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Are You Raising an Entrepreneur?

Whether they choose entrepreneur, doctor, pilot, artist or chef is up to them—but being entrepreneurial is a great life skill for any path.

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Some parents read their kids bedtime stories. Every night with my daughter, I ask her a question instead: “What’s one thing you tried and failed at today?”

I also read her stories and ask other questions. But this one is key, in a few ways. It lets me define failure for her. In our house, failure is an opportunity to learn and a positive thing not to be feared. It teaches her to look for challenges every day. It’s also created some great conversations as we both share our failures of the day.

I’m not one to push my kids toward any career path, but I do secretly hope they’ll pick up a few entrepreneurial tendencies. Whether they choose entrepreneur, doctor, pilot, artist or chef is up to them—but being entrepreneurial is a great life skill for any path.

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Preparing your kids for entrepreneurship has probably never been timelier. Job tenure and security have been declining for years. The gig economy boom has turned millions into enterprising side hustlers. And now, the pandemic has pushed even more of us into business ownership and entrepreneurship—a trend that shows no sign of waning.

My own parents passed down the spirit of entrepreneurship to me and my three brothers, through lessons both implicit and explicit. Today, all four of us are running our own businesses. But even if we weren’t, the fact that we’re able to be self-starters, embrace failure and problem-solve would serve us well at any corporate job, too. Thinking like an entrepreneur is great training for any career.

I want to pass these ideas on to my own kids. They’re under six, which might seem a little young, but this is such an important time for childhood development. We may not be able to dig into balance sheets together, but it’s absolutely the right time to be instilling big picture, foundational ideas.

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In fact, it’s less that I’m trying to “wire” them for entrepreneurship than I’m trying not to unwire them. So many innate childhood traits are central to entrepreneurship—curiosity, fearlessness, a hunger for adventure. I want to nurture these things, not quash them.

I’m by no means the first parent to try it, and there’s some evidence that it works. Spanx founder Sara Blakely’s father did something similar. My own strategies at this stage aren’t exactly data-backed. My daughter is five years old; my son is just two. I haven’t done this before, and I am learning as I go—I’m looking for input as much as offering it. But here are some early tactics I’m exploring in an effort to raise the next generation of entrepreneurs.

Normalize Failure

My bedtime chats are working. The other day my daughter fell off a rope swing and popped up cheerily saying, “Look, Daddy, I failed!” She was genuinely excited to jump back up there and try to conquer the swing again.

The goal is to equate failing with making progress and an opportunity to learn—cementing the idea that covering new ground is more important than the immediate outcome. The reality is, in so many arenas in life—from school to work—we’re taught exactly the opposite. An ‘F’ is something to be avoided at all costs, so you stick to the safe, tried-and-true path.

Succeeding in entrepreneurship or in anything challenging and rewarding, however, requires a very different mindset, as no shortage of classic examples shows. The inventor of the Dyson vacuum, for example, had 127 failed prototypes under his belt before he finally created his best-selling cleaning tool.

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Embracing failure is a trait that’s critical for entrepreneurial success, and I’d argue it’s helpful for success in any area—the earlier we normalize that in our lives, the better.

Suppress Your Instinctive ‘No’

Kids are born without a lot of respect for what’s “impossible.” That can be a liability, of course, when they try to fly off the jungle gym. But in so many other contexts, I wonder if we rein them in too early and too often, suppressing that natural assumption that they can do anything. Maybe instead of “no,” parents should be saying, “just try.”

The best entrepreneurs, after all, have to face down “no” and “impossible” all the time. But they’ve trained themselves to keep on trying, nonetheless. How many times has Elon Musk had Tesla written off over the years? Everyday entrepreneurs—and I’m lucky to work with thousands of them—are constantly facing down skepticism and “that will never work.”

I’m not suggesting that the obstacles faced aren’t real, but successful entrepreneurs have a knack for “just trying,” learning from their efforts and finding ways to move forward, often in unexpected directions. In any case, the next time my kids ask if we can build a rocket ship in the woods, I’m not going to tell them it’s impossible. I’m going to say, “What will we use for fuel? What will we make the cabin out of? Let’s do this thing.”

