I wrote a while ago that I was using paper to plan in the last few years. For work projects, I use online tools like Asana, Basecamp or Trello (for work editorial and product research) so I can attach text links, photos, and other files. But for daily running and maintenance of the good ship ‘me’, it’s still paper.

Sometimes, I would drop off from the paper method and started using trello for managing ALL the things in life.  But since I also track my time, I noticed it took too long to get things done with trello. I was spending too much time IN trello rather than completing work.

Trello’s greatness is it’s easy to customise and fun to use. That’s also its weakness; it’s too easy to get sucked in with customising and connecting it to other tools. As far as using it as my primary management tool: it had to go. 

Lately, I switched time tracking apps. And I’m noticing now that the app I no longer use suffered from a little bit of Trello syndrome: the same greatness was also its weakness.

My time tracking app automatically tracked what I worked (down to the filename inside the application I was using) on or was reading online, or what apps I used automagically and showed my computer use to me privately in a chronological timeline alongside my tracked work hours. At first, this was motivational, since blocking distractions was a goal in itself, and a reason I subscribed to RescueTime.

Mind the Gaps

But I started to notice and obsess about eliminating untracked “gaps” in my chronological timesheet. Gaps I felt shouldn’t really be there. I knew I was working all day, I wasn’t goofing off.  I started working longer to compensate, but feeling less satisfied with my work.

Since I was working longer hours, my focus started to suffer.  The mornings after took longer to get into focus mode. The time tracker dutifully showed me how I had been distracted that morning as soon as I was ready to start working seriously and opened the time tracker app to plan the day.

I was starting my day with a sense of failure.

If I stopped you, right before you opened the door to home and showed you all the ways you had let your partner down without noticing I’m sure you would deeply affected and resolve to change– the first time. But what if I did every single day for three months, at the same time, the same moment your hand touched the door handle? How do you imagine you would feel once you hand reached out? Excited? Browbeaten? Would it dim your enthusiasm to see your partner? Would you be angry at them for taking offence or small things even though you are trying? Or you be angry at me for telling you each day?

How the app made me feel about myself was being projected back at the app itself. I was reluctant to sign in.

It also didn’t account for the fact that I needed time between tasks for context switching to refresh mentally or to complete add-on tasks that didn’t involve my phone. For example, when I recorded that I went out to get groceries (the app tracks my trips and geolocation and enters it in my personal timeline as a possible time entry), I still needed to put groceries away and put away my jacket, handbag and shoes and get a glass of water, before dealing with my inbox again.

Switching my timer to use increments of fifteen minutes would have been one solution,  -and was optional- but it should have been the default solution, because:

1. In offices, context switching and these tiny interruptions are more common than when working at home, alone. 

     2. Design is always judgmental. The layout of the day as a by-the-minute chronological timeline made me feel like changing those default settings to fifteen minutes was “cheating” and “less accurate”, so I didn’t use it. Had it shown time in fifteen-minute chunks, it would have felt ok.

But, using the timer in the default settings meant I felt the timesheets were not reflective of the true time it took complete tasks.

Doubting my auto tracked timesheets was now a distraction that played in the background of my mind during the day, as I wondered- “but it didn’t only take 16 minutes to write that email update. Something here is missing.”

I was already distrusting my timesheets. And as David Allen, author of GTD says, when your mind doesn’t trust the system, it starts to resist using the system. 

Remember, the unique selling point for me wasn’t that the timesheets were powered by magical AI time tracking fairies. Or even that time tracking takes time. That’s a minor pain since I was using previously using a free time tracker.

My pain as a freelance user was that my timestamps didn’t match how much time I actually spent at the computer, with all distracting sites blocked.

I signed up for paid tracking software because I believed that taking time to track time was where that extra time was going. 

And I was being proved wrong in an expensive, demotivating way.

2. Mindless working

In the book, Mindless eating, there’s an experiment where people eat soup at a dinner party from a soup bowl that fills up just a little bit slowly over time. Because they’re distracted by conversation, they keep eating the soup. No one stops eating the soup or questions why the soup never empties. They simply report how it’s very “filling”.

Auto tracking my time made working like eating that endless bowl of soup.

It removed natural starting and stopping points in my workday. Not paying attention to how long I worked was functioning as a dark pattern. Like an infinite scroll in a shopping site, it encouraged – in myself at least-  working longer and discouraged breaks (to eliminate those damned gaps) that would make working more effective.

The other way the auto-tracking negatively influenced my behaviour was that while using a work tool (say, illustrator or sketch), I would stop noticing whether what I was doing right now was necessary or a priority. Just like in the mindless eating experiment, I was mindlessly working.

At invoicing time, I had no way of accounting for why some tasks took so long.

So I started knocking off logged time at invoicing. :/

The actual reverse thing I wanted from signing up to this paid software. 

Around about that time, I started flirting with another time tracker. It’s not AI powered. I have to start and stop the tracker. You could ask why I don’t go back to the old, free time tracker in that case. But it solves a pain I didn’t understand I had. A pain I thought would be solved by auto time tracking.

As users, we tend to mis-diagnose our own source of pain.

We’ll jump from app to app until we land on one where someone has done the deep work to figure out why we really want what we think we want and solves that unspoken pain.

In my next post, I’ll talk about how this app I flirted with became my main timer, despite costing more and being less “sexy”.

Think about your product’s USP…

Could it also be its biggest weakness?

If so, to what kind of user? What kind of use case?

(no, you can’t say “idiots” or “people who don’t matter”)

Put a “who is this for?” in your FAQ.

People love honesty. You could even put a button or some other CTA where can request a version that deals with their situation. You can do the math on whether the number of requests justified another version or not.