Interview: Elle Luna, author of ‘The Crossroads of Should and Must: Find and Follow Your Passion’

Living the dream: Artist Elle Luna left a promising career in the tech world to paint.
Living the dream: Artist Elle Luna left a promising career in the tech world to paint.

Artist Elle Luna believes that aligning our lives with what we think we should do — as opposed to what we must do to be happy — is a trap to which we’re all susceptible.

“It’s like putting on a T-shirt, and you forget it’s a t shirt and mistake it as part of your own body,” says the author of The Crossroads of Should and Must: Find and Follow Your Passion. “If unrecognized, these ‘shoulds’ will trap us for sure. They can be subtle. To recognize them takes time and patience and a good dose of courage.”

Luna, who lives in San Francisco but arrives in town Thursday for an appearance at Books & Books in Coral Gables, documents the process with her unique style in Crossroads (Workman, $16.95). The inspirational book — arriving just in time for graduation day shopping — blossomed from a post Luna made on the online storytelling platform Medium that went viral, advising readers not only how to follow their dreams but also how to identify what those dreams are.

Formerly at the design and consulting firm IDEO in Palo Alto, Luna once assumed her future lay in technology. She had worked with teams to design and build Mailbox’s iPhone app and helped redesign Uber’s iPhone app. But a persistent inner voice, along with a recurring dream of a white room in which she could paint, urged her to transform her life and try to make her way as an artist.

“I got to a place where the risk of staying was higher than the risk of giving it a go,” she says of her decision. “It was a very important moment when I had to sit down and admit to myself that all signs are pointing me to a creative life, making art. It was a lights-go-on kind of moment. I had never given myself the opportunity to imagine that was possible.”

Stepping away from the tech industry while living in its Northern California cradle was anything but easy — “I was riddled with anxiety,” Luna admits — but now, after surviving her first show, finding that her work will sell and amassing thousands of followers on social media, she hopes to inspire others to, as she writes, express “the fullness of our gifts.”

Still, Crossroads is not a quit-your-job-and-everything-will-be-wonderful exercise in wishful thinking. In addition to quotes from the likes of Rumi, Eleanor Roosevelt and Joseph Campbell and exercises to sort out your shoulds from your musts, the book is practical in its approach to finances. In short: Don’t forget you have to eat and pay the rent.

“Between a job and a career and a calling, there is no one right answer,” Luna says. “Just because we want to pursue our calling doesn’t mean we need to quit our jobs. Just because we do something for money doesn’t make that work dirty. T.S. Eliot, we think of him as an author, but he was a financial genius, he had a career in finance in London. … Keith Haring was a painter, but he was also a bus boy with an emotionally non-draining job. Maybe that’s why in front of his canvases he could give it his all.”

Luna has also launched The 100-Day Project on Instagram (#The100DayProject), which encourages participants to choose an action and repeat it for 100 days, documenting their work daily on social media (Luna chose to paint a self-portrait every day for her first round). Now, the project has launched more than 121,000 posts across 65 countries, she says.

“One father who has two vegan children is doing 100 days of vegan cooking. One of my favorite projects is a woman who’s doing mysterious videos where she enacts these dances in the middle of a forest behind her house. They’re wonderfully amusing and entertaining. There are hundreds of kids who are part of an online Girl Scout and Boy Scout group, and one kid is making up a new word every day. Two weeks ago his new word was ‘jerkish’ — kind of like, you’re a jerk, but you’re sluggish, a lazy jerk.”

The community aspect of the exercise is what’s important, she adds.

“You commit publicly to doing this on your social media, and the community holds you accountable. One day at 11:58 p.m. I realized I hadn’t done my post. I ran to my paints, and I quickly put something together before midnight. That feeling of ‘I have to do it! They’re counting on me!’ creates an incredible momentum.”

In her latest 100-Day challenge, Luna is painting her dreams every night.

“I share all of my work on Instagram; that’s really my gallery,” she says. “It’s very democratic. … Waking up in the morning, you go through the routine every day. Some days, it yields something that feels fruitful. Sometimes it’s junk, but I post anyway. I posted a ton of things on Medium before that one post, which was the post that went ’round the world. You just never know what’s going to resonate.”

Meet the author

Who: Elle Luna

When: 8 p.m. Thursday

Where: Books & Books, 265 Aragon Ave., Coral Gables

Info: 305-442-4408 or