We invite you to listen to our podcast. In our interviews with fascinating people, we ask all sorts of questions, particularly focused on lessons about business and finance that they learned as children. Scroll down to click on specific episodes. There you will find more detailed biographies for each guest and our show notes. You can also subscribe on iTunes, Soundcloud, Stitcher, and YouTube. Enjoy!

Encouraging Children to Take Risks

Every now and then, I find myself revisiting a timeless question that I'm pretty sure Hamlet must have asked himself every morning before shaving: "To beard or not to beard." I'm currently leaning towards growing the beard, if my current mug is any indication.

It's a struggle because, on the one hand, women typically prefer a man with at least some stubble; on the other hand, there's no question that a smooth face is nice for all the kissing. In any case, my goal is to please my wife, and she has never really been too strict on the question (though she did recently say that she likes the red tint of my facial hair).

Along with my beard, I've been thinking about my hair. Really, your beard and your hair are just two sides of the same coin (unless you have no hair, in which case you somehow have a one-sided coin). I have a fantastic hairstylist and friend, Zac Tipton, who puts up with my hairy indecision, and I'm certain that my next trip to the salon will start with intense conversation over the future of the top of my head. I'm just scared to commit to risky hair.

Speaking of hairstylists and risk, I had a wonderful interview with Peter Anthony Wynn, formerly one of the greatest hairstylists in the world before he closed shop to start up a spectacular practice as a business coach, You Will Change the World. Peter Anthony threw me a curveball when I asked him what he learned about money as a child. He said he was thankful that he learned nothing, which ran counter to my own feelings that all children need a solid financial education before heading out the door.

His answer was quite thoughtful, and I suggest that you listen to the podcast to get the whole thing. For the purposes of this article, I'll just summarize by saying that Peter Anthony thinks that society's current way of teaching entrepreneurship tends to move children away from a place at which they are willing to take the appropriate risks to succeed. His gratitude was that he had not been scared away from doing the crazy things that led to his later success.

If it's the case that society tends to scare us away from necessary risk-taking, I'd like to discuss three things we can do to help our children have a healthy sense of risk.

Give children some independence

My sister Laura taught me early on in parenting that it's good to give children as much leeway as we can give them without placing them in the way of serious harm. I like this philosophy. Yes, children need boundaries; otherwise, their diet will consist of glue and whatever dust particles gather on the food they eat off the floor.

Not only should independence be allowed, it should be cultivated. Include your children in cooking so that they feel confident in the kitchen. Let them spend at least some of their money freely so that they know what it's like to buy something they regret.

Emphasize the excitement involved in the work you're doing, even (or especially) if that work is hard

You don't need to shelter your children from the stresses you're experiencing from whatever work you're doing. But you should also emphasize what it means to you to reach your goals and to overcome your failures. It's possible for your children to walk into the professional world understanding that it's going to be difficult but that there are rewards for taking a chance.

My children have seen my frustration, but I don't allow myself to complain in front of them so that they know I can take a hit with a good attitude.

Share stories with your children about how you and others have overcome challenges

Part of the point of our podcast is to give parents inspiring stories of the childhood successes and failures of today's leaders in business and entertainment. We speak directly to you parents. But some of these stories may be exactly what your children need to hear. Also, you might take time to consider the stories from your own lives that your children need to hear that illustrate how you did something hard and were rewarded for your efforts.

This whole redefining of my hair could turn out to be a disaster—a shipwreck warning to fellow travelers to stay away from the rocks I've crashed. My hair may grow too long and my beard too patchy. But it's exciting to take risks every now and then and to cheer my children on to their own adventures.

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© 2018 Choose the Nickel. Logo created by Jeremy Beck. Website created with


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