What happens to a world's working population between the phases of manual labor and total automation?

Short Version

(During the next 500 years on Earth) How does life change for students during school and after they graduate, to find work in a world where our economy is still based on gaining wealth by providing services but fewer and fewer services and tasks are performed by humans?

(I'm interested specifically in a breakdown of the change over time, assuming the premise below.)

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The Setting

Years ago, anyone who wanted a job and was willing to work hard could get one. Back then everything was done by hand, manually. Then the industrial revolution came and we started automating as many processes as we could.

Eventually, lets set a premise that this will lead to a point where all processes are almost fully automated, and the worlds production, technological advancement, and services, are handled with the help of artificially intelligent computer software, by a few thousand engineers, scientists, and world leaders. That leaves about 99-point-something percent of the world's population free to focus on arts, entertainment, athletics, etc.

At that point, with nearly total automation, people don't need to perform tasks to make the world function, so there's no need for a job. You either choose to have one or not. The world's wealth will be spread based on the entertainment industry, with world government equally distributing goods and automated services, with people competing for more resources (for a more luxurious life) by performing services in the entertainment industry or as a scientist, engineer, or politician. It's a good time to be alive.

Utopian society, you get the picture.

But my question is about the working class during the transition between manual labor and this destination of total automation. The world we'll live in, lets make up a figure and say, during the next 500 years.

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The Question

Here's what I want to know, assuming all of the above premises are true:

Going century by century, for the next 500 years, what happens to education and jobs, to cope with this transition between most people having jobs (now) and most people not needing them (2,516AD).

How does life change for students during school and after they graduate, to find work in a world where our economy is still based on gaining wealth by providing services but fewer and fewer services and tasks are performed by humans?