If you’d been born a hundred years ago, what would you have done for a living?1
This is not the same as asking, “Of the jobs that existed 100 years ago, which would you most like to do?” Because if you had been born 100 years ago, no matter what kinds of jobs existed, you’d only have access to a few of them.
One way to imagine possible answers is to drop yourself into a random family a hundred years ago. For location, pick the same one you were born in, or at least one in the same country. If you were born a woman, there were a handful of safe options (teacher, nurse, hope you get a kind husband, etc.) and many more bad ones (think Kate in Nicholas Nickleby or Fantine in Les Misérables). If you were a man, you could have more possibilities, but how many would depend mostly on your upbringing. All of this is still true in many places.
Another method is to dial back your own particular ancestry 100 years — picture yourself taking one of your great-grandmother or great-grandfather’s place. You might know what they in fact did end up doing (or you might not), but what options were available to them? Could they have gone to college, or owned a business? Given their circumstances and the way they were taught to think, what were their real options?
I have this difficulty because I don’t even know what I would have done for a living if I had been born 33 years ago, and in fact I was born 33 years ago. Many jobs exist now that didn’t exist when I was born or even when I finished high school. Someone a hundred years from now will say I could have been, say, a social media manager, or an investment banker. But “could” is a deceptive word because it hand-waves a thousand invisible constraints. Sure I “could” do anything for a living, including social media or investment banking! Except when the “social media manager” job was invented I was busy doing other things. And except that growing up, I didn’t know any investment bankers, didn’t know what they did, and didn’t know of any reason to pursue it. And except that in order to do either of them now, I would have to give up a lot of pay and spend years of effort to restart my career (a definite penalty to my growing family which we see no reason to take, though that could certainly change in response to circumstances over which I have ultimately no control). And except that I consider investment banking horrifically boring and I also loathe the cynical activity of social media marketing. So I “could” do anything! But in fact, I never will, so actually I can’t. I’m not saying I don’t have options — just that they are realistically limited, far more limited than those who idealize individual willpower would like to believe.
And that’s why I find this question interesting: because by trying to understand the real lack of choice we would have had a hundred years ago, I soon come around to the lack of choice we actually still face today. People today face the same set of constraints: the resources of the families we’re born into, the way we’re taught to think, and even our own desires and aptitudes — which we’re famously bad at figuring out.