467: “Why Not Me?” From Corporate Cubicle to Multimillion-Dollar CEO with Kym Insana

05/11/2025 38 min
467: “Why Not Me?” From Corporate Cubicle to Multimillion-Dollar CEO with Kym Insana

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Episode Synopsis

Today’s topic is a common experience for many listeners, whether in the present, future, or the rear-view mirror. We are discussing the all-important decision to leave the corporate world to leap into entrepreneurship. Our conversation explores the practical and emotional aspects of transitioning from employee to entrepreneur, including overcoming imposter syndrome, building effective networks, and strategically scaling a business. Join us to learn more!Kym Insana, founder of Always On Digital, shares her journey from corporate digital marketing executive to successful entrepreneur. She built a multimillion-dollar, woman-owned agency serving major brands, like the US Air Force, Johnston & Murphy, and Enfamil. When Kym left a demanding NYC career in advertising to build Always On Digital, her goal was to find flexibility and balance as a wife and mother of four. Her company thrives by empowering talented working parents to blend career success with family life. Kym is a sought-after speaker who has shared her journey and expertise on several national stages and media outlets. Show Highlights:Kym’s motivation to transition from employee to entrepreneurComing from the place of “What I NEED doesn’t exist; I’ll create it myself.”Kym’s practical strategies to build your business:Ask, “What do I want this to look like?” (having a clear vision)Work backwards from that point to figure out the details. (Reverse-engineer your dream!)Self-motivation is essential!Dealing with imposter syndromeAccepting that you may not be the right fit for every client, but you are an expertHandling rejection with a “Who else is out there?” attitudeBuilding networks by going to your allies firstHiring people for fractional roles as you build tractionGrowth and scaling phase, as you build momentumTaking the step to commit to full-time employees and serious operational costsFinding the balance between sales and customer serviceKym’s unique approach to building her team Resources:Connect with Kym InsanaWebsiteLinkedIn (Kym would love to connect with you through LinkedIn! Tell her you are a STaR Coach Show listener!)Kym’s profile: AccessSpeakers.biz/speaker/kym-insana-speaker-digital-marketing-expert-business-ownerConnect with MegStruggling to enroll more clients? Sign up today for our Enroll More Clients: Clarity Sprint 5-Day Challenge! It’s free, and we begin on November 10. Get clarity that makes enrolling clients feel natural, not pushy! Get Meg’s FREE download, Finding Your Perfect Match: A Coach's Self-Reflection Guide.Explore past episodes and other resources at www.STaRcoachshow.com. Explore the STaR Coach Community and see what’s available there for you!Visit the STaR Coach Show

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