Women who grew up people-pleasing: what’s the hardest boundary you’ve learned to set?
November 15, 2025
I’m unlearning saying yes to everything. What boundary challenged you most?
29 comments
Standing up for myself and not letting people walk over me.
Such as calling out jabs or weird comments when people make them.
Or “please stop doing (insert harmful behaviour)”
Advocating for myself
It has lost me two close friends and also my parents this year.
Would I take back advocating for myself to change that? Fuck no.
A former student who is now an adult decided to try to convince me to date him after I got divorced. I loved my students and took pleasure in making this kid feel welcome and cared about, because he was having a hard time when he was a teenager, but I have to draw the line with that behavior.
Not sure if this counts as a boundary but saying no or making a statement without an explanation was difficult.
Can’t remember if that was the most challenging but def took a few years of being very aware, push back from ppl/myself and keeping the habit before it became a natural habit.
I grew up with a lot of guilt-tripping so I usually would say yes if I or another felt that my reasoning wasn’t valid.
Advocating for myself.
I used to just let things slide, to keep the ‘peace’, but I stopped all that. I only have one life to live, and I won’t spend most of it letting people walk all over me.
the need to justify myself for a decision.
“No” being a full sentence. Not need to explain, no need to apologize. Just saying no.
To say no to people and walk away after saying no. Even though those people can still be in my life ,the walking away after saying no more than once is very hard. I’ve definitely learned that in being a people pleaser no one ever really listened to me, or heard what I was trying to say. So in some cases now I don’t open up at all anymore to certain people. That does hurt. It’s made me realize that I wasn’t always wrong or that even if you kept up people pleasing ; those people still won’t be there for you, ever. Like ever. That hurts the most it’s actually heart breaking. But I’ve finally kicked people off their pedestals that I put them on. Their just people
That’s it’s ok serve myself ahead of others. It’s ok to be selfish and put my wants and needs first.
Something that is still a massive work in progress and something I realised wayyyyy to late in life.
“If you keep speaking to me like that, this conversation will end.”
Understanding I can only help people who want to be helped.
A bit different to the others here because it’s an internal boundary – but learning that I am not responsible for other people’s happiness. If I catch myself feeling guilty I’m not “there enough” for someone, I really need to examine whether that’s true. There’s a line.
Being perceived as selfish. Anything you do for yourself is considered selfish and people-pleasing means you can never be that
Offering too much help. Never speaking about my accomplishments or downplaying immediately if asked
I was taught to always be as considerate and humble as possible.
I’ve started letting stuff slide because it is not my job to be the mom of everyone around me. And I will talk about the goals I’ve accomplished because I deserve to feel proud of myself without thinking about everyone’s potential petty feelings of jealousy.
The hardest boundary I learned is related to family. Showing up for family is needed but not at the detriment of myself! I was always stressed trying to figure out how to say no to this gathering or that one. The flip side is, I make time to connect with family when I am in a good head space.
Also, I was always someone who felt like I needed to follow authority or “go with the flow” as a people-pleaser. Eventually I realized it doesn’t always work out even when you do what other people want you to do. So, now I’d rather speak out and advocate for myself when something isn’t right whether it be elders in my family or school or a job (especially a job), because I realize it’s better to say something and have clarity than to silently be suffering.
“No” is a complete sentence.
It’s better to say no than over promise and under deliver.
It’s okay to just say no because you feel like it.
“No” gives you power.
Honestly for me, it’s not mirroring ppl or answering/,behaving in a way I know they are looking for me to and just behaving/answering in my authentic way. I’ve found I come off a lot colder if I’m not enthusiastically doing things for ppl and I am still trying to figure that out.
Most relatable question I read and something I have been working on this year.
Taking a stand for myself and any decisions I take for myself without consulting anyone and having people respect me for that.
Setting boundaries with my parents, now that I am an adult and high time I do it (28YO but it’s always been a challenge)
Not having to explain when I say no to something – could be a plan, an opinion, a thought or anything.
Repeating the refusal. The first time I say no is easy. After that its not. Its a work in progress.
I no longer remain in relationships in which double standards are a requirement and expectation. I no longer remain in relationship with anyone who threatens me. I no longer do anything I’ve been voluntold for.
Realizing that other people’s pov is not the default to follow. That my point of view, thoughts , feelings, opinions and needs are just as valid as everyone else’s
Knowing that I would lose some family members over it.
Decided to cut ties with my aunt this year after she (almost) tried to sabotage my wedding.
It hurts, but with my husband’s and MIL’s support, I know I have to make the healthy choice.
Letting people control my life because it was easily handed over to me so I had to be grateful. I don’t even have time to process things because I would always hear “it’s the best for you..” so I just let it be. I never had my own identity. So I stopped pleasing people. I kinda lost my parents on this and had to break off my engagement too. I was perceived as being selfish when I did it.
