Balancing life and business with kids between the ages of five and nine comes with its own unique set of challenges and joys. If you’ve made it through the infant and toddler years, you know the chaos doesn’t end—it just changes. In this stage, parenting becomes a mix of independence, constant interruptions, and unexpected hilarity. In this post, we’ll explore what it’s really like to run a business while navigating the adventures (and occasional madness) of raising school-aged kids.
The Reality of Parenting Kids Ages 5-9
I have to admit—I’m one of those moms. You know, the kind who loves their kids but isn’t necessarily a “kid person.” I don’t love going to the park. I don’t understand why children must yell to have fun. And I’m not one of those people who longs for the baby stage—I actually looked forward to my kids growing up so we could have strategic conversations and share unique thoughts.
But let me tell you, having more than one kid is a whole new level of negotiation. They’ve realized just how different they are and—news flash—they don’t always like each other. One wants pizza; the other wants sushi. One wants to go outside; the other wants to stay in. And guess what? They expect you to be the referee for all of it.
And let’s talk about how this phase of parenting affects business, because, oh boy, it does.
If you’ve been following along, we’ve been diving into the parallels between raising kids and growing a business. Last time, we talked about the toddler phase—both in motherhood and entrepreneurship. Now, we’re moving into the next stage: the five-to-nine-year-old phase, where things start to get fun… and just a little more complicated.
The Shift from Survival to Strategy
In those early days, whether with babies or brand-new businesses, it’s all about survival. You do what you have to do. You power through the exhaustion. You make decisions quickly because there’s simply no time to second-guess yourself. But then, your kids (and your business) start to grow up. They become more independent. You have a little more breathing room. And suddenly… the overthinking starts.
What should I be doing now? What am I missing? Should I be doing more?
It’s the same with kids and business. When they hit this stage, we start to believe that because we can be more strategic, we must overcomplicate things. But just like in parenting, sometimes the simplest approach is still the best one.
Navigating the Noise (and the Drama!)
At this stage, our kids are navigating friendships, independence, and emotions—often in very loud and dramatic ways. One minute they love their best friend, the next they never want to speak to them again. The playground is basically a social experiment in real-time.
And, honestly? The online business world isn’t much different. We see trends come and go, strategies rise and fall, and we wonder if we’re missing out by not jumping on every new thing. But just like we teach our kids to navigate the chaos of friendships with resilience, we need to do the same in business.
Taking It Slow and Enjoying the Journey
One of the biggest lessons from this phase—whether in business or parenting—is that you don’t have to do everything at once. You can’t do everything at once. The best results come when you take your time, focus on one thing at a time, and give yourself the grace to figure it out as you go.
So let’s make a pact, okay? Let’s stop overcomplicating. Let’s stop trying to do all the things just because we think we should. Instead, let’s embrace this season for what it is—a time to refine, grow, and actually enjoy the process.
And if you need support along the way? We’ve got you. Join the retreat, connect with the community, and remember—you are not alone in this.
Because whether in business or motherhood, we’re all just figuring it out one step at a time.
The Business Parallels: Growing Pains and Overthinking
Running a business when you have young kids is like raising another baby. In the early stages, you just do it. You’re sleep-deprived, overwhelmed, but you push through because you have to. There’s no time for second-guessing or overthinking—you’re in pure survival mode.
But then, as both your kids and your business grow, something shifts. You gain a little more freedom, and suddenly, you’re overthinking everything. You start questioning decisions, worrying about the next move, and maybe even spending money on things you don’t need because it feels like “the next step.” Sound familiar?
I’ve seen this pattern in myself, in clients, and in so many moms. We hit that phase of self-doubt and overcomplication. Why? Because thinking too much is a trap.
When we have space—whether in our homes, our schedules, or our businesses—it can feel freeing. But that space can also be a breeding ground for overthinking. Suddenly, every decision feels monumental:
- Is this the right move for my business?
- Will this fail?
- What if it succeeds beyond my wildest dreams? What then?
One of my clients once spent an entire hour spiraling about what would happen if she succeeded. She was convinced it would mean losing her family, traveling all the time, being too busy for her husband, and ultimately leading to a miserable, isolated version of success. Sound familiar?
The Trap of Overthinking
I’ve been reading this book called Don’t Believe What You Think, and it dives deep into the difference between thought and thinking. When you’re in thought, you’re in flow—you have ideas, you execute, and you move forward. When you start thinking, that’s when the self-doubt creeps in.
