Am I alone in having difficulty estimating how much time a task will take, even after years of experience in the field?

Not if other humans, systems or servers are involved.

I always over-estimate the time it is going to take me to do something and procrastinate. When I finally do it, I am surprised by how little time it actually took.

Not at all, Loli. Any given task might be a Pandora’s box of unanticipated issues and problems.

I can’t say that you’re alone, and I’ve certainly made some wrong estimates during my years as a freelancer. One of my dependable rules of thumb was that every job has its problem.

But because of the way I tracked my time on task, I got good enough at estimating my jobs that I could come in within half an hour on a job that was going to take, say, 80 hours. I always built in some leeway (proportional to the size of the job) for what I called “admin,” which took in those odd hours of overhead.

And there were a few times that I simply wrote off the extra time for the sake of client goodwill.

An important point was that I wouldn’t estimate work on any job sight unseen. (Learned that the hard way.) I had to get a good sense of it before I’d quote my rate and my time.

I’m pretty good at it, but I usually put a large cushion in for something going wrong. I used to track my time, because I billed hourly, so maybe that helped.

I see the difference between my husband and me for tasks around the house or errands. He is much more rigid and expects everything to go as planned (I actually joke he should have been born in Germany) and I find his way of thinking stressful.

Are you a deadline person? Some people like to work under deadlines and I find they give themselves tighter time frames. I’m happy to finish up early, I don’t need a tight deadline.

As my old pappy used to say, never do anything today that you can put off until tomorrow. Sage advice.