.