The 4 C’s of Entrepreneurship Fail Forward to Success with Jen Myers

This week, I had an honest, and truly inspiring conversation with Jen Myers about her struggles starting a business with her husband, the points where it almost broke her, and how she came out on top by learning some invaluable lessons…

Episode Quote
I quit believing this lie that I was telling myself – that in order for me to go to the next level, he had to come with me

Jen Myers

Episode Highlights: 

00:02:55 Trying to fit into the wrong box
00:05:17 Wasted energy
00:8:00 Finding a community
00:09:00 A thousand pounds lighter
00:12:05 An outside perspective
00:15:44 Homeschool CEO

Read The Full Episode:

Welcome back to another instalment of the Digital Breakthrough Podcast, Fail Forward to Success series. 

This series is so close to my heart because it’s all about learning from our failures. I always say that your successes are inspiring for a second, but it’s what you were able to learn that really energizes me. I named the series Fail Forward because that’s actually what failures help you do. They help you move forward and create opportunities to learn. I like to say we don’t Fail, we have a Fun Attempt In Learning!

I am so grateful to share the amazing conversation I had with my guest today. Jen Myers is the founder of Homeschool CEO, a global community for entrepreneurs who also homeschool. She has 17 years of juggling marriage, motherhood, entrepreneurship, and homeschooling. Jen speaks from real life experiences regarding successes and failures of balancing motherhood, marriage, and business. When she isn’t coaching clients about how to streamline their business and life, Jen can be found spending time with her husband, four kids, and two dogs in small town, Iowa. 

Through talking with Jen, I realized there were 4 specific principles that she gained from her failures. Once she was able to realize her need for these principles, she was able to set healthy boundaries, level up in her business, and find peace and positive communication with her family and spouse. So, let’s discover what these principles are, and how you can learn from Jen, and apply them yourself!

The 4 C’s of Entrepreneurship


1. Counselling 

As simple as this first C sounds, believe me, it is one of the critical pieces that will help every other step fall into place. 

Jen started her failure story at the moment she realized she and her husband should never have gone into business together. Their first business together was a power sports/ATV based business, and Jen’s approach to entrepreneurship was drastically different from her husband’s. Mainly, that she wanted to run her own business, and he didn’t. Their communication was struggling, and with it their marriage. She realized they were spending so much time fighting and she was trying to make him conform to a mold she thought was best, that she didn’t have any energy left for her business. 

The first, super important step to Jen’s growth out of their failed attempt at working together was to find an objective, 3rd party advisor who could help her and her husband get perspective. They went to counseling together, and individually, and it became the first step out of their failures. 

Jen was able to gain really great insight into the reasons why she and her husband were struggling so hard to own their business together. And through that, she learned to step into her own power as an entrepreneur, and help hundreds of other women build strong foundations for themselves, too. 

If you are in a space where you feel stuck, and you just can’t seem to understand how to solve a problem you’re facing, it is really helpful to get perspective from an outsider. You could reach out to a coach, a counselor, a friend, or a mentor. You want to make sure that person cares about your success, but is also able to approach your situation objectively.

Episode Quote
“Get an outside perspective because they’re going to help you go farther and faster than you could ever go on your own

Jen Myers

2. Cooperation

One of the first lessons Jen learned was that she had been trying to fit her husband into a box he just wasn’t made for. Jen is an entrepreneur through and through. She strives to create offerings that can positively affect people worldwide, and truly wants to put all the work in required to build that kind of a business. 

Her husband is just as driven, but in a different way. Where she wants to run a business, he wants to be an employee, but probably not her’s. So, when Jen woke up every morning at 4am, but didn’t see her husband wake up until 11am, she would think that meant he didn’t care as much as she did. 

It got to a point, Jen reflected, where she was putting the business before her partner and her family. She thought they didn’t care as much as she did, but in reality they just saw the world differently, and that is ok. 

Jen found herself constantly exhausted. She was spending all her energy frustrated that her husband did work the same exact way she did. And because of that, her business began to suffer, too. 

The second she realized that two people in a marriage do not have to define success in the same exact way, she felt the pressure lift almost immediately. She thought they had to be invested in the same way, on the same page. But as long as they are able to hold space for each other to be their best selves, they will be successful no matter what.

For the longest time, she just didn’t understand why he didn’t have the same love for entrepreneurship as she did. She wanted him to conform to what she thought was best. Through counseling, and being able to expand her perspective, she realized he simply has different strengths than she does. It’s not better or worse, it’s just different. 

And by realizing that, Jen was able to release her husband from their business. She learned that it’s ok for him to not want to be an entrepreneur. And more importantly, that she is still able to pursue her passions in business on her own.


Episode Quote
You can be in love with somebody that is really different than you And doesn’t define success in the same terms you do. And that is ok

Jen Myers

3. Confidence

As Jen reflected on the difficult time struggling to be on the same page with her husband, she realized she was actually holding herself back this whole time. 

Jen realized that she had been telling herself the lie that she needed her husband in order to get to the next level in the business. Step by step, as he distanced himself from the business and she started to understand the differences between their passions more, she realized that he actually did not have to come with her every step of the way. 

Once you are able to give yourself credit for your own passion, you realize that you do not need anyone else’s validation along the way. This is your passion and your business and you don’t need anyone to give you permission to get to the next level. 

Jen realized her marriage could survive without the business, and her business could survive without her husband, everything fell into place. She stopped looking to someone else to validate her success, and started giving herself the credit she deserved. 

With the help of counseling, and setting her husband free from entrepreneurship, she felt a thousand pounds lighter, and started reaching amazing heights in her business.

4. Community

Jen gained so much clarity and found success in her business when she was able to step out on her own. But, part of realizing she needed to release her husband from entrepreneurship was also realizing that she needed to find other people to talk to about that world. 

She now invests in masterminds where she can find like minded women who are as driven as she is, and understand the pride she takes in waking up at 4am. And because of this new space, her marriage is so much healthier and happier. 

And, she now has more energy to dedicate to her business and impacting the lives of women around the world. 

Jen’s company, Homeschool CEO, is founded in community. They have an entire community on facebook, where homeschooling, entrepreneur moms can find others who relate to everything they go through. She is also active on Instagram and Clubhouse. If you are on that app, check out the Homeschool CEO club. 

Jen has used her company to develop a global community of moms who are facing the same challenges and can share in each other’s successes. 

She has not only created a powerful community, but also offers business and life coaching, and a paid membership to really find that comradery from other moms who understand completely what you might be going through. It’s more common to have business friends, or homeschool friends, but at Homeschool CEO, moms get to build a community of business AND homeschool friends. 

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