Raising an Entrepreneur: Eight Tips for Success

“Dad, I want to start my own business.”

I felt equal parts of pride and terror as I gazed at my fourteen-year-old son, who had approached me after dinner. His arms were hugging a notebook, and his face was alit with earnestness.

“What kind of business?” I responded warily.

I’d been encouraging entrepreneurial skills in my children from an early age, embarking on projects that would hone their interest in risk-taking and financial literacy and increase their tolerance for failure. We grew vegetables in our garden and allowed Maya, my youngest daughter, to sell them to neighbors and friends. She took such joy in artfully arranging baskets and delivering them, struggling to add up figures, and finding new customers with adorable enthusiasm. Naomi, who has the enviable skills of an excellent marketer, often runs a lemonade stand in the summer. Her advertising campaigns are a marvel, and she creates compelling artwork to draw in thirsty people. Posters emblazoned with big, tall glasses with ice, drops of condensation flicking off their frosty rims.

However, my eldest hadn’t expressed interest in projects like these in some time. I’d assumed he’d simply gotten too busy with sports and school and a suspicious, growing interest in spending time at the shops.

“You know how I like dogs, right? And we’ve been talking about me picking up a part-time job if I wanted. Something just after the summer. But I thought I should start now to get customers on the hook before vacation season starts. And…”

“Whoa,” I chuckled, and held up my hands. “What exactly are we doing with dogs in this business of yours? Washing them? Feeding them?”

Ivan grinned. “Oh, all of that. Pet sitting. I want to start a pet-sitting business.”

Developing a Plan

That evening, I helped channel all that excited enthusiasm into developing a plan. While it may seem complicated to involve kids in the detailed nuisances of creating a business plan, a simplified version of that process is extremely helpful. My son and I chatted about the need that his business was designed to meet, the services that he would provide, and his approach to targeting a customer base. I was shocked by how smoothly this conversation went, how thoroughly he’d thought out most of his proposal before he’d even come to me. When I complimented him, Ivan grinned.

“I know how things work around here. You’ve been having me do this stuff for years.”

I wiggled my eyebrows in mock derision. “I had no idea you were paying attention. It must have been the constant use of earbuds that fooled me.”

Ready, Set, Go

In the following weeks, Ivan worked hard to drum up customers. I lent assistance, mostly in the form of my wallet, to secure some business cards. He was great at building a rapport with both animals and kids. A natural. After pet sitting once or twice for some friends on an overnight trip, he landed a significant gig. Ivan would be taking care of a high-maintenance sheepdog, whose penchant for chewing holes through walls had left the owners wary of leaving the house even to get groceries. They’d be gone a whole week. A long, long week, during which that dog could dig a hole straight to China if he felt so inclined.

Ivan was nervous. I was nervous. But I couldn’t let anything undermine his confidence. Successful entrepreneurs take risks and make hard decisions. Even when their dads can’t stop envisioning the costs of drywall and plaster and hours of labor.

“I have not failed. I’ve just found 10,000 ways that won’t work.” Thomas Edison

Surely you must have guessed by now that there was a disaster? Isn’t there always? But it was a minor one. A couple of bite marks on a kitchen chair and a shredded roll of toilet paper were the only causalities. And Ivan learned a lot from that experience that allowed him to approach other jobs with confidence and develop his business idea into a successful endeavor.

These days, if you want a dog sitter, I know a great one. But he’ll have to check his calendar. His skills are in serious demand.

Here are eight tips on how to raise a successful entrepreneur and set them up for a lifetime of success.


  1. Practice Problem-Solving Skills


Things happen. Often. The ability to anticipate what those problems might be and solve them before they happen is crucial to success. You can teach your kids to practice effective problem-solving by helping them to verbalize problems and then work out solutions. Get out the chalkboard and white board, scratch out a list, and watch your kids diagramming their way to improved critical-thinking skills.

  1. Learn from Failure


One of the entrepreneur’s most essential traits is the ability to learn from failure and turn it to advantage. Sometimes, initial mistakes can feel crushing and threaten to squeeze the hope out of your kid’s budding business venture. To help your child learn from failure, I suggest using the infamous Sandwich Method, employed by managers the world over. Start with something positive to provide encouragement in the face of failure. Then follow that with criticism framed as a suggestion for improvement. Sandwich it at the end with another piece of praise, not only about what went right but also about your child’s positive attitude when faced with adversity.

  1. Decisions, Decisions


Sometimes we don’t give our kids enough credit. We second-guess their capabilities and unintentionally undermine their confidence. To foster independence, offer more choices. If they’re toddlers, you can give them more control such as choosing what they’re going to wear or which vegetable they want with dinner. Exposing them to what it feels like to make decisions is vital in helping kids feel more empowered.  But be careful not to overwhelm them with a myriad of choices. Keep it simple and age-appropriate. As they get older, you’ll have lots of opportunities to trust them to make bigger decisions.


  1. Mastery Achieved


Entrepreneurs often take huge risks, but they didn’t become comfortable with uncertainty overnight. While kids are young, give them the freedom to test their boundaries and master their fears. Offer assistance at first, stretching out a hand to bolster an unsteady one. But then, as their steps grow firmer, let go. They may fall, but each step they take will be toward greater confidence in the face of failure.


  1. Challenge the Status Quo


Society requires adherence to rules, especially from children. This is actually a trait that inhibits entrepreneurship. I’m not saying they should constantly buck the system, but you can teach ways to challenge the norms constructively by voicing their rationale. What do they think needs to change and why? What would they suggest instead? Teach them to advocate for themselves in an acceptable and diplomatic way.


  1. Why, Why, Why


I know. Having to answer why the sky is blue or if bugs have feet is not easy when you’re driving in traffic or trying to deal with a migraine. But it’s essential that children be encouraged to puzzle out things for themselves. Rather than supplying an answer, turn the question around. Ask them to follow their own logic to a conclusion. And if it’s an incorrect one, perhaps provide some guidance along the way.


  1. Hire Your Kids


Encourage your kids to earn money by hiring them during their holiday breaks. You can have them do some research, produce an invoice, take notes, or even organize files. Such activities exercise their minds, help them develop a work ethic, and encourage financial management. Keep it age appropriate, though. Your preschooler probably isn’t ready to design PowerPoint slides. Not yet.


  1. Take a Look… It’s in a Book


Have I not extolled the virtues of reading enough? I probably have, but I’m going to do it one more time.

Create voracious readers. Once they’re virtuosos of the written word, they’ll be able to use it to open windows to all sorts of careers. Between the sacred covers of a book or the overflowing miracle of information that is the internet, they can learn everything from car maintenance to accounting.


Giving your child the gift of a successful career is invaluable, so start sowing the seeds of entrepreneurship early and watch your kids flower into prosperous adults.

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