Comparing Paper vs Trello vs ClickUp vs Monday.com vs Asana vs Basecamp vs Jira vs Linear vs Github

I've come to terms with my life being too complex to fit in my brain. I write content, read papers, write software, give presentations, meet with community members, and more. On top of that, my ADHD is pretty bad, so I do not naturally want to stick to one project. If I choose priorities based on emotion, I will always ride my motorcycle. And you can't write software on a bike. The only solution that works for me is externalizing my executive function to a system.

Further, since I am an engineer and manage projects for other engineers, it's simply a non-starter for the state of tasks to live in my head. Nobody can have a shared vision on a project this way.

When I began my career as a software engineer, we used a system of Sharpies, index cards, and bulletin boards to manage tasks. Paper and pen remains my favorite system; I also believe it is the healthiest system for our meat computers. The small index cards created a physical boundary to prevent over-scoped work; we could see who was doing what by scanning the office floor for cards, and software specs were collaborated on paper, where deep work was more readily achieved. However, in the years following, physical space became rare and expensive in North America. So, collaborating physically in an office is a pipe dream.

So, my approach to selecting a task management solution will be the following:

  • Digital Task Manager: a coarse-grained personal task manager and the team's single source of truth
  • Paper Planner: an hour-by-hour personal task manager

My weekly cycle will look like this:

MoTuWeThFr Copy today's tasks digital -> paper
Fr Plan next week's tasks

This is a slight oversimplification of the routine because, for example, sometimes planning in longer cycles, like two or four weeks in software development, makes sense. I will also only work some weeks. However, these aspects don't affect what solution I adopt.

Paper Planner

I shopped at the Muji stationery department for my paper planner, which I consider the highest quality inexpensive stationery selection in North America. Muji always has planners, so I drove to Metrotown Shopping Centre to buy one. I wanted something with the following features:

  • Daily planner to do hour-by-hour task planning
  • Blank pages to brainstorm or write notes on
  • Opens flat so spirals don't get in the way of my hand when writing

I chose one with a daily planner on the left side and a grid paper on the right. Sorry I can't attach an image to this post for some reason.

Digital Task Manager

Use Case Analysis

This task is challenging, so I've been procrastinating on solving this solution problem for myself for months. I currently use Linear for task management. Overall, I love the software. However, it comes with some limitations that are dealbreakers:

  1. No mobile app. I often have to manage projects with team members on the go and also frequently need to interact with tasks from my phone. There is a mobile web app, but it's flaky, and the session times out often, so I don't consider it usable.
  2. Guest contributors cost money. Many people I collaborate with only work on a single project. It's a big pain in my pocketbook that I must buy an entire seat for them. I prefer a more limited feature set if I can freely add limited contributors.
  3. Inflexible UI concepts that are specific to software development. This is both a pro and a con. But I run non-software projects, too, so it's mostly a con.

But, there are features from Linear I can't live without:

  1. Projects
  2. Teams
  3. Effort estimation
  4. Prioritization
  5. Burndown charts
  6. Cycles / Sprints
  7. Roadmaps, OKRs, or similar

Task Managers Considered

I am including Linear and any competing task management system marketed at software developers with over 100k users. I pulled these statistics from the internet or by making hair-brained assumptions, so their quality is hearsay at best. Don't make financial decisions based on them.

Here's the table sorted by the estimated userbase:

Name Founding Year Estimated Userbase Funding Revenue (2022) Funding Status
GitHub 2008 100,000,000 $350mm Not disclosed Acquired by Microsoft
Trello 2011 90,000,000 $10.3mm Not disclosed Acquired by Atlassian
ClickUp 2017 8,000,000 $537.5mm $150mm Series C
Monday.com 2012 4,650,000[3] $384.1mm $519mm IPO in 2021
Asana 2008 3,675,000[1] $453.2mm $547.2mm IPO in 2020
Basecamp 2004 3,500,000 Negligible Not disclosed Self-funded under 37signals
Jira 2002 1,625,000[2] $210mm $2,800mm Created by Atlassian; IPO in 2015
Linear 2019 Not available $52.2mm Not disclosed Series B

Endnotes:[1] Asana: Calculated based on 147,000 customers with an average of 25 users each.[2] Jira: Calculated based on 65,000 teams with an average of 25 users each.[3] Monday.com: Calculated based on 186,000 customers with an average of 25 users each.

Must-Have Features Matrix

Doing some research using each tool's pricing and feature matrix webpages, I created this feature comparison matrix:

Features GitHub Trello ClickUp Monday.com Asana Basecamp Jira Linear
Mobile App Free Yes All plans Free All plans Yes Yes No
Projects Free All plans All plans Free All plans Yes Yes Yes
Teams Free All plans All plans Basic All plans Yes Yes Yes
Effort Estimation ? Premium Business Free Advanced Yes Premium Not specified
Prioritization Free Premium All plans Free Starter Yes All plans All plans
Burndown Charts Free Premium Business ? Advanced Yes Premium Not specified
Cycles / Sprints Free Premium All plans ? Advanced Yes All plans Yes
Roadmaps, OKRs Free Premium Business Free Advanced Yes Premium Yes
Price per User $0.00/user-month $12.50/user-month $12.00/user-month $14.00/user-month $24.99/user-month $15.00/user-month $16.00/user-month $8.00/user-month

From a value standpoint, GitHub is looking stellar. I'm unsure if the UI will be practical for non-technical folks. And things are only free for open-source projects. However, this is fine for most of my use cases because I emphasize open-source software development until I'm making revenue.

Conclusion

GitHub is looking stellar from a value standpoint. However, I think I will find the following:

  1. It will excel at pure-text tasks like software development and writing
  2. It will be onerous to use for physical tasks like home renovations

I may have to accept that I will use more than one digital task manager.