What I was wondering about was more along the lines of what his mind comes up with to fill in the blanks between someone arriving at work in the morning and leaving for the evening. In other words, what does he think the functions of a given job are, or has he even grasped that concept? He sort-of understands the idea, but there doesn't seem to be much depth to that understanding.
It definitely is a mystery but as others have said, his influences of work is like mostly come from the media he consumed. In the early days, he said he would like an "office job" but never could elaborate. My guess is, he just sees it as sitting down most of the time, and playing around on a computer. I imagine his idea of going into marketing early on in community college, was that he would draw an ad or two, or else look at other people's work and approve or disapprove the designs. Sort of like a test audience picking things they'd like or not like, but instead, Chris would be in charge.
When we got to the begging Sega for a job, he wanted a corner office, and an assistant, who, much like his sweetheart, would do all the work, whereas Chris would I guess, make decisions? Yell into a phone "buy!" or "sell!" based on something?
His roleplay he did with the Legos seemed to shed some light on it, as in Chris had no idea what his wife did other than have a hard day and get yelled at for whatever.
It's absolutely insane how much time Chris has spent around other people in various times of the day, talking to many different people, yet he has absolutely no idea what they do. I guess it culminated in his "real player one" nonsense where he thinks everyone is just some sort of barely thinking zombie, just going to work, shopping, watching tv, fucking, and doing everything like in the Truman show.