The Freedom to Disappoint

Breaking the Bounds of People Pleasing

Jessica Contessa
Identify Her Daily
4 min readJul 16, 2021

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Photo by Retha Ferguson

Twenty years into the new millennium we’ve only just begun to tap into the striking power of “no”. We’re a generation that has collectively grown fed up and tired of the way things have always been and it’s been decided that that’s just not gonna fly with us anymore. There is so much power and authority in a “no” that we now use it as a full-length sentence ready to destroy any expectation that requires us to set ourselves on fire for others' benefit, their emergencies, and undisclosed agendas.

I think I can safely speak for everyone when I say that our childhoods have deep-rooted issues that we’ve carried well into our adulthood. For myself, my abusive childhood taught me to be extremely afraid of disappointing people. If my parent called me a name that was demeaning and I didn’t like it, I couldn’t dare tell them what to do because they were the adult and I was the child and I had to just take whatever they said or did. I couldn’t voice to my parent what I disliked or didn’t want out of the fear of punishment for it. Fear of disappointment, punishment, and rejection creates the toxic and boundaryless cycle of people-pleasing.

My toxic people-pleasing attracted narcissists, I had to begin to take responsibility as to why I allowed certain people into my space. Yeah, they were toxic but so was I. I had to get to the root of my own issues of people-pleasing and begin to set boundaries.

Everyone fears rejection but that fear that goes unchecked can and will lead to some of the most toxic symbiotic and codependent of relationships.

Narcissistic types love a good people-pleaser, someone who is unwilling to let them down, someone that they can count on.

Unlearning people-pleasing in adulthood is a brutal but crucial process. You’ll need to begin to undress from every “truth” you’ve ever relied on about yourself, believing you were just super nice when in actuality, your need to please was a trauma response to not upset people. We’re breaking the chains of people-pleasing and in doing so we can’t be afraid to disappoint people with no guilt. Letting people down to help rebuild yourself is like a muscle that needs stretching and flexing and you need to become strong AF.

At the root of every disappointment is an unexpressed or unrealistic expectation. It’s okay to have expectations but they always need to become laid bare so that mutual parties can reach a common understanding. Whatever expectation that goes unexpressed, someone becomes prisoner to it.

Free yourself! If you once committed and can’t anymore, express that. If you committed before you knew the terms, gracefully bow out. If you said yes and after began to see who they really are and everything else for the truth, be free! There is freedom in freeing yourself from people’s unrelenting expectations of you. As you continue to practice and meditate on this, it can and will get lonely. Sadly you will begin to see how many people became your friend only because they became reliant on you to solve their emergencies, serve their agendas, and execute their plans all while you were just trying to be accepted by them or become a genuine friend.

Tips for How-to Break the Bounds

Here are a few tips that help you identify and break people pleasing.

  1. You are too easily accesible and reliable, they trust you to say yes, they trust you to carry them because they know you will most likely hold them up. Your constant yes opens you to be manipulated.

When you open yourself up by saying yes to what they want all the time then they will never count on you to tell them no. They will make selfish plans that, by their will, include you before they’ve even asked your permission. Your job now is to set boundaries in place but also test them by saying no and watch how they respond.

2. Know that not everyone else's emergency is your emergency. If it’s not life threatening then gracefully exit stage left.

3. Keep it real with yourself. If you feel depleted and unable to give then say no.

4. If they take more from you than they are willing to give back in reciprocation, then say no.

5. Why are you saying yes? Question yourself and your reasons as to why you may feel the need to say yes. Do you really want to help their cause or do you value their acceptance? If it’s for the acceptance, then do the soul searching to why you feel you need to be accepted by them.

6. Know their expectations. Stop saying yes to things before you know what they expect, ask them upfront to communicate what they expect from you in the friendship or the situation. You also don’t be afraid to communicate your own expectations. You want to know what you’re getting into so you’ll know if you’ll be the one disappointed or if you’re going to have to end up disappointing them.

Their disappointment in your boundaries are not your responsibility and if they aren’t accepting of them then they will show you who they are when you can’t be their reliable slave anymore. Your no will protect you, your sanity, your space, and your mental health. Say no and disappoint them anyway.

Be free. Disappoint them.

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Jessica Contessa
Identify Her Daily

Author and Publisher at ForthRivers.com, Writer and Editor @identifyherdaily and @eightyforth