> First, "living on the dole" has a bad connotation. You are already setting social norms as you say it. Implying that it would be shameful to do so. This plays into the idea that people's needs for esteem is driven by societal norms.
It's not an arbitrary "social norm", it's a human near-universal, at least to some degree, to stigmatize freeloading and value at least some sort of productive activity. After 30 seconds of reflection you can probably figure out why, and after a further 30 seconds of reflection you can also figure out how these attitudes are already engrained at a deeply emotional level for many.
> Second, as it stands, those two options don't afford you the same produce and sercices. Working still raises your standard of living higher but what if it didn't, and in fact, paid less? That is the hypothetical I am talking about.
It's not really a hypothetical--lots of people are in either a welfare trap or a disability trap where they are capable of working and would actually like to work, but doing so would jeopardize their eligibility for benefits, and they can subsist off the benefits more reliably than they could subsist off of their work. These people are almost universally incredibly unhappy with the situation.
Furthermore, if you look at other situations--retirement, winning the lottery--where there is no economic need to keep working in order to earn an income, there are still high levels of depression, suicide, and drug abuse that soon follow. This is one of the reasons that people at the top of social hierarchies--executives, politicians, judges--very, very rarely retire once they reach a "normal" retirement age. If you're powerful enough, you can reduce the scope of your actual job to the point that you can still do it. At that point, the main barrier is retaining the capacity to work.
> Third, you've moved the goal post. Because this isn't about the choice between not working and working a bad job. I'm talking about the choice between not working, or working towards a good job. And which one would feel more rewarding?
Let's look at the jobs you pointed out as "bad jobs":
> an oil driller, an iPhone manufacturer assembler, a McDonald cashier, a dishwasher, a house cleaner, etc.
First off, your choice of "bad jobs" alone comes from a place of arrogant upper-middle-class ignorance, because those jobs don't really have much to do with each other.
Oil rig workers have good pay--averaging around six figures, actually--and long career paths with lots of opportunities for advancement (https://money.cnn.com/2012/05/10/news/economy/oil_workers/in...) (https://www.jobsite.co.uk/worklife/work-oil-rig-18734/). Oil rig work is an entire sector of the economy you obviously know nothing about if you're comparing it with washing dishes in a restaurant or cashiering at McDonalds. Just like factory work, farm work, and construction work--nobody thinks its fun, but the people who do that work take pride in it, and are right to do so.
> But the reality is that, it doesn't make sense to have people do things that aren't needed.
There is also no shortage of things that are needed.