You’re not raising your kids to follow the rules—you’re raising them to question every single one. And if you want them to know how to bend the world to their will, create opportunities out of thin air, and refuse to accept “that’s just how it is” as an answer, you need to show them what that looks like. Starting a business isn’t just about making money or building something for yourself—it’s about giving your kids skills that schools, universities, and corporate jobs will never teach them.

The Skills No One Else Is Teaching

Here’s the thing: your kids are growing up in a world where 20% of parents are literally attending job interviews with their college graduates. Let that sink in. We have an entire generation that can’t look a waiter in the eye and ask for ketchup without whispering to their parent first.

Dana shares a story about her daughter Joe at a restaurant. The waiter came over and told her he’d been working there for several years, and every time a kid quietly leans over, whispers in the parent’s ear about what they want, and then the parent tells him. He’d never had a child look him in the eye and ask for something directly.

The bar is incredibly low. And that’s exactly why your business matters.

When you run a business, you’re forced to develop skills that most people never learn: how to handle conflict, how to communicate clearly, how to assess risk, how to bounce back when things don’t work out. And your kids? They’re watching every single move you make.

What Your Kids Actually Learn When You Build a Business

Krista, another Boss Mom team member, watched her 16-year-old daughter Bri land her first job after observing her mom’s approach to business. Krista explains how she researched local businesses, found gaps in their marketing, made custom PDFs showing opportunities, and walked up to business owners at the local market. She got three businesses to say yes on the spot.

Bri absorbed that lesson. Now her employer tells Krista that Bri is unafraid to talk to anybody, has strong opinions, works harder than any teenager she knows, and she forgets Bri is only 16 because she’s so reliable.

That didn’t happen by accident. It happened because Krista showed her daughter what it looks like to:

• Create your own opportunities instead of waiting for permission
• Walk up to strangers and start conversations
• Research, strategize, and take action
• Pivot when something isn’t working anymore

Think about your own childhood. Did you ever see your parents take a risk? Did they talk about failure, rejection, or hard conversations? Or did they hide all of that behind closed doors, leaving you to figure it out on your own later?

Stop Hiding Your Hard Work From Your Kids

This is critical: Your kids can’t learn from what they don’t see.

If you’re working out only when your kids are asleep, they never learn that exercise is a priority. If you’re reading only after bedtime, they never see that adults read too. And if you’re building a business in secret—grinding after everyone goes to bed, hiding your struggles, never talking about the hard parts—they miss the entire lesson.

Dana puts it bluntly: show your kids the things you’re actually doing. Tell them something was really hard. Tell them somebody said something mean to you. They’re dealing with kids at school who are jerks to each other all the time—you’ve got to teach them how you handle it.

The goal isn’t to have a perfect business. The goal is to show them what trying looks like.

Breaking Rules vs. Following Them

Dana is passionate about this. She wants her kids to know that the way towards freedom isn’t to follow the rules—it’s to break them. But you have to understand the risk and consequence of breaking that rule.

Uber broke rules. Instacart broke rules. Every major innovation happened because someone looked at the status quo and said, “Screw that.“

Your business doesn’t have to change an entire industry. But it does teach your kids that when something doesn’t work for you—whether it’s a 60-hour corporate job, staying home without any creative outlet, or the way “everyone else” does things—you can create a different path.

Krista adds her perspective: she wants her kids to have autonomy. She never wants them to feel beholden or restricted, like they can’t do something or have the life they want just because someone told them it has to be a certain way.

When Krista had her kids young, everyone told her she’d either have to stay home and give up everything for herself, or go get a regular job and never see her kids. Someone even called her spoiled when she said she refused to accept either option. She was going to do both—be available to her kids and build something for herself. That decision shaped everything that came after.

The Self-Development Journey You Didn’t Know You Signed Up For

Starting a business is one of the most intense self-development journeys you’ll ever go on. And that’s exactly why it makes you a better parent.

You become more self-aware. You learn to manage stress differently. You figure out your boundaries. You realize you need a therapist, a coach, better nutrition, or all of the above. Half the people in entrepreneurship end up healthier, not because they set out to be, but because building a business forces you to level up in every area of your life.

