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The Debrief with Dr. Natasha

Why setting boundaries can feel so wrong (even when it’s right)


Hi Reader,

If you struggle with people pleasing, perfectionism, or overachievement, you’ve probably noticed that setting a healthy boundary doesn’t always feel good.

In fact, it might feel downright wrong—and that feeling might be strong enough to make you avoid setting the boundary altogether.

The good news? This is normal.
The bad news? It’s also really frustrating.

In this week's post, I break this topic down into three parts:

  • Guilt can be useful when it’s aligned with your values.
  • But it can also be completely misplaced, especially when it’s triggered by someone else’s unreasonable or arbitrary standards.
  • Clarifying your values will help you differentiate helpful guilt from misplaced guilt.

I also share a personal story about when misplaced guilt took over.

It involves a 🩺 cancelled doctor's appointment, ☕️ thinking about working at Starbucks as a barista after getting my Ph.D., and 📦 moving into a new apartment.

Here's a quick summary of the actionable content if you're pressed for time:

  • Use your values as a litmus test: Ask yourself whether your guilt is pointing to a real misalignment with the kind of person you want to be, or if it’s coming from someone else’s unreasonable expectations.
  • Expect that even when you make a values-aligned choice, guilt may still show up, especially if you’re unlearning perfectionism or people pleasing.
  • Boundary work isn’t just about communication- it’s also about learning to tolerate discomfort while your emotions catch up to your beliefs.

💬 Have you ever felt guilty for setting a totally reasonable boundary? I’d love to hear what helped you hold the line.

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The Debrief with Dr. Natasha

If you're a woman of color in any kind of leadership role, you already know the challenges, and how rare it is to find a space to share those experiences and turn them into action. My monthly letters are that space: a place to pause, cut through the noise, and find your voice again.

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