What They Don’t Tell You About Being A Messy Entrepreneur & A Mom



I’m coming at you 36 weeks pregnant with my second baby, a toddler running around, and working from my bed today! (No shame here!) 

I feel like the idea of being an entrepreneur is a bit of a double-edged sword, and something isn’t sitting right with me regarding our expectations vs. reality… so I think bringing light to these topics will help others choose life and motherhood on our own terms.

For me, motherhood has always felt like something I was disconnected from. I didn’t know whether or not I wanted children, and my partner Bill and I were on the same page about that. We were in our early 30s and had never contemplated it. We loved to travel, so we lived a nomadic lifestyle for a while… which didn’t necessarily seem conducive to having kids.

It wasn’t until I got pregnant for the first time around five years ago that I realized I did want children. Deeply. However, examples I’d seen and conversations I’d heard of motherhood made it sound all-consuming, and like we had to want to stay home 24/7 with our kids. I thought I had to feel certain things in order to become a mother. (It’s what we’re shown in movies, social media, etc.… and it just wasn’t what I felt.)

I’d built a life I really loved, so for that reason, I felt disconnected from the idea of motherhood.

My parents were both entrepreneurs, and my mother had raised 4 of us with the help of nannies. She wasn’t the type to be home all the time. She’s the perfect example of someone who had multiple businesses, traveled all the time, AND had multiple kids. (She’s been to more places than anyone I’ve ever met! She lives for traveling.)

This was my own mom’s example, yet here I also had society telling me what mothers should be like, and something just wasn’t adding up. As soon as Coco arrived, I realized I had a tough balance to figure out.

One day while breastfeeding Coco, I had a moment with her where she looked up at me with her huge blue eyes. It touched the depths of my soul and deeply connected me in a new way to my mother, and I had an intense realization: “Oh my god… the hours she spent with me doing the same thing!” It was an almost out-of-body, deep experience thinking about how almost all mothers have had similar experiences.

It deeply connected me to my mother, and of course, my daughter.

When I think about my mom and my experience of watching her as an entrepreneur, it was an incredible gift to see her raising 4 kids and not letting go of her passion for travel and entrepreneurship.

Growing up, I was hyper-analytical and critical of my parents. I used to wish they’d done a lot of things differently. Then, becoming an adult, I had a lot of my own work to do in facing various traumas from growing up, like a friend of mine committing suicide in grade 9, to a case of sexual assault when I was in the care of one of our nannies.

In a way, motherhood has been a gift to heal and overcome those traumas. The path I’ve had to carve out has turned me into a person who is evolved, transformed, and changed from who I was as a child.  

Having a daughter has put me on a path to do the work because I don’t want to pass those things on to her.

Someone made a comment the other day that they meant well, but I realized I was triggered and needed to sort out why. They’d said, “Oh, you work a lot!”

As I started unpacking my own response, I realized I was triggered because I perceived judgment around the identity of being an entrepreneur for the “freedom,” while having the appearance of NOT having freedom.

The truth is, I do keep my work commitments each day because I thrive on structure, and that way, I can have freedom on other days and at other times.

I have the freedom to go to whatever country or province I want to go to at the drop of a hat. I don’t have to ask anyone’s permission anymore. My best friend can confirm this: I used to be SO afraid to work in a different place that I would literally dress up at the airport so no one would recognize me! I could fly wherever I wanted to, but I was terrified someone would see me. (I had THAT much anxiety about what I did before I became an entrepreneur!)

Now? I don’t feel one bit of shame anymore about the fact that I’m literally working from my bed.

The other piece to navigate in entrepreneurship, motherhood, and life is realizing that I sometimes need to rest in the middle of the day. Sometimes it’s a 1-2 hour meditation, sometimes it’s literally a nap, and there’s no one stopping me! I can even get in a workout, or if I know my daughter needs a little more from me that day, I am here for it.

THESE are what’s most important to me. “Freedom” isn’t just wiping my schedule whenever someone wants to do something. For me, it’s about freedom and flexibility around my family and what I need at that moment. Some days I don’t need anything and I can cruise through it and feel awesome. On other days, I need to recuperate and get out of “fight or flight.” I have the empowered life to be able to do that!

So I think the reason I was triggered upon hearing that comment was I took it as a challenge. “Are you really an entrepreneur that has freedom? Or do you work a lot, and that’s what other people perceive?” After considering the many things I really appreciate about being an entrepreneur, I realized my bucket is so full. I’m incredibly grateful.

In summary, entrepreneurship and motherhood are what you create them to be. You don’t have to do anything you don’t want to do, despite the impressions you get from society. Whatever impact you want to make, you can make. They can work together beautifully.

I was fortunate enough to be raised by a good example of balancing everything, and sometimes it’s still very messy… but on the other side, you can still have a great impact on your kids and what they think is possible! I love that I can work from home and hear my daughter all day long.

If you’re questioning how everything goes together and what it can look like, I hope my reflections can be helpful- even when life gets chaotic, and you don’t feel like you have your shit together!

Key Takeaways From This Episode:

  • I thought building a life I loved and not feeling what people said I should feel meant I was disconnected from the idea of motherhood.
  • Having a daughter put me on a path to becoming a more evolved, whole human because I didn’t want to pass on any past trauma to her.
  • I used to wish my mom had done things differently, but now I realize she gave me the gift of realizing it’s possible to raise kids and not let go of your other dreams.
  • Entrepreneurship and motherhood are what you create them to be.

Don’t forget….. If you loved this episode, screenshot it and share it to your IG stories and tag me @theashleyshaw.  I would love to connect with you!

About the author 

Ashley Shaw

Employee account created by MemberMouse

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