Why did I make no progress on my side project?

I’m starting to experiment with a sustainable approach for startups this year: instead of the traditional “go big or go home” prevalent in Silicon Valley, I decided to take a job, and figure out a way to build bootstrapped businesses on the side, after folding the startup I went all-in for 2.5 years. A lot of other people have tried their own version of this: “How to fail at almost everything and still win big” by Scott Adams, “A portfolio of small bets” by Daniel Vassallo, this indie hackers community, and heck, the vast majority of businesses in the history and outside of tech. So I guess it’s doable? 🤷‍♀️

However, it’s not going very well so far... I can barely find any time or mental energy to make progress on my side project. To be exact, the total time I’ve spent on my side project so far this year is less than 2 days.

I’ve pondered on why and made a lot of adjustments along the way. Disclaimer: this is a run down of the thinking process without a definite solution, spare yourself the 5min read if you’re not interested.

Assumption 1: perfection is the enemy of progress

To prevent me from falling prey to the common “perfection is the enemy of progress”, I started the year with the goal to “validate an idea a month”. I hope this would force me to be scrappy and get in the habit of constant experimenting and tinkering. The result? Idea #1 is still in the planning phase. What I found is I’m not stuck trying to perfect ideas/products before unveiling them to others, but rather not enough motivation to find time to work on them.

Assumption 2: shiny objects syndrome

This is another one a lot of people who do side projects claim getting into the trap of. It refers to the tendency to chase the new idea, new trend, or whatever the next shiny distraction is, and leave the current project unfinished. However, given I’m barely on idea #2, this cannot be me.

Would the “validate an idea a month” experiment cause the shiny objects syndrome involuntarily? I’m making the following two precautionary rules to prevent that:

1. All my ideas should be saas related. This ensures all the learnings are transferrable.

2. Only start on the next idea until the previous idea is rejected by experiments.

Given I’m still on idea #1, I have no way to tell whether these rules are effective or not.

Assumption 3: I need ideas that excite me

If motivation is the problem, is it because the idea doesn’t excite me enough? This is a hard one and puzzled me when I was running my first startup.

The common (and obvious) thought is you need to work on the idea you’re passionate about. However, the notion of “an idea I’m passionate about” is kind of whimsical for me. Truth be told, the passion I had for any ideas never survived a night’s sleep. To not let passion get in the way of getting started, I’m using interest as my criteria right now:

To adopt an idea, I need to be at least slightly interested in both the market and interacting with the end-users on a daily basis.

The ideas I have are definitely in this bucket.

Assumption 4: I need accountability

What about complementing the lack of motivation with accountability? I’m blessed with a bunch of accountability buddies who are founders or work on their own side projects as well. We check in with each other on a monthly to quarterly basis on the status of our new year resolutions. Even though it’s indeed unpleasant and embarrassing to admit I made no progress each time, I seem to be thick-skinned enough to maintain it that way. 😓

Assumption 5: I need a schedule

If motivation is hard to come by, maybe what I need is a schedule to turn this into a habit? I did make a schedule a couple of weeks ago: listing the weekday nights and weekend hours I should be spending on my side project. Has it worked? Sadly no. Work from my day job easily bled into these hours despite my constant struggles. Why?

1. sometimes it’s necessary

2. it’s more satisfying, at least in the short term: since it’s worked on daily with high intensity, the feedback loop is shorter (e.g. a pat on the shoulder by coworkers certainly strokes my ego well, etc). Human brains (or is it just me?) can get addicted to that easily.

3. it’s also easier: wrapping up work I already have full context loaded VS venture into a new set of problems - seems like a no-brainer to the brain running out of juice at the end of the day/week.

Assumption 6: I need a system

From the observations above, just carving out the time is not enough. I need to create a system that can rewire my brain to make the right choice at those times, as the saying “You do not rise to the level of your goals. You fall to the level of your systems.” So here is the system’s architecture after some research online:

• make it easier:
  • document in great detail the next step to minimize the cost when context switching. For side projects, the gap between contexts is huge and it might take a long while to get back to this context, therefore it calls for extreme measures.
  • break down the work into tasks of very fine granularity, like “change the text color”, “think up a tag line”, etc. This makes it easier to make progress in fragmented time and also to ease into the zone for harder work.
• make it satisfying:
  • build in public: sharing work-in-progress frequently with anyone who would listen. This article serves as an example of this. Hopefully, it can provide the reward or satisfaction as in the day job when building something alone.

I’m going to give this a test run. Fingers crossed that this will end my agonizing search for the answer to “Why did I make no progress on my side project?” and I get to write a how-to article then. We’ll see 🤞

If you're interested in following along with my experiment or side hustle in general, here is my newsletter with only a handful of friends. Would love to befriend more internet strangers!