Navigating a career while raising a family comes with unique challenges, and often, we face pivotal moments that require us to make tough decisions and take leaps of faith. In a recent Boss Mom podcast episode, Dana Malstaff sat down with Kendra Hennessy, founder of Mother Like a Boss, to explore these key turning points and the emotions behind major business shifts. This conversation offers valuable insights for moms and entrepreneurs looking to evolve their businesses while staying true to themselves.

How Pivotal Moments Shape Your Business Journey

A pivotal moment can be any life event or decision that changes your path. For Kendra, that moment came when she transitioned from running a successful cleaning business to creating an online brand focused on teaching moms home management skills. After years of working in the field, she recognized that it was time to move on—an experience that was both exhilarating and scary.

Kendra’s Key Takeaway:

“I was grateful for my cleaning business, but it was time to move on. I wanted something new, something that allowed me to be home with my kids and focus on what I loved—helping other moms. It was terrifying to let go, but that change was essential for growth.”

As Kendra shared, such pivotal moments can feel risky, especially when they involve leaving behind something successful. But as Dana pointed out, these moments often spark our greatest growth. Moving from a comfortable place into something unknown challenges us and helps us discover new strengths and passions.

Embracing the Grief of Moving On

Leaving a career, business, or role that once fulfilled you can feel like a form of grief. Kendra described the bittersweet feelings of letting go of her cleaning business, recognizing it as a necessary step to make room for her online business.

On the Emotional Side of Pivotal Moments:

“It was a grieving process. That business was part of my life, and moving on was hard. But it’s okay to feel those emotions. Letting go doesn’t mean you’re giving up—it means you’re ready to grow.”

 

Dana and Kendra discuss how grieving doesn’t just apply to business but can also occur when we transition into motherhood, when our children grow up, or even when we outgrow friendships. Allowing ourselves to process these emotions is vital for personal and professional growth. It’s through these pivotal moments that we can build the next chapter of our lives.

Freedom to Pivot Without Guilt

Many women feel pressured to justify their choices, especially when they involve career shifts. Dana and Kendra agree that a big part of entrepreneurship—and life—is knowing when to pivot and recognizing that it’s okay to do so. As Dana mentioned, we don’t owe anyone explanations for the choices we make; sometimes, moving on is simply the best decision for us.

Dana’s Thoughts on Justifying Your Pivotal Moments:

“You don’t owe anyone an explanation. If a path doesn’t feel right, you have the right to change it. Entrepreneurship and motherhood are journeys of constant growth and adjustment.”

 

This freedom to pivot is especially crucial for moms, who often feel the weight of expectations on their shoulders. By allowing ourselves to make changes without guilt, we set a powerful example for our kids—that it’s okay to follow our intuition and make choices that support our well-being.

The Role of Visibility in Pivotal Moments

Transitioning to an online business required Kendra to embrace a new level of visibility. She had to show up on social media, record videos, and connect with an audience in a way that wasn’t necessary in her previous business. This process was challenging, but it was a critical step in building her new brand.

Kendra’s Tip for Embracing Visibility:

“Start small and be intentional. Have a clear message, outline your points, and don’t be afraid to learn from others. It’s okay to practice and get better over time.”

 

Dana adds that confidence in visibility doesn’t happen overnight. It’s a skill that develops through practice. For moms building online businesses, showing up authentically can make a real difference. By being visible, we connect with our audience and inspire others who may be on similar journeys.

Shedding Old Identities to Make Space for Growth

Letting go of an established identity—whether as a business owner, a role within a company, or even as a stay-at-home mom—can be intimidating. But, as Kendra discovered, shedding an old identity can be freeing and open up new possibilities. Dana and Kendra liken this process to outgrowing an old relationship; sometimes, we have to move on to continue growing.

On Letting Go of Past Identities:

“I felt stifled in my cleaning business. It was predictable, and I wanted to do something different. Moving on allowed me to grow in new directions and discover new passions.”

 

Pivotal moments often require us to let go of who we were to become who we are meant to be. It’s a powerful shift that can lead to more fulfillment and happiness, even if the initial steps are challenging.

Finding Excitement in Uncertainty

While these changes can feel daunting, they also bring excitement and possibility. Dana compares the experience to skydiving—scary but exhilarating. Embracing the unknown can be a source of motivation and energy.

Dana’s Insight on the Thrill of Pivotal Moments:

“Entrepreneurship is about stepping into the unknown and trusting that the journey will bring growth. It’s a blend of fear and excitement that keeps us moving forward.”

This blend of fear and excitement is a natural part of any big shift, and embracing it helps us move through pivotal moments with more confidence and resilience.

Practical Tips for Embracing Your Pivotal Moments

Here are some actionable steps to help you embrace pivotal moments in your business:

1. Allow Yourself to Grieve: Acknowledge the feelings that come with change. It’s natural to feel a sense of loss when moving on from something that was once fulfilling.
2. Follow Your Instincts Without Guilt: Trust that you’re making the right decision for yourself. You don’t owe anyone an explanation—pivoting is part of growth.
3. Practice Visibility Gradually: Start by showing up in small ways that feel comfortable. Over time, you’ll build confidence in being visible.
4. Seek Inspiration from Others: Follow people who inspire you and learn from their journeys. Seeing others succeed can help you find courage in your own path.
5. Embrace the Excitement of Change: While uncertainty can be scary, it also opens doors to new possibilities. Focus on the thrill of discovering what’s next.

Final Thoughts

Pivotal moments are an inevitable part of life and business, especially for moms balancing family and career. They challenge us, push us out of our comfort zones, and ultimately shape us into stronger, more resilient individuals. By embracing these moments and trusting the journey, we open ourselves to growth, joy, and fulfillment.

For more insights on navigating business and motherhood, be sure to follow the Boss Mom podcast and join the community of supportive, like-minded women. Remember, no matter where you are on your journey, you’re not alone—and there’s always support waiting for you in the Boss Mom community.