With kids, there’s always something happening. There’s no room for sitting around questioning every decision. But as they get older, and as your business matures, you get space—and space can be dangerous.
I once had a client spend an hour spiraling about what would happen if she succeeded—she was convinced she’d have to give up everything, be on the road constantly, and never see her family again. Mind you, she hadn’t even launched an opt-in yet. See how quickly our brains can sabotage us?
The Difference Between Thinking and Action
Moms are incredibly skilled at thinking. In fact, we’re so good at it that we sometimes confuse thinking with action. We can spend an entire day analyzing, strategizing, and planning—only to realize nothing tangible was actually done. And that’s exhausting.
In business, this can look like:
- Tweaking an offer again instead of just selling the one that already works
- Redesigning a sales page when what you really need is to send more emails
- Constantly questioning your approach instead of just implementing and evaluating later
Keeping It Simple: The Key to Sanity in Life and Business
The antidote? Simplicity. When my business started growing, I found myself caught in the “maybe I should” trap:
- Maybe I should add another offer.
- Maybe I should change my branding.
- Maybe I should reinvent everything.
But then I remembered: what I had before worked. People loved it. It didn’t need all the extra fluff. So I stripped it down and got back to basics. And you know what? The quiet simplicity was exactly what my audience needed.
Business Is Like Motherhood
Overcomplicating things in business is a lot like motherhood. With your first kid, everything feels like a big deal. By the time you have your second, third, or (in my case) fifth, you start realizing that some of the things you worried about before just don’t matter.
You still make mistakes, but you recover faster. You recognize patterns. You learn to trust yourself more. And this applies to business, too.
The Awareness Factor
Here’s the thing—you’re probably going to overcomplicate things at some point. That’s okay. Just like our kids have to learn through experience, we do too. The key is recognizing it sooner and course-correcting faster.
Instead of saving you from making mistakes, I want you to see them coming, adjust quickly, and move forward. That’s resilience. That’s wisdom. That’s growth.
Create Space—But Use It Wisely
As your business matures, it gives you more space—just like when your kids get older and suddenly you have five uninterrupted minutes (or even an hour, if you’re lucky). The question is, what will you do with that space?
- Will you fill it with overthinking?
- Will you add unnecessary complexity?
- Or will you use it to dial in on what actually moves the needle?
The more space you have, the more intentional you need to be with it.
The Wisdom You Can’t Teach
One of the biggest lessons I’ve learned—both as a mom and a business owner—is that wisdom isn’t something you can teach. Just like our kids have to learn some things the hard way, so do we in business. You will overcomplicate things. You will take a path that seems right at the time but later realize was unnecessary. And that’s okay.
The goal isn’t to avoid mistakes—it’s to recover from them faster. Recognize when you’re overthinking, course-correct, and keep moving forward. Because at the end of the day, parenting and business are both messy, unpredictable, and full of surprises. And honestly? That’s what makes the journey worth it.
So, Boss Moms, here’s your takeaway: Give yourself permission to simplify. Trust your instincts. And most importantly, stop thinking yourself out of good decisions. Because success—whether in business or parenting—isn’t about getting it perfect. It’s about keeping it going.
The Boss Mom Virtual Retreat: Your Guide Through This Transition
If you’re feeling the shift in your parenting and business journey, you are not alone! That’s exactly why we created the Boss Mom Virtual Retreat—a space designed to help moms transition into summer, a time when running a business looks very different from the school-year grind.
This isn’t your typical summit that bombards you with information. It’s an event tailored to give you inspiration, motivation, and actual action steps so that you can move through this season with confidence.
We designed this event to help you:
- Clear out the mental clutter
- Focus on what really matters in your business
- Take intentional action (instead of just thinking about it)
Because here’s the thing: You can think yourself into exhaustion. Or you can take simple, powerful action that actually moves your business forward.
The Time to Act is Now
If you’ve been stuck in the overthinking cycle, consider this your sign to step out of it. Join the retreat at bossmom.com/retreat, connect with like-minded moms, and give yourself the gift of clarity and momentum. Give yourself the permission to slow down, focus on what really matters, and build a business that works for you.
Because let’s be honest—perfection isn’t the goal. The goal is progress, sustainability, and actually enjoying the process.
Let’s do this together. See you at the retreat!
February 27, 2025
