023 Why People-Pleasing Drains Lawyers (and How to Break Free)

podcast Oct 08, 2025
Heather Mills on The Lawyer Burnout Solution podcast, episode “Why People-Pleasing Drains Lawyers (and How to Break Free),” about how approval-seeking fuels burnout in law and how to build self-trust instead.

What People-Pleasing Costs You in Law and How to Replace it With Genuine Self-Trust

If people-pleasing really worked, why does it leave lawyers so depleted?

Many lawyers were raised to be the “good ones”: the dependable, hardworking, conflict-avoiding high achievers. In law, that conditioning gets rewarded, which makes it even harder to see how approval-seeking quietly fuels burnout. You say yes when you mean no, stretch yourself to look committed, and slowly lose touch with what you actually want.

In this episode, you’ll learn how to recognize people-pleasing as a safety strategy your brain learned long ago, and how to replace it with genuine self-trust. You’ll walk away with simple tools to help you pause the reflex, hold boundaries with less guilt, and start practicing law in a way that includes you in the equation.

What Does People-Pleasing Really Look Like in Law?

People-pleasing isn’t just being “nice.” It’s the invisible rule many lawyers live by: keep everyone happy, stay reliable, and never make waves. In this episode, we look at how that pattern shows up in daily practice: saying yes when you’re already drowning, over-preparing to avoid criticism, or staying silent to keep the peace. You’ll hear why the legal profession not only normalizes these behaviors but often praises them as dedication and professionalism.

Where Does This Reflex Come From?

Heather shares how people-pleasing starts long before law school, often as a childhood safety strategy. Our brains learn early that approval equals safety, so we carry that wiring into adulthood. You’ll hear how this conditioning follows lawyers into their careers and why it becomes a hidden driver of exhaustion, resentment, and disconnection.

How Do I Begin Breaking the Cycle?

You’ll learn Heather’s Fact vs. Thought tool, a simple way to pause before saying yes and examine what your brain is making other people’s requests mean about you. You’ll also hear two word-for-word scripts you can use to say no with clarity and professionalism. Most importantly, you’ll learn how to let guilt or anxiety surface without letting it drive the bus—so you can start rebuilding self-trust, one decision at a time.

Summary

People-pleasing isn’t proof of kindness. It’s a nervous system habit rooted in fear of disapproval. Every time you pause, separate fact from thought, and choose an action that includes you, you build a little more trust in yourself. Change doesn’t happen all at once; it happens one conscious “no” at a time.

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Click here for episode transcript

How would your career look if you stopped managing other people’s perceptions and started honoring your own limits?

 

Welcome to The Lawyer Burnout Solution, the podcast for women attorneys who want to move from survival mode to a sustainable, fulfilling lawyer life. I’m Heather Mills, and every week I share tools, strategies, and mindset shifts to help you reclaim your energy, confidence, and career.

Last week, my husband and I went to see Laura Benanti’s one-woman show called Nobody Cares. She is a Tony Award–winning actor. You might know her from She Loves Me, Younger, or Into the Woods. The theme of the night was people-pleasing.

I was laughing so hard at the absurdities of people-pleasing that she called out that I was wiping my eyes with the backs of my hands. But in the back of my mind I kept thinking, this is what women lawyers do all the time because of our social conditioning.

I started trying to break this habit in my twenties, when I realized I was still dating my high school boyfriend mostly because I didn’t want to rock the boat with everyone else in our lives. It was the first time I saw just how deep my people-pleasing ran.

So it is a habit I know from the inside out. And I have come a long way.
What I know now is how to keep myself in the equation, to check in with my own needs and values instead of outsourcing my worth to everyone else’s approval.

And I see this same pattern in so many of the women lawyers I coach. People-pleasing is one of the sneakiest, most exhausting causes of burnout in law.

So today, we are going to dig into it. You will learn what people-pleasing really is and most importantly what the opposite of people-pleasing looks like, so you can start practicing law in a way that includes you in the equation.

Have you ever taken on extra work from a colleague instead of saying no, because you didn’t want to risk tension in the relationship?

