I think a very fundamental part of all of these discussions (police brutality, student loans, colleges, etc.) that we can ALL learn from, is understanding that other people experience life very differently than we do. It is not just a matter of adjusting a certain variable.
1) People who went to well-known schools with big alumni networks experience post-graduate life differently than those who went to smaller, lesser-known schools. Opportunities are more likely to land, personal networks are more likely to grow and help advance career prospects, etc. It's not sufficient for people with the same degrees from different schools to say "well we got the same degree, we accomplished the same thing, and our life experiences should be exactly the same, therefore you should always choose the more affordable option". It's just not an apples-to-apples comparison. And the cheaper school is not always the best option.
2) People who went to college and entered the job market in the 70s, 80s, early 90s, etc. do not experience life the same way people who entered later did. School costs were lower, debt was lower, less people were educated so white collar jobs had less barriers to entry and less competition for them so they were easier for college grads to land, entry level (white or blue collar) jobs paid much better, homes costed less, and healthcare costed less, etc. What does all this amount to? Prior generations could more easily be educated affordably, land a nicer job, and put more of their paycheck away. They could buy homes instead of forever renting, get married earlier without economic anxiety, raise children in a stable environment. Many millennials, no matter how hard they work, do not have this, or have to work many years to reach a place where this is feasible. So they buy homes later, get married later, the family unit in America suffers, etc. So it's easy for someone from those older generations to say someone is "whining" when all we are saying is that we don't have the same opportunities YOU HAD. But you didn't face these obstacles, so it's easy for you to point and say younger people are "whining". You do not have the same life experience. It is not sufficient to say "I went to college and I worked and I made it happen, you can too". Too many variables are different, the ENTIRE life experience is different. You simply cannot translate your life experience to someone else's, adjust the dates, and say "well hey you should have done it the same way I did". It doesn't work that way.
3) Here's an example we can all relate to or at least understand. Ugly people experience the world differently than beautiful people. When you're beautiful, people envy you, want to be around you, want to date you, laugh at your jokes, take you more seriously, think you're smarter, etc. When you're ugly, these things don't happen. Life is EXPERIENCED differently for ugly people vs beautiful people. I think we can all acknowledge that. So it's not enough to just say "hey ugly people, I got this girlfriend and this many friends and all I had to do was a, b, and c... and make these decisions, and treat people this way.." no. It just doesn't work that way. An ugly person and a beautiful person can make all the same decisions and do things exactly the same way in life and still have completely different life experiences.
4) Black people and white people have different life experiences in America. Especially in our prior history, but even now. There's a common phrase "we have to work twice as hard to get half of what they have". It's easy for white people to point and say "well I worked x hard, I made these decisions, and earned this living, anyone can". No, it simply doesn't work that way. Not every example is the same, and there are exceptions to everything, but as a general rule, a white person and a black person could have the same rap sheet, interact the same way with police, and still have totally different outcomes. I mean, how many white mass shooters do we see walk away unscathed and just put into prison? Meanwhile other people are beaten, killed, etc. If you can corral a mass shooter and put him in jail unhurt, you can do the same with a routine traffic stop, even if the person isn't the most respectful. Unfortunately, black folks are at the **** end of that often. It simply isn't enough to say that every black folk has to make the same decisions your white self made and he'll automatically have the same outcome as you. It just isn't a fair comparison as the outcomes still rely heavily on how a person is perceived and treated by OTHER people.
There are MANY more examples out there of how different people experience life in different ways. We ALL have our own unique experiences and we have all viewed the world in our own unique way, different from everyone else, based on our experience. If there's anything we can take away from discussions like this, it's that it is just not enough for two different people to make all the same decisions in life, treat people the same way, etc. and expect to have the same outcome. It is not fair to assume that because someone didn't have a similar outcome as you, that they must not have made as good of decisions as you made. There are simply too many variables out there that affect how we all experience the world, and unfortunately our own efforts, our own hard work, and our own decisions are just one of those variables.