Not so much a boundary I learnt to set, but an incredibly painful realisation. People that I bent over backwards for because we “were like sisters” (their words, not mine), actually didn’t like me, but they were more than happy to accept and take everything I was offering. Once I learnt (the hard way) to stop saying yes and to instead start allowing people to “be there for me”, I learnt that those people didn’t like me. But I was convenient to them for everything I was doing for them. Once they didn’t need me, they left. So I didn’t even get to the part where I practice saying no. I was only at the start of learning not to throw myself under a bus for people, and waiting for them to ask for my help. Turns out they didn’t need me, nor did they actually like me. So for me they were a major part of my life, but for them I was an option. Once you stop over giving, watch who stays around. It’s a hard truth, but it’s important to know and see the truth.
To answer your question: learning to sit and wait for people to ask for help. I don’t need to offer. I don’t need to fix things. Some people just want to talk about their problems – they don’t want help. They just want to voice it. The people pleaser in me wants to fox it for them, or to offer help. But people don’t respect you if you do that. Wait to be asked. Otherwise they don’t value your help. They assume you’ve got nothing else going on in your life and so you want to vs you hating to see people suffer and you wanting to help/ fix.
Sitting still while that strong desire to help rattles inside me like a metal cup on a cage is hard. But it’s a vital lesson I need to learn to sit with.
Focusing taking care of me. I heard a quote that “in the times you arent taking care of yourself, you also can be the most harmful to others”. Also stop trying to save everyone from themselves. In giving myself all the time to figure out stuff, Ive learned there is so much about me Im discovering and learning. When I was too occupied with taking care of so many ppl, I didnt think of how things feel, what the tangible goals are, planning for a future. Eventually, it was accountability for my life and having the same expectation of others. I outgrew friends but also found friends who genuinely support me and celebrate me. Its reciprocal
Saying no. If I deny someone’s request, I feel like the most selfish person in existence. Killing myself for someone else’s benefit is diabolically easy
Learning that my needs matter too, even when others disagree.
Realizing I’m not responsible for others’ feelings anymore
Not offering to solve or help solve someone’s problems. A lot of people are takers. I genuinely love helping people and making things easier for them, but most people will take advantage of that. The best and healthiest friends I have are very independent and understand give/take.
Also NO is a complete sentence. If they throw a fit when you say no, then they aren’t going to be a good friend.
29 comments
Standing up for myself and not letting people walk over me.
Such as calling out jabs or weird comments when people make them.
Or “please stop doing (insert harmful behaviour)”
Advocating for myself
It has lost me two close friends and also my parents this year.
Would I take back advocating for myself to change that? Fuck no.
A former student who is now an adult decided to try to convince me to date him after I got divorced. I loved my students and took pleasure in making this kid feel welcome and cared about, because he was having a hard time when he was a teenager, but I have to draw the line with that behavior.
Not sure if this counts as a boundary but saying no or making a statement without an explanation was difficult.
Can’t remember if that was the most challenging but def took a few years of being very aware, push back from ppl/myself and keeping the habit before it became a natural habit.
I grew up with a lot of guilt-tripping so I usually would say yes if I or another felt that my reasoning wasn’t valid.
Advocating for myself.
I used to just let things slide, to keep the ‘peace’, but I stopped all that. I only have one life to live, and I won’t spend most of it letting people walk all over me.
the need to justify myself for a decision.
“No” being a full sentence. Not need to explain, no need to apologize. Just saying no.
To say no to people and walk away after saying no. Even though those people can still be in my life ,the walking away after saying no more than once is very hard. I’ve definitely learned that in being a people pleaser no one ever really listened to me, or heard what I was trying to say. So in some cases now I don’t open up at all anymore to certain people. That does hurt. It’s made me realize that I wasn’t always wrong or that even if you kept up people pleasing ; those people still won’t be there for you, ever. Like ever. That hurts the most it’s actually heart breaking. But I’ve finally kicked people off their pedestals that I put them on. Their just people
That’s it’s ok serve myself ahead of others. It’s ok to be selfish and put my wants and needs first.
Something that is still a massive work in progress and something I realised wayyyyy to late in life.
“If you keep speaking to me like that, this conversation will end.”
Understanding I can only help people who want to be helped.
A bit different to the others here because it’s an internal boundary – but learning that I am not responsible for other people’s happiness. If I catch myself feeling guilty I’m not “there enough” for someone, I really need to examine whether that’s true. There’s a line.
Being perceived as selfish. Anything you do for yourself is considered selfish and people-pleasing means you can never be that
Offering too much help. Never speaking about my accomplishments or downplaying immediately if asked
I was taught to always be as considerate and humble as possible.
