For most of my adult life, I’ve worked in professional services where billing was done by the hour, so tracking time was a necessity – which doesn’t change the fact that I’ve always hated doing it.
Even when I was tracking my time, I almost always did it after the fact, meaning – I did the work and then when it was time to complete the timesheet – I figured out how I had spent my time for the previous day (or week).
I’ve been making a conscious effort to track my time in real time. (I’m using the timer in Toggl.) The first barrier to this for me has been that I have to figure out how to categorize this particular block of time, and I want to get started on doing the thing I’m about to. Tracking time is almost never done to just have a log of how you spent your time, but to accumulate time into “buckets” to be analyzed and tracked (and frequently – billed). In the past, I ran into similar issues when trying to start budgeting money in Quicken.
I’ve learned that there is value to getting in the habit of tracking your time even before you’ve figured out how you’re going to categorize it. In not much time at all, I’ve starting thinking – just before starting a new task – “I’m starting something new” and click the button to start the timer.