Artwork for podcast STaR Coach Show
467: “Why Not Me?” From Corporate Cubicle to Multimillion-Dollar CEO with Kym Insana
5th November 2025 • STaR Coach Show • Meg Rentschler
00:00:00 00:42:18

Share Episode

Shownotes

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 entrepreneur
  • Coming 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 syndrome
  • Accepting that you may not be the right fit for every client, but you are an expert
  • Handling rejection with a “Who else is out there?” attitude
  • Building networks by going to your allies first
  • Hiring people for fractional roles as you build traction
  • Growth and scaling phase, as you build momentum
  • Taking the step to commit to full-time employees and serious operational costs
  • Finding the balance between sales and customer service
  • Kym’s unique approach to building her team 

Resources:

Connect with Kym Insana

Website

LinkedIn (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-owner

Connect with Meg

Struggling 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 YouTube Channel! Subscribe today! Join our live show taping on the 3rd Thursday of every month at 1 pm CT. 

Mentioned in this episode:

Mentor Program

If you're working toward your ACC or PCC credential, or if it's time to recertify your ACC mentor, coaching isn't just a requirement on a checklist. It's one of the most transformative investments you can make in yourself and your coaching. I've taught or mentored over 2000 coaches, and I hear the same thing again and again. I came because I had to, and I am so glad that I did. Coaches tell me they walk away with renewed energy, deeper confidence and a community of peers who genuinely support each other. Here's what you need to know right now. Mentor coaching must span a minimum of three months, so the time to start is not when your credential is just about to expire. And if you complete your hours in 2026, you get ahead of the upcoming ICF changes, which means peace of mind along with skill development. My fall cohort is already filling up. Every group is capped at ten. It's small, personal, and powerful. If you've been waiting for the right time, this is it. So head over to Star Coach Show. That’s https://starcoachshow.com/mentor/ to grab your spot or to learn more. I'd love to work with you. Now, let's get into today's show.

Join Mentoring Program!

If you’re a coach who wants to grow—not just check a box—this is for you. I’m enrolling coaches now for my Spring Mentoring Program. Some are here for credentialing hours. Others are here because they want to become the coach their clients rave about. Inside the program, we work on your actual coaching. You’ll hear yourself differently. Learn from other coaches. Develop more presence. And ask questions that create real transformation. If you’re ready to deepen your skills and your impact, I’d love to support you. Learn more at starcoachshow.com/mentor I’d love to work with you.

Follow

Chapters

Video

More from YouTube