Side Projects Are Hard

Side Projects

It's hard to stick to side projects. I start and stop new ones all the time.

I dislike this about myself. I do just fine in a work environment, but not so fine when I get home and work on my personal side projects.

I have a long-term, macroscopic focus problem when it comes to my interests.

I am going to try and solve that.

The Long-Term Focus Problem

I've thought a lot about short-term focus.

I'm proficient at answering questions like:

How do I stay focused on my project for the next few weeks?

But I have no clear answer for something like:

How do I stay focused on my project for the next three years?

It's not that I can't focus, it's that I can't stay focused over longer periods of time. Especially on personal projects.

I can do this:

Finish the essay before Friday.

Finish the new feature for our app, test it, launch on Tuesday.

Build a product roadmap and stick to it for the next 18 months

But I can't do this:

Practice piano once a week for the next 3 years

Read 1 book every month in 2020

Build a personal roadmap and stick to it for the next 18 months

I get enthralled about the idea of learning piano or reading more books. I pursue these new interests with furious passion. A few weeks later, they fizzle out. It's not a concious decision, it's almost like I forget about them.

I'm going to explore this problem, fix it, and then write about it.

But What About Roadmaps?

...but Rob I thought you are a product manager? Isn't it your job to be thinking long-term? Don't you create product roadmaps?

As a product manager at a tech company, the single most important tool for myself has always been the product roadmap. I routinely sit down with relevant people (usually the CEO + engineering lead) and we create a plan for journey ahead.

Creating a "personal roadmap" is the first thing I tried. It works perfectly on a professional level, but there is one specific reason why it's been unsuccessful on a personal level.

Businesses have strong, structural incentives to maintain their product, goals, and identity.

  • Product: "Our product solves <problem> for <target market> with <solution>"
  • Goal: "Make $10,000,000 in annual recurring revenue"
  • Identity: "We create a delightful, user-friendly <product> for our <target market> to help them solve their <problem>"

All incentives align to keep these three attributes static. Especially identity.

When I get to work, I naturally adopt the identity of my organization. This identity has no incentive to change.

I, Robert, help make <company identity> a reality by doing <product manager stuff>.

There are no other thoughts that cross my mind. I love being a part of a team and working towards accomplishing goals. I love shipping products, and my persistence in this role makes me better at it.

I'm simplifying, but the static nature of a company's identity enables long-term focus in a way I haven't been able to replicate a personal level. It's why a "personal roadmap" doesn't work the same way a product roadmap does. I don't have a static identity for my personal projects.

Identity Incentives

Here's a simplified example of one attempt, for which I created a personal roadmap.

  • Product: "A video game."
  • Goal: "Create a roguelike action game in my spare time, and release it on Steam"
  • Identity: "I am a game developer who creates exciting, delightful, engaging video games in my spare time."

Creating a video game is a long-term project, especially if you haven't done it before. It's like learning to play guitar and produce/mix an album at the same time.

I created a roadmap, but I didn't stick to it. My momentum fell off a cliff after I finished the first milestone (in this case, a prototype). I found some new incentive to start a different project and immediately dropped the video game project. Some shiny new object entered my field of view, and that was that.

In my book, I recommend that people ignore any failures in their habits in order to preserve a successful identity:

I skipped my morning run today, but I'm still someone who is a runner.

I didn't work on my video game this weekend, but I'm still a game developer.

I never addressed how to maintain the identity itself. My recommendations had a built in assumption that the reader's given identity is static:

  • I study because I am a student
  • I write code because I am a back-end engineer
  • I run Facebook Ads because I am a digital marketer

When the identity is based on a personal interest instead of a professional role, there are fewer incentives to keep it static over the long-term.

Debunked Reasons

The reason I think it's an identity issue is because I have eliminated the following factors:

  • External validation: my friends liked my prototype and wanted to see more
  • Difficulty: I did not lose interest when things got harder, in fact they got easier as I learned more)
  • Time/Energy: I switched to a new interest with similar intensity. I was not burned out.
  • Motivation: I think identity and purpose drives motivation. Also, I like making stuff.

The Malleable Identity Issue

Now that I'm writing this all down, it's clear that my long-term focus problem is truly identity problem. The identity I adopt when starting personal projects is too malleable to persist in the long-term.

There are some benefits. I've started many side projects and now I have a novice-level understanding of many different things.

