Episode 117 - The Enneagram for People Pleasers Part 2 with Wendy Montgomery
Today, I’m back with part two of my conversation with Enneagram coach Wendy Montgomery. In part one, we explored the nine Enneagram types and how people-pleasing can show up for each one. Now, we’re diving into what healing these habits looks like for each type and how the Enneagram can act as a guide for transformation. Here’s what we cover:
Why self-awareness is key to reducing people-pleasing tendencies
A type-by-type analysis of how the shift away from people pleasing can happen
Why healing is a journey, not an arrival–even with the help of the Enneagram
How to offer yourself grace and compassion when overcoming people-pleasing
A healing message for each Enneagram type
Find Wendy here:
https://www.wendymontgomery.com/
https://www.instagram.com/wendymontcoach/
https://www.facebook.com/people/Wendy-Montgomery-Coaching/
Find Sara here:
https://pages.sarafisk.coach/difficultconversations
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https://www.facebook.com/SaraFiskCoaching/
https://www.tiktok.com/@sarafiskcoach
https://www.youtube.com/@sarafiskcoaching1333
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Transcript
Sara Bybee Fisk 01:00
It was a lot of fun to record this podcast episode with my friend and Enneagram coach Wendy Montgomery. It's in two parts because there's just so much to the Enneagram. It's really hard to narrow it down and we try to discuss as much as possible without firehosing you and I hope we did a good job. In part one, Wendy introduces you to each of the nine types and what people pleasing might look like for each type and then in part two, we look at the healing of people pleasing and what it might look like for each type to become more self-aware and take steps to heal the wounds that cause a lot of the people pleasing and we try to give you a map for finding out your type or for deepening your understanding. I really hope you enjoy the episode. I really want to just talk about the shift that happens for each type as they move along the spectrum of recognizing people pleasing or recognizing some unhealthy habits and patterns that don't serve them and don't work for them. The shift that happens as they move toward healing or health from people pleasing specifically. One of the most beautiful things that you have sent me, I think I asked you one time, we were talking about the healing sentences that each type needs to hear. I would love to end with those just so that if that is something that resonates with people listening, they can take those sentences. First kind of like a type by type shift that happens and then we'll end with those healing sentences.
Wendy Montgomery 02:41
I think what's really helpful is to understand the importance of self-awareness when it comes to the Enneagram because the more self-aware we are, the more we can see the way we're getting in our own ways. That's going to look different from type to type. For me as a type eight, being really self-aware of how I'm coming across to other people has been a game changer for me because a lot of eights don't realize that when we bring a level 10 energy to every engagement where maybe a level two or three would have been sufficient that we can come on way strong. In our mind, we're just being friendly and engaging. My kids say I make aggressive eye contact. I don't even know what that means. I just think I'm looking at you and paying attention to what's being said and they feel like it's like laser beams coming out of my eyes. There is that piece of self-awareness that we can't fix something unless we see it. The beauty and also the tricky confronting part of the Enneagram is it will show you. It'll show you how you're getting in your own way if you let it. It does require a level of not just humility for our own weaknesses and ways we wish we were showing up better. It requires deep compassion and friendship towards ourselves to be like, yeah, of course I show it messy. Sometimes life is hard. That kind of encompasses all of the types, that self-awareness piece.
Sara Bybee Fisk 04:09
It does. Okay, I didn't want to admit this because you're the Enneagram expert here, but I started playing around with each type. And what might it look like from like my work with each of these types, because I have every single type in my practice, either, you know, privately or in group coaching. And so I started writing and I'm going to read to you what I wrote, and I want you to either weigh in and tweak it so that it is more accurate, if that makes sense.
Wendy Montgomery 04:37
Yes. That sounds awesome.
Sara Bybee Fisk 04:40
So type one, the reformer or the perfectionist, before they kind of experienced the self-awareness that you so rightly pointed out, they need to be good, they need to be right. And their responsibility kind of earns them that love, right? They're always kind of earning and earning and earning. And as they become self-aware and self-connected, they realize that being human means I'm going to make mistakes. It is a feature, not a bug. And that begins to create a place for softness with themselves, softness with their mistakes, and it allows them to go from really rigid, constant self-judgment to more of a graciousness or grace-filled view of themselves.
Wendy Montgomery 05:32
Yeah, that is exactly what it looks like. And for all the ones listening, and for all of the types when we go through this part of it, it will be the journey of your life to get there. You're going to get there and it's going to feel amazing. And then there might be a little bit of a slide back and then you'll get there. It will be the thing that we are working towards until we die. It's never an arrival. I mean, I would love for it to be an arrival. It's a journey.
