Fearlessly Facing Fifty And Beyond

EP209: Breaking Free from the Need to Please: A Conversation with Amy Wilson

• Amy Schmidt • Season 3 • Episode 208

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The silences that follow our "no" speak volumes. As women, we've mastered saying the word itself, but it's what happens after—that uncomfortable pause—where we often surrender our power.

In this eye-opening conversation, author Amy Wilson discusses her new book "Happy to Help: Adventures of a People Pleaser," revealing how deeply ingrained the people-pleasing tendency becomes in women's lives. When Amy tells us that people-pleasing is "putting other people's wants and needs before your own," she's describing the unspoken assignment given to every mother, every woman. Yet this societal expectation exacts a serious toll, from strained relationships to physical illness.

What makes this discussion particularly powerful is Wilson's ability to distinguish between life's unavoidable challenges and the optional burdens we assume. "When you've got a sick parent and a sick kid at the same time, you're not a people pleaser—you're just somebody with too much on your plate," she notes, helping listeners separate necessary responsibilities from those taken on purely out of obligation or need for external validation.

The conversation explores "socially prescribed perfectionism"—the researched phenomenon where women internalize impossibly high societal standards—and offers refreshing perspectives on female friendships, writing discipline, and self-compassion. Wilson's advice to her younger self resonates deeply: "When hard times come, they're hard because they're hard, not because there's anything wrong with you."

Whether you identify as a people pleaser or simply find yourself perpetually overwhelmed, this episode provides both validation and practical wisdom for reclaiming your boundaries without sacrificing meaningful connections. Listen now for a transformative conversation that might just change how you respond the next time someone asks for "just one more thing."


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Speaker 1:

Hey, fearless friends, it's Amy Schmidt and back with another fabulous episode as we fearlessly face another one of these F-words this could be fearlessly facing our future, our friends, all sorts of different things we're going to cover in this episode, but I'm so happy just to be back on the air doing this and this is my third interview of today. Actually, I usually try to batch about three every time I'm in the studio and there is so much great energy today and I know that this interview with Amy Wilson is not going to disappoint. That energy level is going to be right there. Amy is an amazing author of a book that was released on January 7th, so not too long ago.

Speaker 1:

Happy to Help Adventures of a People Pleaser. Okay, right there, that's like a mic drop People Pleaser, amy. If you know, you know. It should say at the bottom If you know, you know. Oh my gosh, I just think this is amazing and I've been watching you and following you and, of course, this is being published out of Zivi Books and I'm a big fan of Zivi, I know Zivi and so proud of what she does and continues to do and so happy you're part of that group, me too, me too.

Speaker 2:

Thanks for having me, amy.

Speaker 1:

Absolutely. So let's dig into this because you know, fearlessly, facing 50 and Beyond, I certainly, when I launched this back before I turned 50, a lot of people have said you know, amy, how do you do it all, how do you continue to do this, how do you keep your momentum? I mean, do you feel like you just have to keep up, like you have to please everybody? I get asked that sometimes.

Speaker 2:

Yeah, and I like doing a lot. I like getting a lot done. I think I draw a lot of identity from that and sometimes I think, when we use the term people pleaser, which I think tends to be pretty pejorative, we think of somebody who is so busy wondering if everybody's mad at her, she can't get out of her own way, she can't get out of the starting blocks at all, and I think, well, I have a lot to say about it. But I think that there's a lot of women like you and me and a lot of us who get a lot done, who are quite capable and yet who are hampered by these feelings like we need to be doing more, no matter how much we do, these feelings like we need to be doing more, no matter how much we do.

Speaker 1:

You know, it's funny that you say that. I wrote a part in my book years ago that I talked about. There was a good friend of mine who was living in Connecticut at the time and she, you know, I had three kids and a husband that traveled about three or four nights a week every week, and I was PTA president. I was doing all the things, doing all the things like so many of us do. And my good friend said to me I drove a Honda Odyssey at the time and she said Aime, every time I go past your house, you're never home, You're always doing something, You're always busy. And I had a moment when I really thought about that, because that was one of my dear friends, and I thought you know, am I just filling this circle with like endless stuff? Because if I actually was silent and still with myself, would I like myself?

Speaker 2:

You know it's an interesting transition as you face 50 and beyond that. Those things I think you can keep very busy when your kids are younger, school-aged with saying yes to the things that are asked of you. Our school systems still run on the presumption that moms have tons of time that they will dedicate, for free, to everything. That's the way America runs its school systems and so we do and I wanted to. I loved it. I was there gluing the beards on at the Christmas pageant. I was there cheering on the sidelines of the soccer games. I mean I did it all, I showed up for all those things and it's not that I didn't enjoy them, but I think in my case I took those assignments and didn't work to build the friendships or the relationships while I was there or I wasn't doing sort of work that would help those things keep going.

