Today I helped a 19-year-old try and break in to an apartment.

When my kids were very little they went to Nancy’s house. Nancy is older than me. She had three children of her own and had helped raise others through her in-home daycare. She loved my kids and I loved her. I also needed her. I needed her advice and experience to tell me what to do and how to do it.

When the kids started preschool we had a sitter who was much younger than me, but had a son the same age as my kids. It was weird to adjust to not having an “expert” to rely on for childcare. Instead, Emily and I talked and figured things out together (although honestly, I really think she had it much more figured out than I did).

As the kids got older, we had some sitters older than me, some younger than me, but basically as they grew the roles changed. I was in charge, I called the shots and made the decisions.

These days, the kids are really too old to have a sitter, but one of them hates to play alone and ironically, the fact that I work from home means that I need childcare more not less, since I need someone to keep him out of my hair. So, for the past couple of years we’ve hired a series of college students and teenagers.

I feel like when you have a baby people tell you about how to hire sitters, how to check references and what questions to ask. But nobody ever tells you that eventually you will be hiring teenagers, and when you hire teenagers you aren’t just paying someone to do a job, you’re taking on a responsibility for another child. At 19 our current sitter is much closer in age to my kids than he is to me. He is a child, and he’s in my house, and so he’s my responsibility.

I used my connections to help one young sitter, a recent college graduate, find a more professional job. Then, I had to explain to her how her behavior cost her the job. One of our favorite sitters, a 22-year-old, lost his debit card the day before he left town for a weekend. He cancelled it and then remembered it was actually at bar where he had used it to open a tab the night before, but by that time, it was too late to use it and his replacement card hadn’t come yet. I lectured him and then loaned him $100.

Today, I helped a 19-year-old try and break in to my friend’s apartment. This young man is everything you would want in a teenager. He looks you in the eye and talks to you whether you’re a middle-aged mother, a nine-year old boy, or a contractor working on the house. He is smart, determined, tall, and good looking. He was a two sport athlete in high school and got a partial scholarship to play ball at a prestigious school.

Unfortunately, after one year, he can’t afford to finish school at this prestigious university. My neighbors and I have spent the summer depressed and disturbed at the complete lack of guidance he received from his high school, the high school are children will go to. He could have received a better scholarship from a different school, he could have applied for grants from his current school, if only someone had sat down with him and shown him the math.

Instead of packing for his sophomore year at college this kid is facing the real possibility that he’ll spend a year at home at community college. There is nothing wrong with community college, but for a kid who had a chance at a four-year-degree, it’s depressing.

My friends are out of town and needed someone to stay at their house and take care of their dog. They hired him and today when he left my house, he went to theirs. I remember what it was like to be young and temporarily living at home and how great it was when people would hire me to house sit. I was happy for him.

An hour later, he came back. He had gone down to get their mail and locked himself out with all of his stuff inside the apartment. We called my friends, they don’t have keys anywhere nearby, but are Fedexing a spare set to me tomorrow morning. In the meantime, we watched a video on YouTube about how to pick a lock with a hairpin.

Then, I went over with him to my friend’s house to try and pick the lock. It’s not that I thought this was the best idea, but I definitely thought it was a better idea than sending a 6′ 2″ 19-year-old with no i.d. and no phone on him to go pick a lock by himself. It didn’t work and he’s spending the night at home tonight.

I’m not without boundaries when it comes to these teens and twenties. I did fire the guy who came over and took naps on my kid’s bed. I have not offered to co-sign my current sitter’s student loan. But, sometimes I wonder if what I’m doing makes any sense. If I should be letting myself get involved. If I should be mothering the people I am paying to watch my own children.

But mostly I think it’s a bit of a gift. I ‘m seeing a tiny glimpse of the future. Yes, that future includes unhelpful “guidance” counselors, bad decision making, and stupid mistakes. But it also includes the fact that even at 6’2″ and 19 years old, a boy sometimes needs a mother’s help.

The future also includes these beautiful kids. Young men who not only gladly watch kids for money instead of feeling pressured to mow lawns or something else traditional, but do it well. I came home one day to find the 22-year-old giving the 5-year-old girl from across the street a piggy back ride while playing Capture the Flag with the older kids.

It includes the truth that sometimes these kids will mess up, they’ll lose jobs, they’ll lose money, they’ll date the wrong people, and make the wrong choice, and still, they’ll be ok.