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Why does setting boundaries and putting yourself first make you feel like shit?


Man sitting on a bed at sunset

I’ve finally done it.


I drew a line in the sand and stood behind it.


I’ve turned a corner.


This. Is. It.


I’ve said exactly what I think. I’ve said exactly what I mean. I’ve put myself first.


And more importantly, nothing bad happened.


I wasn’t rude or horrible. I just said what I truly thought, and no one died.


Here we go! Welcome to the new, honest, unadulterated version of me…


But hold on, why do I feel itchy and uncomfortable? Like there’s sand in my brain? Like I’m wearing clothes that no longer fit?


Why am I replaying that conversation in my head? Over and over as if I’ve done something wrong?


Standing up for yourself should feel great, not shitty… right?


Right?!


That little outburst is the recurring internal monologue that I’ve been grappling with since the inception of the Confessions of a Recovering People Pleaser blog.


The battle between giving my authentic opinion and feeling like I shouldn’t have said it because it might upset others.


Do you know what I mean?


Starting this blog marked the start of my conscious effort to rewrite the script of my interpersonal relationships and focus more intently on my people pleasing habits.


And most importantly, breaking those people pleasing habits.


In truth, I feel like I’ve come leaps and bounds in my self improvement since starting this blog and a lot of the reason is because it stays front of mind. 


I feel incredibly fortunate that people now come up to me and want to talk about their own people pleasing, where they think it comes from and what they’re doing to overcome it.


This means I get to have some incredible conversations with people like you about how they’re feeling and realising that my problems, fears and habits aren’t unique. We’re building a great little community of like-minded recovering people pleasers.

The art of saying no and setting boundaries has become a skill I'm actively honing, and my life is gradually becoming filled with more self-respect and authenticity.


Yet, even with my newfound ability to draw lines in the sand, speak up and focus on the things I really want to do, an unexpected companion lingers…


Guilt, accompanied by the relentless orchestra of overthinking and self-doubt.


It's as if the act of prioritising my own needs sets off an internal alarm, warning me of others potential disappointment with my words and actions. Which makes me want to fall back into my old ways. Put on those old comfy, harmonious, people pleasing clothes.


The reason this occurs is because we’re fighting against our social conditioning and the neural pathways that have been forged over years of habitual people pleasing.


And because our brains are wired for connection and approval, we react strongly when deviating from established and familiar patterns. So guilt emerges as a defence mechanism, attempting to preserve our familiar, but outdated, people pleasing habits.


A recent prime example of this which I experienced was when I was reading a fantastic book called “Never Split The Difference” by former FBI negotiator Chris Voss. In the book, Voss gives practical tips on how to get the most out of your interactions in both tense negotiations and also in regular conversations. A big part of his advice is to be curious, ask good questions and get under the skin of what someone really wants in an interaction. And ultimately, be direct in asking for what you want.


While reading some of the practical techniques and scripts he suggests, I remember thinking “But I can’t say that, because that might be perceived as mean, or cruel or make me feel guilty.” 


And something profound dawned on me. These techniques he suggests are not mean. They’re not evil. They’re not negatively emotive. They’re just direct.


So there’s no need to overthink them. They only seem “nasty” to me because I’m filtering them through my people pleasing lense. Most people don’t think like that.


A good thing to remember is; the things you say are interpreted at the listeners ears or readers eyes, not when they leave your mouth or when you type them out. So if you take a step back and remove those people pleasing glasses, you can see much more clearly that this might actually help set healthy boundaries and allow you to be your authentic self.


So, what can we do to help not “feel like shit” when we try to overcome these people pleasing tendencies?


To change into and embrace the new you, equipped with the ability to set boundaries and hopefully not feel guilty, will take some time.


So, why don’t you try and practice some self-compassion?


It’s important to understand that the journey towards self-assertiveness is a process, not a destination. It’s going to take time, effort and just like a muscle it needs to be worked on to get stronger. So be kind to yourself as you grow into your new authentic self. This version of you probably hasn’t seen the light of day for a while so it might be shy. But why not let it come out and be the star of the show? Be proud of this new version of you! Once you’re proud of them, then others will be too.


This is a bit harder to do, but you can also try to mentally reframe those feelings of guilt. Shift your perspective from guilt to empowerment by recognizing that boundaries are an act of self-love, not selfishness. You’re doing this for you, and that’s a good thing!


Will some people not like the new you? Yeah, probably. But if they’re only around you for your agreeableness then they probably don’t have your best interest at heart. As Winston Churchill remarked, "You have enemies? Good. That means you've stood up for something, sometime in your life."


So try going out there and transform your guilt into empowerment, and stand tall in the face of resistance!


So to answer the question, why does setting boundaries and putting yourself first feel like shit? It’s because you’re changing. Evolving. Become a new version of you.


You gotta give that version of you some time to get comfy in your new skin with these new habits!


As with a lot of things during my people pleasing journey, I’ve had to realise that getting past this is like working out a muscle. I’m going to go through good days and bad days. And ultimately, I hope I can leave behind that nagging feeling of guilt, and embrace my authentic self.


Get comfy, being uncomfy. You’re going to be better for it!

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