Krista explains how once you start doing things differently, you get introduced to all the other people in the world who do things differently. Then you all start hanging out, and suddenly you’re deep in conversations about adrenal health and mobility and things that have nothing to do with your actual business.

Your kids get to watch that transformation. They get to see you become someone who doesn’t just accept the default.

But here’s what Dana wants you to understand: if you don’t look at having your business as a self-development journey, you could have a business and never develop in that way. And maybe you just end up teaching your kids that following your dreams hurts. That’s not what we want.

What Happens When You Don’t Do This

Think about Dana’s cat. She watched him try to catch a bug and realized he just taps it. He has no urgency. There’s no reason he would ever actually take it down, even though it’s a natural thing for him. Everything is so comfortable.

That’s what happens when we over-protect, over-shelter, and make everything easy. We raise kids who can’t handle discomfort, who don’t know how to take risks, and who freeze when life gets hard.

Krista says you are going to have to do hard things at some point. There’s no value in sheltering and protecting them so much that they never have to do anything. They’re gonna fall on their face sometimes, and they need to know what that looks like. They need to know that you’ve done it and you were fine.

If they never learn how to take those risks or do something hard or put themselves intentionally out of their comfort zone, they’re gonna end up like Dana’s helpless cat. And nobody wants that for their kids.

It Doesn’t Have to Be Huge to Matter

Not everyone needs a million-dollar business. Your business could be:

• An Etsy shop that brings in vacation money
• Teaching other moms how you homeschool
• Reviewing products on Amazon
• A seasonal business that fits around your kids’ ages and stages
• A micro-business that you only work on a few hours a week

The size doesn’t matter. What matters is that you’re showing your kids what autonomy looks like. What problem-solving looks like. What resilience looks like.

Dana believes 100% of moms should have a business. Not because everyone needs to be a CEO, but because our kids are watching. And they’re going to grow up and face the same desires, the same emptiness, the same need to do something meaningful. If we don’t show them how we figured it out, they’re going to be lost.

The World Your Kids Are Inheriting

Here’s what’s real: the world is changing faster than ever. AI is unlocking everything. The rules are being rewritten constantly. Your kids need to know how to adapt, how to question, and how to create their own path when the old one stops working.

Dana and Krista talk about how most of the population still believes you graduate, go to college, get married, have kids, and retire. That’s the 80%. You might think that’s outdated, but it’s still the dominant narrative. And honestly, you and I probably don’t hang out with those people, so it feels like the whole world thinks differently. But they don’t.

Your business—no matter how small—shows your kids there’s another way.

Dana is sick of rules that everybody tells her are set in stone. She doesn’t want her children growing up and going, “Well, it is the way it is” or “That’s just how it works.” The whole point of entrepreneurship is to question. And over the last decade, we’ve watched a world that has changed so rapidly—the opportunities, what we can do, how money is made, how we’re happy, who we figure out who we are. AI has unlocked everything and changed all the rules.

So entrepreneurship teaches us as moms that we can change the rules. And our kids? They can change the rules too.

Which means if we are miserable, we have a choice to figure out how to get out of it.

Start Showing Them Now

If you’re already building a business, bring your kids into it. Talk to them about what you’re doing. Let them see you research, strategize, fail, and try again. Show them the brave parts, the hard parts, and the “I have no idea what I’m doing but I’m figuring it out” parts.

Krista had Bri sitting next to her when she was researching businesses and creating those custom PDFs. She told her daughter exactly what she was doing and why. That wasn’t performative—it was just real life. And Bri learned by watching.

If you haven’t started yet, know this: your kids don’t need you to have it all figured out. They need to see you try.

Because one day, they’re going to want something different for their lives. They’re going to feel that same drive you feel right now. And when that happens, they’re going to look back and remember what you did—or didn’t do—about it.

The greatest gift you can give them is that feeling of autonomy, the ability to have control, to take things and make what they want happen. Dana wants her kids to know they should be breaking rules and understanding the risks. Krista wants her kids to never feel restricted by what someone else thinks their life should look like.

What do you want for your kids?

Ready to surround yourself with moms who get it? Join Boss Mom+ and stop feeling like you’re the only one thinking this way. Because you’re not—you just haven’t found your people yet.