People pleasing doesn’t look dramatic.
It looks generous. Helpful. Even accommodating.
It looks like being the “easy” one.
It can even feel good – like a quick dopamine hit.
But underneath it? It’s often the slow erosion of our own boundaries.
And the tricky part is that most of us don’t even realize we’re crossing our own lines
- until resentment creeps in
- or exhaustion
- or that quiet internal voice that says, “Why did I agree to this?”
Today I want to talk about how to recognize when your boundaries are at risk — and what it actually looks like to practice holding one in real time.
Because boundaries aren’t about being harsh.
They’re about being aligned.
America’s Best Doctors and Other Sales Pitches
I was recently nominated for an award called “America’s Best Doctors.”
Now — I’ve seen these awards come across my inbox before. The kind where you “win” and then have to pay for the privilege of being recognized.
Historically? I’ve given it a hard pass. I blink and move on.
But this time, I did some homework. I researched the company. The website was impressive. It didn’t feel like a scam. It offered an opportunity to write articles and promote my brand. So I booked the 10-minute follow-up call.
A lovely woman interviewed me. She gathered quotes and congratulated me. She told me all the wonderful things that came with the award.
And then she told me the price. $2,000.
Then here comes the moment that matters.
While she was explaining the packages… I recognized something in myself.
Not irritation.
Not pressure.
Clarity.
I have spent hundreds of thousands of dollars in education to become who I am. I do not need to spend thousands more for external validation.
And spending money on accolades is not in alignment with my goals this year. Or any year.
And that clarity – it didn’t happen in the moment.
It happened long before — because I’ve spent a generous amount of time reflecting on my values. My financial priorities. My business direction. And my personal goals.
So when the ask came, the answer was already decided.
I simply said: “I do not intend to spend any money on this today.”
- No apology.
- No justification.
- No over-explaining.
And then she countered. Lower price. More perks. Personal sponsorship. Eventually we got all the way down to… $14.99 a month.
The most interesting part for me was that at some point — when the price became negligible — I almost caved.
- Not because I wanted it.
- Not because it aligned.
- But because it would satisfy her.
What???
That’s the moment most of us miss.
That tiny internal shift where the goal stops being alignment… and starts being someone else’s comfort.
But because I was paying attention, I caught it.
And I repeated the boundary: “I do not intend to spend any money on this.” Holding the line.
Most Important Tactics When Holding Boundaries
This experience reminded me that strong boundary setting requires a few things:
- Recognition
You have to notice what’s happening internally.
The urge to apologize.
The desire to soften.
The pull to make the other person comfortable.
I caught myself apologizing — I literally added the word “sorry,” despite teaching this work.
That awareness is step one. Then you need…
2. Clarity + Brevity + Repetition
Boundaries don’t need to be outlined in paragraphs.
They need clarity.
- Clarity
- Brevity
- No apologies
- Repeat as needed
Sometimes you will have to repeat yourself.
And sometimes the real firmness in boundary setting is not with the other person — it’s with yourself.
Why This Matters More Than You Think
Had I caved and purchased the membership, I would have gotten a small dopamine hit.
I would have felt generous, supportive, and nice.
But I would have quietly eroded trust with myself.
And every time we override our own clarity for someone else’s comfort, we weaken that trust.
And trust with yourself? That’s leadership.
Bringing It Home
But here’s the harder part.It’s not usually a salesperson pushing your boundary.
- It’s your mom who wants you home for the holidays.
- It’s your colleague asking you to cover one more shift.
- It’s your boss asking for the presentation a week early.
It’s people you care about. And then it becomes so easy for guilt to cloud your judgment.
So the real practice is this:
- Recognize.
- Find alignment.
- Speak clearly & briefly.
- Do not apologize.
- Hold the line.
And when you walk away from that moment?
You build confidence.
You build self-trust.
You build strength in what I like to call your “boundary muscle.”
Like an isometric hold — it gets stronger the longer you practice.
I got off that call and laughed. Not just at the price.
But at how powerful it feels to know:
I can trust myself to say no.
I’m still working on this. Are you?
Create Action
Where are you currently overriding your own alignment for someone else’s comfort?
Where are you apologizing when you don’t need to?
Where are you saying yes… and quietly feeling resentment grow?
Because boundaries aren’t about being rigid. They’re about protecting what matters.
- Your time.
- Your energy.
- Your financial goals.
- Your leadership presence.
- Your self-trust.
And if this episode hit a nerve — in a good way — I want you to know something:
Boundary setting is not a personality trait.
It’s a skill. And it can be strengthened.
I’ll soon be hosting a course called Boundaries That Stick — because most women don’t struggle with knowing they need boundaries. They struggle with holding them under pressure.
If you want to be the first to know when it opens — and get early access — join the waiting list at womenmdleaders.com/boundariesthatstick-waitlist
Let’s build boundaries that don’t crumble under guilt, pressure, or people pleasing.
Because your leadership — and your life — deserves that level of clarity.