One Disneyland Map, Two 10 Year-Olds, No Parents

One of the most challenging books I have read on parenting is Free-Range Kids: How to Raise Safe, Self-reliant Children, by Lenore Skenazy. Modern-day parents live in a world where worrying is billed as one of the most essential character traits of good parenting. Skenazy argues in her book that this obsession with overprotecting our kids is a relatively new development in child rearing — and she challenges parents to take a reasoned look at whether our safety-crazed culture is actually beneficial to our kids.

As I read this book, I began to think about how I might apply the ideas/challenges within it to Harrison as he grows. The central story in Free-Range Kids is one where Skenazy allows her nine year-old son to travel from Bloomingdale’s in New York City all the way home (using busses and the subway system) by himself. As in all alone — with no parents or other adult chaperones. He was nine, and he was flying solo.

This was something that her son had asked to do for some time, so it’s not like she just dropped him off and wished him luck. He knew how to ride the subway, he knew how to read public transportation route maps, and he wanted to do it on his own. People called her the “Worst Mom in America” for allowing her son to do this. Her book is an explanation of the worldview behind her choice to allow her son so much freedom — and it’s very compelling.

Since reading this book, I have been looking for ways to allow my son to experience age-appropriate levels of independence, and you’d be amazed at how hard it has been to fight against the prevailing winds of culture. I recently began to wonder what it would be like to have been in Skenazy’s shoes, how it would feel to actually allow my nine year-old to do something at that level of independence and self-reliance. Then I began to wonder what — specifically — that would look like in our lives. We don’t live in New York, so allowing my son to do what Skenazy’s son experienced would be irresponsible of me. But what would be our New York subway excursion?

Well, I think I’ve found it.

Heidi and I have talked this over and we have resolved that, when Harrison is about 10 years-old, we will take a trip to Disneyland with him and a friend; we will enter the park together, take family pictures at the Mickey-head flower bed, and then we’ll send the two of them off with a Disneyland map and $20 each (adjusted for inflation, of course). They will be free to explore the place that Walt Disney built for kids, as kids.

I’m sure many people will think this is crazy. To be quite honest, I’m not even sure if Disneyland would allow it. But every time I see the picture below of children running through the archway of Sleeping Beauty Castle for the very first time in 1955, I can’t help but hope that Disney still encourages the mixture of wonder and adventure that these kids had on opening day:

Talk about free-range kids. I can only see one adult, and I’m pretty sure he’s a Cast Member, dressed as one of the Knights of Camelot. How many of these kids do you think were abducted, injured, or otherwise harmed?


All we have to do now is wait until Harrison is 10, then we’ll get the chance to put our money where our mouth is. If you are a Disney Executive and would like to offer us a few practice runs over the next few years, we’d be happy to accept. Actually, if you do work for one of the Disney parks, I’d love to hear your thoughts on this. Does Disney allow self-relient, well-behaved children to explore the park unsupervised like they did in Walt’s day?

As for the rest of you, I’d love your feedback as well:

What are your thoughts on this idea? Would you take this challenge with your kid?



I’m not going to lie, this plan gives my stomach equal amounts of excitement and nervousness. This time we live in as parents is a very untrusting, skeptical era — one that wants parents to control and supervise children at all times. But Mom and I want to push past our worries and allow you to live your own adventure. If we try to make sure that nothing ever happens to you, then nothing will ever happen to you. Live your adventure, we promise to try not to stifle the independent spirit that lives in you as it does in each of us.

  • Uncle Jared

    Wow. I sometimes have a hard time letting Emsleigh just climb into and out of her highchair by herself (because she could fall). Unfortunately, our world is very different than 1955. Our world is even different than it was in 1985 when I would walk independently to and from friends’ homes to play….or go up to the local 7-11 for a drink and some candy….or ride my bike to the grocery store to pick up something for my mom. Can’t wait to hear the stories though when the “Disney On My Own” trip happens. :)

    • http://DearHarrison.com/ Michael Gray

      Interesting you should say that our world is different than in ’85. The author of this book does some research on crimes committed on children and she found that kids are safer now than in the ’70s. In fact, 1985 was probably among the peak times of violence against children.

      For me, I think the hardest part of this whole thing will be to experience Disneyland without Harrison, because that’s one of the best parts. Perhaps I’ll think differently when he’s 10. Hahaha.

      You’re going to have a tough decision to make when Emsleigh’s 10 and we call you asking if she’d like to go to Disneyland with Harrison.

  • http://www.facebook.com/kevin.phillips.7583 Kevin Phillips

    I think that is a great idea. I would
    trust Disney more than I would trust New York, sure there are strangers everywhere
    but at least with Disney the strangers are paying a ton of money to go enjoy
    themselves and will most likely be more focused on the park than two unattended
    children roaming around. I have a six year old daughter and would probably
    allow her to go with Harrison on this adventure, so don’t worry you aren’t the
    only one who feels this way. As for whether or not Disney would allow it, I’m pretty
    sure they wouldn’t care as long as the kids were behaving themselves.

    • http://DearHarrison.com/ Michael Gray

      I agree with you — Disneyland is probably the safest place for a responsible kid to explore on his own. Still, it’s a big place, and a LOT could happen. That’s what keeps parents tied up in knots — what COULD happen. But no one can live a fulfilling life just trying to avoid the “coulds”.

      Good to hear from you, Kevin!

  • Mary @ A Teachable Mom

    I love your blog and the sentiments you share with your child and your readers. I have such a hard time letting go and wrote a similar post on my blog about Lenore Skanazy and Free Range Parenting. I have to say, Disneyland is a brilliant idea – one entrance/one exit and a closing time plus extensive security. Perfect. I think I’ll start smaller though, say letting my kids wander away from me at the grocery store! Great post!

    • http://DearHarrison.com/ Michael Gray

      Thanks, Mary. I noticed your most recent post sort of deals with some of the negative things that can happen when a child is let loose on the world. Thankfully, the vast majority of setbacks are minor and very temporary in hindsight. If we don’t teach our kids to fight through discomfort and get back up on the horse (or bike in your daughter’s case), then we will be sapping the independent spirit right out of them.

      Thanks for commenting, and thanks for refusing to let your feelings dictate how you feel about Ava and her freedom.

  • WEK_Esq

    Fantastic stuff, Michael. Planning to take a look at this book. I’m looking forward to the day that you post about Harrison’s adventures in Disneyland. I can tell you that at the age of 11, I was turned lose in Disneyland with four friends with the only restrictions being checking in at lunch and then meeting at the gate to leave. I still remember it–it was fantastic.

    • http://DearHarrison.com/ Michael Gray

      Thanks, man. I guess if a kid like you can make it through a day without parents, then so can anyone! :) Kudos to your parents for being so confident in their only child. Sometimes I think that parents of only children tend to be MORE protective than average.

      • WEK_Esq

        Agreed, and I think they fought that instinct for a while. They’ve both said that with my personality so strongly developed as a kid, they realized fairly quickly that the best way for them to maintain control was to turn me loose and give me freedom whenever it was possible to do so. That made for some stressful times, obviously, since I preferred to learn things the hard way.

        One thing they’ve told me since then is that they knew if they could just get me through adolescence alive and without a permanent record I’d be fine. They were always of the belief that the things that made me such an enormous pain back then were the same things that would bring me success later–and I don’t think there’s any question they were right. God has blessed my path with a unique set of circumstances where being single-minded and strong-willed has been more of a benefit than a burden overall.

  • Lenore Skenazy

    Go for it! And have Harrison drop me a note when he’s done! — Lenore “Free-Range Kids” Skenazy