Lessons learned from working on multiple side projects: Goals and Partners [Part One]

Side projects are a great way to enhance your CV, learn something new, gain work experience that would allow you to transition to a new job, start your startup without risking it all, or simply get some extra income.

For the last five years I’ve started multiple side projects, ranging from an on demand T-Shirts printing, a board game, a desktop app, a web app and others.

Here are my lessons learned and things that I consider when starting a new project:

Usually when starting a project

You need to have a clear goal on why you are starting a particular side project. I’ve started projects for many different purposes:

  • With the sole purpose to make some side money;
  • With the purpose to learn a new technology;
  • To test if a friendship could become a business partnership (I usually do this on a small project that I wouldn’t care much if things don’t work out);
  • To enhance my CV and get a better job;
  • Pick your own.

If you don’t think about it and write it down I can guarantee that after X months from starting up you will be wondering if you didn’t just waste your time. (Especially if things didn’t work out as planned)

Your side project typically can’t or shouldn’t have multiple purposes simultaneously. E.g learn new thing + make money + get a better job. It may sound really logical to mix the goals, but what will happen is that eventually you will have to make a sacrifice and ditch one of the goals and you will get disappointed. Maybe you will have to change the technology, maybe you will decide that this project won’t help you get the desired position, or it will turn out that there is no market for your product.

Don’t get me wrong — starting a project will most definitely have many benefits — you will most definitely learn something new, it could make you money etc, however, when the going gets tough, you better be clear from the beginning with your partner what’s the main purpose so that you don’t have to make such decisions on the go. Consider everything you gain besides your main goal as a bonus.

Know exactly why you are doing it from the very beginning. Aim as high as you would like to achieve.

I cannot stress enough on this. I’ve always considered myself to be extremely picky, but after every project, I’ve come to the conclusion that I’m not even picky enough. Here are a couple of bullet points to consider when choosing your partners:

  • Your business partner should be a person that you like to hang out with. You will most definitely have to spend hours with him, and if he is someone that you don’t love to spend time with — this is going to become a nightmare at some point. Trust me on this, at one point you will start regretting that you are spending all of your free time with a person you don’t like to hang out with — no matter how smart or motivated he is. On the other hand, if you enjoy your time together — it will feel like you are not working, while you are pulling 20–40 hours a week. This is the sweet spot.
  • Your business partner should be motivated to finish the project at least to the extent that you are. If this side project means everything to you and he’s not eager to work on it, can’t wait to get his hands off the project or you have to push him every time so that he completes his duties on time — you don’t have a partner, you have an employee and you are losing your precious time. Either pay the man to finish the job on time, or find yourself a new founder that is motivated not only to do the bare minimum so that his work is considered “done”, but to be willing to put the extra effort to make your product even better. On the other hand, if you are not very motivated and he is — make it clear to him. It’s awful to give false expectations, don’t be that guy.
  • If any or both of you are inexperienced it will most probably take lots of time. If you are starting a startup as a side project, with the purpose to quit your day job and focus on it — you need a strong partner with definitive knowledge in what he is doing. Otherwise, you are risking to spend months on learning, experimenting and by the time you get proficient you will both be already turned out by the lack of real world progress. In some occasions you can even be too late for the market (been there). However, don’t get me wrong — with the right mindset and motivation you can make up for the lack of experience, and whatever you are starting — you will most probably going to have to learn new things and adapt.
  • Priorities and free time — One of my big mistakes was not to put huge weight on this one. Thing is, the more experienced and motivated people you have on your team, the less free time they have. They will either be working on something else that they want to start by themselves, or they may be doing lots of pro bono work, or they will most likely spend a huge amount of their time learning new skills — all typical things that successful people do. It’s easy to assume that experience or connections will make up for the lack of time, but no matter how good you are — if you can spare just a few hours a week, you will not be able to complete enough things or complete them with the desired quality. Free your time and don’t do too many things simultaneously.
  • Proper distribution of responsibilities — two business people can’t start an IT startup, two typical programmers can’t do it successfully either. Your team needs to have a proper distribution of their responsibilities. If you are starting an IT startup get an experienced front-end developer, get a separate back-end developer, get a designer, get a business/marketing person. Aim for people with “T-shaped” skill tree. Everybody should be an expert in his field, and optimally have at least general knowledge in what everyone else is doing:

These are the top things that I’m looking at when starting a new project so that I can guarantee I’m starting on a solid foundation. No matter how good your business idea is — your team is everything.

In the next post I’m planning to write on how to pick the correct project for your goal.

It’s your turn — what can you add to my list? Do you agree with it? Share your experience!

If you like this post, please click and hold down the 👏 button for 10 seconds to show your support!



Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store
Stoimen Iliev

Pro Bono Machine Learning Consultant | Senior Product Manager & Certified Scrum Product Owner | MBA at Cornell Johnson | Fulbright Scholar | Software Engineer