Skip to main content

Growing my skills with side projects

Someone lifting weights — practicing to get better.

I recently started working on a new side project and noticed it’s starting to paying off both personally and professionally. It got me thinking about all the projects I have done before it and one of the common threads that stuck out was that they each helped me feel happier and healthier. They created a space for me to break away from work, practice my craft, and experience new things.

Now, as a father of three kids with a very demanding job, I will be the first to admit that it’s hard to make time for this kind of thing but just like just like exercising, I believe that taking on projects outside of work is something I need to prioritize to be on the top of my professional and personal game. As I reflected back, I thought I’d share some of the projects I have worked on and how they’ve paid off:

Hundred days of sketching

A little over a month ago I committed to a hundred days of sketching as part of the hundred day creative challenge. At the end of most days, I open my sketch book and spend some time running through a number of exercises until I’m happy with the end result or my page is full. I almost always start with the date and then reflect back on my day while sketching all kinds of things. After I’m done, I post the sketch up on a blog I created just for this very purpose so I can look back over time and also hold myself accountable.

The mental pause from work, and everyday life, is very relaxing. In some ways it’s like therapy as I process my thoughts and express them visually. I have also found myself rediscovering old personal interests like nature, patterns, numbers, and letters. The every day practice of exploring and being creative feels like it’s rubbing off on my work because it feels easier for me to come up with more comps when I’m evaluating solutions to a problem.

I have begun looking forward to this time everyday and look forward to continuing with this practice hopefully beyond the hundred day challenge.

Design Herald

A couple years ago, I wanted to have a go at creating my own app and looked at my personal interests for inspiration. Since I like staying up to date with the news, and also get lots of enjoyment from apps like Yahoo and Google News, I thought why not create a news app for designers. I came up with an idea for an app called Design Herald that would aggregate and curate the top UX design news from across the web.

It was a lot of fun coming up with the name, doing some branding work, and designing the interface. From a development perspective, I decided to go with React Native because it’s a JavaScript language, which I know how to write, and it compiles to multiple platforms like iOS and Android — plus it was what everyone was talking about at the time. I dove right in to the code and learned as I went. I built a backend tool with Drupal that collected all the news and aggregated it into a single source that could be consumed by the app.

After a couple weeks, I had a fully functioning app working on my local machine. That’s when I ran into problems because I couldn’t find any documentation for actually publishing the app to the various App Stores. I was a little disappointed but not overly worried because I learned a new programming language and had lots of fun in the process. A month or two later, I started a new job at Automattic and was happy to find out that they used React as their code base for Thanks to my side project I was able to jump right into the code and add extra value by executing my own a/b tests and project work.

Design Herald — take two

Although my initial attempt at launching Design Herald didn’t work, the idea didn’t die there. Almost two years later, an opportunity to revive my idea presented itself when I was promoted to Design Director of the UX practice at Automattic. I was assigned seven direct reports and one of my responsibilities, as their director, was to level up their skills in the UX discipline. Sharing the latest design news and articles seemed like an obvious first step in doing that but regularly posting links into our Slack group got annoying very quickly — that’s when I remembered Design Herald.

I dug up my old app and spent a bunch of time trying to get it running again but that wasn’t going anywhere so I thought I would approach it from a different angle — this time I had the idea of combining WordPress and IFTTT. With IFTTT, I was able to “watch” any site’s RSS feed and then, if the feed updated, I could post the article to my new WordPress site. Compared to the app that took me a couple weeks to develop, this new approach only took me a couple days to get up and running. All I needed to do was create a site, gather up my sources, and setup all my “Applets” in IFTTT.

One of the first things I noticed after setting it up was there was a lot of sponsored content coming through. An update to my IFTTT settings allowed me to set the posts as drafts rather than publishing then publicly right away and that was all fixed up. This new work flow also meant that I needed to spend a little extra time to review the posts but that actually turned out to be a good thing for me because now I’m staying up to date with all the latest UX news.

Personal site

When I first read about progressive web apps my imagination went wild thinking of all the different things you could do with them. Unfortunately the role I was working in at the time was unrelated and didn’t afford me the opportunity to explore those possibilities. I therefore decided to pursue this interest on my own time and created a side project to dig in and learn more.

My idea was to rethink my personal website as a progressive web app. At the time, I had been blogging with for a couple months and the site I had was more than enough but when I looked at what some of the competitors we’re doing, there were parts of it that were outdated. The new format of a progressive web app gave me the opportunity to incorporate some more modern blogging features along with some of the benefits that progressive web apps bring.

Once I completed my new design, I took the opportunity to practice my React skills and started coding. Looking back, I can easily say this was the most ambitious coding project I ever worked on and in the end it payed off because not only did I get a new site but I also learned a lot about developing with React. Thanks to all those extra hours of practice, I feel more confident taking on development projects in my day to day work and have also become a regular contributor to our development efforts.

Hundred days of patterns

The first time I heard about the hundred day creative project was back in 2014. Cassie Slack, a designer colleague at Shopify, introduced me to the idea while presenting her work to the rest of the design team. Her work inspired a number of us to try the project or for ourselves. Some people created visual art like portraits and illustrations, some wrote stories and limericks, and others played music — I chose to design patterns.

My first patterns were replicas and then I moved on to making my own. Early on in the project, I noticed that I liked working with colour too so that introduced a whole other dimension for me to experiment with. I tried all kinds of combinations and even went monochromatic for a while. The constrains I placed on myself lead to some interesting outcomes.

I noticed the creative practice rubbing off on my day to day work as a marketing designer. It started getting easier for me to come up with lots of different ideas for our campaigns and I also experimented with colours I would never dream of using before. The overall experience left quite an impression on me because I often tell people about it and I also just decided to pickup another hundred day challenge again.

Wrapping up

If you made it all the way down here, thank you for reading. I hope you can see how beneficial these projects have been for me. If you’re working on a project yourself or have any ideas for a new one, I’d love to hear about them — just reach out to me over LinkedIn.


Signup for occasional updates from my blog.