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Embracing The Pivot: How To Overcome Business Doubts And Thrive w/Kendra Hennessy


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Navigating the rollercoaster of entrepreneurship, particularly for Boss Moms, involves constant shifts, uncertainties, and tough decisions. One of the most daunting challenges is the pivot – transitioning from a known, successful path to something uncertain.

It’s not just about the business; it’s about the emotional turmoil that comes with it. Doubts creep in – Will the change be worth it? What if it fails? 

Contrary to popular belief, us moms don’t have it all figured out so where do we go from here? How do we overcome the fears that come with a pivot in business?

In this episode, founder of Mother Like a Boss Kendra Hennessy joins me to talk about the emotional components of pivoting when owning a business, the ups and downs in entrepreneurship and how she took her in person business to the online world.

It feels really scary to leave something behind that is successful for something that is unknown. -Kendra Hennessy

Things You’ll Learn in This Episode

  • Is change necessary?
    How do we ‘shed our skin’ to step into a new phase of who we are and what we want to become.
  • The explanations behind our reasoning
    Why don’t we have to justify our reasoning to those around us?
  • Letting go and moving on
    Is it okay to grieve a part of our life that may be over? How do we move on?


Guest Bio

Kendra Hennessy is the founder of Mother Like a Boss where her mission is to make house cleaning more doable for regular moms so you spend less time tidying your space and more time enjoying your life.

Just Clean It 365 guide is 52 weeks of done-for-you cleaning routines that fit your life and take the trial & error out of daily tidying, even if you struggle to stay consistent or hate to clean.

Visit her WebsiteMother like a boss guide | Instagram | TikTok | Podcast

Dana Malstaff

Dana Malstaff

Dana Malstaff is the Founder of Boss Mom and creator Nurture to Convert.
She is a mother, author, speaker, messaging strategist, podcaster, blind spot reducer, and movement maker. She believes that too many brilliant moms are struggling to figure out how to grow their business while balancing all that is required to be a good mom, partner, and woman. So many moms are trying to grow their business using trends that feel inauthentic and aren't realistic for their inconsistent schedules. She has helped thousands of women become known for their brain and not their dance moves

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