Sara Bybee Fisk 06:00
Yeah. And the question that you asked, I think, you know, of each type is, is so important to be asking as a way to facilitate this kind of movement toward more health and more and habits that just serve you and your relationships better. Okay, so type two, before they kind of have the self-awareness, they are also doing a lot of the gaining self-worth by meeting others' needs, giving people the cookie that they baked, you know, from scratch this morning, anticipating others' needs, and they're neglecting their own desires. They are really resentful kind of in there because they're always so outwardly focused. And what a two looks like as they journey toward health and out of people pleasing is that love, they learn that love doesn't require them to be constantly hypervigilantly doing their thing. And that they actually are worthy of receiving care without feeling guilty and without feeling ashamed. They go from like the self-sacrificial type of love to more of self-worth as love for themselves.
Wendy Montgomery 07:21
Yes. And to be able to accept other people's help and care for themselves. That's so hard for it too.
Sara Bybee Fisk 07:29
Yeah. Yeah. Okay. So for three, the achiever, you also mentioned that they would kind of shapeshift, right? I'll just be whoever you need me to be. I will be really good at reading the room and I will show up and meet people's needs both so that you can admire me and so that I avoid being seen as a failure. So their shift would look like understanding that they're worthy of receiving, that worth isn't tied to how they perform. And as I've seen threes kind of make this journey, there's almost this softening or relaxing into letting themselves be seen as someone with needs who is authentic and comfortable with being kind of a regular human like the rest of us.
Wendy Montgomery 08:25
Yeah, and less than shiny and perfect. Yeah.
Sara Bybee Fisk 08:28
Yeah, I love that. Okay, good. I feel like I'm getting a good grade on this so far. Yes.
Wendy Montgomery 08:34
Yes, you nailed it.
Sara Bybee Fisk 08:35
It's awesome not to be a people pleaser and seek your approval right now Wendy.
Wendy Montgomery 08:42
I mean, not the people-pleaser part. You're nailing this part.
Sara Bybee Fisk 08:45
Type four, the individualist. So they are kind of on that teeter-totter seesaw of too much, not enough, and kind of wanting to be special. I need to be more special. I'm not special enough to earn a place, to earn belonging, to earn the right to kind of exist in their groups. And they go from that to knowing that they just who they are, however they feel it, however they see it, however it is in their lens or their circumstance, it's right. And it's enough. And that they are able to connect, not just by being the most special or the most unique, but through shared emotional experience that doesn't have to be the same level of emotion. Yes. So they go from like maybe like a longing for significance through their emotionalness, their specialness, to just really being at home with who they are and how they feel. And they just belong.
Wendy Montgomery 09:56
Yeah, I love all of that. And I would also add that they stop putting shame on themselves for their big feelings. They let themselves have them. Cause society, especially if you're a male type four, like my husband, society is like, why are you like, and it's not like he's a crier or anything, but it's like, he's going to feel something deeply. And then there's a level of shame. Like I can't let people know how much this is affecting me. Women as well, you know? And when they get to just feel what they're going to feel, regardless of what society tells them is okay, they don't have to feel that need to people, please.
Sara Bybee Fisk 10:30
Yeah, this next one was fun for me because Dan is a five. So before they come into a lot of self-awareness and begin that healing journey, their protection is through withdrawal. And like intellectual control of either the conversation or whatever is going on. I've talked with Dan in the past that sometimes his boundaries felt like electric fences, right? Oh, that's so accurate for fives. When he needed space and he needed time because fives do need more space and time to themselves and there can be very protective of their free time and their personal time. And I think that the switch I've seen him make and other fives make is that they develop the capacity to open up and participate without controlling the intellectual property in a conversation. Oh, that's so good. Or in a situation, and they actually trust that their needs will also still be met. Sometimes those boundaries that feel like electric fences are fives who worry that they won't have enough free time for themselves, they won't have enough of their own resources for themselves. But as I've seen fives and especially Dan kind of relax into trusting other people, like talking about what they need. Like the reason it's hard for a five to trust that their needs are going to be met is sometimes they feel like they're the only one looking out for themselves. But as they open up and they share their emotional experience, they learn to trust that other people will show up for them and meet their needs as well. And so it really is a shift from like a withholding as a way to protect myself to engaging with a lot more trust that their needs will be met. Because part of what we need as humans is emotional community and communing with each other on an emotional level.
Wendy Montgomery 12:31
You said it so well. For fives, they fully believe that their energy, their bandwidth is finite. It will be over at some point, so they are fiercely protective of it. So their growth work, like what you were explaining, is almost a generosity of their time and their knowledge. And even if it feels like it's coming at an expense, it's worth it because I love this person or I love this group. And there will be more. Once it's over, it's gone and the well is empty. Yeah, so good.
