We’re so excited to share this incredible conversation with Michelle Dempsey—the force behind Moms Moving On and the Moving On Method. Michelle’s journey from hands-on divorce coach to certification leader is packed with insights on what it means to level up and still stay true to who you are. Her story shows that by facing fears, embracing growth, and focusing on legacy building, women can create a big impact.
If you’re growing your business, shifting from one-on-one work to mentoring others, or wondering what it takes to lead without losing yourself, this episode is for you. Michelle and Dana dive into everything from tackling imposter syndrome to overcoming the guilt of “leaving the trenches.” They also chat about what it really means to create a legacy that empowers both clients and future leaders.
For a lot of women, stepping back from hands-on work to a leadership role brings up emotions we don’t always talk about. There’s guilt, hesitation, and a little voice that says, “If I’m not right there doing the work, am I still valuable?” Michelle shares her experience of stepping back from client coaching to build her certification program and the hurdles she faced along the way.
One of Michelle’s biggest fears? Losing her “relatability” as she leveled up. So many of us feel that if we’re not in the trenches, we lose touch with our community. Through self-reflection and some good ol’ therapy, Michelle realized that relatability isn’t about doing everything yourself. It’s about staying authentic and aligned with your purpose. When you level up, you don’t lose touch—you expand your reach.
Another big piece of Michelle’s journey was figuring out the difference between ego-driven decisions and choices fueled by passion. Letting go of the need for constant validation? Not easy! But it’s part of creating a legacy focused on others, not just what feels good in the moment.
Michelle explains how stepping back from client work allowed her to build a team of skilled coaches and increase her impact. It’s a mindset shift that many of us need: sometimes, we can do more good by teaching others to thrive than by doing it all ourselves.
A huge takeaway from Michelle’s journey is the value of legacy building. By creating the Moving On Method certification, she’s forming a community of skilled divorce coaches who are making a real difference. Dana and Michelle talk about the power of mentorship and why training people to do what you do—even better than you do it—is one of the most powerful ways to build a legacy.
Michelle’s certification program reflects a big shift toward practical, real-world education. As Dana points out, programs like Michelle’s can offer even more value than traditional education. They give real skills and mentorship without the student loans and rigid schedules.
Michelle’s certification isn’t just a course you finish and forget—it’s a community. From mentorship calls to continued learning, her graduates get much more than a certificate; they join a network that supports them long after the course is over. This is the kind of legacy that builds itself, creating ripple effects that go far beyond what any one person can do alone.
Michelle’s transition from client work to running a certification program is a roadmap for anyone who wants to grow their business without burning out. But don’t think it was easy! Michelle talks about the thought, planning, and focus that went into building the Moving On Method certification.
The Moving On Method covers everything from legal support to child psychology in divorce. Michelle’s experience shaped this curriculum, ensuring her coaches truly understand how to support clients. It’s a blend of real-world knowledge and empathy that only someone like Michelle could create.
Michelle opens up about her own imposter syndrome when launching the program. Overwhelming demand for her certification showed her she was on the right path. Her story is a reminder that feeling unsure is just part of leveling up—it’s what makes us human.
Michelle’s approach to legacy building goes way beyond growth for growth’s sake. She set high standards and even created a code of ethics for her certified coaches. For Michelle, scaling means ensuring her work has a positive, lasting impact. It’s about integrity and keeping her mission in focus.
Michelle and Dana both agree: if you’re going to be a leader, you need to make time for big-picture thinking. Running a business isn’t about staying busy; it’s about creating space for planning, vision, and relationship-building.
Michelle’s Moving On Method certification isn’t just a “one-and-done” course. Her graduates receive ongoing support through mentorship calls, alumni education, and her network. This community-driven legacy is rare and powerful. It shows her graduates they’re not alone and that Michelle is there to support them long-term.
Michelle Dempsey’s journey is a powerful example of how to create meaningful change by empowering others. As she shifts from client work to training a new generation of divorce coaches, Michelle shows that true impact comes from building a legacy of skilled, ethical professionals. Her story is full of valuable lessons for any woman ready to embrace her next chapter and make a difference.
Curious about Michelle’s Moving On Method or want to know more about her certification program? Visit MichelleDempsey.com to learn more.
Michelle is a repeat guest! Listen to her first BossMom episode here.