Speaker 2:

When your kid doesn't take ballet anymore and you miss seeing those moms you used to see at ballet, drop off, it's work to keep those relationships going and I realized first because of the pandemic and then as my kids left the age of being an age when they needed me around that I couldn't depend on that to have a life that was fulfilling and full of friends.

Speaker 1:

You know there's a part here that when I was reading a little bit about you, it said you know, being a people pleaser, and always being a people pleaser, took a toll on your health. Let's talk about that.

Speaker 2:

Well, yeah, I mean, I think being a people pleaser. The most basic definition of it is putting other people's wants and needs before your own, which I think is the assignment for every parent, certainly any mother, Every mother has put somebody else's wants and needs before her own. I think from a young age, we're told to do that. So we're just following the assignment, some of us more assiduously than others, and it does catch up with you because there's not enough room for you. So in my case, I still don't know if this is because I was a people pleaser or because I got an early version of COVID, but I developed an autoimmune disease and the doctor asked me have you been through anything stressful? And this was in 2021, after 18 months at home, with everybody you know, incessant, three meals a day, Zoom, school. And I said, yes, yes, I have been under something stressful.

Speaker 2:

And the doctor said, not that, I mean something like a car accident, something really stressful. And I got really angry because I thought what does this guy know? This counts. The pandemic was that stressful for me. And then I thought, well, one he doesn't know. And two, it wasn't just the pandemic that I had been living at this high level of stress for a long, long time and so that autoimmune disease which was being put back on me that you've caused this by being too stressed all the time to think like, okay, I have been pretty stressed, but when were the times I had a choice about that and when were the times I didn't like 18 months?

Speaker 1:

of a pandemic Right?

Speaker 2:

Wow, we don't always have a choice. Being people pleaser is what we were told to do, and then, when we're overwhelmed that that label is fed back to us as proof of our own insufficiency, and I don't think it's sufficient, I don't think it's really a fix, and I think chasing what's wrong with me instead of demanding the changes in the situations around us is never going to get us where we need to be, and the situations around us is never going to get us where we need to be.

Speaker 1:

Right, right, you know I talk about it as well. I mean, a lot of people have said this. This is nothing I made up, but talk to yourself as you do. Your best friend, I like to say, you know, treat yourself as a guest of honor.

Speaker 2:

How many?

Speaker 1:

times do we welcome guests in our home, we treat them with kindness, we treat them with love, patience, all those things, and we don't do it for ourselves. That's right.

Speaker 2:

That's right. I mean what I want when I express that I need help or I'm overwhelmed. I think what I want more than anything is for somebody to say to me I get it, you're handling a lot, this is nuts. I see how much you're doing Right, and then maybe let me help you, let me take this one thing off your plate, but you want recognition that, objectively, you are handling a lot, and I think that women we, I think, know to do that for each other and I would be that friend. You're right, I would offer that support, have offered that support to friends who are going through some real tumble dryer sort of times. But when it's you yourself, you think what's wrong with me? Why am I not doing this better, faster, more happily?

Speaker 1:

Well, you said the four-letter word in there. It doesn't start with an F, but it started with an H and that was help. We are kind of raised as women to not ask for help because we look weaker or we're not going to get there as fast, because if I do it and I'm in control of it, I'm going to get there further faster, I'm going to take care of all of it. So we don't ask for help enough. Don't you think that's a part of if you're a people pleaser, you're not asking for help.

Speaker 2:

Yes, when you take on more than your share, traditionally you do it because people keep telling you you're so good at it that they don't know how you do it, and you think that their faith in you has to mean something. I'm not sure I really can take on this other task, but everybody else seems to think so. Everybody else seems to think it can only be me, and so that's got to be a vote of confidence that I can't let them down by not doing it Right. And so I think then you do get tricked into over delivering time and again.

Speaker 1:

Yes, exactly, I love the way you say. No is a complete sentence. I love that. That should be everybody listening and watching right now. Write that down, put it somewhere, because it's a complete sentence.

Speaker 2:

Yes, but I'm going to say yes, but to that because no is a complete sentence, I think, is also kind of incomplete advice, because I know how to say no and stop. I know I know how to do that part. What has stopped me in the past is that when you set a boundary, when you haven't done it in the past, when you say no in that complete sentence, when you've never done that before, the people that you're with, the group that you're in, their first reaction is going to be silence, is going to be confusion, not even resistance, necessarily. Just what? What did she just say? Is something new happening? And the people around you? There's a hard reboot of everybody else's systems.

Speaker 2:

And the mistake I make is not that no isn't a complete sentence, but in the silence that follows, that no, to not start talking again, to not start a new sentence which includes well, let me just do it for six more months. Well, maybe I could be the vice chair. I guess I can stay until you find somebody else. Right, All of those things. You take back what you just handed over. So I think that is what people are trying to say when they say no is a complete sentence. Stop there, but it's like stop there and don't pick it back up.

