What happens when you spend 10 years at Amazon, love your job, love your team and then parenthood shakes everything up?

That’s the story of Jane Dashevsky. Becoming a mom of two under two made her start asking the big questions: What do I really want for myself? For my family? That entrepreneurial spark she’d carried deep down finally pushed her to walk away from stability and build something of her own.

Jane is now the founder of The Starter Set, an AI-powered service that helps parents cut through the chaos of baby product shopping. Because let’s be honest, the last thing overwhelmed parents need is another late-night Google spiral about strollers.

In this episode, Jane gets real about:

• Leaving a steady job after a decade at Amazon
• The identity shift that comes with walking away from stability
• Parenting while building a startup (the real messy middle)
• Testing ideas piece by piece and finding her way in Seattle’s startup world
• How to not let numbers or social media dictate your worth

This is a conversation about courage, resilience, and choosing yourself, and your family, even when the path ahead is messy and unclear.

🎧 Listen now and connect with Jane below.

Connect with Jane

• LinkedIn
• The Starter Set
• The Starter Set Instagram
• Listen to Getting Started with Baby

Episode Sponsor:
This episode is sponsored by Dwellspring. It’s an app I’ve been using that helps with sleep, focus, and just finding a little calm in the chaos. Think soundscapes, white noise, even custom mixes, all offline and totally ad-free.

If you want to try it, just search Dwellspring, like wellspring with a D, in the App Store or Google Play. And if you use the code Flipper, you’ll get a free month of Premium.

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Submit your story:

Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com.

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Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.

🎵 Music Credits

Season 1: Intro & outro music by Audionautix.com

Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio

And hey, remember my favorite question: What’s the best that could happen? 💫