Happen To Your Career - Meaningful Work, Career Change, Career Design, & Job Search From 20 Years of Misfit Jobs to Creative Entrepreneur: Amy's Career Change Story
Oct 9, 2025
In this insightful conversation, Amy Haggerty shares her journey from a 20-year struggle in unfulfilling jobs to becoming a creative entrepreneur. She reflects on how coaching and family life prompted her quest for autonomy and fulfillment. Amy reveals the pivotal moment of starting her business and the mindset shifts that helped her embrace failure and momentum. She emphasizes the importance of community and practical habits like the 'one thing a day' approach, along with the powerful decision to let go of her old career identity.
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Tasks Aren't The Whole Story
- Amy focused on daily tasks when choosing roles and missed larger life fit factors like autonomy and values.
- She later realized themes beyond tasks explained why roles stayed unfulfilling.
Life Stage Clarified Career Needs
- Growing family responsibilities clarified Amy's need for autonomy, control, and flexibility in work.
- Coaching helped her articulate a life vision that revealed entrepreneurship as a better structural fit.
A Clear Decision To Create And Own
- Amy had a clear realization and wrote it down: she wanted to be a creative entrepreneur but didn't know the 'what' initially.
- She connected her love for creating content, design, and communication with the desire to run her own business.