Stayed awake replaying an email you sent to opposing counsel, worried you came across as too harsh or not responsive enough?

Taken on the “quick” client favor that turned into hours of work, because you didn’t want them to question your dedication?

Sat silent in a strategy meeting when you knew the plan had holes, because you didn’t want to embarrass the person who suggested it?

Signed up for the bar association committee or the office volunteer event, not because you wanted to, but because you didn’t want to look unhelpful?

And outside of work, have you ever agreed to dinner plans with friends or family when you were completely exhausted, because you didn’t want to disappoint anyone there either?

That is people-pleasing. On the outside, it looks like being thoughtful, helpful, “nice.” On the inside, it is exhausting.

And in law, it does not just sneak in. It gets rewarded. You are praised for being reliable, a team player, always available. The trouble is, those rewards create a cycle: approval feels good for about five minutes, then resentment sets in. And before you know it, you are right back at yes again.

To really understand people pleasing we have to go way back - usually to childhood. For me, people-pleasing did not start in law. It started way earlier.

I remember getting stress headaches about homework in the fourth grade. I did not want to disappoint my teachers or my parents. I was the good girl, the one who got the gold stars, the teacher’s pet. Yeah, you can imagine how popular I was. 

By high school, I was collecting every good-girl badge you could imagine: straight A’s, student government, yearbook, band. I did not just want to do well. I wanted to look like the kind of kid who had it all together, the one adults could brag about.

I even carried it into my first serious relationship. I dated my high school boyfriend through college, and those same themes of people-pleasing and over-accommodating showed up.

I kept telling myself that if I could just keep him happy, keep his parents happy, I would feel safe and loved. Breaking up with him was one of my first wake-up calls. I finally knew what I did not want. But here is the harder truth: I still could not name what I did want. That was the real pattern underneath. I had spent so much energy pleasing parents, teachers, boyfriends, bosses, that I did not have a clue what I wanted for myself.

When it came time to pick a career, I froze. I could not answer the question because I honestly did not know. I never put it in these words back then, but I was stuck in this impossible calculus: what would please everyone else? Mom? Dad? Professors? My boyfriend’s family? I had no idea what would make me happy.

And law school, of course, was the perfect breeding ground for this pattern.

Yes, there are charismatic, outgoing, argue-in-courtroom types who end up in law. But there is another stereotype too, the one I fit into. High achievers. Book-smart. Introverts. People-pleasers. Highly sensitive people who do not like risk.

Law is full of us: people-pleasers, perfectionists, high achievers who were already wired to chase approval. And the legal culture doubles down on that wiring.

Because in this profession, people-pleasing does not just slip under the radar. It looks like success. The associate who says yes is praised as reliable. The lawyer who smooths over conflict is seen as a team player. The one who is always reachable at all hours is celebrated as client-first.

On the surface, it earns you gold stars. Underneath, it costs you your energy, your boundaries, and honestly, eventually costs you your sense of self.

It’s that reward → resentment loop. You get the praise. You feel good for five minutes. Then you are left holding the resentment, the exhaustion, the Sunday night dread.

Here is the truth: people-pleasing is never about generosity.

For me, it was an attempt to make people think I was kind. That I was nice. That I was the good student, the good associate, the good daughter.

It was not actually about caring for others. It was about managing what they thought of me.

That is why I call it what it really is: my brain’s safety strategy. As a kid, I honestly believed that keeping people happy was the best way to stay out of trouble, to avoid conflict, to feel safe.

Safe from my parents’ disappointment. Safe from conflict. Safe from the sting of rejection or abandonment.

If I was the good student, the helpful daughter, the easy girlfriend, then maybe I could avoid someone being mad at me or pulling away. My amygdala was running my life, and it linked approval with safety.

The problem is, that same wiring followed me into adulthood and into law. And what once felt protective started burning me out.

So what is the opposite of people-pleasing?

It is not pretending you do not care about anyone else. That is not it at all.

The opposite is realizing you cannot control other people’s thoughts about you. Their thoughts live in their brains, not yours.

It is shifting the focus to what you think about yourself, your own beliefs, your own values, your own priorities.

