I am struggling with the point that one should never ask a black person "what is like being black in [some setting]?" more or less the way I struggle with it if you replace "black" with "gay" or "girl" or "socially awkward" or "obese."
How are whites possibly going to understand white privilege if they are never taught what it is to not have all those default advantages? (never having to waste extra time at airport, never having to waste time in courts, never having to not be helped purchasing expensive items, never having to be asked to explain the actions of whites, never having to feel guilty for the actions of people who only look like you, etc etc.)
This is more or less the same thing that happens to rich or wealthy people who cannot understand that not everybody has an iPhone or can blow $10k to go to Hawaii.
First, I totally understand your perspective. It's essential for people to have empathy about the conditions of those unlike themselves and part of empathy is curiosity about another's world.
That said, there are two topics of this question: the general and the specific.
The general question is both easier to ask and much harder to answer. How /are/ things for black people in silicon valley? That's a big question for anyone - much less a single person who spends most of their time living life and not doing ethnographic surveys of black people in silicon valley. This is the question that people don't like being asked because they are constantly being asked to stand in for huge, diverse sections of the population. How has it felt when people ask you how the "tech industry" feels about its reputation in San Francisco?
The specific version of the question is, "How are things for you in silicon valley?" It doesn't mention being black, because obviously the person you're asking is black and they'll be answering it as such. That is a question we can all answer and are generally happy to answer - because we can just answer for ourselves and not for everyone is is "like" us in some way. It is also an answer that is almost entirely about the person answering the questions, though obviously it will reflect their experience with race in some way.
So to answer your question about how to learn - seek out people who have chosen to give their answer to the general question in public and use that information to inform your understanding of the specific answers you get from people you meet. Keep in mind that the general answers are always wide and generalize, while specific answers focus on the circumstances of the person and aren't reflective of their thoughts about things "in general."
> How are whites possibly going to understand white privilege if they are never taught what it is to not have all those default advantages?
There are plenty of people volunteering to teach you about those things. Heck, there are entire public awareness organizations, university departments, and other institutions devoted to providing education on that issue.
Its not the job of every person of color you meet on the street to be your racial-experience teacher. The same is true, mutatis mutandis, for LGBTQ, female, socially awkward, or obese people.
"Heck, there are entire public awareness organizations, university departments, and other institutions devoted to providing education on that issue."
They promote specific, biased views given most of them are liberal & pushing similar claims. I meet many Blacks in the South, from other cities, and from other countries whose views contradict points I learned from such organizations. There's a whole spectrum of opinion. Certain things most will agree with for sure but the differences can be pretty big.
Funny thing is people involved in the organizations you mentioned often argue with those views until I say they came from Black people. Then they still argue with them. So, do they represent Black people or a subset of them's views? I'm leaning latter. Means I listen to them, read blogs of many types of people (Black or otherwise), talk to individuals about the issues if they bring up the topic, and listen to white opposition, too. Learned plenty by listening to people from all walks of life instead of just the most vocal groups.
From there, the question remains about how best to do that without causing people discomfort. Seems 90% art 10% science if that. I get mixed results...
How are whites possibly going to understand white privilege if they are never taught what it is to not have all those default advantages? (never having to waste extra time at airport, never having to waste time in courts, never having to not be helped purchasing expensive items, never having to be asked to explain the actions of whites, never having to feel guilty for the actions of people who only look like you, etc etc.)
This is more or less the same thing that happens to rich or wealthy people who cannot understand that not everybody has an iPhone or can blow $10k to go to Hawaii.
Maybe this story is a good way to start: "It's not easy being either one of us right now" https://www.yahoo.com/news/not-easy-being-either-us-00000038...