The Problems With Planning Too Much

I was reading an article on Medium today about how planning is more like escapism than actually making progress on anything.

I’ve read similar articles and books where they convincingly put forth the idea that when we imagine things happening, we feel like we have made some progress towards them actually happening. While this may help with things like confidence, it can harm our motivation and sense of urgency.

I can understand the point that the article was trying to make and agree that we have to be careful about that when we are planning, but I take issue with the lack of solutions offered! Whenever I have a problem, I’m immediately thinking up solutions to tackle the problem and won’t draw a lot of focus to the problem until I have some idea what to do about it. The idea might be to just avoid it, but when it’s something that so many people seem to benefit from, that seems like a missed opportunity to really dig into it.

We are bad at estimating time


One point made in the article is that we are generally bad at estimating how long tasks will take us. I agree, I’m not great at it, but I found that my estimates of routine work tasks are usually no more than half an hour off because I didn’t start estimating how long my tasks would take until I had actually tracked how long they usually took.

I used Toggl in my browser to track different tasks and sub-tasks while working on them for about a month before I started making estimates of how long upcoming tasks would take. In the beginning, my estimates could be off by hours, but I was learning what threw off those estimates and how much extra time I might need. For example, if I need to implement some sort of change and I’m sure how to apply it, I now add an extra hour onto what I think I need and that usually works out. If there are particular changes in the market that could affect our company, I expect up to two hours of interruptions per day until things die down, because that’s what I’ve seen happen before.

When you track your time in an app, you can also usually add notes for context. When you look back and wonder why something took you double the time, seeing those notes will save you from a lot of head scratching.

We’re overly optimistic

Another point made is that we are usually overly optimistic about our abilities and don’t factor in downtime. This is absolutely true, but it doesn’t mean that we should stop planning! No, instead we should plan downtime as well, because it’s going to happen, we aren’t machines. I have my one hour lunch break every single day, and to get that sometimes I have to accept that I won’t fit in all the work I want to do. That’s okay, because I wouldn’t be anywhere near as productive if I didn’t give myself that break and scenery change halfway through the day.

When I schedule my tasks, if I have any that take over an hour, I won’t put more than two of those back to back, because during those hours anything could come up and two hours becomes three. When they do, I’m glad I didn’t try to fit another hour long task in that window, and when they don’t I have an extra slot where I can move up my schedule from later on in the day, insert a small task from my ‘quick wins’ list, or just take a short break for a cup of tea or a chat or catch up on a blog.

We plan more actions than we take


The final point I am going to address is one of the important ones, planning everything out in detail might make us feel good, but when we have too many action steps we can end up ignoring all of them and only doing the most urgent things because they jsut have to be done. My proposal against this is just to not plan everything at once. Nothing ever goes perfectly and planning too far ahead is definitely a bad way to go. When I have a lot of projects to complete, I make sure to add them all to my projects list (as many as I can remember anyway) and then forget about them until I have a random idea to add or am actually starting the project.

Planning in advance can be a lot of fun and feel like a really positive move, but unless you’re taking action on the steps you planned out, you’re going to start feeling a loss of momentum and it’s going to undermine the plan you made. Only go into detail on the steps you can take now and then don’t go any further until you’ve taken them.


Planning can be a lot of fun and a form of escapism, but we can indulge in anything too much and that’s the key, focus and moderation.

With that in mind, here are a few guidelines for planning:

  1. To build good estimates, start tracking your time, and always track tasks you’ve estimated against so you can refine them further.
  2. When planning tasks together, leave yourself windows for interruptions and complications, don’t put lots of tasks back to back.
  3. List out the top level tasks you need to do, but don’t start planning them until you’re ready to get started, and only plan the steps you can take now or soon.

There are more but I think those guidelines cover the issues raised in the post I mentioned, and that’s all I aimed to do today, so this part of my plan is done!

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