I appreciate the response, and I will try to explain more where I'm coming from.
The automation I see coming for the 'creative' jobs doesn't need to completely eliminate professions to cause a problem, just reduce the number of people required. As a Netflix animator, I've watched as the software we use gets better to the point of doing many things for us. My job used to be done by about six people, so a smaller workforce is required. I can imagine a day when software automatically poses character rigs to storyboards, and then uses machine learning to generate keyframes. Then animators would just check that they look okay, adding details where necessary, and hitting a button to build extremes and then inbetweens. The inbetween stage, which smooths out the animation, is almost entirely automated now.
Lawyers will still be around, but they'll need far fewer people to do all the research. Doctors can double check a machine-generated diagnosis and so see more people. Writers have already been replaced in generating business and sports articles. There will always be writers doing more creative things, but the more formulaic stuff will be computer-generated.
It should be a great that we can do more. (Newgrounds is certainly a better place for it.) My view is that those gains should benefit society, instead of just whoever happens to own the machines doing the work. There was a break between productivity and wages in the 1970s. I think we're all overdue for a raise... even the people that have been put out of a job.
Jobs are of course being created by technology, but an order of magnitude more are being taken away. I don't see how retraining is going to fix the problem. Maybe those displaced can be retrained to find something new, but it's the speed of change that will cause a lot of damage. Maybe you've seen how few people Netflix employs, and how many jobs were done away with when Blockbuster disappeared.
I'm guessing you live in the States. You might look at the low unemployment rate and think things are fine, but it's only the service sector expanding. This means that all other jobs are shrinking and people are forced to do more fast food jobs or things like driving for Uber. Automation tends to go for the highest paying jobs first... it's why there are giant robots in car manufacturing, while low-paid Chinese workers still put together our phones. As machines become cheaper than people, a lot of people are going to suffer.
In your view, and a lot of others, there is a nobility to work that enables us to become deserving members of society. If one does not work, they are freeloaders and deserve nothing, etc, like the person with the truck you mention. This puritan work ethic runs into problems once there aren't enough jobs for everyone. So the response is usually denial and saying that there will always be jobs, you can create your own job, etc. I found it interesting to read accounts from the Great Depression about how conservatives with such views came to accept government handouts as 'just the way things are now,' once they found they weren't able to get work.
I think that we have certain axioms about work and justice that we form in our teens, which lead to our overall political view. These things are deeply rooted and almost impossible to change. Whatever evidence we see in the rest of our lives, we tend to pick and choose to fit our worldview. It takes a long-term, conscious effort in order to expand our ideologies.
So maybe nothing I can say will change your view. But I hope you can keep an open mind and try to see where others are coming from.