Raising a Little Entrepreneur (Pray for Me)

Somebody should have warned me that entrepreneurship is basically an incurable disease, because I would have liked to have had that information before I caught it.

And the really inconvenient part? I’m pretty sure my son already has it too, and he’s ten.

Let me back up, because his story actually starts in second grade when my kid figured out something most adults haven’t…it’s easy to start a business, but keeping it going is a different story.

He was earning “school bucks” for good behavior and high test scores, totally wholesome, very on track to be a model employee for some corporation someday.

Then one day, he used five school bucks to buy a pack of stickers from the school store and turned around and sold individual stickers for a buck each, walking away with fifteen school bucks and apparently zero guilt about it.

I did not teach him that. He was completely his idea. I want that on the record.

Fast forward to this school year, when some kids in his class started a little rubber band bracelet business, and my son came home ready to declare himself a co-founder.

I had to explain to him, very clearly, that “I want in” is not a business plan, and that if they’re doing the work, it’s their business, not his just because he has entrepreneurial energy and a lot of enthusiasm.

He sat with that for a couple of weeks, came back to me, and asked if he could use his Christmas money to buy a bracelet-making kit.

I said yes, mostly because I was genuinely curious what he was going to do with it, and also because I’ve learned that this particular kid doesn’t let things go.

He had his sister teach him how to make the bracelets, put three of them on his own wrist, walked into school, and sold them right off his arm before the last bell.

The next day, he sold five and came home with actual real dollars, which is when my parent brain finally caught up and said “hold on, we need some guardrails here.”

I made him check in with the other kids’ parents and looped his teacher in (because I was not about to let my child accidentally run an unlicensed elementary school economy without adult supervision).

Then one morning, my husband dropped him off, and a teacher he had never seen before called across the parking lot, “Hey, do you have bracelets to sell today?”

Word had spread to the whole school, and my fourth grader had apparently built something resembling a “personal brand.”

He kept showing up with five bracelets on his wrist every single day and coming home with none, then making more that night and doing it all over again.

But, like most “hot trends,” it ran its course after about eight weeks.

Kids (and teachers, apparently) stopped buying so he stopped making them.

He didn’t even recoup his original investment, and honestly, he was completely fine about it because when you’re ten, “failure” only costs you $20 and some afternoons you could have been playing Xbox, and then you just go eat a snack and move on with your life.

When you’re a grown adult with real bills and real stakes, failure costs a lot more than that.…

like sleep, margin, presence, peace, and sometimes years of pressure while you keep building something you genuinely cannot stop thinking about even when it’s not working.

(ask me how I know!!)

When Inspirational Stories Stop Being Inspirational

And you want to know what really, REALLY drives me crazy? The stories of all these famous people who failed over and over and then finally “made it.”

You’ve heard them…

Michael Jordan missed a lot of shots, Oprah got told no, J.K. Rowling collected rejection letters like a hobby before Harry Potter found its audience and exploded into a world all in and of itself.

And from a comfortable distance, those stories feel like proof that failure is just a step on the way to greatness.

Buuuut when you’re the one in the middle of it, when the rejection is landing in your actual inbox or being said to your actual face, those stories don’t feel motivating at all.

They feel like a Cinderella story that applies to other people, and you’re just sitting there with a rotting pumpkin.

I want to acknowledge that, because I think you deserve to hear it said plainly: the messy middle is hard, rejection is genuinely terrible, and it’s okay if you’re not feeling inspired by someone else’s comeback story when you’re still in the part where nothing is working yet.

But I also know that the only guaranteed way for those stories to never be yours is to actually quit in the failure moment.

Because every time something doesn’t work, you learn something real that gets you closer to finding what will.

That’s not a motivational poster; that’s just the actual mechanics of how to build something that works. Period.

But I also want to be honest about something that doesn’t come up enough in these conversations. Not everybody is built for this life, and that’s not a character flaw.

The highs of running your business are legitimately obnoxious. Like, coffee-fueled, can’t-sleep-because-you’re-too-excited obnoxious.

And the lows are the kind of low where you find yourself curled up under the covers binge-watching some cheesy Netflix series, actively choosing not to look at a bank account that is reaching dangerously low levels.

And if you have the “entrepreneurial bug,” you know that feeling well, because you’ve been there, and you came back anyway.

But if you’ve been white-knuckling your way through entrepreneurship because it seems like it should be right for you, and you’re exhausted not just from the work but from the relentless uncertainty of it all, that’s worth sitting with honestly.

Weekly Challenge

This week, I challenge you to do a real reflection. Not the “I’ve got this, I’m a boss” kind, but the kind where you get quiet and actually ask yourself the hard question.

Are you someone who keeps coming back after the hard stuff because something in you genuinely can’t NOT build?

Or have you been trying to force yourself into a life that isn’t actually what you want, because you feel like you SHOULD want it?

Both are honest answers, and they lead to very different paths, but either way, you deserve to be on the right one for you.

If you’re staying in the game, start treating your failures like data instead of verdicts. (I’m literally preaching to myself right now.)

And if you’re realizing this isn’t the life you want, give yourself permission to choose something different on purpose, instead of letting the uncertainty make that decision for you.

Both take courage and intentional action.

All that to say this…if you’ve got the “bug” and you’re not looking for a cure, but you are looking for a way to make the messy middle significantly less messy, I want to talk to you.

I work with entrepreneurs who are done surviving their business and ready to actually run it, using AI-powered systems to move faster, stress less, get more done, and make more money without needing to hire a whole team to keep up.

If that sounds like exactly where you are right now, DM me with the word BUG on FB or LinkedIn and let’s talk about what that could look like for you.

Because the messy middle doesn’t have to stay messy forever. It just needs the right systems to make it survivable, sustainable, and actually worth it.

Btw, in case you were wondering, my son literally walked in the door from school today as I was getting ready to publish this very newsletter and announced that he started a new business selling little plastic ducks…and “business is BOOMING!”

I think it’s too late to save this kid, he has got it BAD! 🤣