Kid Hustle: Encouraging Your Child’s Entrepreneurial Nature

Remember the kid who ran a business in the school hallways during lunch break, selling handmade bracelets, hawking candy or scalping concert tickets?

Who were these kids that hustled you for pocket change? Years later, when you went to high school reunions and found out how everyone else’s lives turned out, these oddballs never showed up. Why? To them, high school might have been but a tiny blip on their radar screen, a small step along the road to bigger and better things. Some may have ended up as entrepreneurs or business owners, having learned lessons about supply and demand early on in life. But did they hustle out of necessity or were they taught to use their heads to earn their livelihoods? Either way, it was a game worth learning to win.

Author, speaker and CEO coach Cameron Herold gives TED talks on how to encourage kids who have entrepreneurial tendencies toward a life of lucrative creativity – often the most underrated trait recognized by academic institutions. He defines an entrepreneur at any age to be “a person who organizes, operates, and assumes the risks for a business venture.” He speaks of one of his earliest talents as a child – public speaking. But he laments, “No one ever thought of getting me a speaking coach. Parents tend to hire tutors for what kids suck at – like French. I still suck at speaking French.”

When we think of education and even overall society, we think of how children are routinely told to earn good grades and build up an impressive CV in order to become attorneys, doctors, engineers, nurses, scientists, etc. While Herold speaks of how not a single MBA program in existence teaches anyone how to be an entrepreneur, he admits it’s not something most academics knows how to teach. “These programs teach them to go to work for corporations,” he says. The problem, he acknowledges, is that entrepreneurs are simply not students. They are people who figure things out on their own.

So what traits might clue you in on whether your child has these tendencies?’s Larry Alton, in his article 6 Signs from Childhood You’re a Born Entrepreneur, says curious kids tend to choose a wide-ranging collection of courses, even when given easier options to get good grades. “Entrepreneurs force themselves to learn about diverse things and not just rely on their strengths,” he says. “If you see that your child’s schedule looks like a hodgepodge mess with no real core, that’s a good thing. Check out what other electives are offered and talk to them about how they’ll shake things up even more next term.”

These kids also seem to know when to call it quits and move on. In my own entrepreneurial daughter’s case, she made it clear when she had lost interest in doing even things she was naturally good at it, like violin, soccer, and track and field, all of which kept her interest for a while, but eventually felt unrewarding to her. By her junior year, her favorite class was a creative one, where students were asked to make videos using the school’s state-of-the-art computer system and equipment. “Some children keep taking saxophone lessons for years because they don’t want to disappoint their teacher, parents, or whoever else they think it’s important to,” says Alton. “However, if you decided to speak your mind and tell your parents you’re no longer interested (after giving it a fair shot), that bodes well for an entrepreneurial future.”

In one of my earlier Psychology Today articles, I talked about the mistake parents make when constantly praising their kids for merely participating in something. I reasoned that they could well be setting their kids up for a fall later in life, when they discover on their own that failure is painful. Instead of painting failure as a series of steps that lead to a higher level of knowledge, these pampered kids tend to give up more easily because their parents may have sent them the message that as long as they do something, they are winners.’s Nadia Goodman agrees that tomorrow’s business leaders will be today’s young kids whose parents have raised them with an entrepreneurial spirit. “It’s a skill that is increasingly important as young people flood the startup world and the freelance economy grows,” she says. “As a parent, you inspire entrepreneurship by fostering the emotional skills your child will need, such as comfort with risk, effective problem solving, and a positive attitude toward failure.” Goodman goes on to quote Dr. Andrea Vazzana, a clinical assistant professor of child psychiatry at New York University’s Child Study Center. “It’s all about shaping the child’s behavior. Social emotional skills are important and the earlier you can help a child with them, the better.”

“To prepare kids to find business ideas in everyday life, bolster their problem-solving skills while they’re young,” says Goodman. “As a parent, you influence your child’s willingness to try, fail, learn, and try again — an essential skill for entrepreneurs. To do this, frame criticism as a learning opportunity by helping your child practice the skill or brainstorm what they could do differently next time.”

No prospectively lucrative opportunity slipped by Cameron Herold as a child. He delivered newspapers, cut lawns, collected golf balls from golf course lakes and re-sold them, and even went door-to-door selling license plate frames. When he became a parent, he decided not to offer his kids allowances just so they could learn some of the same creative survival tactics he had taught himself. “Allowances teach kids to expect a paycheck,” he says. Instead, he suggests his kids go around the house and yard looking for things that need to be done. Once they’ve got their lists formed, he asks they come back to him and negotiate what they might get paid if they get these things done. He also makes sure they place a certain percentage of their income in a separate account for charitable giving, another percentage for investment, and still another for mad money, when they want to buy something they want. Now? “They each have their own stockbrokers,” he says.

Encouraging your child’s hustler side (used in the most positive of terms), you are effectively giving them tools they can use for a lifetime, preparing him or her for the real world, whether negotiating a salary or starting a business.

First published in Psychology Today

Interested in more parenting posts?

Dena tackles issues surrounding parenting challenging kids, emphasizing the need for parents to raise empowered young women and enlightened young men as she writes The Unedited Offspring blog for Psychology Today.

Dena Kouremetis
Dena Kouremetis


You may be a successful business person, a brand leader or an edgy entrepreneur, but none of it prepares you for parenthood. Dena Kouremetis writes The Unedited Offspring for Psychology Today, sharing her perspectives on parenting as the real life mother of the author of #Girlboss.

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