There is no way to fully reject the privilege you come from, though. I cannot change my silver tongue or my private education or the color of my skin, nor should I wish to. The pen merely served as a reminder of how easy it is to believe we live in separate worlds from incarcerated individuals, when really we're as close as the address on that envelope.
As a child, I was told that people who wrote to incarcerated men were sick in the head or incredibly lonely. I don't feel I'm either of those things, and I would certainly still be in touch with my mentee if he hadn't recently ended up back in for a parole violation. Still, it feels taboo. I rented a P.O. box for my return address. Some people ask me, "Why go through all that trouble? He screwed up. You're wasting your time..." etc. And I wonder, Why give up on him now, when he probably needs support the most? Can you look back, right now, and capture a moment when someone had compassion for you when you were at your worst? When they saw through your screwup and reminded you that your mistakes don't have to define you? Do you remember your relief?
Still, it must be this belief that we outsiders should not cross into "their world." As if we might catch a contagion and become criminals ourselves. Or as if we are dabbling in darkness. Or playing "white savior." Or getting duped. Or "why care about someone whose life isn't like yours?!" Any number of things. However, I see it as I'm writing a few words of encouragement to a friend, someone who is away for now but will be back in a matter of several months, likely with far less than he has now. I don't pity him, but I understand his circumstances and have seen how hard he worked to try to push past them. I never had circumstances like his.
Last summer, I invited my mentee to my parents' lake house. On the ride there, he admitted, "I had to Google what a lake house is. I don't know what to expect." My mentee frequently opened up to me; he hid a lot of things from the world that I wished he weren't so afraid to share. Conversely, I didn't tell him much about myself until that day, a year after we had been working with each other on a weekly basis. Perhaps I was shielding our differences from him.
"Oh, it's just a regular home but on the lake," I explained, but I instantly felt stupid for simplifying it. I didn't want to act as if a second house is nothing, or that such thing as a "regular" home exists.
I thought it would be nice to show him this beautiful lake, our good barbecue food, and my parents' hospitality. But more than that, I wanted my family to meet him. He was timid and shy - luckily, he brought his rambunctious younger sister along to break the ice - and told me he was worried he'd be judged at every turn. I assured him my family was friendly, but I withheld discussion about what judgements they might hold and who cares. I was proud over how my family made a sincere effort to get to know him and make him feel comfortable and welcomed. Then I misplaced my phone, and my father quietly accused my mentee's 7-year-old sister of taking it. I felt enraged at this ignorance, yet I knew I had to expect that sort of behavior from my father, who is generally always surrounded by people with similar backgrounds and status, similar stories and political views, and anything outside that seems scary and suspicious. I admired my mentee's bravery that day, going somewhere he knew would be a bit uncomfortable - perhaps to be nice, or perhaps to learn about where I came from, or perhaps to simply enjoy it.
My mentee texted me afterwards: Thanks for a great day. Sorry I didn't talk much but I had a great time. I hoped he was being sincere.
I continue to hate the phrase, "We come from different worlds." Sure, it speaks to how our lives can be so different. But we come from the SAME world, and everything we do influences other people, and how we live might determine how others will live, and we all are observing and being observed by strangers with different problems and hopes and beliefs. Our paths intersect constantly - but it's up to us to notice it, appreciate it, learn from it. In the case of my mentee and me, our differences - in how we grew up and the things we each knew and the people who always surrounded us - gives dynamic to our friendship, rather than complication. More people need to pursue friendships where they will learn and expand, rather than just feel comfortable. I'm not here to save my mentee from where he's from or change him to be more like me; I'm here to exchange something rare that continues to help us both grow.
So in this letter to him, gripping the cold steel of my fancy-pen, I write...Just wanted to say hello, you're in my thoughts, and I'll be here for you. I don't want to tell you things you already know, but sometimes it feels good to hear it - you will get through this. You are strong and you will see much better days.