Here is my interpretation of how we should examine privilege, in terms of living our lives as successes (in whatever capacity we think success is: education, happiness, financial independence, whatever). Hint: you're not supposed to feel guilty, so you don't need to get angry and refuse to feel guilt. But it's nice to be grateful, so read on.
Most of the things we want out of life aren't handed to us for free. We see what we want, and we evaluate it (a new car... scoring top of the class in the exam...). We decide if it's worth it. If we want it, then we make it our goal. We figure out what we need to do in order to achieve that.
Perhaps we have to save money, get a promotion. Perhaps we have to study hard. Life can still spring things up in our way to foil our attempts, but by and large, getting it requires personal effort.
So when we get that something (the house we saved ten years for, the scholarship we worked towards) then we are justifiably proud that we did it. If you put some hard work into the widget machine, out pop the widgets.
Except that we often forget that it wasn't always hard work alone. Particularly in things that require competition against others (we got the job, we bought the house, we landed a scholarship). We tend to think about these things in a vacuum, as if nobody else had to LOSE so that we could WIN.
Someone had to lose. We had to tread on heads to overtake people on that ladder.
Big deal! - you say. They should have worked as hard as I did.
Well sunshine, perhaps they did.
Perhaps they studied longer, but couldn't get proper sleep because they were cold. Maybe their parents couldn't send them to college. Maybe they didn't get a scholarship because it's hard to study with five small siblings in the house with you. Maybe they were too hungry to concentrate in class. Maybe they skipped middle school any time their mother's babysitter cancelled. Maybe the girl missed out, because the scholarship went to a boy who was more confident on the debating team. Maybe she was late to exams because of her crutches. Maybe his accent ruined his marks in English class.
Maybe it's far simpler than all this: "people who start with a disadvantage still have options to succeed, they'll just have to try harder." It is amazing how often this comes up. "Sure, you can't afford college, but you can still get a scholarship!" These sorts of things. Stop and think about it for a moment. The underprivileged kid has to try so much harder. The privileged kid can just sail in on average marks because there is a way for them to pay their own way through if the scholarship doesn't happen (their parents' savings, etc). Stop and think about it. Life is very unfair for the kid who has no other choice but to go after that scholarship. It's their only shot. And they're up against middle-class kids who just don't WANT to pay for school. Even more unfairly, the middle-class kids will still get to go, even if they fail to get the scholarship...
Now this does not mean that your success wasn't earned. You worked for it. Your hard work got you over the line. But for most people, hard work was not the only thing that got them there.
If you are still not convinced (hey life's not fair, suck it up) then let's go to working life. You got to be successful in your job because you worked hard. You have put hard work into the widget machine, and a good job came out. You earned it.
Or maybe the other guy didn't get that promotion because they're black and your boss gave the job to you. Maybe she quit because the baby's coming. Maybe he couldn't work while on dialysis. Maybe the power was disconnected, maybe they didn't have a phone, maybe they didn't look as good as you at interview because their clothes had a hole. Maybe the car broke down and they didn't have savings to repair it, because they had student debts.
So now you're thinking about their poor planning? Well maybe you had student debts too! But when their fridge broke, their dad didn't loan them the money. Nobody in your house stole your wallet to pay for a drug habit. You're probably not disabled. You're probably not transgender. You're probably healthy - or if not, you can probably go to a doctor.
The thing with having disadvantages is that they often breed more disadvantages. Things that the happy graduate or worker usually hasn't even considered. Car breaks down, it's inconvenient! But imagine there was no money to fix it, so you spent the rent to get it repaired. Then the rent will have late fees so you won't have grocery money. So you take a payday loan.
Then you can't pay it back. So they take the car, so you lose your job. And you can't pay rent. So you're evicted.
Perhaps at this point you're "lucky" enough that a friend takes you in.
How long will it take to try and save the deposit for a new flat while living on a friend's living room floor with no job? Oh and furniture too - you didn't have any money for a U-haul, so the landlord threw it all out.
Homeless and jobless - all because of a $100 repair on the car. Things that would never have happened to someone who had just $100 in the bank.
So the next time someone says to you, "Check your privilege" - they're not saying that you haven't earned your success. They're reminding you that perhaps you forgot about the people who lose. You forgot that some people work just as hard as you - maybe harder - and are not lazy just because they haven't achieved what you did.
They just haven't had all your privileges.
Say a word of thanks.
And if you are a hair's breadth away from being that someone who could be ruined by a $100 unexpected bill, don't sit idle for even a second. Every spare second should be used to figure out how to save one spare dollar, earn one spare dollar, from somewhere, anywhere. If that means eating nothing but rice for a week, doing surveys for 20c on the internet, then so be it - you never, ever want to learn the "hundred-dollar terror" the hard way, and it might mean all the difference to things in a years' time - it may even be an opportunity to hone the frugality which frees you from it.