Nobody Ever Plans to Fail, They Fail to Plan

I got a lot of feedback on my blog about Girl Scout cookies and teaching kids sales skills. This got me thinking about another lesson that’s very important for kids to learn: how to plan.

As many of you know, I travel around the entire country with my son Crosby to see every Major League ballpark. It’s one of my favorite things and we started that exercise when he was around 10-years-old.

I wanted to do this to spend quality time with my son Crosby. Being able to travel, just me and my son, without interruption was important, plus it was just fun to see all the different ballparks and explore the cities they’re in. On top of that, I was able to show him the business side of sports. We’d evaluate the best food, souvenirs and everything surrounding the game. It was always great to show him the difference between each club from city-to-city. (Like in Cincinnati, one of my favorite things is Graeter’s Ice Cream).

One of our first trips was when we went to Wrigley Field in Chicago. It was right on the top of our list as one of the last remaining old-time ballparks. I wanted to give Crosby the experience of planning a part of trip. This was just about 10 years ago. The Internet was picking up, so there was Travelocity and Priceline.

Wrigley Field Panorama

Crosby had a favorite rib joint in Chicago, so I told him, “I’ll take care of dinner reservations,” and seeing this as a good opportunity to teach him something I continued, “And you take care of the travel plans.”

So, he comes back to me about three hours later and says, “Dad, you’re not going to believe this. I searched and I found this website that got us a direct flight from White Plains to Chicago for only $200. It was $100 cheaper than any other site and I think this is the flight we should book.”

“Good job Crosby, you did well. You learned how to not waste our money. Good job.” We booked the flights and off we went. Chicago bound.

When we got off the plane in Chicago we’re talking about our great seats for the Cubs game and the rib place we’re going to eat at for dinner. Then, Crosby turns to me and says, “Dad, where are we staying?

I said, “I don’t know I thought you were making the reservations. Where are we staying? What hotel did you put us in? You were taking care of the travel and I was taking care of the tickets and the food”

He gives me a very puzzled look, but we figured we would work it all out later. We went over to the Navy Pier and Crosby turns to me again with a serious look of concern and says, “I think we should take care of this.”

“The reality is,” I told him, “when you’re taking responsibility for something, you have to plan ahead. You have to think about ALL details of a trip weeks ahead of time.”

Needless to say, it was a valuable lesson learned. Always look at the whole situation. With me being a former hotel-guy, I knew there’s always a room to be found. There’s always a room available even if a hotel says they’re sold out. Though, there happened to be two major conventions in Chicago that same weekend, so, on this particular day me an hour and a half to find a room.Thank god for American Express’s concierge service because they came through in the end.


Nobody wants to fail, but people fail to plan all the time. Get your kids thinking EARLY about what it takes to be accountable. Show them how to book a vacation. You don’t just hop on a plane and find yourself in Disney World. Walk them through the steps of calling the travel agency or booking something online. Help them understand how you’re going to get from A to B to C and do everything in between. Show them the costs. In the end, teaching them how to plan will make it much easier for them not to fail later on.

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