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Letting go of implied expectations is one of the hardest—and most liberating—skills we can learn. In this conversation with Kaitlyn Westendorf, Anne explores the unspoken pressures we inherit, the ones we place on ourselves, and the ones we unknowingly hand off to our partners and children.
Kaitlyn reflects on the example set by her mother, the contrast between her father and her husband, and the subtle ways we look for someone to blame when the real conflict is internal. Together, they unpack the cost of saying “yes” to everyone else, the importance of letting your kids make mistakes, and the reality that we often create our own suffering through expectations no one explicitly asked of us.
We dive into generational work ethic, parenting adjustments, relationship standards, emotional boundaries, staying in marriages “for the kids,” and the difficult discipline of letting children experience their own skinned knees. It’s a grounded, honest look at what it means to break generational patterns, plant new seeds, and give yourself permission to live by your own standard.
If you’ve ever felt weighed down by invisible expectations—or unsure how to stop carrying burdens that were never yours—this episode offers clarity, compassion, and practical wisdom.
Kaitlyn Westendorf is the first of three girls born to her parents that spent the entirety of her childhood working multiple jobs to support her family's agricultural retail business while demonstrating unparalleled work ethic and the importance of family. She is a first-generation college graduate, with a Bachelor's Degree in Marketing. After watching her parents' hard work come to fruition with the business turning the corner to success, Kaitlyn planned to enter sales that involved agriculture. Life had different plans for Kaitlyn and she ended up being wooed into Aviation. Kaitlyn spent the last 20 years working with Colorado Airports for the state's Aeronautics Division.
Kaitlyn married her high school sweetheart after graduating from college and they've been blessed with four amazing children and a friend group that is unmatched. Kaitlyn enjoys playing and watching sports, especially if her kids or nieces and nephews are playing. Some may say she has a card addiction, but it could be worse. Kaitlyn works hard and plays hard and she is extremely luck to have a life partner that feels the same. Kaitlyn is involved in her community in a multitude of ways and enjoy how it feels to "give back".
This podcast dives deep into real, raw topics—think vulnerability, triggers, and childhood trauma. But just so we're super clear: I’m not a licensed therapist, mental health professional, or anything close. I’m just a human sharing stories, lessons, and life hacks based on personal experience and a whole lot of curiosity.
So, while you might find some golden nuggets here, this is not therapy and should never replace professional mental health care. If you or someone you love is going through it, please—seriously—reach out to a licensed therapist or healthcare provider. You deserve the real deal.
Need Help Now?
Here are a few amazing resources:
· 988 Suicide & Crisis Lifeline (U.S.): Call or text 988
· NAMI HelpLine: 1-800-950-NAMI (6264) or nami.org/help
· Therapy Directory: psychologytoday.com
· Crisis Text Line: Text HOME to 741741
The opinions expressed on this show are ours and ours alone—no official organizations are responsible for what we say (or how much we overshare).