I recently had a twitter discussion about why I don’t like using Basecamp.

It’s a bit weird, I love Rails and it originated from the need to create a stable framework to create Basecamp. DHH and his colleagues were generous enough to share it with the rest of us and I’ve been using it for years to great effect. I admire DHH and the guys at the company and have read their books. But I hate their product. Using it makes me feel depressed.

I can’t see the flexibility others see anywhere. They are a poster child for great design and easy UI and it’s pretty dull and obvious, maybe that’s what the fuss is about. I’ve used it off and on for years and it doesn’t seem to have substantively changed in all that time, yet there are allegedly changes and improvements happening to it constantly. It’s also boring, even more boring than the bazillion sites you see built on top of Twitter Bootstrap – because they usually have some metaphor the coders are exploring and bootstrap’s a quick way to make it presentable while they experiment.

But the main thing is I can’t stand todo list apps.

This comes out of the way I work and think. I will write todo lists on paper and cross them off, but for anything bigger than just me (and up to 5 items) I need to visualise it and look at the flow and commitment of work. You can’t do this with static text-based lists without doing a lot of counting in your head. As far as I can work out you can’t create a different visualisation (in Basecamp) where you have a private list taken from other lists of things you care about today in the order that matters to you without creating another list that isn’t linked to the original tasks so you’d have to close everything twice. It hasn’t changed in years.

In the physical world you can do this with sticky notes or file cards and a bit of blu tac to put each piece of work into something that can be visualised and moved about. It doesn’t have to be complex, but nicking ideas from scrum and kanban around allocating points for pieces of work and limiting your work in progress (WIP) you can come up with something that lets you look at your pipeline and your commitments so you can start to have grown up conversations with other people about priorities and schedules. Limiting your WIP also gives you a far better chance of actually getting something worthwhile done. This is a big win over boring lists, but harder to understand at first.

Todo lists are, I think, a great tool for linear thinking and controlling.*

The metaphor lists give you is the linear instruction manual, codes, all you can do is change their priority and create more items. They also suffer from being unbounded, so you can just keep adding to them and never finish. There’s a very interesting time management book by Mark Forster called Do it Tomorrow. In it I found the idea of a closed list. This is a list you don’t add to and work on until it’s done – he’s discovered this makes you more productive and also you start tackling the tasks you really don’t want to do because you can’t close the list off until you’ve done them. This is a great antidote to procrastination. It’s also limiting your WIP. In fact it’s a different take on the same idea as a personal productivity booster.

So, in essence, for me the list metaphor stifles your ability to think and visualise without a lot of effort breaking out of the mental straightjackets it puts you in. There are better metaphors that allow you to easily move work about and discuss it properly with stake holders. So use them a little for small tasks, but for the big stuff – use bigger metaphors. I also think gantt charts cause similar cognitive blindness when you use them for anything other than checking if you are still on track.

* Aside: I was going to use the phrase command and control. The original meaning of this was simply that military operations have a designated officer who is responsible for seeing the mission through. How that officer does it is not defined. Some systems thinkers, for example John Seddon, use this term to mean enterprises where the people doing the work are not expected to show any initiative and be told what to do all the time so everything costs a fortune and is badly done by people who could do a much better job if left alone to do it properly. Military operations don’t work like this, people are trusted to do what their training tells them so they can achieve their objectives, see commander’s intent. Seddon’s meaning seems to have triumphed in systems thinking debates, however.