Sara Bybee Fisk 13:06
All right, type six, the loyalist. So they're people-pleasing. When I was looking at, you know, different clients and people I know looks a lot like aligning with strong leaders, that loyalty piece of just like parroting, like strong leaders or strong groups for safety. There's a large number of sixes and a lot of, you know, conservative religious groups because that is what they do for safety. And because so much of their people-pleasing is just towing the party line. And there's very little self-trust that can be built when you're just kind of towing the party line, allowing the thinking to be done for you by people that you trust to keep you safe. It is the opening to I am trustworthy. I have an internal authority that I can cultivate that actually creates safety for me so that I can disagree so that I can have my own opinion so that I can take a stand that aligns with maybe more who I am deeply and authentically than just the rules of this group. It looks to me like the shift from an externalized trust. I'm going to trust this group to take care of me and their laws and their rules and what they want for me and what they tell me to think to more of an internalized bravery or courage or centeredness. And it's not even either or it's not like the loyalist has to leave the group, but it's their own internal compass and trust comes online and is at least equal to that of the group to which they belong and hope will keep them safe.
Wendy Montgomery 14:56
Yeah, I totally agree with that. I think sixes thrive when they realize that the assurance that they're looking for is best found inside themselves. Yeah. It's there.
Sara Bybee Fisk 15:07
Yeah.
Wendy Montgomery 15:08
And they have to trust it.
Sara Bybee Fisk 15:09
All right, seven, the enthusiasts. I have a strong seven wing, avoiding pain by let's go do something fun. But I think there's a lot of accommodating and being very agreeable that also happens for sevens. And so slowing down, like I just remember in a lot of my seven, just high, just action, action, action, action, action, doing, doing, doing, doing, and so slowing down to stay present with emotions.Because for a lot of people pleasers, we are able to just skip past the heaviness of the guilt, the resentment, the fear, by just staying in motion. So for a seven in particular, slowing down, staying present, and a shift from like constantly being in action, trying to not feel to just being comfortable feeling and letting and trusting that those emotions have really valuable, important information for us about what is good for us, what is not good for us, and letting some of those emotions lead the way.
Wendy Montgomery 16:24
Absolutely. I call it bright siding that sevens do, like when they stop bright siding other people or a situation and like see it for the truth of what it is and let that be good enough, you know, and feeling that perfect. It's perfect.
Sara Bybee Fisk 16:41
All right, type eight, the protector. Okay, hurt my feelings. Mine too. So that fierce like self-protection, not wanting to be controlled, not wanting to be trapped in in anything, is the armoring up that I see for myself, like I can do it, give it to me, I'll take care of it, I will take care of that and that and that and that. And so you become this, this almost self supported thing, because you don't allow a lot of other people to step in and do a lot for you. Especially because having needs feel so vulnerable, it feels like you're, you know, standing naked in front of everyone not knowing if they will want to support you the same way that you know, you are you are supporting and protecting everyone else. Will I be protected the same way that I'm protecting everyone else? And so allowing softness and allowing mutual care, that letting other people in is not just an act of courage, but that it's an act of courage. And it's not weak. And it is what actually gets me the protection and the care and the mutual equity that I so often resent that I don't have. And so it's a shift from like being the strongest, or like being the one to have power over by moving all the chess pieces on the board for everybody else, to just be equal, right power with and softness with connection with
Wendy Montgomery 18:28
Yes. All of that. 100%.The other thing I was thinking when you were speaking is, oh, another way that people pleasing shows up for me is my overuse of apologies. Because I automatically assume if something's gone sideways in a relationship that it's my fault. Because eights feel that a lot, especially female eights were too loud. We have too big of an opinion. We're too harsh. So I assume I said something unkind or I did something that was thoughtless. And then I start realizing I'm like, I am taking far more accountability and ownership of things that I was not the problem, if that makes sense. So that's a way that I find that I'm trying not to people please is apologizing when I do get it wrong for sure. But not taking other people's stuff and making it mine.
Sara Bybee Fisk 19:17
That's right. Just letting, just letting whatever awkwardness or discomfort is there, be there without owning it and trying to smooth it over. Yeah. Yeah. All right. Last one type nine, the peacemaker. So the peacemaker, as I understand it, really is about disappearing my own needs just to keep everybody else happy. So I'm going to, if I'm a nine, I'm avoiding conflict and I see the nine, you know, in, in me a lot, deferring decisions. What do you think? What do you want to do? Chameleoning just so that everybody is harmonious and that there's no conflict. And so out of that comes a lot of people pleasing and nines when they find their voice. And when they say, this is what I want, this is what I need. It's almost like the switch flips and they become more of, I would call like an, an active participant in their life, not just the one kind of curating the experience for everybody else and just trying to keep it everybody happy and smiling. And so I see their shift from like not having any needs. That's what gets me loved and accepted to, I am a person who has needs that deserve to be met just like everybody else. And I feel comfortable saying what those are and holding my place of equality in a group.