I’ve started letting stuff slide because it is not my job to be the mom of everyone around me. And I will talk about the goals I’ve accomplished because I deserve to feel proud of myself without thinking about everyone’s potential petty feelings of jealousy.
The hardest boundary I learned is related to family. Showing up for family is needed but not at the detriment of myself! I was always stressed trying to figure out how to say no to this gathering or that one. The flip side is, I make time to connect with family when I am in a good head space.
Also, I was always someone who felt like I needed to follow authority or “go with the flow” as a people-pleaser. Eventually I realized it doesn’t always work out even when you do what other people want you to do. So, now I’d rather speak out and advocate for myself when something isn’t right whether it be elders in my family or school or a job (especially a job), because I realize it’s better to say something and have clarity than to silently be suffering.
“No” is a complete sentence.
It’s better to say no than over promise and under deliver.
It’s okay to just say no because you feel like it.
“No” gives you power.
Honestly for me, it’s not mirroring ppl or answering/,behaving in a way I know they are looking for me to and just behaving/answering in my authentic way. I’ve found I come off a lot colder if I’m not enthusiastically doing things for ppl and I am still trying to figure that out.
Most relatable question I read and something I have been working on this year.
Taking a stand for myself and any decisions I take for myself without consulting anyone and having people respect me for that.
Setting boundaries with my parents, now that I am an adult and high time I do it (28YO but it’s always been a challenge)
Not having to explain when I say no to something – could be a plan, an opinion, a thought or anything.
Repeating the refusal. The first time I say no is easy. After that its not. Its a work in progress.
I no longer remain in relationships in which double standards are a requirement and expectation. I no longer remain in relationship with anyone who threatens me. I no longer do anything I’ve been voluntold for.
Realizing that other people’s pov is not the default to follow. That my point of view, thoughts , feelings, opinions and needs are just as valid as everyone else’s
Knowing that I would lose some family members over it.
Decided to cut ties with my aunt this year after she (almost) tried to sabotage my wedding.
It hurts, but with my husband’s and MIL’s support, I know I have to make the healthy choice.
Letting people control my life because it was easily handed over to me so I had to be grateful. I don’t even have time to process things because I would always hear “it’s the best for you..” so I just let it be. I never had my own identity. So I stopped pleasing people. I kinda lost my parents on this and had to break off my engagement too. I was perceived as being selfish when I did it.
Not so much a boundary I learnt to set, but an incredibly painful realisation. People that I bent over backwards for because we “were like sisters” (their words, not mine), actually didn’t like me, but they were more than happy to accept and take everything I was offering. Once I learnt (the hard way) to stop saying yes and to instead start allowing people to “be there for me”, I learnt that those people didn’t like me. But I was convenient to them for everything I was doing for them. Once they didn’t need me, they left. So I didn’t even get to the part where I practice saying no. I was only at the start of learning not to throw myself under a bus for people, and waiting for them to ask for my help. Turns out they didn’t need me, nor did they actually like me. So for me they were a major part of my life, but for them I was an option. Once you stop over giving, watch who stays around. It’s a hard truth, but it’s important to know and see the truth.
To answer your question: learning to sit and wait for people to ask for help. I don’t need to offer. I don’t need to fix things. Some people just want to talk about their problems – they don’t want help. They just want to voice it. The people pleaser in me wants to fox it for them, or to offer help. But people don’t respect you if you do that. Wait to be asked. Otherwise they don’t value your help. They assume you’ve got nothing else going on in your life and so you want to vs you hating to see people suffer and you wanting to help/ fix.
Sitting still while that strong desire to help rattles inside me like a metal cup on a cage is hard. But it’s a vital lesson I need to learn to sit with.
Focusing taking care of me. I heard a quote that “in the times you arent taking care of yourself, you also can be the most harmful to others”. Also stop trying to save everyone from themselves. In giving myself all the time to figure out stuff, Ive learned there is so much about me Im discovering and learning. When I was too occupied with taking care of so many ppl, I didnt think of how things feel, what the tangible goals are, planning for a future. Eventually, it was accountability for my life and having the same expectation of others. I outgrew friends but also found friends who genuinely support me and celebrate me. Its reciprocal
Saying no. If I deny someone’s request, I feel like the most selfish person in existence. Killing myself for someone else’s benefit is diabolically easy
Learning that my needs matter too, even when others disagree.
Realizing I’m not responsible for others’ feelings anymore
Not offering to solve or help solve someone’s problems. A lot of people are takers. I genuinely love helping people and making things easier for them, but most people will take advantage of that. The best and healthiest friends I have are very independent and understand give/take.
Also NO is a complete sentence. If they throw a fit when you say no, then they aren’t going to be a good friend.