Greg·Wolanski —designer

Questions to ask yourself before starting a design side project

1. How does this design side project fit in with the things I want to do?

In a perfect world, I would like to work remotely with people on useful software and be able to openly share my acquired knowledge.

For several years, I worked on side projects that were supposed to bring me money. It didn’t go well. I realized it’s unwise to do things over and over and expect radically different results. I decided to take a break from side projects. After catching my breath, I decided to try design side projects that would not bring me money. As I was thinking about it, I came across two areas of design side projects: pro bono projects for NGOs and open–source projects.

Pro bono projects for NGOs have the advantage that you can talk about them openly. They also have the bonus that you’re working with people, not in isolation.

Open–source projects are also transparent. And they’re generally developed online, remotely. They’re exactly my style.

I’ve done two solid design pro bono side projects for NGOs and a few smaller good deeds in this category. Now, I say no to NGOs and focus on open source.

Keep interested in your own career, however humble;
it is a real possession in the changing fortunes of time

Max Ehrmann, “Desiderata”

2. Do I want this design side project to be a one–time thing or a regular thing?

After many years, I noticed that most of my side projects (well, all of them) are one–off. I do something, I achieve the goal (or not), and I stop.

One–off side projects have value. Yet, they’re not worth limiting yourself to. Why not? Regular side projects help train other things.

Until recently, all I knew about myself was that I could come up with a side project, hook up, grit my teeth, and ship it. I’d categorized writing and publishing one text in English every month as a pipe dream. I only thought it – I didn’t feel I was able to do it. So many years of thinking about doing it and… nothing.

To know you’re an effective stubborn person who can turn down quality time with friends is one thing. To be aware that you’re able to regularly fasten up for a short time and ship something unplanned in time – that’s something completely different. Both have value. I recommend both. Not necessarily at the same time, though, especially at the beginning.

One interesting idea is the seasons of regular mini design side projects (articles, podcasts, […]). I haven’t tried working in a season format yet, but I’m getting ready for it. However silly it may sound, it’s hard for me to stop between successive monthly texts, look at this initiative from a distance, and reflect on the nuances and strategy. And – again – I just have to get my act together and do it. Even if it means a month or three of no writing and trying the seasons.

3. Don’t I have already some side project?

Personally, I try to take on only one one–off and one regular design side project at the same time. That’s already a lot.

It’s better to be able to brag about one shipped design side project than to talk about nine that are in a state of neverending progress.

4. How much am I willing to spend on this side project?

I treat the money spent on design side projects as an investment in myself.

If I had had to look after the servers myself, several of my side projects would never have been created.

If I hadn’t made room in my personal budget for editing my English writing, I would either not write or write in Polish, not English.

5. Is it possible to write a valuable case study on this side project?

This is an important question for me. If I think about a design side project and realize it would be difficult to write a case study on it, I consider what I can change about it. If I can’t come up with anything, I postpone it.

6. What constraints do I want to impose on myself in this design side project?


  • Technology: Next.js
  • Visual language: Material Design
  • Number of characters: 3,600
  • Duration: Up to 30 days

7. Do I need to involve anyone else in this project?

Another important question.

Sometimes I like to do things with others. Sometimes I prefer to do things by myself. I think it’s worth experimenting with both scenarios.

You can involve people in various roles: client, test user, consultant, service provider, subcontractor, etc.

Experimenting with involving people in various roles is a source of interesting experiences and a treasury of knowledge.

8. What do I want to learn from this side project?

Most of the time, I think about this when I consider whether it’s possible to write a valuable case study on the side project.

Aim to come up with one to three answers to this question.

9. Do I want to speak publicly about this design side project before shipping it?

Apparently, some people are motivated by this. It doesn’t work like that for me. I hate the feeling of shame associated with a unshipped side project.

10. What do I risk with this side project?

Health? Reputation? A relationship? The depletion of your personal budget? These are real threats.

11. How much free time do I have?

At the beginning of my adventures with side projects, it was very difficult for me to estimate how much real free time I had.

Such an estimate is important because it sets the perspective: If you have an hour of free time a day, you have seven hours a week for the project. That’s more or less one day of a full–time job. What can you do in this time over six months?

When I was younger, I assumed I had 60 minutes a day for a side project. And I did what was necessary to organize these 60 minutes. Even if it meant working past midnight.

These days, I’m for 25 minutes of work a day on a side project. I do usually work several times this timespan on the weekends. And I’m nice to myself when I don’t work on a side project for a day or two.

12. Can I drop any bad habits while working on this project?

I recently got rid of conventional chairs in my apartment. If I want to keep working in my free time on design side projects, I have to treat my spine well.

An idea I’m going to test: A design side project I’ll only work on without caffeine.

13. Why do I want to do this?

The answer to this question will get you through the hard times in the side project.

It’s important to have an answer to this question for yourself. Sometimes, someone asks me, “Why are you doing this?” Generally, I don’t have a universally convincing answer, but I just let myself not have one and feel good about it. It wasn’t always this way.

14. Do I just want to do this design side project to get a job in a particular company?

I’ve been here before. Actually, more than once. If I can suggest something from my experience, I’d say you should try to get yourself recruited in the conventional way first.

15. Why not use this time to do some freelance work?

A reasonable question.

After years of trial and error, I know that freelance work after 40 hours of regular work a week is not for me.

There are other ways to diversify your revenue.

16. Do I want to do a side project as a part of my everyday life or during vacation?

This is a real question I was asking myself when I was younger.

I know myself well enough to know that trying to do side projects during vacations doesn’t work for me.

Can you do a design side project during vacation? Speak up, I want to meet you. :)

17. Do I want to get an email every time the author of these questions publishes something?

June 2018