How to support a challenging child
One of my children has a challenging personality. Within my family, we are aware of it, and deal with it, and love him oh-so-much. As he is getting older, I can see how the outside world (teachers, coaches, neighbors) favors him less than my others. He's not as socially adept, athletic, comfortable around adults, etc. I don't even know what my question is, really ... but suggestions on how to support him? I KNOW he will become aware of this, if he isn't already.
He knows it, or will soon -- just as everyone does who has traits outside the favored bounds. Ask a poor student in a wealthy district, or a person of color where the color of power is white. Ask short men about the humanity-negating effect of women who cite, “I can't wear heels!” as grounds to reject them. Ask a beanstalky kid what it's like in the 5th grade hallways where disappearing into the crowd is a sacred mission. Ask fat people how warmly embraced they feel by 21st century America. Ask people on the autism spectrum, or their families.
People who don't check some preferred box can make a childhood's work -- a life's work, even -- of navigating an outside world that “favors them less than others.”
I'm not reeling these off to minimize the challenge your son faces or you face in raising him to be comfortable in his own skin. To be emotionally well-adjusted can be an adult's most precious asset, and building confidence in childhood is where that starts.
And yes, the biggest obstacles to it are often next to us at the dinner table. We accept there are smarter, prettier and more athletic/talented/charming/fortunate people out there somewhere -- but it can torment us to feel nth-best in our own home.
That is, if we think about it that way.
The healthiest way to teach your son not to think that way is for you not to think that way.
That's why I reeled off those other challenges. Maybe this son has the hardest path relative to your other children, but your sample size doesn't have to be that small and might not serve your son that way. Instead, look around at how normal his challenges are. We all have ours, he has his. Treating him as typical is itself a form of support and validation.
Typical kids have areas where they need extra help. Make sure he gets what he needs -- screenings, tutoring, social-skills training, [blank]? His teachers might have ideas.
Once any needs are being met, then consciously shift to his strengths. Society might fawn over X and Y, but he's got Z. Z is interesting. Identify Z, support it, play to it, celebrate it. Teach him to cultivate it. Think of ways you're better for having Z in the family. Even if Z itself is challenging, be mindful of how Z makes you ... less complacent? More empathetic? Slower to judge?
Kids who are by nature socially adept, athletic and comfortable around adults can make you look like a great parent, but the ones who aren't are where great parents are made.
Your son will see himself through your eyes, not just society's. The warmth you reflect will warm him to the task of finding his way.