06 May The Diary of a People-Pleaser #2: I Thought Being Kind Was Enough. It Wasn’t.
The Diary of a People-Pleaser, Series 2
On people-pleasing, societal conditioning, and the slow cost of a pattern I mistook for a virtue.
The people-pleasing pattern cost me something I could not name for years — because everything around me confirmed it was the right way to be. Work hard. Be kind. Help others. Put your head down and success will follow. These were not just professional values. They were moral ones. The kind of person who operates this way is a good person. A reliable person. Someone others can count on. I believed this completely. And for a long time, the evidence seemed to support it.
What I Noticed But Could Not Explain
Somewhere along the way I started to notice something that did not quite fit the story I had been telling myself. The people getting promoted were not always the hardest workers. Some of them were not particularly kind. A few had what I would generously describe as an attitude. And yet there they were, advancing, being recognised, taking up space without apology.
Honestly, it made me furious. It seemed so unfair. I had been doing everything right. And so my response, almost automatically, was to work harder. To be kinder. To make myself even more indispensable. Because surely, eventually, it would be noticed. Surely being the person who never said no, never dropped the ball, never made anyone uncomfortable would count for something.
It did count for something. Just not what I expected.
The Compounding Nobody Warns You About
Here is what actually happened. Slowly, so slowly I almost missed it. Each small act of people-pleasing compounded. One yes led to another. One absorbed discomfort made the next one easier to absorb. One moment of swallowing what I actually thought in a meeting became a habit so ingrained I stopped noticing I was doing it.
And then came the part that still surprises me when I say it out loud. The more I did for everyone around me, the more guilty I felt. Not less guilty. More. I was giving everything: my time, my energy, my weekends, my opinions carefully softened so nobody would feel challenged. And yet the feeling underneath was not satisfaction or pride or even relief. It was a persistent, low-level sense that I was somehow still letting everyone down. The people-pleasing pattern cost me the very thing it promised to protect: the feeling of being enough.
The Prison Nobody Sees From the Outside
From the outside, things looked fine. More than fine, actually. There was progress, achievements, the kind of professional profile that looks, by any reasonable measure, like success. But inside, something had started to shift in a direction I did not have words for yet.
The kindness — the genuine and deeply felt kindness that had always felt like one of my best qualities — had started to feel like a role I could not put down. Like a coat I had worn so long I had forgotten it was not my skin. Being perceived as the kind one, the reliable one, the one who always came through — it had stopped feeling like an expression of who I was. It had started feeling like a condition of my belonging. Like the price of being accepted in the room.
I was not being kind because it felt good anymore. I was being kind because I was afraid of what would happen if I stopped. That is not kindness. That is a cage that looks, from the outside, remarkably like virtue. Research on burnout in high performers consistently shows this pattern: the most conscientious people are often the most at risk.
What I Did Not Know Then
I did not know that the people-pleasing pattern is not a character trait. It is a strategy, one that most of us learned very early, in environments where being agreeable kept us safe, loved, or accepted. I did not know that the guilt I felt was not evidence that I was failing people. It was evidence that the pattern had compounded to the point where no amount of giving would ever feel like enough.
And I did not know that the people advancing around me — the ones with the attitude, the ones who took up space without apology — were not doing something wrong. They were simply operating from a different set of rules. Rules nobody had explicitly taught me. Rules I was only beginning to suspect existed. This is exactly why high-performing directors stop getting promoted — not because they are not good enough, but because the rules that built the career are not the rules that unlock the next level.
Understanding this did not fix anything overnight. But it was the beginning of something. Because once you see it clearly, once you understand that what you mistook for kindness has become a condition rather than a choice, you cannot entirely unsee it. And that is where everything starts. If you are ready to explore this work, you can find out more about my executive leadership coaching programme.
Where This Leaves Me
I still catch myself in it sometimes. The automatic yes. The smoothed-over opinion. The guilt that arrives before I have even done anything wrong. But now I recognise it. And recognition is not the same as freedom. It is, however, the only honest place to start.
Read the first entry in this series: I Caught Myself Doing It Again.
Learning to please yourself, one step at a time.
Danguole Litvinskaite, The Leadership Coach Exceptional & Exhausted Senior Leaders Eventually Find
Frequently Asked Questions
Why does working harder and being kinder not lead to promotion?
Because the qualities that earn early recognition — reliability, agreeableness, never dropping the ball — gradually stop signalling leadership potential and start signalling availability. The people advancing around you are often not working harder. They are operating from a different set of rules. Rules nobody explicitly teaches. Understanding that those rules exist is one thing. Learning to operate by them while keeping everything that makes you exceptional is where the real work begins.
Why do high-performing people pleasers feel guilty even when giving everything?
Because the pattern, once compounded, creates a threshold that no amount of giving can reach. Each yes leads to another. Each absorbed discomfort makes the next one easier to absorb. Eventually the guilt stops being feedback about specific actions and becomes a constant background condition. Recognising that the guilt is a signal about the pattern rather than evidence of genuine failure is the beginning of something important. Getting from recognition to freedom is a different journey entirely.
Is people-pleasing a personality trait or can it actually change?
It is not a personality trait. It is a strategy, learned early in environments where being agreeable kept things safe. That distinction matters enormously because strategies can be expanded. The warmth, the care, the commitment do not have to disappear. What becomes possible, with the right support, is that those qualities begin to come from choice rather than compulsion. That shift changes everything, including how others read your authority in the room.
What does it mean when kindness starts to feel like a condition of belonging rather than a genuine expression of who you are?
It means the pattern has moved from a strategy into an identity. The coat has been worn so long it no longer feels like a coat. At that point, recognising it is necessary but not sufficient. The question becomes how to rebuild, from the inside, the capacity to belong on your own terms rather than on the terms the pattern negotiated years ago. That rebuilding rarely happens alone, and it rarely happens quickly. But it does happen.
About the Author
Danguole Litvinskaite is an executive leadership coach based in Switzerland, specialising in helping exceptional and exhausted senior leaders advance without losing themselves in the process. With 14 years in investment banking across 4 countries, an ICF PCC credential, and 3,000+ executive coaching sessions, she works with senior leaders in tech, finance, consulting, and global financial institutions. Her 3-month intensive, The Integration Method, addresses the overdelivering pattern at the level where it actually lives, combining corporate strategy, leadership psychology, nervous system regulation, and career navigation. Clients include senior leaders at the largest tech companies, Big 4 firms, and global financial institutions.
ICF PCC certified — verified profile
Book a Free Turning Point Call
or email info@coachandyou.com