These are the Productivity Tools I’ve Tried– and This is Why They’ve Failed Me


At first, everything seems wonderful. I throw myself in headfirst. I want to know everything about my new companion. I let myself believe… This time I’ve found The One.  No, I’m not talking about dating, but rather my relationship with productivity tools. 💔

I’ve tried every productivity tool under the sun. And while they’ve all had a lot to promise, they’ve invariably failed me. There’s a pattern to these failed productivity tool relationships. A hot new tool arrives on the scene. Everyone’s talking about how it’s changed their life: streamlines their workflow, frees up their time and generally transforms their life. I jump in, eager to experience the magic.

And more often than not, after a few weeks or months, I’ve realized it’s not the right match for me.

What I’ve come to learn is that this process is important. We all do this. It’s ok to take that fancy new tool out for a spin and see if it works for you. It’s fine to move on if it doesn’t. But I’m no longer forcing myself to use the productivity systems that seem to work for others. If there’s no chemistry, it’s best not to force it. 🙅

Let’s take a look at the tools I’ve tried, and how it turned out.

Productivity Approach #1: Project Management Tools homepage

What it is: is a platform to coordinate teams remotely and run projects. It’s one of many similarly designed project management tools like ClickUp, Asana, and now Google Tables.

What it promises: Monday promises that it works for “any process, any department, any industry, anywhere”.

How I used it: For managing my marketing tasks and as a work tracking platform.

How long our relationship lasted: 2.5 years.

I really wanted to love—and for a time I did. I think this is a tool that works really well for some people, but it didn’t scale with me or the pace of my work. Project management tools like Monday are great for teams where you have long project timelines, plans are set quarters in advance and you don’t expect much movement. Working at a startup, though, things rarely look like this. I’m used to fast-paced change and racing against the clock to deliver. Taking time out to maintain my project management tool just doesn’t make sense.

Why we broke up: While I loved the organization I gained from Monday, maintaining it became just too much. A productivity tool that was eating into the time I needed to get stuff done wasn’t working for me.

#thankyounext: Monday helped me learn to identify when a project management tool works—and when it doesn’t. I’ll always look back with fondness on those calm quarters of neatly organized projects, each with clear tasks and due dates… But I also know that’s not the reality of my work (right now).

Productivity Approach #2: Bullet Journalling

Photo by Matt Ragland on Unsplash

What it is: Bullet journalling calls itself “the mindfulness practice disguised as a productivity system.” Using good ole fashioned pen and paper, a bullet journal is part day-planner, part goal-setting tool, part diary.

What it promises: According to the creators of Bullet Journals: “The goal of the Bullet Journal is to help its practitioners (Bullet Journalists) live intentional lives, ones that are both productive and meaningful.” Fans claim benefits from getting organized all the way up to improving their creativity.

How I used it: As a highly-customizable productivity tool to create a productivity system for myself.

How long our relationship lasted: 3 years.

My relationship with my Bullet Journalling ended only recently in July 2020 (#RIP). Three years ago, I’d bought myself a Leuchtturm 1917, the German journal brand much-loved by bloggers around the world.

The best thing about my Bullet Journalling system was how I could adapt it to my needs over time—I fine-tuned it over the many months I used it, so it was a truly personal system.

Why we broke up: At a certain point I realized that far from helping my productivity, my Bullet Journal was actually hindering me.

There are three big reasons for this:

1. A lot of overhead time spent setting up my journal for each month. (We’re on a mission to eliminate work about work like this at Charli AI)

2. Not enough flexibility week to week without just creating a glorified to-do list.

3. The paper-based system was increasingly not needing my needs… I wanted access to my information everywhere.

#thankyounext: The minimal system was appealing to me, and as someone who is into creating productivity systems, the process could be quite fun. But when I realized that it wasn’t actually doing what I needed it to, I knew it was time to move on. The art of actually being productive seems to rest on how many of these productivity tools you say no to in the end.

Stay tuned for part 2 next week where I’ll dive into a few other approaches that worked…then went stale and one that is still working.