What Matters to Jessie McGuire

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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.

Jessie McGuire is a designer, dreamer, realist, and mom who believes in big ideas and small actions. She is leading the charge as the first managing partner at New York’s ThoughtMatter.

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

Imagining the future.

This goes back to elementary school, where I’d end up in the principal’s office telling stories about how the world should look in the future. It turns out the nuns at my Catholic elementary school were more interested in the past than the future. Today, my imagination takes shape during dinner conversations with friends, colleagues, or family. If you end up late in the night with me, just know that we will be talking about “what’s next.”

What is the first memory you have of being creative?

Sitting at the edge of my lawn in Schenectady, NY in a brown, beige, and orange woven lawn chair. An open burgundy briefcase propped next to me with friendship bracelets hanging from the interior pocket. A hand-drawn sign with prices of individual bracelets that were priced by the number of colors they featured. I was probably nine years old— apparently with big dreams of selling out.

What is your biggest regret?

Regret is a tough word, because as soon as you say it, you’re disappointed in yourself. Disappointed that you let it happen, that you didn’t do it or that you did do it. It just feels too sad to talk about. I feel sad every day when I have to say “no habla español.”

How have you gotten over heartbreak?

Of all the questions, this one is the hardest for me. I wanted a witty, fun response, but honestly, I compartmentalize and distance myself from negativity. So, what heartbreak?

What makes you cry?

Extraordinary feats of sacrifice. Every November, I get a good cry from watching the NYC marathon. Recently, I cried at the end of Avatar: The Weight of Water, and not because it was three hours long. It was the end that got me.

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

I tend to move quickly from one accomplishment to the next. I have never been good at enjoying the present moment (see also: thinking about the future ALL THE TIME, as I mentioned in Question 1). I will say, however, that these past few years of living through a global pandemic with a 2-year-old and 6-year-old has forced me to slow down, confront and reflect on my thoughts, accomplishments and failures. For this I’m thankful, as time is finite, and I realize I must not speed through it.

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

Like praying, I believe the afterlife is for those still in this life. I often pray to loved ones, hoping my prayers can provide support and guidance. I always imagine a board or council of loved ones, and I hope one day to be on one of these special boards for my children. I believe the afterlife— or belief in the afterlife— is for protecting the ones you love.

What do you hate most about yourself?

I have a hard time saying thank you.

I have been tremendously lucky all my life, starting with being adopted at a young age, so my difficulty in conveying my gratitude certainly isn’t because I don’t have a lot to be thankful for. It’s more that I get nervous that I’ll get it wrong. I overthink it and the moment passes by. I’m learning that it is never too late to say thank you.

What do you love most about yourself?

I never give up.

What is your absolute favorite meal?

PIZZA—specifically homemade pizza. My retirement plan is to open a local pizzeria on a beach so I can enjoy pizza made by hand every day.