The Power of Side Projects

The OurGoods Team, 2012
The OurGoods Team, 2012

Side projects have been a big part of my world over the years, and I want to encourage you to do them!

Here are some emails and artifacts from my archive of 25 years of side projects:

How Do They Do That With HTML?

1995. High school. Wanted to learn HTML, so I innocently made a website about how to make websites. It took off and ultimately helped a million people make websites.

A year later, web pioneer Jeffrey Zeldman sent me this nice note:

1998. “My modem is still 2 weeks old."

A kid from the Philippines found my HTML guide and wrote me. He was 15, I was 19. I got a lot of fan mail for my website, but this email kicked off a 20+ year pen pal relationship.

I even visited him in Manila in 2015. Yay internet!

Immanuel from the internet

Immanuel from the internet

Going to the Philippines led me to write an article about the history of laundry. Why? Because I was curious about how laundry was done in the Philippines, and had long conversations with Immanuel about it.

This was my first Medium post. Then the Atlantic’s CityLab reached out and I wrote a piece for them about the same topic.

It was the first time I got paid for a piece of technology writing!

The Microsoft Interview

1998. “I felt like an apprehensive lemming." I was rejected by Microsoft for a college internship. I wrote a cathartic story about my interview experience and posted it on my website.

This got me a mention in a book about tech interview questions, called “How Would You Move Mount Fuji?" ๐Ÿ—ป

Student Internet Services

1999. Cleveland, junior year at CWRU. On the side I created a student-run web host with Greg McGuire and Andy Reitz. Then we convinced the university president to give us summer jobs to expand it, and to let us work remotely from Boston.

After I graduated, this project on my resume helped me land my first job, at Zipcar. With Student Internet Services, I was able to demonstrate leadership and initiative that wasn’t as clear in my other college jobs and internships.

Lost In Translation

2002. I made a funny side project called Lost in Translation that used language translation APIs to add interesting distortion to English text:

Programmer Ward Cunningham built the web’s first wiki in 1995. It’s still around. It’s called “wiki.”

One day he found a link to my site on wiki. He wrote to thank me. Thanks for the encouragement, Ward! :D

2003. “Bruce Sterling showed me this."

William Gibson blogged about my translation project, which made my day.

2003. Artist Petra Cortright found my Lost in Translation project and used it for years in her art practice.

Fast forward to 2018, Rhizome invited us to do the Seven on Seven art + technology event at the New Museum. We made a generative art project using Photoshop and Petra’s paintings. Here’s the GitHub repo for the project.

Here’s our talk from that event.

The Flag of Equal Marriage

2009. I designed a Flag of Equal Marriage. Like an American flag, but it only had stars for states with legalized same-sex marriage.

This project got several nice press mentions. One day in 2009, WNYC had a “pride flag redesign” contest. I submitted mine on a whim. Then Isaac Mizrahi raved about it on the air. ๐Ÿ”ฅ ๐ŸŒˆ


2011. I helped create a bartering network in NYC called OurGoods.

OurGoods illustration by Louise Ma

It was a big side projectโ€”there were 5 of us: Jen Abrams, Caroline Woolard, Louise Ma, Rich Watts, and me.

A year in, we applied for a $100k Rockefeller grant. It was a WILD long shot. And we got it. ๐Ÿ’ฐ

We also got a lot of press for OurGoods: The New Yorker, Paper Magazine, Bloomburg Business, the New York Times…

Wine Flavor Wheel

2011. I made a visualization of wine flavors in Processing, based on a data set I found of 5,000 wine reviews. I did it as a favor for an ITP@NYU prof.

The Washington Post’s wine guy found it. El Bulli’s sommelier reached out too, and we did a small collaboration. ๐Ÿท

Sourdough Experiments

2016. I made really great sourdough bread at home, after 17 failed attempts. No press, no grant money, no fame. Just me, flour, water, and salt. Very satisfying.

View this post on Instagram

OMG we did it!!! Nailed the Tartine Country loaf, after 17 failed attempts. And it is soooooo tasty! Thank you @dchowser for being my bread guru throughout this process. ๐Ÿ’–๐Ÿ’–๐Ÿž๐Ÿž #breadbaking #wildyeast #tartinebread #bread #sourdough #homemadebread #๐Ÿž

A post shared by @ kitchensf on

2019. I saw that the domain was available, so I registered it and compiled a repository of queer healing resources.

Screenshot of, 2020

Screenshot of, 2020

This project still needs a lot of work. But, it’s up! It exists!

Work in progress: The Beauty of Networks

2020. Here’s a work in progress: After writing What Developers Should Know About Networks, I started designing a giant poster about the TCP/IP protocol stack, called The Beauty of Networks:

I’m excited about this one! As Bret Victor told me, if you want to learn something, make a poster about it.

I also have dozens and dozens of unfinished and abandoned side projects. Which is to be expected. A food truck map, field recordings of Balinese frogs, a generative music plugin for Logic, unfinished podcasts I made with friends.

Here’s a painting I made in Evernote, because I thought it would be funny to turn Evernote’s crude annotation tools into painting software:

I never aimed to pay rent with any of these projectsโ€”and I never did. Instead, I got to follow my curiosity, have fun, get creative, learn, collaborate with amazing people, feel connected to the community, and be of service.

So, what’s your next side project? ๐Ÿ’ช โœจ