Letting Go Of Implied Expectations With Kaitlyn Westendorf

Letting go of implied expectations is one of the hardest—and most liberating—skills we can learn. In this grounded and deeply human episode of the Let’s Get Naked Podcast, Anne Karber sits down with Kaitlyn Westendorf to unpack the invisible pressures that quietly shape our lives, our relationships, and the way we parent—often without our conscious consent.

This conversation isn’t about rebellion or detachment. It’s about awareness. About recognizing how much of our stress, resentment, and self-betrayal comes from expectations no one ever explicitly asked us to carry—but that we picked up anyway.

The Inherited Weight of “Should”

Anne and Kaitlyn begin by naming something many people feel but rarely articulate: the heaviness of unspoken rules. The expectations passed down through family culture, work ethic, gender roles, and generational survival patterns.

Kaitlyn reflects on her upbringing as the daughter of parents who worked multiple jobs to support their agricultural retail business—modeling sacrifice, grit, and relentless responsibility. That example shaped her deeply, instilling discipline and loyalty, but also an internalized belief that rest, boundaries, or choosing differently might equal failure.

What starts as admiration can quietly become obligation.

“We inherit work ethic,” Anne notes, “but we also inherit pressure—and if we don’t examine it, we end up living someone else’s definition of success.”

When the Conflict Isn’t External—It’s Internal

A powerful thread throughout the episode is the idea that we often look for someone to blame when the real conflict is inside us.

Kaitlyn shares the contrast between her father and her husband—two men who represent different models of partnership and presence. That contrast forced her to confront an uncomfortable truth: sometimes our frustration with others is really grief over expectations we never communicated—or standards we never questioned.

Anne and Kaitlyn unpack how easily resentment grows when we say “yes” out of habit instead of alignment. Over time, those yeses compound into exhaustion, bitterness, and a sense of being unseen—when in reality, we never fully showed ourselves.

Parenting, Pressure, and Letting Kids Have Skinned Knees

One of the most impactful parts of the conversation centers on parenting and generational patterns.

Anne and Kaitlyn challenge the idea that good parenting means preventing all discomfort. They talk honestly about how the urge to overprotect—emotionally, socially, or physically—often comes from our own unresolved fears, not our children’s actual needs.

Letting kids make mistakes. Letting them fail. Letting them scrape their knees.

These aren’t signs of neglect—they’re signs of trust.

Kaitlyn reflects on the discipline it takes to step back and allow children to build resilience, rather than inheriting anxiety or perfectionism. Anne reinforces that rescuing too often teaches kids they’re fragile, when what they actually need is confidence in their ability to recover.

Staying “For the Kids” and Other Quiet Contracts

The episode also takes an honest look at relationships and the unspoken contracts people stay bound to—especially marriages held together by obligation rather than connection.

Anne and Kaitlyn discuss how staying “for the kids” can sometimes model the very dysfunction parents hope their children will avoid. Kids don’t learn from what we say; they learn from what we tolerate.

Breaking generational cycles often means choosing discomfort now over dysfunction later. It means modeling boundaries, emotional honesty, and the courage to live intentionally—even when it disappoints expectations.

Emotional Boundaries and the Cost of Over-Giving

A recurring theme is the cost of chronic over-giving.

Kaitlyn speaks candidly about community involvement, family loyalty, and the genuine joy of giving back—but also about how easy it is to confuse service with self-erasure.

Anne reframes boundaries not as walls, but as clarity. They protect relationships by preventing resentment. They allow generosity to come from fullness instead of depletion.

“You can be kind,” Anne says, “without being available for everything.”

Planting New Seeds

At its core, this episode is about permission.

Permission to question inherited standards.
Permission to choose a different pace.
Permission to live by your own definition of success, partnership, and fulfillment.

Kaitlyn’s life story—first-generation college graduate, two-decade career in aviation, devoted wife and mother of four, deeply involved community member—illustrates that honoring your roots doesn’t require repeating every pattern.

You can keep the values and release the pressure.
You can honor the past without living inside it.