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Spend A Night In Jail And 4 Other Things I Want My Sons To Do Before They Turn 16

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As life goes, my 2 boys — Henry, 9, and Maddox, 6 — have it pretty damn good. Here are just a few of the many things they get to enjoy every day:

  • A world-class education
  • Grandparents who spoil them rotten
  • An Xbox and a WiiU
  • Clean drinking water
  • Multiple vacations a year
  • 3 pet fish
  • Overnight camp, guitar lessons, basketball … you get it.

Living in it, it never feels like too much. Most days it all goes unnoticed because it’s just our lives. But occasionally I step back and look at it from the outside and can see the absurdity of some of it. And at those times I have to remind myself that their mom and I work our asses off to give the boys a nice life.

And they are great boys. Great boys with enormous hearts, impeccable manners (occasionally needing a little prompting) and, generally, as much appreciation for their lives that I can reasonably expect (or would want) from a 9 and 6-year-old.

The biggest reason the boys have decent perspective is that they have a mom and dad who – while divorced – are aligned on the values we want to instill in our kids.

This past Thanksgiving she and I agreed that Henry should volunteer at a soup kitchen. I signed him up (via school) not even thinking that other volunteers would be 10 years his senior (Juniors and Seniors looking to fulfill a community service requirement? It’s so cynical of me but I was that age once). He wasn’t exactly thrilled about going (I think he was nervous), but I dragged him to an unfamiliar neighborhood on a cold fall night and we did our duty – prepping and cooking and serving and cleaning and cockroaches and all. And he loved it! Because he got special attention for being so young. Because it made him feel good to “sneak” the kids at the soup kitchen 2 deserts. Because he saw how proud I was. And because he’s been raised right.

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Henry, far right

But as great as the boys are, I’m always watching for the smallest sign of entitlement — using it as an opportunity for a teachable moment.

So when the other night at dinner (at a restaurant, which I’ve recently realized they are far too comfortable with) a debate broke out about a new Xbox game Henry wanted, I saw a chance to teach them both a lesson.

First he wanted me to buy it for him. No way, kid. Then he decided he’d borrow the money. I agreed to front him, but only with interest and late payment penalties. His mind was blown – this was the first he’d ever heard of interest. He asked a lot of questions about how it all worked, the payment schedule, fees and more. It got his brain working in a new way. And led to a conversation about buying houses, cars and using credit cards beyond a person’s means.

He decided to sleep on the offer.

The next night at dinner (again at a restaurant, but at least a cheap neighborhood diner this time) I told them I’d been thinking about our conversation; and that I came up with 5 things I’m going to make them each do before they turn 16 (each corresponding to a core value I think makes for a good human being).

Here’s what I laid out for them:

Buy Something On Credit And Pay It Off
I want you to walk into a bank, introduce yourself and work something out with the manager where you borrow $500 and pay it back with interest. There’s no more valuable personal finance lesson than learning that a $500 bike actually costs $505 or $510 or $600.

 This one’s a double-whammy. First, I have no clue how you’ll convince a bank to loan you money. But I’m certain it can be done if you get clever about it. But the real lesson here is about having a sense of personal financial accountability – a lesson so many adults will never grasp.

Ask A (Super Hot) Girl On A Date 
I’m not talking any girl. I’m talking the most attractive, out-of-your-league girl. The girl who’s 3 inches taller than you. The girl who dates the starting QB. The girl who doesn’t know your name. The girl who’s so pretty she doesn’t use Instagram filters.

There is nothing more brave than asking out a girl who’ll probably say no.

But you’ll learn that it’s no big deal. Life will most certainly go on. And if she says yes (which does happen – it’s happened to me once or twice, if you can believe that) you’ve got a date with a beautiful girl.

 Spend A Night In Lock-Up
This one’s a bit tough, logistically. I don’t actually want you to break the law, but I wouldn’t mind if you slept on a concrete slab for a night, surrounded by people who scare you a bit.

I spent about 5 hours in lock-up as an 18-year-old (sorry, mom, if you’re just finding this out). Fortunately it was just for walking around a baseball stadium parking lot with a beer. But it sucked. And was a little intimidating.

Guess what I’ve never done again in the 25 years since? Carried a beer somewhere I’m not supposed to. Appreciating the consequences of your actions will help you make smart, kind, and interesting decisions in your life.

Play Hooky From School And Do Something Totally Irresponsible (Even Better If I Never Find Out)
Speaking of consequences … sometimes consequences be damned. Leave for school on a Tuesday morning and don’t show up. Grab a friend with access to a car. Do something irresponsible. Whatever floats your boat. Just don’t be an idiot about it … irresponsible doesn’t mean dangerous.

The car part is important. There’s something magical about the freedom of being a teenager and driving with the windows down. I can’t describe it, but you’ll see (I’m still a sucker for road trips).

 Do Something Nice For Someone, Anonymously
Frankly I don’t care if it’s a stranger, a teacher, a friend or your mom. Write an anonymous note telling them why they are important. Buy them a small gift you know they’d like, because you pay attention to their words. Send a $20 bill to a charity with no return address. On Valentines Day get to school 10 minutes early and drop a rose on the desk of the girl who isn’t in the popular group.

Generosity is nice. Unconditional generosity is remarkable and so rare. To do something without expectation of acknowledgment means you did it for the right reason.

Those are the 5 things I told them at dinner, all met with questions and laughs and objections. It was a fun conversation.

The next morning Maddox came bounding into my bed asking nervously if I was “tricking” him. No, kid. No I’m not.

Well, I don’t intend to trick them. Am I really going to make them do all these? No (Besides, remember when I said their mom and I are aligned on values? We are. But we are probably much further apart on methodology. I’m pretty sure the jail idea wouldn’t fly with her).

But do I think even talking about it has value? Yes. Because if I can raise 2 little boys who grow to be accountable, brave, conscientious, independent and generous teenagers … that would be my greatest accomplishment.

Ian is a 44-year-old father of 2 kids: Henry and Maddox. He lives in Chicago and works in advertising.