Do you feel like it's impossible to figure out how long something will take? Do you find yourself at the end of the day wondering where the time went, your un-done to-do list mocking you? Don't fret! You are certainly not alone.
The esteemed Daniel Kahneman and his colleague Amos Tversky first proposed the Planning Fallacy back in the 70s, explaining that humans have a bias towards optimism when estimating their own time regardless of prior knowledge to the contrary. (But interestingly, humans have a bias towards pessimism when estimating the time it will take someone else to do something!)
If you've ever been involved with a construction project, you'll know how true the adage is that for any estimate, "you'll need to double the time and increase the units" (so, 2 weeks becomes 4 months).
It's important to realize that much of our satisfaction/happiness is based on expectations. So, of course we should strive for accuracy, but in the end, if you overestimate the time it will take by giving yourself a buffer, you will be much happier with the result than if you underestimate.
So, humans are bad estimators. True. But, we can take some steps to get improve:
Define the Next Steps
Sometimes our inability to estimate accurately is due simply to missing information. If you've ever had an ill-defined task that you were dreading because you thought it would take a long time, and then simply sat down to start and realized it wasn't that big of a deal, you'll know what I'm talking about.
If you can clearly define the components of a project or task, in as much granularity as possible, it'll be much easier to accurately estimate the time it will take.
This works especially well for travel, but works for big projects as well. Figure out when you need to get somewhere, or get something done, and then work your way backwards, making sure not to leave out any components, to figure out when you need to leave/start. Allocate a little extra time for each step so you have a buffer. Don't assume that because you need to be there at 7pm, and the drive is 30 minutes, that you can leave at 6:30pm. If you do that, you're bound to be late because you haven't factored in parking among other things.
And if you've got kids, you'll know all too well that you need to allocate at least 10 minutes for finding and putting on shoes!
Block out the time you think it will take to get something done on your calendar. Then, update the calendar as you go to see how much time something ACTUALLY took. If you start doing this regularly, you will start to find patterns in your thinking. You'll start to notice the things that take longer than expected, and those that take less time then expected. Once you start noticing this, you'll start to improve at your actual estimations. Or, you can look back at your calendar to check how long something took. For instance, if you notice that it usually takes you about 1.5 times longer to pay bills than you are allocating, you can start to add 50% to any time estimate you give yourself for this activity.
If you've effectively time-blocked, and been diligent about updating your calendar to reflect reality, you can do a simply daily or weekly review of your calendar to get a sense of how long things take you. And you can incorporate that knowledge as you plan for future tasks and projects.
Use a time-tracking app
There are tons of apps out there to help you track how you are spending your time. One that is free and simple to use is Toggl.com. Using a time tracking app will make it more convenient to track how you are spending your time, and if you are tracking where your time goes, it will become easier to estimate how long things will take.
So where does that leave us?
In short, the key to getting better at time estimation is to actually track how long things take you. As Peter Drucker so famously said: "What gets measured, gets managed"