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Breaking Free From People-Pleasing and Expectation With Jennifer Sherwood


Are you saying yes when you don’t want to? Feeling irritable, overwhelmed, or stuck? Have you ever stopped to wonder WHY - beyond the obvious stuff going on around you. What’s really driving how you feel?

Our host Jen Sherwood gets in the hot seat and shares her should story. From wanting to fit in, to the pressures of early career and motherhood. So much of Jen’s driver was fear of judgment and not doing everything exactly right. She was incredibly mean to herself until she got sick and tired of being sick and tired and had to make a change. Life is so much better now.

That’s why she’s so passionate about exposing the lies of the should and sharing these stories. Jen hopes other women will hear themselves in these stories and realize they’re not alone AND they’re not stuck.


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Welcome to the I Don’t Give a Should Show – a podcast exploring ALL the ways that women SHOULD all over themselves. How many times do you find yourself acting out of obligation or doing what everyone ELSE expects from you without stopping to consider why? Where do all those beliefs that are driving you come from? If you’re tired of feeling resentful, overwhelmed, stuck, exhausted or pissed off you’re in the right place.

Shoulding all over yourself is a real thing, but it doesn’t have to be in the driver’s seat.

I’m your host Jen Sherwood, and I spent waaaaay too many years trying to prove that I was good enough and worrying what other people thought while avoiding conflict at all costs. Today, I don’t give a should – well not as many anyway and neither should you. I’m talking to women like you who figured out how to stop shoulding and start LIVING.


Hi, Jen!

Hi - hello to your listeners, it's so interesting to do it this way. I love this whole paradigm of interviewing the interviewer to help her audience get to know her a little bit.

So before we get started, my name is Jen Liddy. I am a content and copy strategist - I help women who want to get their ideas about their marketing out of their head and into the world and clean up so people can see them. The reason that Jen and I are talking today is because she has so much experience and we want to pull it out of her head and share it with you.

So thanks for being here today and here we go.


Before you jump in, I just want to say you know your introduction of yourself to anybody listening? Jen is amazing at what she does - we are friends, but I have worked with her as well.

So I just want to give you that little, little plug before we jump in.


So Jen, when you and I started working together, you were and still are a life coach. But one of the things you were really struggling with is what's my way into working with people? Who am I as a life coach, which I think is something a lot of life coaches struggle with?

And very quickly, we kind of learned this idea of people shoulding all over themselves, and having these ideas about what they should do or have to do or are obligated to do.

I'm wondering, before we dive into your story, how did it feel for you to identify that little, like that little crack in the door where you saw the possibility for the road? You could be on in terms of your own messaging and purpose?


Oh, I have no, I don't think I've really ever thought about that before. I think it felt like just a pull in the right direction because I understand this.

This coming from expectation, this really worrying about what people think because that doesn't change between your personal life and your professional life. If you're somebody who worries about what people think of you in general, then you're going to worry about what they think about your product, or how you said something in a promotional video or the way you present yourself.

I mean, it's universal how we do one thing is how we do everything so when I could see that it just felt like the right way to go because it's such a painful way to live.

That's what I'm really drawn to is helping women who feel this way about themselves have a different approach and have a different experience.

It was helpful, and it just really felt like the right way to go.


Yeah, and it was almost like you were able because I was there for I witnessed it.

It was almost like you were able to put a label on it, and almost like put it on a shelf and be able to take it down and examine it and like it, you can see how it's how shoulding seeps into everything and then I think you also could see how it was everywhere around you with the people and the like, it was outside of yourself.


Oh, yeah, yeah, it's interesting how you said, you know, you've kind of labeled it and I've actually been doing a lot more of that in my coaching recently, I'm really helping people, women to take sort of these overarching stresses, like overwhelm and anxiety.

Let's break this down a little bit further, because it is too much when you're like, I'm just overwhelmed, because then you can't get out of it and so taking my client and sort of breaking it down to like, Oh, here's what it's feels like when you're shoulding on yourself and then you know other various things, but that should, like you said like it's it's almost this bucket, it's this category of things that we do to ourselves and identifying it helps us to be able to move through it.

