4 Lessons I Learned as a Pregnant Entrepreneur

After months of deliberation and weeks of preparation, I was ready to hire my first major employee. I wanted to legitimize my business, grow it into something bigger, and become more institutionalized. I wanted to really boss-lady this thing. Gangbusters!

And then, I found out I was pregnant one week before sitting down with my first big hire to tell her she had the job.

In fact, the meeting was set before I even saw those pink lines.  We were (and are) thrilled beyond belief at our growing family. This was what we wanted and hoped for, so it was good news all the way. But boy oh boy was it some heavy timing for me. I felt conflicted. I couldn’t tell if this was a sign to halt the Gangbusters Plan, or permission from the heavens to pursue the hustle.

In the end, I learned that it was all perfect timing. It was the moment to learn a few lessons about myself that only some pressure and tension could induce.

1. I was trying to “legitimize” my business up to someone else’s standards.

I got it into my head that my business was only legit if it had employees and payroll and a dozen accounts going at once. This frenetic pace that I couldn’t keep up with was the goal as outlined by others – to grow the business so that it was beyond me. Then, only at that point would the business become real.

Well news flash: you don’t start a business to make someone else happy. You don’t run a marathon or dye your hair to make someone else happy either. You do it for yourself and your soul.


I quickly realized that I had been making these growth decisions out of a place of feeling “not enough”.

Feeling that what I had built wasn’t good enough for someone else. Which brought me to a much more important question: Was it enough for me? Was it too much for me?  It was. The more I tried to hustle in any direction, the less peace I felt. I had built the business for a few people, but farther and farther away from my dream.

2. There is no perfect solution.

The only thing I could think about was what I would do once the baby was born. It became my sleepless, anxious, obsession for three months. Should I hire even more people? Would I want the full six to eight weeks of maternity leave? Will I want part time help? Where would I work from? Would people understand?

There was and is no perfect solution. No way to “do it right” in maternity leave, or otherwise. Heck, the jury is still out on whether staying home with your kids or putting them in day care is better for them - we may never know. While I searched for the perfect approach to this whole mom-preneur thing, all I could do was listen to what my heart wanted and could manage.

I realized the perfect solution for me meant doing what would: one - strengthen my family, and two - respect my employees and clients. In that order. Because whether what I chose was “right” or not, it was meaningless if it weakened my family or disrespected the business and those people impacted by it.


3. What I needed was already in front of me.

I actually started this company with my future family in mind. My hope was to create an environment where I would have flexibility and freedom - both of which I cherish and adore. It’s true I am about to lose them a bit with a newborn coming, and yes that freaks me out, but the whole model was prepared for this. For me to be remote, control the number of hours I work, and to be able to scale up or down as needed.

What I learned after many (I’m talking dozens) leadership meetings, phone calls to mentors, talks with my husband, etc. was that it was time to pull the flexibility lever on my business. I had created it to flex, and now was the time. To slow the pace, downsize, focus on core clients, and let the rest wait.  The solution I was looking for was baked in - I just couldn’t see it at first.

4. Hustle doesn’t pay, consistency does.

With all the ramping up I did trying to “legitimize” the business, and then the downsizing I did to refocus the business, I learned that hustling just for the sake of it is not what pays your bills. Doing good work does! Loving on your existing clients does. Being your best self each day does. I’ve actually had more business opportunities come through the door now that I’ve stopped hunting them down, and have a lot more peace of mind and heart. It’s created less stress and more happiness during a time where that is exactly what I want to cultivate.

As someone who has struggled her whole life to be perfect and in control (which is impossible and exhausting and no fun at all), I can tell you that throwing a baby into the mix can do just that – mix things up! It will impact your thoughts and feelings, it will change you. For me, it has done so in the best of ways.

I needed to kick the desire to create something perfect away.

I needed to slow down and reevaluate what I wanted. Sure, the timing created tension on all fronts. But it took my biggest dream being realized for me to lean into the discomfort and grow into my greatest role (a mom!).

Photos by: Valerie Moreno


Bailey Van Tassel

Bailey is a writer, wife, and mother, as well as the Director of Generosity and Culture for Auric Road, a petite resort hospitality brand, where she creates unforgettable experiences for guests and the community. She brings a wealth of knowledge from over ten years of studying the way the private sector interacts with the social sector, and how cause marketing can change the world. She founded her own social responsibility firm, Abel Impact, and has worked with companies like Google, Sysco, MasterCard, Club Corp, and many others. Bailey’s ultimate passion lies in writing about home and happiness, along with her love for her family, yoga, cooking, and doing anything outside.