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Make DIY the Default

I vividly remember a tantrum I had as a six-year-old, begging my parents to phone the store for me to check if they had the book I wanted. Instead of dialing for me, my dad gave me the phone book and told me to call and ask myself.

This obviously isn’t a dramatic sink-or-swim moment, but the self-empowerment lesson stuck. This basic concept—either you find a way to do this, or it won’t get done—is so central to entrepreneurship. You may not always be an expert or have all the resources needed, but can you find a way forward? Can you learn the skills required; can you improvise with the materials on hand; can you reach out to the mentor who can get you through a challenge? Successful entrepreneurs I know do this countless times a day, every day.

As a parent, I hope I can instill some of this git‘er done spirit. There’s a twist here, though. As important as it is to cultivate self-reliance, raising an entrepreneur also means letting your kids know you are there for them. Entrepreneurship inevitably entails risks and delayed gratification. Knowing I had a support and safety net behind me made it far easier for me to take the plunge when I was starting to pursue my own business dreams. I hope to provide my kids the same balance of DIY and security as they get their hands dirty.

Get Real About Money—Beyond Allowance

I don’t think it’s ever too early to learn the nuts and bolts of money and business. In fact, I have a friend who’s been spinning a multiyear saga about owning a chocolate factory with his grade school-age daughters. They cover supply chain issues, pricing models and budgeting, all through storytelling. I’m sure by the time they’re in high school, they’ll be ready to give Hershey a run for its money. They’ve even published a book about their collective story and are working on another.

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But my friend’s playful economics lesson is an exception to the rule. Considering how much it rules our lives, money—how it’s made and lost, invested and leveraged—is conspicuously absent from childhood education. Only 17 percent of public high school students have taken a personal finance course, in fact, making it little surprise that the financial literacy rate for adults in the U.S. is just 53 percent.

For entrepreneurs, financial literacy is obviously table stakes, but it’s something many of us learn too late or through painful lessons. I see so many entrepreneurs held back by the inability to model revenue flows or mismanagement of balance sheets. Even a basic understanding of assets and liabilities can mean the difference between long-term growth and insolvency. The sooner we get familiar with these concepts, the better. (And of course, like all of these ideas about entrepreneurship, financial literacy is essential regardless of the career path kids choose.)

Model What ‘Entrepreneur’ Looks Like

One positive thing about COVID and working from home: My kids have gotten to see exactly what entrepreneurship looks like in action. Granted, most days it’s Daddy in sweats staring into my Zoom camera, but they’re at least seeing the real deal.

It may seem basic, but there’s real power in “career representation”—seeing a job helps you understand it. Or, in some cases, aspire to it: 43 percent of entrepreneurs surveyed in one study by 99Designs said they had at least one parent who ran their own business. It’s easy for kids to understand concepts like “teacher” or “doctor” or “pilot,” but it’s harder to imagine business ownership for yourself, unless you understand what that actually is day to day.

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(Side note: I love that when my daughter walks in on my Zoom meetings, she sees a mix of gender and color on the screen and sees that as part of “business.”)

My kids are too young to understand exactly what I’m doing (or what an online course platform even is, frankly), but I do talk to my daughter every night about what I did that day. Sometimes, it’s, “I had a great meeting,” and sometimes it’s, “I had a really hard conversation at work today and Daddy cried.” I believe in showing vulnerability and being transparent about challenges—after all, that’s a big part of what entrepreneurship really is.

One big caveat: I don’t think we’re all meant to be entrepreneurs, and I don’t think entrepreneurship is a higher calling than any other. Raising an “entrepreneur,” in my mind, is really about teaching kids to be confident, curious and willing to forge their own path. Whether they wind up at the helm of their own startup, or choose a completely different path, I hope these are lessons that are going to serve to make them happier and more fulfilled in whatever they do.

Greg Smith is the founder and CEO of Thinkific, the leading platform for creating and selling online courses.

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