It is creating safety internally, by managing your brain with mindset work and through deprogramming your thoughts so you do not have to outsource your safety to everyone else’s approval. I do this with my clients using tools like the TEA Practice and the Mindset Matrix.

It also means being willing to disappoint people in order to put yourself back into the equation. To say, “I matter here too. My opinion matters too. My needs matter too.”

And it is taking responsibility for what you want, your own dreams, your own desires, instead of living life by what will keep everyone else happy.

That is the shift. From trying to look nice, to actually living true. From managing other people’s perceptions, to building trust in yourself.

So how do you start unwinding this reflex in real life? The first step is to notice when you are in it.

The next time you catch yourself saying yes automatically, pause and run a quick check I teach my clients: Fact vs. Thought. This is the first part of the TEA practice.

Here is how it works: Facts are neutral. They are the pieces of reality that everyone could stipulate to in court. “My colleague sent me an email.” “The meeting is scheduled for Tuesday.” “A client asked a question.” That is it.

Thoughts are the sentences your brain layers on top of those facts, usually in a split second. Those thoughts are opinions. Spin. Not the truth. And those thoughts create the pressure you feel.

For example:

Fact: “A partner didn’t reply to my draft right away.”
Thought: “They must be disappointed in my work.”

 Fact: “I was invited to speak on a panel.”
Thought: “If I say no, I’ll miss my chance and let people down.”

 Fact: “My kid’s teacher requested parent volunteers.”
Thought: “If I don’t put my name down, everyone will think I’m a bad mom.”

See the difference? The facts are neutral. It is the thoughts that generate the guilt, the anxiety, the pressure to please.

When you can pause long enough to separate the two, you create space to ask: Do I want to act from this thought my brain is serving up? And if not this thought, do I want to come up with a new one?

That is where real choice begins.

Once you see the difference between fact and thought, you can start practicing a new response. That is where simple scripts can help, because they give your nervous system a safe way to try something different.

Here are two you can borrow this week:
“Thanks for thinking of me. I can’t meet Friday, but I can deliver a solid draft Monday at noon. Does that work?”

Or try this one:
“Before I confirm, what can drop from my plate so this gets the attention it deserves?”

That spike of guilt or anxiety? That is just your nervous system learning something new. Just feel the anxiety or guilt. If you actually feel it, it will pass. And you will not die even though your body thinks you will. It is just an emotion to feel.

So anchor yourself here:
My goal isn’t to look good or nice. It is to be a whole human, to remember that I matter too, and to practice law from there.

When I was practicing, I said yes to too many assignments and too much volunteer work I did not have capacity for. I would stay late, miss dinners, and drag myself home feeling exhausted and resentful.

It took me years to see: my yes was not really about the work. It was about managing perception. I wanted to be seen as reliable. As kind. As good. As competent.

But every yes that betrayed my limits disconnected me further from myself.

What finally started to shift things was not better time management. It was beginning to rebuild self-trust. It was reminding myself, again and again: I get to matter too.

Before you say yes to the next request, take 30 seconds for a quick check: Fact vs. Thought. What is the bare fact of what was asked? And what is the thought your brain instantly adds about what it will mean if you say no?

From there, try something simple, like: “Thanks for asking. I can’t this week, but here’s what I can do…”

Then pause. Notice the discomfort. Breathe. That is not failure. That is you building capacity.

People-pleasing is not proof you are kind. It is an attempt to look kind, to manage approval and avoid risk.

And every time you pause, separate fact from thought, and include yourself in the decision, you are building a new reflex. You are building self-trust.

It does not have to be a massive overhaul. One rep at a time is how you loosen this old pattern.

If you are ready to stop people-pleasing and start practicing law from self-trust instead of fear, I would love to help. Book a free call with me at heathermillscoaching.com/call. We will look at where you might be caught in patterns that once made sense but no longer serve you, and map out your next step toward deeper self-trust.
 

That is it for today. Thanks for listening. Remember to be kind to yourself this week, even when you’re caught in that people pleasing loop. And I will see you next time.

 

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