Three Things I Learnt from the One Side Project per Year Challenge

Dec 4th 2015, I wrote an article about the idea of an One Side Project per Year Challenge here on the Mission. In the article I shared my frustration of wanting to work on too many side projects and struggling to get any of those done. I also introduced some simple rules for the challenge: commit to one side project per year, and write a project update every month.

The article got popular with 1.1K recommendations, thank you all. By Jan 1st 2016, I got 56 fellow creators to join me in this adventure. Very quickly, we had a publication, a Slack group, a content calendar, a Twitter account, and a lot of ambitions.

Everything looks beautiful and I thought 2016 would be the most productive year ever.

Until it started falling a part.

Among those 56, only 22 wrote an update at the end of January. And the monthly update chart looks like this after that:

Along those who do update, the common theme went from goals and plans, to growing slowly and hops and pivots, to derail and failure, and eventually OMG — Where has the year gone.

It was very interesting to watch this year-long journey. I got many sorry messages over email and Slack on the way. But I really can’t blame anyone because I, too, got slow on my updates and follow ups, and stopped working on it in June 😂.

Looking back, there’s quite a few lessons to be learnt from this challenge and social experiment. I feel obligated to share them at the beginning of a new year, the year 2017, in the hope that we can all learn from the past and have a more productive year forward.

1. Three Months, instead of One Whole Year

First thing first, a year is a very long time frame for side projects and personal goals. No wonder most new year resolutions fail miserably:

Image from: http://www.fitlivinglifestyle.com/failed-new-years-resolution-not-fast/
Image from: http://www.fitlivinglifestyle.com/failed-new-years-resolution-not-fast/

As I was communicating and following up with all the makers and writers in the challenge, I heard about a lot of things happened this year — life events, career pivots, relocation, finding new interests and projects, and more. I’m sure there were even more stories that I don’t know as many just stopped updating silently.

Maybe life is too short for us to plan it in the measurement of years. Things happen and we have to change our plans. Maybe it’s even more unfortunate if we just box ourselves in the little box we picked at the beginning of each year and stay that way.

Maybe three months is a better time frame.

Out of the 22 who wrote a January update, 14 sticked to the challenge until the end of March. That’s a 63% survival rate. And by the end of April, that 14 became 5, only 22% stayed committed for more than three months.

If you observe this chart again, you will see a cliff every three months. It could be a coincidence. The sample size is very small here. Or, it could mean that three months might be a better time frame for personal goals and side projects. And maybe that’s also the reason the 100 day challenges / projects got continuous participation.

And beyond that, aiming for three months could mean more than changing the time frame, it could help us to set more realistic goals as well. Maybe side projects shouldn’t be too ambitious to begin with. The start small mentality should be adopted with extra focus here.

2. Find All the Reasons to Hold Yourself accountable

During this challenge, each participant had at least three factors to hold them accountable:

  • Promises to themselves
  • Public announcement they made to their followers.
  • Pressure from the community. I sent out reminders for each writer for about 4–5 months.

That’s already more than what we would usually have, which is just a promise to ourselves. And you can easily tell how the public and community peer pressure pushed our writers forward. Many of them addressed such feeling in their updates.

However, that’s still not enough. Once the heat of the community and excitement die down (which is not uncommon), what can hold us accountable? A bet with friends? A hunger for pay checks? A habit?

I don’t have an answer yet. But when I was deep in finding my way through the maze of Redux, I knew I really need a strong reason to keep going. And if you are starting a side project, find all the reasons to hold yourself accountable — that may still not work, but at least you’ve tried.

3. Prepare an IFTTT Style Plan for Failure

Observing and reflecting on this entire journey, I realized that failure is inevitable. Things happen in our lives and we are not in full control. Unless you are Batman himself, you will break one of your promises at some point.

So what do you do when you break your own promise? What do you do when you miss an update or a day of exercise?

This is a particular weak spot in humanity. We are so easy to just gave up on ourselves at a small failure. In her famous book The Willpower Instinct, Kelly McGonigal described this what-the-hell effect:

Many dieters would feel so bad about any lapse — a piece of pizza, a bite of cake — that they would say, “What the hell, I already blew my diet, what’s the point, I might as well eat the whole thing.”

Similarly, once you miss one project deadline you set for yourself, there is a tendency for you to say: “What the hell, I’m a failure already, might as well just forget about my plans.”

Among the 56 participants, only 3 had skipped at least a month’s update and came back. The remaining 53 — once they missed the update for a month, they never came back. Myself included.

According to Kelly McGonigal, such reaction is driven by shame and is best handled with self-compassion — don’t blame yourself, know that lapses will happen. The very thought that we can keep all our words if we try harder is mainly an illusion after all.

To better prepare for the inevitable small failures, one thing we could try is to put a if this then that (IFTTT) plan for ourselves:

  • If I miss an update, I will pick it up next month
  • If I wasted a weekend not working on my project, I will spend 30 mins each day for the following week to compensate.
  • If instead of an hour I can only work 20 mins per day on my project, I will adjust my plan and keep going.

The more if else logic you program for yourself, the more prepared you are. I don’t think we should act like we are codes snippets, but it might give us some guidance in slow times and help us fight the what-the-hell effect.


When we wave goodbye to 2016 and say hello to 2017, I hope this recap can help you live a more productive new year :) If you enjoy this post, definitely give it a 💚 recommend as always.

As you can tell, I don’t have all the answers and I’m keenly seeking for them. If you have thoughts, experiences, and tips in this area, please share them in the comments! (And maybe write full articles, too, because why not both.) I can’t wait to read them.