Dear Anonymous,

This is tricky, and I completely understand where you're coming from. What you’re feeling is incredibly common; thousands of people struggle with advocating for themselves, setting boundaries, and especially enforcing them.

 

Here’s what helped me: I started practicing saying “no” as a daily goal, and I offered zero explanations. It was almost physically painful at first. I felt awkward, uncomfortable, and guilty as I walked away. It sucked.But then something shifted. People adjusted, as long as I held my ground. You may need to remind someone of your boundary once, but only once. After that, if they continue pushing, it’s intentional or it’s rude.

 

A good way to gauge fairness is this: Would I do the same or ask the same of them? If the answer is an instant “no,” then the behavior is no longer acceptable for you.

 

For example:“Holly, would you please stay late and help me finish my presentation?”

Do not apologize when establishing a boundary. You’re not doing anything wrong.

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"I can’t stay today. I’m sure you’ll figure it out though - you’re amazing at this!” Then leave. Quickly.

If they push: “Why not?” Give them a calm, steady look and maintain eye contact. You: “Because it’s your work, not mine. Have a great night.” Then leave. Or: “Because I’m off at five, which is now.”

 

Use whatever version feels most natural to you. You don’t owe anyone an explanation, including your boss. After five o’clock, they’re not your boss, they’re just annoying. Best of luck as you move through the discomfort. You can do this, and you’ll be so proud of yourself!

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Best wishes,

Holly

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