What would you do if your kids were in school with kids who thought dressing up in blackface was cool? Fortunately, it’s not something I’ve had to deal with, but after last week, add that to the list of my worries about my choice in where I’m raising my sons.

The events of last week—standard fare for Halloween, as we all know—gave me pause and yet another reason to agonize over what it means to raise and educate our kids in communities where there’s no guarantee of respect for our cultural experience or sensitivities. How’d that all spring from the latest blackface faux pas? This is an internal debate held by Black parents all over the country and one that rarely gets easier.

Martha’s Vineyard, home to the young woman who posted the most notorious of this year’s Halloween blackface images, mirrors the Connecticut suburb where I live with my boys in many ways. In fairness (mainly to me, because I’m certain you’re judging right now), there are important exceptions. The Vineyard’s affluence makes our neighborhood look poor (which it definitely ain’t). And I didn’t move my sons here to separate them from other Black kids; I chose based on the quality of the schools. Connecticut is stratified much like the rest of America, and less diverse overall. The best public schools here are in richer, Whiter towns—while the most diverse districts are underfunded and underperforming. I moved here in a position my mother had never been in while raising me: I had more money to afford a better-performing district than I had time to look for a place to live. I split the difference. We set up shop in the best-performing, most-diverse district near my job, in a house with a deck and a big backyard that borders a synagogue (imagine the summer Saturdays when I wake up, open the doors to my deck and crank Hov or Jeezy through the surround sound). My oldest son wound up in a high school on US News & World Report’s top high schools list, where student body is 64 percent White and less than 10 percent Black.

Which brings me back to Halloween, blackface and those wacky White kids from MV. Not every person from a homogeneous community becomes a racist jackass. But growing up in relative privilege—the kind of privilege that comes with insulation from other races—often does engender cultural insensitivity and ignorance. Even worse, it can birth a “go along, get along” coping mechanism for those in the minority. Because of where we live, I feel a need to remind my sons of certain things: The n-word from a white kid who thinks he or she is “down” is never OK and assimilation. Passive-aggressive insults are not the cost of making friends. I encourage them to challenge anything that doesn’t pass the “THAT’S RACIST!” smell test. And so far, we’ve had no problems.

My worries over how my kids are adapting to things they may not even be aware of leads to plenty of second-guessing about my parenting and how I instruct them. I'd never want to deprive them of friends or social experiences just because most of their peers are white. I allow them to keep company with whomever they choose, as long as they're choosing kids who aren't into drugs, crime or too much mischief. It's tough, but necessary, to explain to a 16-year-old that his White friends will be judged differently than he will by authority figures—today and always—and that should they all get in trouble together, benefits of doubt will be shown to them that won't be to him. It's just as hard, and necessary, to explain to them in front of a mixed group of friends, how following certain rules should they ever be stopped by police can be a matter of life and death. None of that can be left to chance. 

Beyond the natural concern for their safety in this sort of environment, those of us raising children in spaces where they are the minority also grapple with anxiety over what this might mean for their self-esteem—how might going all day without seeing a familiar face take a toll on them at school? Do they feel like less than? What happens when they make a natural, childlike mistake? I also worry over how they’ll view and treat brothers and sisters whose parents didn’t have my newly-acquired means, and about who they’ll choose to date and why.

I’d be lying if I said I didn’t also lament having to choose whether to sacrifice cultural comfort for safety and the quality of education. From my earliest classroom experiences through my time at the great Coppin State University, I took for granted that I lived and went to school where everyone looked like me and shared at least one common value—that being Black was, indeed, beautiful. That immersion is non-existent for my sons, but so, too are the suffocating violence, crumbling streets and schools I survived. My boys can walk to their high-performing schools and their first jobs without worrying about getting jumped, robbed or shot because I never forgot that none of the above were options for me.

There's no city, no town, no suburb on this planet where you can raise a Black child without worry—and if you feel otherwise, I have to question your commitment as a parent and/or your knowledge of the world. However, it's frustrating to know that no matter what our best option may be, it, too comes with a price.

Keith Reed is a senior editor for ESPN The Magazine. Tweet him: @k_dot_re