As a working parent or someone contemplating parenthood, you’re navigating a complex landscape. If you’re an entrepreneurial parent, or aspiring to be one, the challenges can feel overwhelming, leaving you anxious, torn, drained—or even experiencing all three. It’s easy to feel isolated in your journey.
And why wouldn’t you?
Each parent has a distinct story. Every entrepreneur travels a unique path. Therefore, no two self-employed parents, or parent-entrepreneurs, share identical journeys.
Even if you and a neighbor both work in the same industry, are freelancers, and have children around the same age, your choices will differ. You will lead your families in diverse ways and perceive your work through different lenses. Nevertheless, all those who identify as entrepreneurial parents encounter significant shared challenges. Balancing child-rearing with non-traditional work structures introduces certain realities, pressures, and certainly some benefits, too. Whether you’re an entrepreneur contemplating adding to your family or a parent considering striking out on your own, it’s wise to be aware of these realities—to fully grasp what lies ahead. Why navigate the road ahead blindfolded when a clear view can be yours?
We are about to share vital insights on entrepreneurial parenting, gathered directly from the source. These insights come from a wide array of parents who have lived through these experiences, sharing lessons they’d wish they had learned sooner. After absorbing their candid advice, you’ll face some tough questions—queries that could help refine your entrepreneurial aspirations and boost your confidence.
Truth #1: Entrepreneurship and parenting can reflect each other.
Indeed, they can resonate both practically and emotionally. Both roles demand immense commitment, especially in their early stages.
Truth #2: There’s no perfect time to transition into becoming an entrepreneurial parent.
You’ll need to make decisions regarding timing—without seeking external validation or approval. There is no universally accepted right moment to have another child, increase your workload, or shift careers. The same principle applies here. If you’re looking for the perfect moment to become a working-parent entrepreneur, be prepared for a long wait. Carefully consider the advantages and disadvantages before making your choice. Trust in your decision, as encouragement may be scarce.
Truth #3: The business model you choose is crucial.
It’s not only about possessing a sellable skill or a brilliant concept. You must devise a revenue strategy—one that takes your parenting obligations into consideration. As straightforward as it may seem: Understand how you intend to generate income. Don’t assume that being self-employed automatically makes your situation parent-friendly. Be truthful about the time you wish to dedicate to your children, and strategically manage your income and expenses accordingly.
Truth #4: Robust systems and infrastructure are vital.
Without them, you risk spending a disproportionate amount of time away from your children. Being your own boss can provide incredible liberty, adaptability, and the opportunity to focus on the broader vision. However, it also places the onus on you to oversee all underpinning operations: IT management, tax obligations—all those fundamental systems you might have overlooked while working for others or within a larger framework. Unless you are practical, inventive, and disciplined regarding these requirements, they might soon become overwhelming.
Truth #5: Monitor your expenses.
As a working-parent entrepreneur, it’s essential to increase your vigilance regarding expenses. In a larger organization, budgetary constraints exist, but ultimately it’s the company’s resources rather than your own. Once you shift to self-employment, this separation often erodes: your personal finances and professional finances may become intricately linked. This necessitates a more thoughtful approach to both expenditures and savings.
Truth #6: Expand your business at a pace that suits you.
Be intentional and clear about what that pace looks like. The narrative of someone who founded a business and sold it for a fortune within a couple of years is intriguing. Who wouldn’t desire such swift success? However, as a parent, rapid growth could lead to more time spent away from home and potential stress or burnout. Clearly establish your growth goals, and remain committed to them.
Truth #7: Family-friendly benefits are not limited to large corporations.
You can sometimes create similar advantages for yourself. Things like corporate childcare services, lactation rooms, and networking opportunities for working parents are all valuable. Yet, if you can find or establish comparable resources within an entrepreneurial venture or through self-employment, these benefits don’t necessarily have to dictate your career choices.
Truth #8: Your family and community will be essential in raising this child.
Be pragmatic about the support you require and innovative in securing it. The more assistance you can garner, the better. Approach this creatively and systematically, identifying those who can lend support.
Truth #9: Flexibility might evolve into something entirely different, necessitating a new approach, or may be hard to pin down.
In reality, you may find yourself working more than ever. Entrepreneurship does not equal free time; it often involves increased responsibility and accountability, which can demand significant effort. While there might be positives, you need to carefully deliberate on how a career as an entrepreneur would impact you and your family.
Truth #10: The good news is: you have the autonomy to set your own boundaries. The bad news: accomplishing this may be challenging.
In a corporate environment, or while working for someone else, the delineation between work and personal time tends to be clearer. Now, with the shift into self-employment, those boundaries may blur, be dynamic, or be difficult to establish. You will need to create them on your own terms, without established protocols or explicit consent from others.
Truth #11: Taking a break can be challenging.
Or it could come with tangible repercussions. It can be quite difficult to step back when you bear full accountability for outcomes or lack paid leave, so explore the idea of different types of breaks compared to what you’re accustomed to.
Truth #12: Being self-employed allows you to design a fresh and improved model for working parents.
This benefits both you and fellow working parents. By forging your own course, you position yourself as part of the solution.
* * *
Now that you have a clearer understanding of the ever-present, unavoidable truths of entrepreneurial parenting, both positive and negative, perhaps some of your anxieties have eased. But a new question arises: How do the realities we’ve discussed intersect with your personal circumstances, career goals, aptitudes, interests, and family life?
Whether you’re just starting to contemplate the possibility of becoming an entrepreneurial parent or have been navigating this path for years, these questions will prompt thoughtful reflection on how to best combine your career aspirations and your life with your home responsibilities. Visualize discussing your responses with a nurturing friend or mentor—someone who embodies support and encouragement, who won’t criticize or make you feel foolish, and who won’t settle for surface-level answers. Imagine that person gently pushing you to be as honest and open as possible.
If you wish, you can engage in this conversation with a trusted partner, but utilizing the imaginary mentor concept is also a valuable tool for introspection. Regardless of the approach, the objective is to clarify what it means to operate independently and entrepreneurially within your life—and what potential decisions or actions you may want to consider moving forward.
As you ponder these questions and examine your answers critically, you might uncover personal insights: maybe you realize you need to rethink your business’s IT strategy, or that you prefer to hold off on freelancing until your twins are in school. It’s also possible you feel a bit adrift, lacking definitive responses to these inquiries. Even if that feels unsettling, it’s completely acceptable.
Keep in mind: an entrepreneur is someone who organizes and manages a business, assuming the risks and responsibilities of doing so. As a parent-entrepreneur, it’s not essential to predict every future outcome or have all the answers neatly outlined. What matters is your willingness to navigate and direct your career and family life while accepting responsibility for your choices. By grappling with these reflective questions, that’s exactly what you’ve accomplished.
Now, whether you’re putting in significant hours at a startup, considering the leap into entrepreneurship, or have ultimately decided against pursuing that path, there are effective strategies to align your distinctive career with your family commitments.
