The philosopher Galen Strawson has a knack for translating big, abstract questions – the kind of things you might assume were of little interest outside philosophy lecture halls – into puzzles so personally troubling I can’t continue with my day until I’ve figured out where I stand on them, or at least been distracted by a sleepless baby or enticing cheeseburger. He does this repeatedly in his invigorating new book Things That Bother Me (which, incidentally, would be the title of many more books, and most opinion columns, if we all had his candour). For example, take the timeworn conundrum of “free will”, or rather one specific part of it: for which of my accomplishments in life am I entitled to claim credit? We’d surely all agree that some Trumpish child of privilege, born to wealth, deserves no credit for striking it rich. But as Strawson vividly demonstrates, the matter goes deeper – and gets a lot more uncomfortable – than that.

What if you’re super-rich but got there thanks to your intelligence? You were just lucky to be born intelligent. What if differences in intelligence are down to nurture, not nature? Again, luck: you didn’t choose your parents or most of your teachers; and in any case, you might not have been gifted with the self-discipline to learn from them.

OK, but what if you taught yourself the self-discipline? Still luck: you were gifted with the sort of character capable of cultivating self-discipline.

On and on it goes: whatever your station in life, you got there by following some course of action. But even if that course of action were wholly your doing, you still had to be the kind of person able to pursue it; and even if you became that kind of person by the sweat of your brow, you still must have already been the kind of person who could raise that sweat…

Eventually, working backwards, you will reach some starting point that can’t have been your doing. The troubling conclusion is that the person born in poverty, with no parental support, who scrimps to put himself or herself through college, finally achieving success through ceaseless suffering, owes their triumph no less to luck than, say, Eric Trump does. Or, as Strawson pithily puts it: “Luck swallows everything.”

Among other things, this has interesting implications for the way we talk, these days, about “privilege”. Some people undoubtedly have advantages over others thanks to their gender, race or class. But if it’s true that luck swallows everything, there is also a sense in which differing degrees of privilege are the only thing there is: your social situation is a matter of luck, but then so are your underlying skills and character.

We should fight, strenuously, to make society less sexist and racist. But the result won’t be a world in which accidents of birth matter less; it will be a less sexist and racist society, in which accidents of birth still account for everything.

I realise that plenty of people, some much smarter than me, don’t buy this view of free will at all. I’ve never been able to find a flaw with it, though. It’s dizzyingly unsettling, but that’s just my tough luck.

Listen to this

Galen Strawson, Helen Beebee and Simon Blackburn discuss the brain-pummelling puzzle of free will in a fine 2011 episode of the BBC’s In Our Time

oliver.burkeman@theguardian.com