The Hardest Habit to Break

Habit #8: The Disease to Please

Why we learned it, why it helped us… and why it can hold us back.
Welcome back to our 12-week series breaking down the habits that quietly (and sometimes loudly) hold us back from our next raise, job, or promotion.  This week, we’re diving into Habit #8: The Disease to Please.  And I’ll be the first to admit this one hits home for me.

My People-Pleasing Origin Story

I didn’t become a people pleaser in adulthood, I mastered it early on.  Like so many women, it was a safety mechanism long before it became a professional habit.

I learned that if I made everyone happy, kept things smooth, and managed the emotional temperature in the room, then I was okay. People pleasing wasn’t about being “nice.” It was about keeping my nervous system calm.  I believed if they liked me, they wouldn't harm me.  (And I was rewarded with words like "you are such a sweet girl" and "it is so nice to have you around").

And honestly? It worked for a long time.  Until it became unsustainable.

If I could anticipate a reaction and soften it before it happened, I didn’t have to deal with conflict, disappointment, or unpredictability. My little-body-turned-big-body learned: “If they’re okay, I’m safe.” No wonder we carry this into our careers.

But doing this is exhausting! It takes a lot of energy to always try to anticipate what will make someone else happy and go out of my way to please them while ignoring my own needs.

On the flip side, while people-pleasing is often talked about like it’s some terrible flaw, it's not ALL bad.

It actually is nice to work with someone who is pleasant, cooperative, and thoughtful. Someone who doesn’t create drama for sport. Someone who sees the whole room, cares about the impact of their words, and wants harmony.

There’s value in your ability to read people, build relationships, and create ease.  It may even be your superpower. But the problem is when we use that superpower against ourselves.

The mantra I come back to again and again and the one I tell my clients: Please others when it also pleases you.

Not instead of you, not at the cost of you, and not as a way to "earn" belonging. 

The How Women Rise authors highlight that over-pleasing can derail talented, capable women because it keeps them from being authentic.  We end up watering ourselves down to be palatable.  

We hesitate to speak up, disagree, or offer a bold idea if it risks someone’s discomfort, which ultimately silences our truth.  This slows or even stops our advancement because leaders need to take a stand, make decisions, and hold boundaries - not constantly seek approval.

People pleasing also leads to overwork.  We say yes when we mean no and we take things on because it’s “easier” to do it ourselves than disappoint someone by setting a limit.  And it also erodes confidence. Because when we chronically put others first, we subconsciously reinforce that their needs matter more than ours.

So what can we do instead?

This isn’t about swinging from “people pleaser” to “I don’t care what anyone thinks.” (Those people are the real problem in the workplace.)

The shift is learning to check in with what pleases YOU too. Say yes with intention, not obligation. Let people manage their own reactions because the reality is they’re going to have them anyway and their reaction isn't your responsibility.

Sometimes you have to disappoint others in order to not abandon yourself. This feels really uncomfortable for many of us because if we disappoint them, we don't know what will happen to us.  But we have to trust that our truth, spoken clearly and kindly, is not only allowed - it’s required.

This week, notice where you’re over-functioning to keep the peace or avoid discomfort. Ask yourself these questions:

• Does this please me, too?

• Am I saying yes out of desire or fear?

• What would authentic honesty look like right now?

And as a small nod to last week's note on perfection - progress is the key.  Small shifts here can create real improvement in your career and well-being, even if you are still people pleasing at times.  It is all about starting somewhere.

If this one hits you like it hit me, you’re not alone. This is one of the most common habits I coach women through and one of the most liberating to unlearn.

Personally, I've made so much improvement in this area, and yet I still occasionally find myself saying yes to someone out of habit, especially if I am stressed, tired, hungry, or overwhelmed.  If I am already struggling a bit, I revert to the old habits that kept me "safe".

But the more I notice it, the more I am able to revert to my mantra above: Please others when it also pleases me.

You deserve a life and career that pleases you too.  That's not selfish- it's sustainable success.

Cheers to people pleasing that includes YOU,
Sharon

PS - Here are the 12 Habits we are walking through (from How Women Rise by Sally Helgesen and Marshall Goldsmith) - Links to previous newsletters:
1 - Reluctance to Claim Your Achievements
2 - Expecting Others to Spontaneously Notice and Reward Your Contributions
3 - Overvaluing Expertise
4 - Building Rather than Leveraging Relationships
5 - Failing to Enlist Allies from Day One
6 - Putting Your Job Before Your Career
7 - The Perfection Trap
8 - The Disease to Please
9 - Minimizing
10 - Too Much
11 - Ruminating
12 - Letting Your Radar Distract You

We all need support

You are not alone.  The reason these habits resonate is because they are common and difficult to overcome on our own.  I help women define what success means to them and achieve it with more joy and less stress.  We figure out the habits that are helping you and ones holding you back so we can adjust accordingly.  Imagine feeling fulfilled, happy, AND successful?  It is totally possible, with the right support.

The first step is to schedule a free 30-minute strategy session to explore where you are and where you want to be.  SCHEDULE HERE.  It takes 30 seconds to schedule and will help you move forward.  Don't delay!  I'm offering discounts to those that schedule this call before the end of November.

Life is too short to stay stressed and stuck. Don't let another season slip by.  I've helped so many people reclaim their life.  I will help you too.