As for me, I've had a much different relationship with the tax system. I spent about...30 minutes yesterday getting all of my taxes done. This wasn't a testament to my intelligence, but rather a reflection of the speed of the software that's currently in place. Even as I type this, my taxes have already been officially sent to and accepted by the IRS and my refund should be here within the week. It's incredibly simple and, while I understand some people have incredibly complicated tax situations out there, for most of us, it should be a breeze.
And yet, every year, thousands don't file returns. Many that do, try to do themselves themselves. Others assume they're "bad at math" so they pay ridiculous prices to "their guy" who will "get them a great deal" and do their taxes for them. The tax prep pros have done an excellent job selling their tax-prep software to DIY-ers by promising the process is easy...while simultaneously convincing people that doing your taxes is still really really hard. It might have been difficult 25 years ago, but by now, it's as simple as taking a Facebook quiz or buying something on Amazon. The stigma remains based on the past practice.
In education, I think I see this all the time as well. Our profession and our students are full of dread about tasks they assume to be difficult which have long since become simple. Finding online sources, conducting reviews of content for background research, locating secondary sources, and editing for grammar/spelling are all infinitely simpler than they were...and yet still haven't moved past them. Rather than zipping through these now-simple steps and moving to move complex learning, students (and teachers alike) continue to just dumb-down instruction and understanding on these topics so they take just as long. It used to take two weeks to find sources and take notes...and we still take the same amount of time. Just as technology as improved to help students; the students have decided to bring less and less to the table, which nullifies the process.
How can this be improved? I'm sure the IRS is asking the same thing when it comes to taxes. At the end of the day, neither teachers nor the IRS is interested in the process...they just want the learning (or the money) in the end.