Using ClickUp to organize my side quests

In a previous post, I discussed how I use Obsidian to organize my work, and that system has remained largely the same since then. However, I recently encountered a challenge that led me to rethink how I manage both my full-time job and my side projects.

What prompted this shift? Well, I decided I was going to start really trying hard.

It all started when I read this insightful blog post from Aaron Francis about pushing yourself to truly give your all. The message resonated with me deeply. I realized I wanted to place more focus on things that mattered to me—writing, personal branding, and social media. More importantly, I wanted to embrace the things that make me feel alive, like giving talks, writing, and building side projects in my (limited) spare time. It’s part of who I am, and I don’t want to diminish it just to “look cool” and make it look like I’m not trying hard.

Honestly, I’m not sure I have ever succeeded in looking cool anyway.

You can read more about why I write here, but the gist of it is that I write because I enjoy it, because it helps me improve at my job, and because I want to create more opportunities for myself down the line. It also helps me organize my thoughts in a more concrete way than I do without writing them down.

The decision to “try really hard” meant adding a lot of new tasks alongside my regular work. Initially, I just added those extra to-dos onto my usual workflow—using Slack for quick ideas and Obsidian for tracking my day-to-day progress.

But soon, I realized that combining everything into one workflow was overwhelming. It blurred the line between my full-time job and personal projects, making it hard to focus on what I was doing at any given moment. I needed a way to separate the two.

During a retreat weekend at Skamania, I came to the conclusion that I needed a distinct organizational system for these “side quest” tasks, so I could clearly differentiate between work and passion projects. That way, I could focus entirely on my full-time job when necessary, and when I had time for side activities, I could easily access everything related to them.

At the same time, I was taking Aaron Francis’s course on screencasting, preparing to overhaul my Zoom and video recording setup. (Side note: I promise this isn’t just an Aaron Francis fan club post. I have been following him recently because I’m amazed at what he gets done as a fellow twin parent, and it is motivating me to get more done, too!)

In the course, Aaron briefly shared how he uses ClickUp to organize his projects. This reminded me of how I used ClickUp at Hippo Education and how customizable it is. So, I decided to give it a try for organizing all my side quest activities.

I needed to re-create some workflows that had worked for me in the past, such as capturing quick ideas in Slack, but also add new elements that Obsidian couldn’t quite handle—like recurring tasks. Here’s how I approached it:

Organizing projects

The first thing I did was create a project list for each of my side activities. These include the Balanced Engineer Newsletter, my blog, web comics, meetups, talks, social media accounts I’m active on (or want to be), and a section for other side quests—personal or side projects like crocheting patterns or building websites for friends.

For each of these projects, I created tasks for individual actions, and categorized them using the following workflow:

• Idea: I’m still debating whether I want to pursue this.
• Planning: I’ve committed to this project and am figuring out the approach.
• Researching: Gathering resources—articles, videos, etc.—to help me dive deeper.
• In Progress: Actively working on this—writing, recording, etc.
• Editing: The draft is complete, and I’m refining it.
• Ready: Everything is done, just waiting to be shared or posted.
• Complete: The project has been shared and is officially finished!

By organizing my tasks this way, I can quickly view the status of everything I’m working on. It gives me clarity on what’s in progress and what needs attention next.

Organizing each of my tasks and their current status in this way means that I can get a board showing the current status of each thing in my list, which is awesome for knowing what I currently have in progress and figuring out what to do next. I’m also using it as a way of knowing when I have too many side quests on my plate and should finish some things up before starting anything new.

Capturing quick ideas

One habit I’ve established over time is capturing quick ideas via Slack. I jot down thoughts in a note and use the “Remind me Monday at 9 AM” feature to get a reminder.

This process works well for everything from remembering work tasks to jotting down comic ideas or interesting articles I want to read. But as I started managing more side projects, I realized this system wasn’t scaling.

I wanted to keep using my Slack workflow but integrate it with ClickUp. Fortunately, ClickUp offers an easy-to-use Slack integration tool that lets me create tasks directly from Slack messages. It’s been a game-changer!

I integrated this tool into my “Cool Tech Kids Club” Slack channel, where I chat with friends and follow RSS feeds. It’s working really well so far.

Making reoccurring tasks

One thing I’ve learned about building a social media presence is the importance of consistency. And while I’ve never been the most consistent social media user (except on Discord), I’m actively working on improving that habit.

To help with consistency, I created a posting schedule with recurring tasks in ClickUp. I’m curious to see if this system helps me stick to a routine.

Organizing docs about my side quests

Although I’ve done a good job writing and organizing content in Obsidian, I wanted to separate my “content” from my “content about content” (like social media strategies and course notes). The goal is to make it easier to link these resources to specific tasks in ClickUp.

To solve this, I used ClickUp’s document feature to store my notes. For example, this “Social Media Strategy” was created with the help of ChatGPT. Thanks, internet!

Conclusion

This was a really fun and rewarding exercise during my retreat weekend at Skamania. I love organizing things, and if managing digital workflows were an Olympic sport, I’d definitely be competitive!

By creating a system to separate my full-time work from my personal projects, I’ve found that I can focus more effectively on both. The result? A more organized, productive, and stress-free approach to managing my work and passions.