Happen To Your Career - Meaningful Work, Career Change, Career Design, & Job Search

The Messy Middle: What Career Change Actually Looks Like Before You Have the Answers

September 21, 2026·39 min
Episode Description from the Publisher

Holly Dixon spent 20 years in the legal field, never once argued a case, and walked away without a single job lined up. She is still happening to her career and figuring out what comes next. Most career change episodes on this show share a complete story from start to finish. This one does not. This episode is the messy middle — the experiments that did not work, the grief nobody warned her about, the identity crisis that came from letting go of 20 years of who she thought she was, and what she has learned about living in uncertainty on purpose while still moving forward. What You'll Learn: Why the experimenting is not the detour on the way to clarity and how every experiment Holly ran gave her specific, useful information she could not have gotten any other way What happens to your identity when you walk away from a 20-year career and why grieving who you used to be is not a sign something is wrong How Holly co-created a four-month exit plan with her boss instead of giving two weeks notice and why that approach set everyone up for success including herself Why the survival instinct that tells you to just pick something and get back to work can be one of the biggest obstacles to actually finding what fits What living in uncertainty on purpose looks like in practice and how it becomes a skill you can build rather than a personality trait you either have or you do not Our book, Happen To Your Career: An Unconventional Approach To Career Change and Meaningful Work, is now available on audiobook! Visit  happentoyourcareer.com/audible to order it now! Visit happentoyourcareer.com/book for more information or buy the print or ebook here! Want to chat with our team about your unique situation? Schedule a conversation Free Resources What career fits you? Join our free 8 Day Mini Course to figure it out! Career Change Guide - Learn how high-performers discover their ideal career and find meaningful, well-paid work without starting over. Related Episodes Six Career Experiments To Help You Discover Your Ideal New Role (Spotify / Apple Podcasts) Should I Quit My Job? How to Know It's Time (Spotify / Apple Podcasts)

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