Home Advice For The Young At Heart Seven Ways To “Grow” An Entrepreneur (Instead Of A Boomerang Kid!)

Seven Ways To “Grow” An Entrepreneur (Instead Of A Boomerang Kid!)


by Michael Houlihan, coauthor of “The Barefoot Spirit: How Hardship, Hustle, and Heart Built a Bestseller

Your child may still be in elementary school but you’ve already started worrying about the “boomerang” syndrome. It’s a valid concern. Most kids come back home after college to “crash” until they find a job. But as the months (and years) crawl by and your child still can’t find anything that doesn’t involve cash registers, coffee machines, or polyester uniforms, it becomes clear that their career prospects are what have actually crashed.

The good news is that this less-than-ideal fate needn’t befall your child (or, let’s face it, you.) Today’s job market cries out for street smart, innovative bootstrappers who think and work like entrepreneurs. (It also calls for actual entrepreneurs, as “jobs” are pretty scarce.) Those skills may not be taught in school — but they can be taught and nurtured by parents who commit to helping their kids develop an entrepreneurial foundation.

Here’s how:

Have them read all about it. (Entrepreneurship, that is.)

Encourage your kids to read stories and books (or even watch movies and documentaries) about individuals who tapped into their strengths and built successful businesses. (The options are plentiful, from Henry Ford to Steve Jobs to Mary Kay Ash and more.) Afterward, you can have a conversation with your children about what qualities and habits helped these entrepreneurs reach their goals.

For a twist on this theme, challenge your children to find one example per month of an under-capitalized startup that was successful. After learning about each month’s company, your child can report to you. You and your children might be surprised to learn that many of today’s Fortune 500 companies were started in proverbial (or actual) garages on shoestring budgets!

Emphasize hard work and effort.

Promote focused effort and patience. The fact is, when we see a booming business, we all tend to forget how it started. Challenge “easy way” overnight success stories and explain to kids that such things rarely happen. Instead, glorify “get rich slowly” schemes and reinforce patience when you see kids displaying it.

You can teach them the value of deferred gratification in many ways, ranging from saving money for a toy to planting and cultivating a simple garden. As you pursue these projects, point out parallels between them and real-life businesses. For instance, your child’s peppers and tomatoes required her time, commitment, effort, and knowledge to get to an edible state, and successful companies require the same things to grow from humble beginnings.

Don’t fill up the college fund for them.

Yes, making sure your children are able to get a higher education is a valuable gift indeed. But don’t feel that you’re obligated to pay every penny. Expecting your children to pay for part (or maybe all) of their schooling will increase the odds that they’ll value it more. Plus, if they work part-time while attending college, they’ll also develop skills like time management, discipline, professional social skills, and an understanding of how money is made — none of which can be truly taught in the classroom.

If your child does work a part-time job, be a curious parent. Ask him questions about how his company makes money, what a typical day is like, whether he thinks the organization is well-run, and how he thinks it could improve, for example. You can also take the opportunity to ask him how satisfied he is with the current work he’s doing. He might be learning some valuable lessons about the value of the education he’s getting: It will allow him to go on to do something that he finds more fulfilling.

Encourage them to start a kid-sized business venture.

Don’t make your kids or yourself crazy — too many American households are already over-scheduled — but if it’s feasible, encourage your children to launch an age-appropriate business. Lemonade stands, babysitting, tutoring, and yard work are classic examples (but don’t limit kids to them!). If they use their imaginations, they may be able to come up with creative ideas of their own. When you’re coaching them, explain that they’ll be setting themselves up for the most success if they can create value as opposed to simply taking value.

Insist that they help out financially.

If your child wants a more expensive item that doesn’t fall into the birthday-or-holiday-gift category (like a bike, laptop, gaming system, skis, etc.), ask her to help pay for it. She can save up birthday money, her allowance, or paychecks from any official or unofficial jobs she may have. Along the same lines, don’t buy her every “little” thing she asks for. Going without — or figuring out how to pay for it herself — will teach your child self-reliance.

Whenever possible, guide your child on the path to self-reliance. For example, you might encourage her to find clever ways to be fashionable without using tons of money. If she has only $20 to spend, go on a thrift-store shopping trip together and find treasures you’ll both get a lot of use out of. Remember, getting by with less and being resourceful is at the root of successful entrepreneurialism. When your child does find a way to pay for something on her own, be sure to praise her!

Reinforce entrepreneurial behaviors.

Whenever possible, direct them toward creative toys like Legos that expand the imagination. Encourage activities that don’t require pre-manufactured toys at all: building a tree house in the backyard or a fort in the living room, for instance. The idea is to show them there are many alternatives to “cookie cutter” thinking.

It’s common knowledge that kids like to be praised. Take the opportunity to do so whenever you see your child using his imagination to solve problems, giving credit where credit is deserved, going above and beyond the bare minimum, and connecting face-to-face with other people, to give a few examples. Also, keep your eyes open for “teachable moments” that can help your child develop and stretch his skill set; for example, inviting him into an adult conversation.

Help them find mentors.

As your child gets older, encourage her to seek out and talk to individuals who have successfully started their own companies. If your teen can land one, an internship at a small business can be invaluable. And interviewing an entrepreneur can turn into a truly educational school project for kids of any age. If your child takes advantage of the opportunity to learn from a real-life entrepreneur, make sure she expresses appropriate appreciation.


Michael Houlihan, coauthor of “The Barefoot Spirit: How Hardship, Hustle, and Heart Built a Bestseller“, started the Barefoot Wine brand with Bonnie Harvey in their laundry room in 1985, made it a nationwide bestseller, and successfully sold the brand to E&J Gallo in 2005. Starting with virtually no money and no wine industry experience, they employed innovative ideas to overcome obstacles and create new markets.