As someone trained to be a risk-averse lawyer, entrepreneurship wasn’t originally in my life plans. Yet here we are, 9 years into Mindful Return and 2 years into running my own law firm, and I feel like I’ve finally fully embraced the entrepreneur title.
For me, this career shift toward entrepreneurship wasn’t a giant leap but rather a years-long pivot. What started as a nighttime “passion project” became a “side gig,” which over time became my mostly full-time role supporting working parents through Mindful Return. (I say mostly full-time, as I still do practice law for about 10% of my workweek.) I’ve learned a million things from this journey. Trusting myself. Knowing what to stick with and what to abandon. How to find and connect with supportive communities. And perhaps most importantly, I’ve learned that getting comfortable with sales is a *must* in entrepreneurship.
If you’ve ever flirted with the idea of “striking out on your own,” this post is for you. I’m delighted to introduce you to Elizabeth Hubley, founder of The Mama Love Collective. Elizabeth not only runs her own business that supports new parents through the postpartum period, but she also leads mentorship circles for parents who are just starting or are in the early years of starting their own small businesses.
Heed Elizabeth’s advice and ask yourself these key questions, if you’re thinking about whether entrepreneurship is for you!
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Last spring, my friend Lauren called. Without even saying hello first, she jumped in with, “Why didn’t you tell me how awesome working for yourself is?! I mean, you did tell me, I just didn’t understand until now. But it’s so worth it. You have to tell everyone it’s really worth it!”
She had started her “dream job” nine years ago. But two kids, a move, and a pandemic later, she was completely overwhelmed and underappreciated. She also felt stuck, because her position provided steady income and the family’s health insurance.
Personally, I’m coming up on my 10-year anniversary of being self-employed. While entrepreneurship certainly has its challenges, I know it’s the best choice for me and my family—something I share often with friends and clients. And while it’s not for everyone, I’ve had hundreds of conversations with parents about how having kids can often make us reconsider our priorities and make dramatic changes. But how do we know we’re ready?
Here are three questions that can be helpful in guiding you in your consideration. My favorite way to do this exercise is to write each question at the top of a blank piece of paper. Then write whatever comes to mind. There are no wrong answers!
- Why do I want to leave full-time employment?
This is not usually a challenging question (so many reasons!). But getting clear on the answer can be really helpful. Our motivations can range from positive and forward-thinking, to a “get me out of here!” reaction to a toxic work environment, to a shift in priorities, or something else entirely. In fact, it’s often a mix of many different things.
Some parents are inspired to create something new as a result of their own experience in pregnancy, birth, and parenting—like Lori founding Mindful Return! Similarly, a dad in our community created fatherhood circles to create a much-needed space for new dads to connect.
Economics can also play a role. A mom I worked with who gave birth to twins realized that almost her entire full-time teaching salary would go to paying for daycare. She decided to start a part-time tutoring and student advocacy business to spend more time with her kids and earn more per hour to pay a part-time nanny.
Writing down all the reasons you want to leave your full-time job can help you clarify what you are looking to create. It can also help you identify what specific areas you should pay attention to as you start something new.
- What is holding me back? In other words, what are the barriers to entrepreneurship?
This is another question where your answers might fill the page, starting with big thoughts like, “what if I fail?” and “what will other people think?”
Another common challenge is guilt or uncertainty around “giving up” something you’ve been working on or toward your whole life. It’s a huge identity shift to transition, for example, away from a successful career as a Pediatric ER doctor and start a gluten-free bakery.
The fear of not having a regular paycheck is also real! In our summer Mentorship Circle, every single person cited variable or uncertain income as a top concern when leaving full-time employment. The shift to more of an ebb and flow of income is a big one. Plus, having no paid vacation, sick time, or parental leave all factor into the earnings equation.
These are all real challenges. But the benefits of starting one’s own business often provide enough positives to make it worth it.
- Who are my support people and communities?
This is often a little harder than the first two questions, but it’s a key piece of the puzzle. Here are a few to consider:
If you have a partner, having them on board in entrepreneurship is pretty essential. Many aspects of your shared life will change. This includes finances, daily timing, the mental/physical load of managing your home and child(ren), and so much more.
Friends and family are great to have in your corner when you’re having doubts or need someone to proofread your website. These are also people who will celebrate your successes! Some people hire accountants, marketing firms, business coaches, lawyers, and others as they start and build their businesses. These people can be a wealth of knowledge and expertise.
A final essential element is other people who are “in it” with you. This can be friends, mentors, or acquaintances who have started their own businesses. Even better if they are parents, so they can commiserate with you about how many Bluey episodes it took to finish an important email.
Now that you have 3 pages filled with motivation, challenges, and support, you may be ready to take some next steps. You may also realize that a shift in your schedule, a different position, or staying right where you are is best.
If you’re feeling inspired to keep exploring, here are a few next steps for those considering starting their own business:
- Reach out to others in your prospective field or business area to see how they got started.
- Talk with your partner or spouse about your idea and how it would impact your family.
- Sketch out a rough budget for household expenses (so you can see what you’ll need to earn to make it work).
You have my friend Lauren and I cheering you on! After some serious work and consideration, she secured a part-time contract with a great hourly rate, purchased health insurance through the exchange, and gave notice to her employer. She told me last week that she’s sleeping better, actually has patience for her kids, and loves making her own schedule.
Elizabeth Hubley is a certified holistic health coach, group facilitator, yoga instructor, and director of the Mama Love Collective. She has worked with hundreds of parents through Mamas Circles, Parenthood Circles, One-on-one Coaching, Motherhood Redefined, and the Mentorship Circle for parents who are starting their own businesses. Elizabeth lives in Silver Spring, Maryland with her husband and two young children.
Want more practical tips on working parenthood? Check out my book, Back to Work After Baby: How to Plan and Navigate a Mindful Return from Maternity Leave
