This piece originally ran on Good Men Project earlier this week. It is part of my series there, My Son's Walkabout.

This week I will travel to a wide-open, western state to visit my 14-year-old son at a boarding school attended by other wealthy kids with behavior problems. I am immensely grateful to my former in-laws who shell out the $100,000 annual tuition that keeps Luca nestled in a rustic mountain valley, where he receives 24/7 staff supervision and state-of-the-art equine therapy.

Were it not for Luca’s paternal grandparents’ bottomless pockets, my son would be living the life of troubled kids from families who can’t afford to contain them. He would be truant. Peddling drugs. Running with a gang, locked up in juvenile detention, or living on the street.

I work with those kids at a state-funded adolescent residential facility. Their brief, turbulent lives have been shaped by circumstances known only to those residing in the nether regions of the 99%.

These are the kids whose parents are frequently psychotic, in jail, or missing. Many of them have ping-ponged from one foster home to another, where they were emotionally, physically and sexually abused.

Most of the kids I work with do not get better. They have nothing to go home to that resembles a family. So they end up in prison. They get pregnant while on heavy-duty psychotropic medications and quickly lose their babies to foster care.

One of the boys on my caseload – I’ll cal him Kyle – could be Luca’s doppelganger. Like my son, he is 14, slight, compellingly handsome, and sports a Justin Bieber coif. Like my son, he initially charms adults and instantly pisses off his peers. In session, I struggle with my countertransference – therapy lingo for the feelings clients evoke in the clinician – which leads me to tear up when I see Luca’s eyes gazing out at me from Kyle’s face. When Kyle starts cursing, I give him the eye --- that mother’s look --- and, unlike Luca, Kyle reels himself in with an endearingly formal “sorry, Miss Pauline.”

Once a week during lunch hour, I lock my office door and call Luca’s therapist for our phone session. It is a strange kind of parallel universe phenomenon. I am a therapist at an adolescent residential facility treating lower-income kids. But for that hour, I’m a parent speaking to my son’s therapist at a swanky therapeutic boarding school for 1% kids.

Luca’s therapist updates me with tales of my son’s “entitled” behavior that involves sneaking around rules, getting peers to do things for him, diva-like demands of adults, and a blind eye to the rights of others.

In a recent e-mail describing the crux of Luca’s treatment, the school’s director wrote, “we need to make sure we shut down his entitlement and narcissistic traits.” This has long been the locus of my own struggle with Luca, who has both feet firmly planted in the tippy-top terrain of the 1%.

Luca’s dad and I were an opposites-attract couple. Previous generations of my family had had money, southern plantations even, but lost it all through bad business decisions or when they were called to the church and left commerce behind.

My mother taught at the private school I attended, so I got a fancy education for free. We traveled, but on a shoestring, and I don’t remember a time when my parents weren’t worried about getting by. My father was a minister and my mother’s parents were Presbyterian missionaries, so values such as empathy and generosity were pretty much piped into the drinking water.

What I didn’t acquire was a healthy sense of entitlement. Maybe it was because I was adopted and always felt I was hovering on the margins. Maybe it was because I was an introverted, thin-skinned kid. Whatever the reason, I grew up feeling that I didn’t have a voice, and that I was less “equal” than others.

Although I didn’t recognize it when I married Luca’s dad, I was swept away by his innate sense of VIP-ness. White, uber-rich, highly educated, charming: my ex-husband acted like he ruled the world, and in a way, he did. He didn’t have to work and he still got to boss people around. His confidence was addictive and for many years I felt buoyed by the hit I got off of it.

I thought my ex wanted someone who wouldn’t push him relentlessly the way his parents did, someone with whom he could make an emotional connection. I imagined that we were coming together to balance each other’s extremes, to give our children the qualities we had lacked growing up.

But I hadn’t married an individual. I had married into a brand, an influential dynasty that dictated how others, especially their own, should be. There were lots and lots and lots of rules for how to hone one’s image, and especially, how to acquire more property. But there was no message about the importance of giving back. In fact, the opposite was true.

I remember one holiday dinner, many years pre Occupy Wall Street, when talk of corporate bonuses was bandied about the table. The gist of it was, the more the better, even if a CEO’s company was in the toilet. I mentioned something about how undistributed wealth hurt the greater society, that perhaps CEOs and Wall Street titans owed more to people who enabled them to do their jobs. The conversation screeched to a halt. Several pairs of eyes stared at me as if seeing me for the first time. I wasn’t one of them. I was soft. I was perhaps unhinged. Certainly, I did not belong in the 1%.

Fast forward through one bloodcurdling divorce and years of co-parenting hell. For a variety of reasons, my daughter has been able to balance her 1% and 99% DNA and emerge well-rounded. She is confident, assertive in just the right dose, naturally empathetic, a helper.

Luca is entitled in the worst sense of the word. I have often felt that my son looks down on me, his 99% mother. He has little interest in my relatives and my values seem to have slipped off him as if he were Teflon. This could be in part because his dad’s life is non-stop fun, full of 5-star vacations, parties, and entourages. My husband and I work long hours in professions that aren’t glamorous. I’m sure we look dull and tired in comparison.

Luca is adept at getting others to do things for him, a skill that is not altogether bad, especially if used for the right reason. But coupled with his tendency to see others as a means to an end, with no real interest in genuine connection --- and he could do some serious damage.

It’s a blessing that my son spiraled so wildly out of control that he landed first in a wilderness camp, and now in a boarding school. Finally, he’s in a place where tantrums are shut down, not rewarded, where he has to work his way up a strict level system to earn privileges, the same as everyone else.

He’s just 14, still young enough to change, to learn the value of hard work and self-reliance. The catch is, at some point he’ll go home, back to the 1% life he was born into.

People who come from money often have to work harder than the rest of us to grow up --- especially when their parents offer to swoop in and clean up their messes. This is what Luca is used to and I think he has been led to believe that I don’t love him because I don’t rescue him. I don’t do his homework for him. I don’t blame his problems on other people. And I can’t afford to motivate him with front-row seats to sporting events.

What I can do is love him regardless of the college, profession, or life partner he chooses. I can set reasonable expectations for him and tolerate my own anxiety if he opts not to live up to them. It is that part --- accepting that our jobs as parents are finite --- that is, for me, the hardest part of being a mother.

Later this week I’ll show up for Luca in the small ways that I can. I’ll sit in on his school classes, observe his group activities, join him in a family therapy session. If he’s on level --- meaning he’s following his program --- I’ll be able to take him on an off-campus outing. And I hope, in those moments, the 99% and 1% will slip away, and we will just be a mother and son, hanging out together.

Luca at boarding school