Thoughts on side projects

I recently visited my best friend from college.

We were both city boys who caused trouble as teenagers, and connected over our free spirited willingness for fun. Since our friendship began 10 years ago, he has taken up farming and lives in Oregon on a nine acre plot with crops, animals and a seasonal business. I ended up in New York city, married, and working at a tech company as a programmer. Both of us studied philosophy and literature, both of our lives took unexpected directions, and I think that we both ended up exactly where we want to be. At least for the time being.

I wouldn’t necessarily call the farming a side project, but I also don’t think my friend will be a farmer for his entire life. He spends his days and nights farming, but his dreams are around writing and his real income comes from highly successful real estate deals. If all of his time goes toward one thing, and all of his money comes from another, then which is the side project and which is the job?

Similarly, my income comes from a consulting contract, but the majority of my time isn’t spent at work. In one sense, this is because I found a great company to work with, but in another it is because I prioritized finding a source of income that allowed me to spend a lot of my time on side projects. In my own defense (not that I need one), my time spent on projects makes me much more impactful in the other areas that I end up working in. But I don’t consider them work.

Given the two cases where a side project ends up becoming the main allocation of time, I conclude that a “side” project doesn’t necessitate a minor allocation of time.

For the past seven years, every winter, I have taken on a side project.

In 2013, I traveled around the US and built an artistically laid out website that described an educational pedagogy. In 2014, I went to India and learned enough Objective-C to make an iOS app. In 2015, I made a hotline for people to share their breakup stories. In 2016, I built a ruby API and bot that traded stocks (very poorly). In 2017, I built a deep learning machine and trained some amateur image recognition models. (Surprisingly I never used this to mine crypto.) In 2018, I indexed millions of street art images and built a web application to explore them online. All the while in between, I was playing around with unfamiliar tech and building out personal projects for fun.

This winter, I haven’t “built” anything, but I have been thinking a bit more deeply about what the output of all my side projects have been. I have a nagging feeling that while each project was unique and fulfilling in its own right, I don’t have any concrete products to point to. Once the project becomes too expensive (or no longer interesting) to maintain, I often let domains expire or spin down servers.

My usual process is this: The output of the side projects is a website, possibly with a registered domain, and some efforts to gather attention. This results in a boost of page views/downloads while the promotion efforts happen (ie. Reddit/hacker news posts), but then eventually drops to a crawl. The remaining traffic normally comes from search, and otherwise never surges again. At the point that the traffic doesn’t feel worth the small but real cost, I start sunsetting the project.

This brings me to the question of why I do side projects, and also what more I think could come out of the projects.

While reading a great book about note-taking (How to take smart notes by Sönke Ahrens), I was intrigued by the idea that all notes should be taken with a purpose in mind. In the book, Ahrens states that notes should be taken with the mindset of needing to write about the material being read. In the same way, maybe defining clearer purposes for side project, could ease my feeling that more could have come out of old projects.

(I preface this thinking with an important point: Doing a side project for the sake of doing it alone is absolutely a good enough reason. I think if every side project must have a predetermined purpose or end goal, you will end up a person with boring side projects. And you would likely become a boring person. For example, if you feel all side projects need to result in becoming a business or passive source of income, then the pursuit itself will result in a series of unoriginal projects that are hard to maintain over time. Personally, doing projects out of sheer interest and a desire to learn or experiment has been the greatest force for sustaining my excitement and investing my time into producing something new.)

Now, let’s assume there is some definition of a side project. It’s a pursuit of some idea, which, in my case often revolves around technology, and results in a product (ie. an app, hardware), a community, or a collection of knowledge (ie. research, blog post, dataset, academic article).

That being said, the yearning sense of looking back at projects and not having some clear value to point to s concerning to me. With some projects requiring well over 100 hours, and in some cases hundreds of hours of time, I do wish I could point to something concrete that crystalized my effort.

Value I have derived from side projects:

  1. I can honestly say that the projects I decided to work on made me more interesting and have something worth talking about.

  2. If I was just doing “work”, I would feel dull.

  3. In the process of learning something new for a project, I regularly made new friends to expand my knowledge and perspective on a problem.

  4. Along the same lines of being “interesting”, by making something new, I felt I established some authority as a developer or product maker.

  5. I established more confidence in my ability to contribute to other people’s projects.

  6. When in work atmospheres that were less than exciting, side projects gave me something to be motivated about when work was not.

Moving forward, concrete things that I’d like to do

First, I need a lessons learned blog post and some kind of summary of the project. I don’t know if this is a series of gifs and screenshots, or some kind of gallery that can be previewed. Or at least a document or single place of reference that explains the project would be great.

Second, if data or an untapped area of interest is involved (ie. my street art project), I strongly feel publishing in an academic journal article would be possible. I don’t know what the process is like to submit to an academic journal if you aren’t affiliated with an academic institution or research entity (except I sometimes treat my projects as research entity), so understanding that early and then pursuing the project accordingly could be interesting.

Third, wouldn’t it be nice if all side projects resulted in some $$$? It’s not possible and shouldn’t be the goal in most cases, but in some cases the project could be wrapped up as a deliverable to someone who wants to buy it. When doing explorative projects, there are certain decisions I have made that I didn’t consider too seriously. If I had considered a sale of the overall codebase/community as an original goal, I imagine I would make different decisions along the way.

Anyway, I’m sure I will come up with something to work on this winter. If this year’s project doesn’t survive a year from now, and doesn’t become an academic study, and no one buys it, I think it’s still okay. I’ll still be happy working on something.