That's what it's like for me is looking at that particular behavior, how it impacts their lives and how do we shift that because then when we do the outcome is so good.


So I want to take you back to a place before you really identified that you were shoulding a place far before you even knew you could do anything about the shoulding, right?

What was that like for you? What was your life like?


You know, it's like I said to you before we started.

I've been not really trying to think about this because I want to be very organic.

This is the one place that I did think about, like, how long have I been shoulding on myself?

It's my whole life and if you think back, I mean, I'm not that different from everybody else. But when we're young we really want to fit in and that's a lot of shoulding like, you know, and I think there were some things in my background that really, again, not unlike other people that really took a hit my self esteem took a lot of hit, there were some bullying, there was some things that just left me really craving, fitting in and feeling validated and feeling good enough and I really think that's where the shoulds originated for me.

Just like I was thinking today, Jen, you and I are 80’s kids, you know, we really are in school and man, you know, I just wanted the Jordache jeans.


Oh my God, why wouldn't my mother buy me Jordache jeans?



They were the shit, youngsters, if you're listening Jordache jeans were the shit in the 80’s. I just thought if I could just have the Jordache jeans that I would fit in and people would like me, you know, it's that same process and so that was like, really through all my schooling and college and what were the shoulding really, like?

I think that's kind of what happened or, you know, broke my awareness. I don't know what you call it. I've had enough.

I'd had enough of motherhood (pause for laughter), you know, when I had my kids, I had two girls and it was just this tight.

You hear people talking about motherhood, they're like, oh, motherhood, and I just went off, it was the same but I was so buried under should’s and perfectionism - I didn't know it at the time. But like, I just wanted to be so good at everything and all of that was like trying to look like I had it together trying to make people see me a certain way, because I felt pretty damn inadequate at every turn.

I've got two kids - I'm in my professional career at this point And I just don't, I feel like I'm dropping the ball everywhere. And I'm worried that somebody's going to figure it out - I don't know what I'm doing anywhere, anywhere in my life And that it wasn't just limited to, you know, we hear the term imposter syndrome. Often that's about work and man did I have impostor syndrome at work and it's just ironic.

This is just how impostor syndrome is but I'd been in my career, I was a pediatric audiologist with clinical experience and then I was in a big state program where I was doing consulting, and I've been in that role for years. I still felt like somebody is going to figure it out that I don't know what I'm doing.

I have a freaking master's degree in audiology, and I'm still like, somebody's gonna figure it out. Then you go into this motherhood thing where I don't have a master's degree, and I don't have years of experience. I'm trying to figure out what the hell I'm doing. Everybody around me seems like they know what they're doing - their kids are sleeping through the night and like, I just couldn't win in any arena.


And what did you do at that point?

You have this awareness and the heaviness got so heavy that like you couldn't, there was no escaping it?

Because now it's not just like, I'm in - I'm in should survival for myself would be fine. I can't do the Jordache jeans.

Okay, fine, I'll do something else - like, yeah, you get to parenthood and now you've got people who require your attention all the time. You're just so like, they're like, sucking the life out of you and then it's like, you can't figure it out on your own anymore.

So you had this like, awareness smack you in the face? What did you do at that point?


Yeah, so the sucking the life right out of you.

I don't want to gloss over that - I really want to stop for a second because if anybody is listening, and they really feel stuck, and they just feel like, this is good as it gets. That's where I was and I want to be really clear about this. I had the life I had dreamed up, I have a great husband.

I have two healthy kids, we had a home, we had friends like on paper, I should have been really happy and should have been, you should, I should have been really happy but I wasn't. It just kind of happened to where I just think I got sick and tired of being sick and tired and so once I looked, I had no idea that I was the one creating these ideas of what life was supposed to look like. I finally just decided to get some help like this was beyond something I could figure out on my own and so I worked with a therapist, and I think that was really important.

At the same time this was happening I was burning out in my career and audiology is this very narrow topic. I was also at the same time considering, like, what else could I do with the things that I love about my career and then coaching just started talking to me.

