The Generosity Project

Last Christmas season, I thought it would be nice to try out a little mini-project that had been percolating in my brain for a few years. Unfortunately, I got a late start on my idea and it never really had the chance to get rolling. Well this year, I have given myself and any other participants plenty of lead time, and I’d like to ask you again if you would consider being involved.


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What “Bruce Wayne” Taught Me About Generosity

Some people in this world make insane amounts of money, but billionaire industrialist and Gotham City playboy Bruce Wayne takes personal income to unimaginable levels of insane. Wayne is filthy rich, to be sure, but there is a side of Mr. Wayne and his globally-dominant Wayne Industries that many people do not see: The Wayne Foundation, his generous philanthropy organization. I got to tour the Phoenix offices of Wayne Industries this week, and I am going to leak a few very interesting secrets about the legendary Bruce Wayne (SPOLIER: Bruce Wayne is merely a secret identity for a well-known superhero).

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20 Questions to Ask Your Kids Each Year

You know you’re getting old when you find yourself telling kids, “I can’t believe how big you are! I remember when you were [insert distant memory here].” The kids roll their their eyes just like we did, confirming our official acceptance in the Weird Things Adults Say Club, and we walk away wondering how we allowed ourselves to become just like the distant relatives and family friends that we swore we’d never be.


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Go Ahead: Judge Your Neighbors

Everyone who truly loves Christmas also loves to see neighborhoods decked-out in true holiday spirit. As we walk/drive/sleigh through each year’s winter wonderland of lights, we see homes with decorations that fill us so full of Christmas Spirit that we could swear we are one carol away from bursting.


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2012 Generosity Project

Giving is gratitude in action. This Christmas, I thought it would be nice to try out a little mini-project I’ve been rolling over in my brain for a few years. I call it the 2012 Generosity Project, and I would love it if you would consider being involved.

The idea is pretty simple: as you’re out and about this Christmas season, look for some opportunities to show some unexpected generosity to a stranger. It can be as simple as buying coffee for the next person in line or it can be something more significant like having your kids pick another family at the restaurant where you’re having dinner, and paying their bill. Perhaps you could leave a jar of homemade spiced tea mix (a Gray family specialty) and leave it on your neighbor’s doorstep. The opportunities are endless.

Then, in order to keep the ball rolling, I have made a business card-sized note that you can pass along to the recipient of your generosity in hopes of inspiring them to do the same for others. I’ve also included a link back to this post where givers and recipients alike can tell the story of their involvement in the 2012 Generosity Project. How exciting to read the different ways that people choose to be generous this Christmas.

So what do you think? Are you in?

If so, you can download and print the 2012 Generosity Project card, or if you are interested in playing a bigger role, contact me directly and I can mail you up to 25 of the custom cards I printed up. These are thick, high quality cards, and I will mail them to you for free.

Also, don’t forget to tell your story by leaving a comment below!

Merry Christmas and Happy Holidays!



Even though your four year old vision of Christmas is Santa bringing you that telescope you asked him for and getting to go sledding at Grandma’s, I hope you grow each year to see that the Christmas spirit really is more about giving than getting. The world has commercialized Christmas, and on some levels I have no problem with that, but if you let the “things” of Christmas overshadow the meaning, then no amount of presents under the tree will bring you the joy that Christmas should bring. Show gratitude by being generous. Read the stories below of people who were generous this year.

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.

Why Your Kid Likes the Box More Than the Toy

Every parent knows what I’m talking about: You find the perfect gift for your 4-year-old’s birthday, wrap it in his favorite Buzz Lightyear wrapping paper, and smile with satisfaction when he opens it and says, “All right! I wanted this! Thanks, Mom and Dad!” But no matter how grand the initial reaction, it never seems to fail that two hours later, that very toy is laying on the couch and your child is in his bedroom playing with the box it came in.


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3 Things to Look for in a Teacher

Teachers oftentimes spend more time with children each week than their own parents do. That makes your child’s teacher a very significant influence. I’ve written before about the importance of hand-picking your child’s teacher, but what are the qualities you should look for in a good teacher? I’ll give you a hint: the one your child wants because he is “the funnest” probably isn’t the one.


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Disneyland Vacation Planner

With Summer quickly approaching, many families are now making their vacation plans. Well, if you’re thinking about taking the crew to Disneyland (or any other amusement park) this year, I would like to offer a FREE, customizable resource that you might find helpful. In preparation of our trip last year to celebrate Harrison’s 3rd birthday, I created a handy-dandy Disneyland Trip Planner.


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3 Reasons You Should Hand-pick Your Child’s Teacher

When I was a kid, teachers were selected for students at random and class rosters were posted on the glass doors of the lobby two weeks before the first day of school. We were at the mercy of the invisible gods of elementary school. Some years, the gods would look on you with favor and you would get someone like Mrs. Olson, and in other years the gods were vengeful and placed you with Mrs. Rushton. The idea of my parents (or anyone else’s) going to the administration and requesting a particular teacher was unheard of.


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