Wendy Montgomery 20:53
That's so good and I'm thinking of, I have a lot of nines in my life, a lot of family members that are nine and I think it'd be amazing if they could do that and it would also be very hard for a nine. I think everything you mentioned across all the types is so beautiful and it will be hard. So I don't want your listeners to expect to be like, okay, well, I've got the magic bullet. This is what I need and now like give me a week or two and I've got this. This is going to be something that we work on our whole life. So give yourself like a lot of grace and a lot of compassion because we're going to do it fumbling and messy, especially in the beginning as we're trying to overcome these people-pleasing tendencies.
Sara Bybee Fisk 21:35
Yeah. And I wanted to offer these shifts as kind of like the lighthouse, right? That we're going toward. Because so many of the women that I talk to that, you know, they know they're people pleasing. They don't know how to stop. And they long for a real authentic lived experience. And hopefully in these, you know, nine kind of shifts that I've just kind of, you know, it's not that any grand bible by any stretch of the imagination, but it's the shifts that I have seen clients make. And it's a continuum, right? It is a constantly evolving set of skills and feeling of self connectedness and sovereignness authenticity that begins to develop that just builds on itself. Yeah.
Wendy Montgomery 22:27
It's so good. I love those shifts. I'm gonna write them down. Thank you.
Sara Bybee Fisk 22:31
I'm so glad. Did I get a good A? Did I get a good grade? Great plan.
Wendy Montgomery 22:34
Plus, you totally pleased me, Sara.
Sara Bybee Fisk 22:39
People-pleased. Excellent. All right, so let's end. Do you have those sentences that you could just read to us as we end? So as you hear these, if you're listening, just notice which ones feel like the warm hug that you wish you could have had maybe or you wish you could have and offer this to yourself because that's the thing that we can do as adults to heal whatever set of wounds and circumstances kind of created each type in us as we can begin to fill that hole for ourselves and heal that wound.
Wendy Montgomery 23:15
Yes, absolutely. So the Enneagram calls these the healing messages or the message your heart longs to hear. I call them for the spouses you're get out of jail free card. So if you're ever in a disagreement and you know your spouse's type, write this down because this is what will soften every conversation. It is also what we need to deeply, deeply embody within ourselves for our type because this is where we find ours, our softness. It's where we find our integrity. It's where we find true peace. So for our type one, the improver, it sounds so simple, but it's so important. Their healing message is you are good. Period. Full stop. You don't have to keep doing and perfecting and making everything better. It's good and you are good right now. So that's type one. Oh, good. Type two, the healing message for the helper is you are wanted and loved. You don't have to contort yourself. You don't have to bend over backwards taking care of every person in your life. You are wanted and loved right now without having to serve or do anything. And then type three, their message is you are loved for yourself without needing to perform. There is nothing we need you to do. You don't need to be shiny and perfect for us. We love you right now, even flawed and messy, right? And then type four, you are loved and seen for who you are. You already are special. You already are unique. You already are your authentic self. And we see that and that is what we love in you, right? And then for type five, their message is your needs are not a problem. They are so fiercely independent. They won't even let you know what they need because they're going to take care of it because they're afraid their needs might be a problem for you. Nope, your needs are not a problem. Let me be here for you. That's a five. And then type six, their message again, it sounds really simple, but it's really important for six is to know you are safe. We've got you, you're safe. And you've got you, right? Type seven is you will be taken care of. Again, a very independent type. That's just like, nah, I'll take care of myself. No, let us take care of you. We will take care of you. That's seven. And then type eight, you will not be betrayed. And that I think they use an intense word like betrayal because eights are an intense type, but that is what hurt feels like to us sometimes is betrayal. And when we know you will not be betrayed, we show up a lot softer with a lot less armor. And then type nine, last but not least, your presence matters. You have a seat at the table, your opinions, what you want, it matters to us. Your voice matters.
Sara Bybee Fisk 26:19
Those are so beautiful. And I noticed several, you know, that just feel really good to say to myself, even though, you know, I'm kind of in that solid eight area of the Enneagram. So whatever feels like that just soft warm hug, please take those healing sentences and start to say them to yourself. Because that is the beauty of being a human is that we can't go back and necessarily relive the past. But we can still heal the things that hurt from the past by showing up as the beautiful wise adult today for ourselves that we needed back then. Wendy, I have loved this discussion with you. So glad I got a good grade on my assignment. You didn't know I took on from myself. If people want to find you find out more about the Enneagram work with you, where should they go to do that?
Wendy Montgomery 27:18
Well, my website is wendymontgomery.com. You can find me on any social media platform. I'm probably the most active on Instagram, where it is wendymontcoach. On Facebook, I'm wendymontgomerycoaching. On a lot of the social platforms, you can find me there. So I love this too, Sara. This was awesome. Thanks for having me on.
Sara Bybee Fisk 27:40
Absolutely. All those will be linked in the show notes and Wendy, thank you so much for your time.
