

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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Early Career In Higher Education
- Amy began her career as an academic advisor helping undecided college students and enjoyed intentional career exploration work.
- She found limited interest in structured advising among peers, which pushed her toward more research-driven roles where she could create programs.
Chronic Career Dissatisfaction
- For nearly 15–20 years Amy felt chronically unfulfilled and kept pursuing new jobs, training, and degrees.
- She describes constantly searching for the next role or credential immediately after finishing each program.
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.