4 Ways I Ensure my Side Projects Can Go the Distance

My first project in 2017 was acquired in ~6 months, led to an awesome job offer and helped me build out a more successful product at the same time.

But I spent all of 2016 grasping at straws, trying to find projects I was interested in while simultaneously trying to learn the tech skills needed to be able to build out my own semblance of an MVP.

This is a lesson to myself on how to ensure the next project I build can go the distance to achieve the results I want.


I was slowly making progress towards creating my own successful side-project/startup. I decided at the beginning of 2016 I wanted to focus on the Rental Real Estate industry here in Australia. It was an industry that impacted almost everyone I knew and after speaking to dozens of customers and agents I knew there were problems to be fixed. Plus I didn’t really know much about the industry so I knew I could learn a lot along the way.

Aside from some great practical coding experience with Node.js and chatbots (remember those), a brief stint in an accelerator and valuable connections, my efforts did land me a spot on a startup mission to Shanghai, where I got to spend a month working with an awesome real estate startup there and experience the local culture and investor scene.

It sounds cliché, but when you’re working in a city with a population greater than your entire country, it definitely broadens your horizons as to what’s possible. In Shanghai I got to experience what it was like to be a small part of a team trying to build something big, and it made me even more eager to start building my own product.

But soon after I returned I realised it was all becoming very forced. Real Estate still needs to be shaken up, but it wasn’t going to be me, I knew there were much lower hanging fruit.

I made a decision to start focusing on creating solutions for eCommerce merchants. I had been working in eCommerce for ~4 years and knew there were plenty of problems to solve. Which leads me to my first point:

1. Find an industry and project you’re passionate about.

This is your side project after all. If you’re going to be working on it in your spare time, it should be in an industry that you enjoy learning more about.

So for me, that was eCommerce. I was excited about how quickly it was growing, I loved how it was enabling new forms of commerce to arise and how quickly it could iterate on new ideas compared to old methods. But I mainly just found it cool how it gave thousands of small entrepreneurs the power to create their own business.

I knew I wanted to build a SaaS product utilising the Shopify App Store, but I was still finding my feet, and didn’t know exactly what problem I wanted to focus on.

2. If you can’t decide, narrow in on a vertical

I didn’t know what I wanted to build, so in the mean time I launched a website called Built with Shopify. Inspired by Indiehackers, I wanted to interview other eCommerce stores to learn about how they started, what they were working on and what problems they faced.

Because this project was in a space I wanted to be in long term, it gave me four harmonious benefits:

1. It let me learn about the problems my customers were having
2. It let me build an audience for my future products
3. It gave me a testing ground for new ideas
4. Everything I learnt building this website could be applied to future projects

All of those points turned out to be incredibly valuable. I got to do real customer validation and create a detailed profile of what eCommerce merchants look like. I quickly started building up an email list of customers and even learnt how I could use the website to launch products when I launched a simple Chrome Extensions.

There’s a problem that many people seem to face, and I wouldn’t even call it analysis paralysis because I don’t think most people get to that stage. They get stuck thinking about an idea and then jump ship completely and lose all their progress if they don’t have a certain skillset. I was guilty of the same thing, so I decided if I was going to start over, I wanted to make sure I had still gained some valuable insight into the industry.

Thankfully, after being hunted I made more progress in the first couple of months with this project than anything else I did in the Real Estate industry. I was a much more experienced developer, but I was also working on problems that I felt much stronger about and could relate to. Which is what my third point is about:

3. You should have a natural inclination to the project

This might sound similar to “be passionate”, but to me when I’m starting a side-project one of the most important criteria is also how well suited I am to the project.

I’m super passionate about blues music and space, but I have no real inclination to start a side-project in either.

For me, the ideal projects lie in the intersection between what I’m good at and the fields I’m interested in (like eCommerce). Finding projects here means I can work on problems that interest me, while knowing I have the skills to overcome the roadblocks that can quickly kill a side project.

But try as you might, a side-project can usually only sustain itself for so long and unfortunately that period is often shorter than the time it takes to start seeing a commensurate amount of value (whether that is revenue or otherwise). Which brings us to point four.

4. Have an exit strategy

“Exit strategy” might be a bit too narrow in this case, what it really translates to is “make sure you know what you want to get out of it, how you’re going to do it and at what point you jump ship”.

I had two different type of milestones that I would want to reach.

The first were development milestones, i.e “I want to be able to build X feature”. These were super important when there wasn’t a lot of revenue or traffic because it gave me tangible goals to work towards for my own personal development and I loved working on new features.

The second were more tangible. Every now and then I would have content partnerships come up or some spikes in traffic that would give a nice little boost of confidence and these always required a bit of work to reach.

I also had clear strategies for how I wanted to earn a small amount of revenue from the site and how I could grow this revenue. Eventually it started matching the time I had to put in to the site which made it somewhat sustainable at which point the focus shifted to “what do I focus on to grow this further”.

I knew at a few stages whether or not this project was something I wanted to keep going. Initially after I had spent some time getting my first 15 interviews, I wanted to see how well it did on Product Hunt. The success helped me validate the idea and keep going. From there it was a bit trickier, I knew it would take some time to get to the point I wanted but I constantly evaluated whether this was the best use of my time and if the growth was still strong.

But you also have to be open to bigger possibilities. Side projects often revolve around the risky ideas that can be tricky to find the value in. But if they pan out, they can become incredibly valuable to businesses that don’t want to take on that initial risk themselves.

I made sure to always talk to other people in the industry which led to some great partnerships and eventually an acquisition with my ideal buyer.

Being able to maintain my side project, even for just the 6–7 months it was active also led me to Shopify, where I’m now working as a Launch Manager for Shopify Plus merchants.

I’ll be writing more about specific parts of this journey, my other side-projects, my time at Shopify and more. If you’re reading this and there are things you’d like me to dive deeper into, leave a comment or send me a message :)