I'm seeing a therapist. I'm feeling better in that way, but I feel like I want something to help move me forward into a new career and coaching was kind of speaking to me. So I thought, well, I should hire a coach. And then Jen, she rocked my world. And she was the first person to help me see that it wasn't the circumstances that I was in that was making me feel how I felt. And she was the first person to make me realize that these ideas that I had, that I was trying to live up to, that they were my ideas, I could change that, right? Like, there was this way, that not as a blame, because I want to be clear about that.

I was creating this for myself, I'm the one who was like, this is perfection, this is where I need to be. But I'm never going to reach it, and I'll be miserable. So why do I have to try to reach that, and she really helped me see that critical inner voice, and how that was what was actually sucking the joy out of my life, not motherhood.


As these it's an interesting confluence of both the external world and the internal world, right, like the external world is painted for us, like you should do this, you should do this, you should do this.

This is what a good mother looks like. This is what a good worker looks like. This is what a good partner looks like. And there's all of these external things that we take in and then add on to that, what our parents said, what our brownie leaders said, what, you know, our sixth grade teacher said, like all of those things are external. And then they create this internal landscape that starts to rule us.

So we think that it's all this external stuff, which is actually caused by our internal thoughts. But the only way to change any of it is to start from the inside and work your way out.


100% and you don't want to get that until you get it but yes, and that's part of thank you for saying it so succinctly.

That is why I do this podcast because most of us don't realize that we have absorbed this social conditioning, these social ideals, and we think that that's just how it's supposed to be, and don't really think to question it.

Do I really have to have a size six pants and you know, compete with Suzy down the street for all the material things? No, no, but we keep thinking that if I just lose weight, if I have a nicer car, if I have a nicer house, then I'll feel like I'm…fill in the blank.

If we're just chasing these expectations, that society, culture, family, whomever have put on us that is actually stopping, like, do I really care about that?

Do I actually want that, that in my personal experience, and what I see in my clients is when they're chasing those things, without realizing, and you know, when I want to back up, it's not necessarily about the Gucci purse, or whatever, it's really about, like trying to be that ideal of a good mom, or the successful career or I won't feel good about myself until I get this promotion, all that kind of bullshit leaves us feeling exhausted, and resentful, and overwhelmed. I mean, any negative emotion you can think of, there's probably some of this underneath it frustrated, angry.

My hope is that by talking about this and sharing this one, we bring awareness for people who may not see it. And just to, if somebody else out there feels this way, it just might give them a moment to go, Oh, my God, maybe it's maybe I'm okay.

Because I really felt like I wasn't okay, that sort of, internalizing all that stuff that you were talking about was external, really made me feel constantly like I was not okay, I was not good enough. And I lived with that for a really, really long time. That's such bullshit and we waste so much time and energy on that - that's why I do this.


You know, what I think happens is in the life coaching world, no, I'm not a life coach. But in life coaching slash personal development, slash self help, whatever you want to call it world, you get surrounded by people who are doing this mindset work or who doing self care work or whatever.

You forget in your bubble, that there are people out there who haven't done this work yet, right? So you, you become desensitized that like, Oh, everybody knows about inner critic, everybody knows about the shoulds, but it goes the other way too. If you're surrounded by people who complain, who bitch and moan about everything, if you're surrounded by people who are unhappy and toxic and negative, that becomes your norm too.

It might be like, I've heard about this personal development stuff I've heard about everything she's talking about, this is not news to me. But if you're only surrounded by everybody in your house, in your family, in your work, in your community, who you take in online, and it's not that it's not helpful, it's negative, it's harmful, that becomes your norm.

Peeling back the layers is a really scary thing, because it's very possible and I'm sure you experienced this when you started examining your own should’s. Oh my god, what if I stopped thinking that I should do that? What if I stopped thinking I have to do this? What if I stopped doing this thing? Who is it going to piss off? Who is? And will it make the negative people even more negative? Right?

