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The Teaching Journeys Podcast

The Teaching Journeys Podcast

Unbecoming: Ashley Jordan on Grief, Love, and Finding Your True Self

The Teaching Journeys Podcast · Mar 23, 2026 · 54:27

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In this episode of Teaching Journeys, host Dave Roberts speaks with author and journalist Ashley Jordan about her transformative journey through grief and self-discovery.

The Story:

Ashley lost her childhood sweetheart Daniel at age 13—literally on her 13th birthday. Growing up in the Midwest with a culture of "nice on the outside," she buried her grief for 24 years. At 37, while living what appeared to be a perfect life, a spontaneous visit to a psychic medium triggered a tsunami of repressed grief that changed everything.

Key Themes:

The Transformation:

Ashley walked away from her "picture perfect" life—the degrees, accolades, marriage, and material success—to follow her heart. Today she lives a life built on love rather than achievement, sharing her story through her book "Unhappy Achiever" and her journalism.

Core Message: You are worthy of love simply by existing. Grief never goes away—it just gets different. And sometimes you have to unbecome everything you thought you should be to remember who you truly are.

Ashley’s Bio and Contact Information

Ashley Jordan has done many things throughout her life. She’s

been a feminist activist, licensed attorney, public speaker, and

a stay-at-home mother. Most notably, however, she’s a well-

published journalist with her works appearing in The New York

Times, The Washington Post, The Guardian, and HuffPost, among

others. Today, she lives in Milwaukee, Wisconsin, with her

three children.

Connect with Ashley:

• Website: ashjordan.com

• Book: unhappyachiever.com

• Instagram: @msashjordan

To find out more about Dave go to davidrobertsmsw.com

Episodes: The Teaching Journeys Podcast

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