Early Entrepreneur?

Dear Powerless Parent,

Though I do not know your son, I know teenagers in general and showing up with cash in that amount that frequently sounds suspicious. But as a therapist, I am less interested in discovering the truth or facts and more interested in developing rapport with him and providing a judgmental place for him to share what's going on. This takes time. 

Prognosis: Depends on where you all live and past behaviors. I can tell you for sure this definitely is the right time to bring in a professional, even if only for a consultation. If left to his own brain and his friends' influence, he will likely get into academic trouble and possibly legal trouble. This is the time to intervene to help him avoid that mess. 

Parent's Role: As a parent, your role is different in that the facts do and should matter. If he is selling drugs or stealing stuff and selling it on craigslist, you and he are liable. This is where some creative boundary setting would come in. Not your basic discussions about giving him 'tv time' if he gets an 'A' on a report card, but a deep understanding of what motivates him (both rewards and consequences). If he's around shady characters (like I guess he is) getting into trouble might be a badge of honor for him. 

Professional's Role: It's hard to give specifics from afar but this type of family/individual therapy really should start with the parents to help them regain control. If after learning higher-level parenting skills your entrepreneurial son continues to engage in less than reputable behavior, we would start talking about increased levels of care (ie. therapeutic wilderness program, residential treatment, therapeutic boarding school, day treatment). There could also be a very early substance use issue here. There could be bullying going on. Until someone sits down with the individuals and family as a whole, the recommendations really are to find some good professional support. 

How We Would Do It: We work with families like yours all the time and help the parents navigate through the therapeutic process. Sometimes, basic boundary setting and outpatient therapy are all that's needed. Other times, we uncover a super hidden world of substance use and move quickly with treatment. Until then, I recommend you focus on setting some basic boundaries (ie. curfews, grades, homework time) and, instead of asking him where he got his magical wealth (he probably hates lying to you as much as you hate it) simply let him know that you understand he is hiding part of his life from you but if he ever needs to talk with you, you will do the best you can to listen, not judge and help if asked. Making a statement like that and walking away is way more congruent with the adolescent brain and how they process parental dialogue. 

I hope this helps point you in the right direction and normalizes your experience. Lots of parents struggle with their kids doing stupid stuff but with the correct support, his choices do not have to have a permanent affect on his life.