I think you were, I'm curious about when you started to have these ahas. And you started to see, okay, my therapist is helping me, my coach has helped me, how did it actually make your life better? Because it's very scary before you dip your toe into this world, that you might be messing with everybody and screwing everything up?


This is so good.

I'm so glad this is the direction you went – and if I forget to answer your question, remind me. But literally, just yesterday, I was working with a client. We were talking about her creating more boundaries between her and her young adult children so that she has more time. And her question to me was, well, what happens to relationships? If I close my office door? And my answer was, you know, everybody's different, right? But you know, you close your office door, and you make time for yourself, like your kids will figure it out.

Her kids are young adults, they will, but this is a genuine question. I mean, she really was concerned about this. For me, when this started happening, before I was aware of what I was doing, I would worry. And when I worry, I spill that out onto my husband in particular. And I have these like circular conversations about what I should do and what I shouldn't do.

What do you think about this? What do you think that person thought? What do you think about this? So there was a lot of external processing on things. I remember coming home from events or parties, or even just timeout with friends. There were not every night, but there would be nights where I couldn't sleep, thinking about what stupid thing I did, or what stupid thing I said, or like, there was a lot of ruminating.

The relationships that mattered the most to me have benefited exponentially from me doing self development work. I think I show up in my life calmer. I am funny since our conversation was off air, but I am more decisive. And I don't have to go through with everybody around me like and why do you think this meant and and I was hiding a lot too from the people who knew me except, like, my husband, and my kids saw the real me. And so I think they get a much more real version of me now. And it's actually been good. And the people who potentially would be like pushback who want me to stay up, people-pleaser, who want me to do better, they've either just come around, or I don't have them in my life anymore.


It's really hard to believe that you could get to a point where this person who's so important to you and whose opinion matters to you that their opinion won't matter anymore. But it really does happen that way. This has been my case so I didn't start my personal development journey until my 40s.

I was disappointed putting air quotes around a lot of people because I was no longer available for their crap and I don't miss any of it.


Oh, hallelujah - I am with you!

It's so funny, if you ask me, I remember asking one of my kids what it was like, and I wish I could remember exactly what she said. But she just said, Oh, I think I know what it was. Wasn't I apologizing for like, Oh, I wish I could have done it better. And she's like, No, it's so good. Now and then I think my girls learned a lot from watching me decide to stop doing this to stop over giving to stop people pleasing to stop worrying so much about the benefit to my family. I can't even put it into words, I actually should ask them because it was hard when I was always worried and it spilled out on them. One thing I do want to say quickly before I forget, though, is you were saying, you know, people kind of worked out for you, like there became that point where you weren't so worried about their approval.

I would also say I think there is a ripple effect when you start to change yourself dynamics change as well and so it may be hard to believe. But as I changed things, my husband's communication to me came back differently.

That was happening out in the world too and so it is scary, but the potential of what you get on the other side of it is so worth it.

I do not feel like the joy has been sucked out of my life for years.


Right? Right. Right.

It really is about taking that leap.

I feel like that's what you want people to know about - why you're doing this podcast is it can be a scary journey. You might you might be worried you're gonna screw it up, especially if you perfection and people pleasing in your background and that's part of the shoulds but you can't you can't know what's ahead of you I can't think of one person that I know, who has started to put boundaries in place and stopped shutting, whose life has gotten worse. I can't think of one person.


No, I totally agree.

I can't remember what you just said that you reminded me of, you know, when you're in that position, when you're stressed, it's very isolating, because nobody wants to talk about well, I don't have my shit together and, and those Oh, I know what it was. The fears of like, what you're going to screw up, like, the fear that you're going to really fuck up your kids or screw up your marriage or those sort of things and it's very, very isolating.

So hopefully hearing this makes somebody realize you're not alone- you're not a weirdo!

This is so much more common than you realize impostor syndrome is everywhere. Shoulding on yourself is just, it's just what happens. You know, it's interesting from this book called Radical awakening, this psychotherapist, I think she is Dr. Shefali says, women are taught to crave the need for validation, approval and praise.