As a product manager in tech, this is a good thing. I can code, design mockups, use 3d modelling software, use deep learning tools like GPT2, and so on. I'm no expert, but I understand how all of these work to some degree.

On the other hand, I have many projects I would have loved to continue. I'm not full of regret, but I wish I had a solution to my rapidly changing interests.

Rabbit Holes?

I don't think I'm the only one with such problems. I suspect this is an ADHD issue, but I'm not certain.

Once in a while, the ADHD brain finds a different type of distraction: the rabbit-hole.

Sometimes it's a topic on Wikipedia you read for a few hours, sometimes it's a series of cooking videos on YouTube you want to watch.

Sometimes it's a grandiose inspiration.

I'll start a podcast like I always wanted to!

I'm going to learn piano!

I'm going to make a video game!

The identity follows soon after:

I am a podcaster!

I am a musician!

I am an indie game developer!

As soon as you imagine a new identity, a previous identity evaporates.

The salience of the rabbit hole is such that it convinces us to adopt this new identity immediately. There are too many interesting things on Earth for us to stick to a single one. Or maybe it's just me.

Solutions I'm Not Exploring

In Barbara Sher's book Refuse to Choose!, she argues "Scanners" are a specific type of person who are permanently afflicted with ever changing interests. "This is who you are."

The author argues that some interests are only meant to exist for fleeting moments, and their subsequent abandonment is because "maybe you got what you came for?"

(I find it funny how she creates a new identity for people who constantly change identities.)

In some sense I agree with Barbara. Sometimes all I really wanted was some brief creative outlet. In another sense, I refuse to capitulate because I'm a certain "type" of person. At some point, a therapist told me writing a book was not possible for me because "it takes too long for someone like you." Heh.

I want to create great work. Great work takes time, effort, and overcoming gaps in motivation.

I think I can learn how to do this.

Some Data Points

I abandoned my video game project but finished my book. What was the difference?

Writing my book was a full-time project. I had no other job at the time. I took Steven Pressfield's advice from The War of Art and treated this creative process like a full-time job. I had no side-projects while writing. I never got distracted, and never felt the need to be "disciplined".

Perhaps the nature of the side project is to blame? Something like "oh I don't really need to keep working on my video game."

It's hard to be objectively analyze what's behind my motivation. Is it because writing the book was purpose driven, while the video game was identity driven?

Maybe identity is not a great explanation?

Potential Solution 1: Purpose

A friend of mine argued that what I'm looking for is purpose in these side projects, rather than an identity. Perhaps if a project was intrinsically tied to a purpose, the identity malleability problem would become irrelevant. It seems true enough for my book.

I haven't spent enough time directly thinking about purpose. I just do things I like doing. Perhaps that's the issue?

I'm going to actively think about purpose rather than identity going forward and see what happens.

Potential Solution 2: Doing Less Stuff

I just started reading Digital Minimalism by Cal Newport. He argues that we spend way too much time on our phones/computers. This is a pretty straightforward point and I agree.

I wonder if the constant bombardment of tantalizing information on the internet makes me more likely to find some new project to pursue. If I shut myself off from complete-waste-of-time activities like checking Reddit, would I be less prone to jumping around from topic to topic?

I was going to try to use less technology anyway, but I'll keep track of how this affects my focus.

Potential Solution 3: Discipline

I've always struggled with the idea of discipline. Whenever I have really stuck to a task or project, it has always felt natural to keep going. Obstacles were challenging, but overcoming them was fun. There was no required "push" where I needed to harness discipline.

While not every task has been so simple, I never felt like I needed more discipline to finish my book. Yet I completed it in 3 months and worked on it every day. Does this mean I'm already disciplined? Or does this mean I got lucky with one project?

It's rare for me to consciously avoid a difficult activity, but I also don't live a robotic life. Am I disciplined? I genuinely can't tell.

Discipline is a skill worth building, and I have Discipline Equals Freedom by Jocko Willink on my reading list. I was going to explore this anyway, but perhaps my identity would be more static if I was more disciplined about it?

If avoiding shiny new projects is a function of discipline, then perhaps that's the solution.


I'm going to explore these three potential solutions and see what happens. This is a problem I've found with many others (not just those with ADHD) and it's worth exploring further. People deeply desire the ability to stick to long-term side projects.

I'm also actively interviewing people about this idea. If you have some feedback or comments, please send me an email.

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