10 min 39 sec

Artistic Cartographer Maps Out Successful Side Hustle

A designer with an enthusiasm for both maps and art merges the two to create hand-printed mazes that zig-zag through the hearts of iconic cities.
Arts & Crafts Product Product Development Unique Ideas

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What It's About

These iconic city maps will a-maze you!

Business Model
Arts & Crafts
Skills Required
Design & Product Development
Profit Potential

Words of Wisdom

Michelle has always been a big believer that early efforts don’t need to be perfect. In her book, it’s better to start with something, get feedback, and grow. And she learned a lot by sharing her map art at craft fairs where she could get feedback directly from a wide range of people and improve her prints and website.

Fun Fact

So, is it true that all roads lead to Rome? Well, at least in Europe, they do! A map visualization from this Vice article shows the 500,000 routes to Rome across the European continent.

Notes from Chris

Episode 861
Need to get from the Golden Gate Bridge to Sutro Tower in San Francisco? Well, you’re in luck! Today’s featured side hustler, Michelle Chandra, can take you on the longest, windiest route imaginable.

Michelle is a graphic designer with a love for the outdoors, adventures, learning, and art. From her life as an undergraduate seeking to be a creative writer to her current life as an artist with a mapping style all her own, Michelle’s journey has been full of twists and turns.

She began her adventure when she entered college, discovering a new world of travel, poetry, and art. She connected with a community of artists all over San Francisco—ultimately inspiring her into a labyrinth of projects.

The “x” at the conclusion of her journey was artistic cartography. And the intricate world of mapping was love at first sight. Michelle landed a full-time job with a Bay area startup creating web map visualizations, and that’s where she stayed putting together maps for three years.

While at a work conference, she attended a talk on maze-generating algorithms utilizing grids. As a traveler who worked in mapping, Michelle immediately connected the dots: cities are planned on grids as well!

Always keen on a puzzle, Michelle took on the challenge of designing her first map maze, using actual street grids. Although the journey was at times difficult and took 3 months and over 100 hours to solve, it was also a ton of fun. And it occurred to her that perhaps others would enjoy the challenge as well.

To get Dirt Alley Design started, Michelle created a maze map using screenprinting for two of the country’s most iconic cities: her hometown of San Francisco, and Brooklyn.

For the San Francisco maze, she decided to start at the Golden Gate Bridge with it ending at Twin Peaks, in the heart of the city. And for Brooklyn, nothing would suffice but to have it start at the Brooklyn Bridge winding its way all the way to Coney Island. She realized pretty early in that people would want to solve these without damaging the original designs, so she also sends along an extra print of the maze for you to solve.

Her first year, she brought in small profits of around $3,500. The year after that, her profits doubled to $7,000. Her goal is to keep doubling every year. Not only that, but Michelle recently realized that she was learning way more running a business than she was at her main job. With that in mind, she opted to set off on her own path—leaving her day job to focus entirely on her growing side hustle. Luckily, she was able to take the leap thanks to savings and living a minimalist lifestyle.

Looking a bit further down the road, Michelle is aiming to convert more maze enthusiasts by getting her art featured in new places and boosting online marketing so she can spend more time creating and less time at festivals and art fairs. She is especially excited to start exploring different art forms.

Most of all, Michelle feels fortunate to have the opportunity that her hustle has given her to create a new lifestyle. She looks forward to the twists and turns ahead.


  • Dirt Alley Design: Learn more about this winding side hustle over on Michelle's website!
  • Shopify: Michelle used Shopify to set up her site for Dirt Alley Designs, and they're offering a 21-day trial and exclusive discount for all Side Hustle School listeners!
  • The Jealous Curator: A popular, curated art blog we featured in Ep. 818
  • Kottke: One of the oldest blogs on the web. Written and produced by Jason Kottke, this blog covers the essential people, inventions, performances, and ideas that increase the collective adjacent possible of humanity
  • HauteLook: A "members-only" shopping website offering flash-sales and limited-time sale events featuring women's and men's fashion, jewelry and accessories, beauty products, kid's clothing and toys, and home décor
  • Art Biz Success: A website run by my friend, Alyson Stanfield, that focuses on helping artists successfully manage the business side of their operation
  • Forbes | Holiday Gift Guide 2018: A holiday gift guide that highlighted some of Michelle's products back in 2018

Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,


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Quote of the Day
"In the beginning, you might just have an idea or an invention, but until you share it and get feedback, you won't be able to learn, grow, or build it something bigger!​​"
—Michelle Chandra #SideHustleSchool

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To infinity and beyond,

Chris Guillebeau