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When you think about planning for your legacy, what’s the first thing that comes to mind? Stacks of paper? Boring legal terms that mean absolutely nothing to you? Admit it, you’re overcome with dread.

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“It’s a scary topic,” says artist and illustrator Julia Rothman, speaking from her studio in Brooklyn. “It makes you feel sad and think about being separated from your loved ones. That’s not a fun thing to think about.”

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She’s right. Estate planning is not an easy thing to ponder. But over the past several months, Ms. Rothman has been doing exactly that as the illustrator behind a new estate-planning app called FeedingBird. The app is filled with her hand-drawn illustrations, which appear throughout the experience. “Using illustration,” she says, “is a nice way to make it a little less unfriendly and stressful; because the drawings have a warmth and a playfulness to them.”

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Ms. Rothman has spent the past decade working in illustrated journalism and is the author and illustrator of 15 books and counting. (Maybe this is a good place to mention that Ms. Rothman and the author of this article had a column in The New York Times for five years together as well as co-authored three books.) Over the years, Ms. Rothman has tackled plenty of difficult subjects: racism, war, depression, economic hardship and even death itself. No matter the topic, she brings the same approach: she uses her distinctive, handmade style to soften heavy ideas and make them more approachable.

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“I think you can tell when something is made by hand,” she says. “Every single thing on this app was done with a piece of paper, using paint, using hands. There’s a warmth there. It gives it humanity and comfort. And for an app that’s talking about something so delicate, they did a great thing by deciding to use illustration. Especially illustration that was completely made by hand and not drawn on a computer or by AI. It really makes it special.”

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The whole purpose of FeedingBird is to transform legacy planning from something that feels heavy or intimidating into an experience that feels meaningful, empowering, and even a little exciting. Rather than presenting it as a rigid checklist of legal tasks, the app encourages users to feel proud about thoughtfully shaping the legacy they’ll leave for their loved ones. 

When speaking with Shreya Patel, co-founder and president of FeedingBird, she explained that one of the app’s central goals is to make complex legal jargon easier to understand. Incorporating hand painted illustrations into the app’s design helps make the experience feel more accessible and less intimidating.

“We want to break down intimidating concepts into clear, approachable guidance,” said  Ms. Patel. “By weaving art and illustrations directly into the experience, FeedingBird turns guidance into a natural part of the app’s flow. Visual storytelling helps make each step feel engaging and surprisingly uplifting rather than bureaucratic.”

With this approach in mind, Ms. Rothman’s illustrations throughout the app rely on metaphor instead of literal depictions. “I have to think about how to convey an idea without showing people,” she explains. For example, guardianship is visualized as an umbrella, symbolizing protection from the rain. Marriage and children are represented through objects that evoke warmth, comfort, and gentleness.

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Money, she says, was the hardest. “How many ways can you show money without always using a money bag?” She’s had to think outside the box here.

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Ms. Rothman also likes to keep things light. “I put in little jokes,” she says. When the app addresses business ownership, the illustration is a mug that says Number One Boss. “I’m trying to get people to smile a little. Even though they’re thinking about something sad.”

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The light touch works. And maybe from now on when you think about planning for your legacy instead of freezing up with dread, you can imagine a small hand-drawn umbrella keeping your loved ones dry and safe.

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