3 Lessons I Learned About Taking Risks in my Business from Middle-School

bizmom business advice business coach mompreneur organization overthinking risk-taking Jan 23, 2020

How many times in the last 24 hours did you think to yourself, “I wish I could just settle for being normal and get a “real” job?”

If you could just get over this feeling you were meant for more, life would be easier, right?

You keep telling yourself there is nothing special or to be noticed about your business but deep down you know that’s a lie you tell yourself to stay safe. A lie that keeps you from taking chances.

I know that voice too, I know that wish, and it keeps me up at night sometimes thinking about all the times I’ve given into it. 

But not this time.

When you were in middle school you probably spent a ton of time thinking about similar things. As a mom of teenagers, I realize from watching my daughter this is where most of us start this type of thinking. We want to be noticed for anything in the sea of hormones, honor societies, and competitive sports. It’s the period of time when friendships, role models, and even parents start asking us to get in line with the status quo. And because we’re all individuals we rebel against it, some more than others but we all want that lucky chance to be seen for exactly who we are even when we have no clue yet who we will become.

I’ve been thinking about this a lot lately. Transitioning to providing business development training to women solopreneurs from leading a multi-level marketing team has been what I knew was my next “more” to take a chance on to be seen. I knew it to my core I was meant to make that leap. I knew I wasn’t supposed to settle where I was, even though to the rest of the world it would have made perfect sense to stay. I knew staying safe there or going back to corporate would make my life easier in some ways. 

How do you convince yourself that you're one of the lucky ones who has this driving force for more? All the while, caring for yourself in a way that encourages your determination when there’s no one admiring you? It can feel a lot like those days in middle school when the girls who conformed were the ones who received the candy graham on Valentines’ Day.

I’ve sat and thought about this and have put together 3 Steps to Stop Overthinking Like a Middle Schooler & to think more like a Mompreneur:


If you aren’t someone who was ever fond of tests this might make you a bit queasy, but I promise you it’s not that type of test. It’s more about developing the skills you need to be able to ace a test. As an entrepreneur, you signed up for a boatload of additional work than what you originally thought building a business would be. You have your area of specialty and that’s definitely where you already know you’ll shine when you’re with your customer, but what about all the other departments that you need to do work in and develop for your business?

Take a few moments and think about all the things you do in your business, maybe even set a timer for ten minutes and brain dump them all onto a piece of paper. Then decide where do they belong? What departments would they fall under if your business was a Fortune 100 company? Marketing? Sales? Operations? Accounting? Customer Service? If you want a few more department names, head to the school of Google, but take some time to test yourself on all the “hats” you’re wearing. Then decide which department you’re going to focus on “studying” for next. 

This is an important test to take. As a mompreneur, it’s important you recognize there might be places you need to conform a little bit. The departments that aren’t your expertise are departments I encourage you to develop a few friendships, a role model or two, and possibly take the advice you’d give your kids and do your homework.


Remember when you got the nerve up to ask the kid you liked since kindergarten to your school’s Sady Hawkins dance in eighth grade? Or maybe you wanted to but you just never took the chance, fearing they’d say no. As a mompreneur, there are going to be so many times you will regret you didn’t take the chance without even knowing it was a chance to begin with. This is why it’s so when you recognize chances to go after more, girl, take it! Taking chances is a part of what it means to know you want more. It’s knowing you’re worth more than what others say you are or deciding to settle for that small dream instead of going after the big one. In order for you to see that dream turn into reality, you are going to have to take the steps toward it.

Once you take a chance, you’re gonna feel all sorts of regrets. You’re gonna feel stupid, you’re gonna overthink how you handled it, you’re gonna wish you thought it through better. Like the fact that you didn’t realize the kid, you’ve liked since kindergarten is two-foot shorter than you while you're dancing together. What I will promise you is once you take the chance there is no going back. The great part is that now that you took the chance others will take notice and admire you for doing it.  

As long as you are taking chances, people will notice. They might not be exactly who we want to notice us but you can’t stop because eventually, it will be the perfect dancing partner. I promise others are watching and admiring you for taking the leap, risking the choice to look like everyone else, and hoping you will take a chance to ask them to be a part of your special plans too.


How many times have you told your kids that it’s ok to ask for help? Something about being a solopreneur allows this middle schooler mindset to take hold of you. You’ll feel like you need to do everything on our own. The reason I believe middle school is where we learn how to overthink instead of taking chances is because it is the turning point for most of us. Friends are transitioning, we can’t count on the same people we always did. It is the time when some of the work gets harder and studying becomes more than memorization. 

You and I can remind our kids over and over again to ask for our help from friends or teachers, but at no fault of their own, the season they are in has been telling them the exact opposite. 

“It’s time to grow up, time to do it yourself, time to be mature enough to figure it out without anyone else’s help.” The same sentences going through your head as you tackle the next chance you’re going to take in your business.

As a mompreneur, you have probably witnessed enough of times where you were able to figure it out on your own. Hell, even Marie Forelo wrote a book about it. I’m not saying she’s wrong here or that you aren’t mature enough to be self-sufficient in your business. What I am saying is to be determined enough to reach your goals of success by knowing when it’s important for you to be asking for the help you need from someone who has the strengths you don’t. Have the perseverance to develop this sort of grit of taking a chance on the help of others who know better than you.

There is no way you are going to completely turn off the doubts, overthinking, or fear you have about being someone who believes you have more potential than what the status quo will provide. Believing you were meant for more is the entrepreneurial mindset you need to reach the reality of your dreams. Take some time to remember what held you back as a middle schooler? What were the tests you wish you aced, or the chances you wish you jumped into headfirst, or the support you realize you had but couldn’t see back then? What’s the advice you are telling your kiddos about the same situations you’re facing in your business? 

It’s time #BizMama to take the test on where you need to study up in your business. Take the chances that will be the ones you are afraid you’ll regret but will be the ones you’re most admired by others. And without a doubt, take the support that is offered to you by those who’ve been determined enough to figure it out and hone their strengths in the areas of your business where you need the help.

Subscribe to @ivealwaysbeengena is a blog for women who believe the reality of their dreams is only as far as their skills and determination are willing to take them, who are raising their family while they are building their business, and for fempreneurs who desire the freedom of a life that is sustainable, purposeful, and profitable enough to invest in what matters most to them. Want to work with Genavieve Rose to learn how to keep your focus on both #MomLife & #BizLife? Then join her next #10DaystoWHY Challenge where finding your WHY leads to HOW & WHAT your business is destined to be!