Do you have side projects? If not, you probably should think about it – they can be helpful in the long term.

But I'd suggest being mindful when you're starting one – otherwise, it can cause unpleasant and unnecessary headache, as it did for me many times. But how can we avoid it? What defines sustainable projects? Let's think about it together.

"Unhealthy" side projects

It is not always smooth. I had plenty of side-projects I wish I had never taken.

Sleepless nights, strict deadlines, demanding users – all of these made me want to finish it sooner and come back to the safe old world, where I had only a full-time job and nothing else.

I know at least one person who experienced the same:

James Corden (Francis Henshall) – ONE MAN, TWO GUVNORS. Credit: Johan Persson

Francis Henshall is the main character of the comedy "One Man, Two Guvnors". This is a setup from Wikipedia:

<...> Francis Henshall becomes separately employed by two men <...>.

Francis tries to keep the two from meeting, in order to avoid each of them learning that Francis is also working for someone else.

It goes normal for a minute or two until two bosses start giving him urgent orders at the same time. As a bonus, the main character holds his own personal interest, which sometimes conflicts with the goals of his employers. What can go wrong?

This is the best illustration of how unhealthy side projects look like.

Honestly speaking, those are not really side projects. The word "side" implies that you have something "main", like a full-time job, family, friends and other areas of your life you aren't ready to sacrifice.

If a side project cannibalises your time and attention from the "main" activities, you're dealing with either of two options:

The side project is unsustainable It is not a side project, and you need to be explicit about your priorities

Which projects are "healthy"?

I've formulated these criteria for myself:

I should know an exhaustive list of goals I'm trying to achieve If I fail a project, only those goals should be affected Those goals should not be time-bounded

Why do I emphasise the part about goals so much? Because I need to estimate a blast radius in case the project fails, which frequently happens with side projects.

– Would I let someone down?

– Would it affect my reputation?

– Would I be affected financially?

– Would it require unexpected extra work?

I want to be able to answer "no" to all of these questions.

How to stress-test your projects

As always, I need someone to demonstrate an example. Today it will be an extraverted Jane.

Imagine that a friend is asking her to build a website. What could be Jane's motivation?

These goals will not affect other duties – she will be fine even if she fails them. But what's about the friend? How urgent is it for him?

That's the best possible response – if Jane doesn't have enough time, she will ask him to find somebody else.

If the time boundaries were stricter, "no" would be a preferable answer. After all, she can learn Typescript in a much more relaxed environment.

Time for the last check.

Is there any chance that this project will become urgent?

At first glance, no. There is plenty of time, why would it become urgent?

But it's not that simple. Imagine them in two months, after Jane built the website:

Then it quickly becomes unsustainable and causes all the pain I've mentioned before.

What if the goals are ambitious?

Does it really mean that you should deny everything if it can become urgent? In the end, all ambitious projects imply potential success and consequential urgency.

This would be quite a thoughtless strategy.

Luckily, there is a way out.

You need to remove yourself from a critical path

If you're building something with high potential – try to spread the load. Build a community, even if it's just a community of two. There will be much less chance that unexpected urgency will catch you off guard.

Being extra explicit also serves the same purpose:

The same approach works with pretty much any system: you can either strictly define the SLA (= agree on expectations) or add more resources (= build a community).

After all, you won't do any good if you're burned out.

Take care*!

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