I’m a Recovering People Pleaser, but I Don’t Want My Son to Become One


Recently, I took my son to a kids’ play space. He was happily playing independently when another child, much older than him, came in and started to remove all of the toys in that area, including the ones in his hands. The older child’s mother stood to the side watching. I stood to the side watching. My son is three but has no trouble telling me when he’s upset with me. So, I waited and observed, giving him space and time to assert himself – to tell this older child he was playing with those things and it wasn’t nice to take them. He didn’t. Instead, he stared at the disappearing toys, visibly upset yet silent. My heart sank. Have I already been failing to teach him how to assert his own needs? Or was he simply intimidated by the age and stature of the older child?    

boy plays with lego

This anecdote bothers me because I am a recovering people pleaser.

I fight my people-pleasing tendencies on a regular basis. Saying ‘yes’ too much and feeling guilty when I say ‘no’. Apologizing when there’s no need. Amending my plans in an effort to accommodate others rather than communicating my own schedule. Forfeiting my true thoughts and feelings about something if I believe they’ll be met with hostility or defensiveness (especially with those I really care about.)

My own behaviors stem from several things. First, I dislike conflict and confrontation. Second, I am uncomfortable disappointing others even if that disappointment is perceived rather than real. Third, and perhaps most importantly, I was brought up with family dynamics and modeling that supported passivity and accommodation over open, assertive communication and boundary setting.

I don’t think it was ever my parents’ intention or conscious desire to teach or model passive communication or people pleasing.

If anything, my parents made deliberate efforts to teach kindness and respect. To put ourselves in another’s shoes and try to understand. To choose our words carefully and not speak out of anger. They modeled fairness and diplomacy. They urged my siblings and me to get along when we had squabbles and to recognize when things weren’t worth fighting about.

Additionally, they chose to keep their own arguments out of sight and hearing. I have no doubt that many of their decisions came from each of my parents’ upbringing and their conclusions about their own childhoods. In one of their childhood households, arguments between man/dad and wife/mom were kept private. In the other, the arguing and tension were visceral and detrimental. In both, because of the era, children didn’t speak out of turn or confront their parents about issues bothering them.

Kindness, respect, empathy, thoughtfulness, self-regulation, fairness, and diplomacy are a strong set of emotional aptitudes to be raised on. At the same time, they are a perfect nesting ground for passivity and people pleaser tendencies to breed when communication and assertiveness are not natural tools to employ. As a parent, I wonder how to teach these skills that at times seem at odds.

Most who know me will read this post and go, “Really? She thinks she has a problem communicating or being assertive?” Many know me as being outspoken in my opinions. Loud. In charge of my space and commanding attention. “Big personality,” most say. But there’s a difference between voicing my opinion in the workplace about a strategy or idea, or about jumping in on a conversation where I know more about the subject than the other person.

man, woman, coffee shop, date

What I’m talking about is being able to assertively communicate my needs and boundaries in the context of my interpersonal relationships. How to be empathetic and thoughtful and still stand up for my beliefs.

I want to be able to say to someone I care about, “You really hurt me when …” or, “It was extremely embarrassing that … please don’t ever do that again.” I want to stand up for myself and say, “Hey, I feel like I’ve done it your way a lot and I’m no longer okay with that.”

I’ve had more than one romantic relationship in my lifetime fail partially as a result of me not being able to communicate my needs effectively because I have been passive and a people pleaser. The thing I’ve found about being a people pleaser is that it’s ‘people’ who end up getting what they need all of the time, but not me. No relationship can really sustain both parties when there is an entirely one-sided approach. I’ve seen the person who perceives they’ve constantly given become resentful of the person who is perceived as constantly taking. And I’ve been on both ends of this equation.

The rub is that as a people pleaser it’s kind of my fault. At least this is what I’ve come to realize. And the hard way.

If I constantly give to the other person whatever it is they need and don’t assert my own needs at all, then I’m granting permission for this dynamic to exist. If I’m not communicating that I don’t like this dynamic, they don’t know any differently and therefore aren’t going to intuit a problem they have to resolve. To them, there is no problem.

When my resentment and true feelings finally appear – which inevitably happens – it’s even worse than it would have been if I had just said something at the outset. By the time the dam breaks and water comes rushing in, there’s now resentment built up. My partner may be angry because I’ve been internalizing issues instead of being forthcoming or honest. It’s easy to see how this pattern of behavior becomes a very large elephant with enough weight to squash a relationship.

silhouettes in sunset

While I know all of this, I have to make an active effort to change my behavior. I continuously must consider whether I’m doing something because I’m truly okay with it or because I’m trying to please the person I’m with. I have to determine when and how to express something that has hurt me, made me uncomfortable, or that I wish to see change. In order to be true to myself, I have to say ‘no’ more and without guilt. I have to apologize less.

I have to make an active effort to try to step outside of myself and witness what kind of role model I am being for my son.

Like my parents, I want to raise my son with kindness, respect, empathy, thoughtfulness, self-regulation, fairness, and diplomacy. But not at the cost of him becoming a people pleaser. I do not want to risk him being unable to communicate his feelings and personal boundaries. I must practice assertiveness, interpersonal communication skills, and boundaries in an effort to model these for him and to show him that it’s still polite, kind, thoughtful, and fair to respect my own being as much as I respect other people.

I want my son to be the kid at the play place who says to the older child taking everything from him, “Hi, what’s your name? I’m K. I’m playing with these, but I would be happy to bring them to you when I’m finished.” In his relationship with me, I want him to be able to say, “Mom, it upset me how you just spoke to me in front of my friends.” Or, with his future partners, “I know that you didn’t mean to come across that way when you did ‘x’ but it really bothered me and I need you to know.” I want for him to learn way sooner than I did that kindness, compassion, empathy, thoughtfulness can exist in harmony with assertiveness and personal boundary setting.

children, boy in skeleton shirt

I’m a recovering people pleaser, but I don’t want my son to become one.

How do you model boundary setting and assertive communication to your child(ren)?

How to raise an assertive child when you are a recovering people pleaser


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