I have a million things to do, and I know I should probably do them all at some point. But it’s hard, I’m tired, and I don’t know what I should do first, so I freeze at the idea of doing any of it. 1
And I know I’m probably not alone in those kinds of thoughts. After all, you’re reading this article I wrote!
As someone who works in project management professionally and does a lot in their personal life, I can say that knowing what to do and when to do them helps give peace of mind, whether in a team or individually. And I also know how easy it is to say all that and how tricky it is to actually do it. I’m by no means perfect at it.
But being perfect isn’t the goal and you don’t do perfect to get what you want done. So here’s an imperfect method you can use to get an idea of how much long something will take.
The method, in short
Ask if something will take a really large amount of time (I usually go with a year). Since most tasks don’t take a year, this will be easy for most people/you to reject. Work your way down (say six months, three months, etc.) until you get answers that are rejected less easily out of hand. Once you get to answers that can’t be readily rejected, you have an estimate.
If you want to get it towards a range, you can do another round where you start bottom up. Ask if it will take one minute, then five, fifteen, an hour, working your way up until answers aren’t readily rejected. Now you have a bottom limit.
And that’s it! There’s the method, you can stop reading if you want.
But why do it this way?
There’s two questions you should consider when thinking about why. I’ll answer them separately.
Why estimate effort or time at all?
The most important reason is to help prioritize what you have to do. You have a lot to do and you need to pick what gets done first (maybe even what gets done at all if you’re on an energy budget). There are two things that help you make that decision: value (which won’t be discussed here but maybe in a different article) and cost. Having idea of cost (here, effort or time) helps you know where you can get the most value for what you give. If you can get the same amount of value out of an activity that takes less effort, then it makes sense to do that first.
Also, it gives you an idea of how much time you might need to budget. If you have reason to think something will have 8 hours to finish, you can think of how to give it 8 hours. Do you split it up by days, or do it all at once in a free afternoon? Maybe it’s something you need someone’s help for, and I found people appreciate when you already considered how much of their time you’ll be taking up when you ask.
Why estimate effort this way?
The most common response I give to myself and that I hear from others when I ask “how long would this take” is “I don’t know” or “It depends”. These replies come from a place of wanting to give a “good” answer but stumbling over all the possible considerations that could get in the way of giving a quality answer. They come from a good place, but ultimately, that’s not the thinking we need to employ when we want to prioritize tasks. Really, what we want is to put our instincts to use to decide the estimate, and that’s the level of human judgement we are trying to extract here.
I’ve noticed that people have a tendency to struggle generating “good” answers, but have an easy time rejecting “bad” answers. This approach uses this to your advantage. After all, in order to say definitively “this task will not take a year, no way”, that suggests the person has a feeling for what a reasonable amount of time should look like for the task. By progressively working away from an unreasonable estimate, we get closer to a more reasonable one.
Should we estimate effort as time?
In project management literature, you’ll commonly see effort quantified in one of two ways: Work time, or story points. (This is a bit of a simplification, PMPs don’t come at me please) My method tries to take advantage of the benefits of story point estimating (which is that relative estimates are easier to come up with than absolute ones) to estimate work time. But is work time even a good measure of effort?
We could use story points and rely on relative weighting, which works great for software teams working on complex features. But those come with the disadvantage of story points being a context-heavy unit. Is five story points a day of work? It can be for some projects and teams, but not always and definitely not for a different team or project.
What you’ll often see in project management is conflating effort with the time it takes to work on something and abstracting away other factors that come with effort. Story points try to account for this fact, unlike work time. For individual creatives, artists, and people trying to do things in their lives, this approach leaves out consequential factors such as energy, recuperation, and emotional resources. Put simply, effort as strictly time spent working will lead to burnout.
So that’s why you trust your gut on estimates
The method of starting large and going down (and vice versa if you want a range) takes advantage of human intuition of the task as a whole. When you ask yourself about the time something would take you to do, a part of you is thinking about what doing the tasks would imply on you and adapting your thoughts for it.
Let’s say you’re thinking about the effort of a energy draining task (maybe something that needs a lot of research and could bring you out of your comfort zone). A lot of the time, the feelings of discomfort might prevent you from starting that task. But let’s repurpose that instinct: When you start estimating and going down in sizes, a part of you should be thinking about how you might need to recover from doing that task. So sure, it might only take a few hours to research something, but if your gut is saying it could take a day to do it, then that might be part of the legitimate effort of keeping yourself sane and healthy while doing that task.
We’re getting the best of story points but keeping ourselves tied to real world units. You’re already thinking of the effort involved and giving yourself that buffer.
This kind of thinking is unusual in professional project management. There’s probably a lot of cultural reasons for that which I might write about at some point. But ultimately, if you’re thinking of just you and what you want to get done, you’re going to need to factor in rest as part of the effort in getting work done so that you can keep going. This is true for anyone, but I’d say it’s especially true for those looking to pursue creative endeavours.
Who should try this?
I think this advise serves individuals and small teams best. If you want advice for enterprise, hire a consultant lol
Ideally, this is to get you a rough order of magnitude so you have a base to decide what you should spend your time on. There are methods to get a more detailed estimate, but I find that is usually not necessary at the scale we’re talking here. Don’t spend more time planning to work than actually working (or resting from working).
What next?
That was all I had for you today! Just wanted to write a quick thing about this trick I use to get an idea about how much time something will take me.
As part of prioritizing your todos, you’ll also want to decide how valuable the things on your list are to you. I’ll be discussing that in a different article and hopefully linking it here if I remember to do that!
Footnotes
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A lot of these feelings I’ve described were reduced (but not eliminated) after I began treatment for my ADHD. Just a thing to think about if you relate to me way too hard.
If you’re in the neurodivergent boat with me, please be aware that a lot of productivity advice out in the wild is designed for neurotypical people in mind. What I put in here are things that actually work for me in my experience, but think with you and your circumstances in mind. ↩