So of course, we're out there trying to do what is expected of us, because that's what we're looking for. And the shift here is to start bringing your validation from within not from without,


Yeah, what do you think if people and I know you're going to explore this as you have your interviews on your podcast, but how have you seen your clients' lives get better when they start to make that shift?


Oh, yeah, this is the privilege of the work that I do.

It's in small ways. It's like, you know, better communication with their kids. That's actually not small when I say it like that. But I was thinking of one client in particular, who says, I literally saved her marriage, that being able to open up and get into a more vulnerable position and say, what she needs to say to her husband, instead of kind of showing up as the duty dutiful wife, she's no June Cleaver, don't get me wrong, but you know, instead of doing what was expected, and getting really honest, they were able to save their marriage, that was a huge one for me.

Other things I've seen women do start businesses, for sure, I have one client who launched a business and then did a total left turn from a coaching business and now owns a brick and mortar boutique, and is like the happiest person that she used to be in corporate raising new jobs. And that all comes from being able to speak up and stand up. But I think the biggest thing is the relationships. I think what happens to people's relationships, in the improvement, those are the most important things to us, the people that we love, the jobs and all of that are important as well, don't get me wrong, but I think central to all of us, is our connections to the people that we love. That when you do this kind of work, when you start coming from a place of value in yourself, you show up so differently, and you're able to speak up, and maybe it's losing a relationship that wasn't good for you. Or maybe it's improving a relationship that was there or finding, oh my gosh, I have one client who found the love of her life in her 40s after really coming into her own.

I think the improvement in how you feel about yourself, how you talk to yourself, impacts how you show up in the world. And then that all ripples out.


My husband will when we look back on where we were before I started because I started doing self development work. And he just kind of came along for the ride and absorbed it by osmosis - he certainly never did any of this but it has made the entire family better.

More importantly, like I just like myself better because when you are in that perfectionistic people pleasing shutting overwhelmed. No boundaries, terrible communication, overthinking everything. You're so exhausted, and you're like I could have done that better. I could have done that better. I could have done that better and it's like you hate yourself all day long. John, and I always laugh about like, I'll do something now. And I'm like, can you imagine if, like what that would have been like 10 years ago. And he's like, Oh my God, and you never would have done it that way. And so yeah, I think that ultimately you get to like yourself better and more easily and it even if you can't believe that, because you were believing all along, like oh, no, the only way I like myself is I can fit into those size six jeans and I have the Gucci purse and we drive this car and I did all the things and I made the I made the cupcakes right like I did all the things that's that's how I like myself, but I promise you that that's not the way and I think that that's what you want people to know by listening to this podcast.


100% - I think you just nailed that piece about you know, it's not about checking off, right and then your doesn't work that way.

No, you're not going to love your life. It's all about liking yourself and when you'd like yourself. It affects everything.


I always laugh because I think about Whitney Houston songs, like the greatest love of all is loving yourself and Michael Jackson's man in the mirror and you have to love yourself and I'm like, I think neither of those two people actually knew how to do that.

That's why they ended up the way that they did. And we're always told, you should like yourself, you need to like yourself, you need to like yourself, it starts from within, most of us have no idea how to friggin do that.

That's why I think your podcast is so important because it's a way in a way that's realistic and reasonable and no bullshit.

Like, let's talk about it because we needed to sing it like it didn't work for her.


I love that.

And, and as we're wrapping this up, I just want to say kind of going back to that the way that women are taught to crave the need for approval, validation and praise.

There's no way that you can love yourself, if you've been conditioned your whole life to look outside of yourself for this. And so, to tell someone, just love yourself.


I'm doing that. Oh, okay - oh, therapy works, I would just stop doing that.


Yes - and so I love that that's where we're at. It's not that simple. It is possible. It's possible to love yourself, but to just go you know, just love yourself. It's a little more complicated.

Yes. Jen, thank you so much for coming here and helping me share my story.

This was way more fun than sitting in front of a microphone alone, which is why I decided to ask you to be here as my guest helping me out today. Thank you for walking me through this.

3 simple steps laid out in 3 bite-sized videos to go from overwhelm to ease (even if you think it's not possible!)



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