Speaker 1:

Wow, that's a practice right there. I think we all could incorporate.

Speaker 2:

That is powerful yeah.

Speaker 1:

No, and then pause.

Speaker 2:

Right, and the pause. The pause is the point, right. It's not what goes in that sentence. It's that the pause that comes after the sentence.

Speaker 1:

Yes, totally Well. You think of standing in line at Starbucks and you're looking around and all of a sudden somebody comes up and is like we're both named Amy here, but I'll use it for both of us. And all of a sudden somebody comes up and is like you know, we're both named Amy here, but I'll use it for both of us. But Amy, oh, how are you doing? And your first inclination is oh, I'm good, I'm so busy. I'm so busy Because we wear this badge of busyness as like a badge of honor.

Speaker 2:

Yes, yes, well, I mean, we do work hard, we do do a lot. We should be proud of that, we should get recognition for that. But again, I think that you take on everybody thinks I'm so good at doing so much that that must be something I have to keep doing, I have to keep leaning into that, instead of saying I have enough right now and again. I think it's about teasing out the differences. When you've got a sick parent and a sick kid at the same time, you're not a people.

Speaker 2:

pleaser, you're just somebody with too much on your plate, right, and I think sometimes we tend to apply the same advice to those times that are optional and to those times that aren't optional, and that's when it gets really frustrating to get back. You know sort of hallmark card. You have to believe in you responses instead of assistance.

Speaker 1:

Yes, exactly, let's talk about fearlessly facing another F word here, which is family and being a member. Most of us in our 50s, a lot of us, are part of that sandwich generation caring for kids, caring for parents, and that's tough right.

Speaker 2:

Caring for kids, caring for parents, and I think then you just have to give yourself compassion that you really are doing your best, that you're meeting everything the best you can. And some balls are going to fall, some plates are, going to crash, that's okay. That's okay. Nobody's expecting you to do it perfectly, even if it feels like they are, and sometimes you have to let some things crash.

Speaker 1:

Boy, that's so hard and I bet people listening and watching are going oh, but that's so hard. Like did you just say to? And I usually am a really attentive listener. But I think you said and doing a lot of things and some of them not well Right.

Speaker 2:

Right Because you beat yourself up like oh, I didn't get to.

Speaker 1:

I love that. You said that Right. That's pure transparency and truth and honesty, and I'm right there with you. Yeah, we're doing a ton of stuff, but we can't do it all well.

Speaker 2:

You can't do it all well, and then you're beating yourself up that you're not doing it all well, right, and you just get stuck there. I've just spent a lot of time grinding my gears in those moments, I think, beating myself up for the thing that I'm not getting right, when nobody could get it all right, and you just have to give yourself grace and, like you said before, amy, I could definitely reflect that back to a friend of mine that was going through those same things. But it's harder to give it to yourself.

Speaker 1:

Yeah, yeah, it really is. Let's talk about friends, because I think these things change as we get older, for sure. Right, I mean relationships change. I mean I just had this delightful young woman on the show who's in her 30s and I talk a lot about opening your circle to a horseshoe and allowing other people to come in and they evolve and change. But you know, so many of our generation is trying to keep up with everybody else just trying to do it all. How do you see your relationships changing as you age?

Speaker 2:

And then I feel dorky about making it a priority Like, oh my gosh, do you really have to spreadsheet your friendships which I don. Let those female friendships, like I said before, be sort of carried along on the tides of whatever my kid had going on or my spouse to show up in those places and talk and make friends. But when those times in our lives, when those ages of our kids go away, part of being the empty nester, I think, is you don't go back to the high school anymore. There's no reason for you to walk in, even if you were there three times a week and building ahead of time what that is going to look like, a framework where female friendships are at the center of my life. My grandmother had a group of friends. She played cards with them every month for like 65 years until they all died.

Speaker 1:

Wow, how cool is that.

Speaker 2:

Isn't that cool. And when I was a child watching it and my grandmother lived with us, so once in a while I'd be like grandma's club is here today. You have to go say hello. And they'd be, you know, their card tables would be set up and they'd be having cake. And they just seemed like old ladies playing cards to me. And when I look back now I realize no, these were women who held those friendships at the center of their lives. Those friendships outlasted their marriages, everything else. And I look back, I treasure that now.

Speaker 2:

I honor that in a way that I didn't when I was younger.

Speaker 1:

Yeah, it's so true. I have a thing with my friends Do you have five minutes? And when you get a text and it says do you have five minutes, it's like pick up the phone, call that person. They need you. They need you right now, oh my gosh, I love that yeah. Yeah, do you have five minutes and everybody knows in my circle of people when you need that, or I may get a text from somebody that says hey, I think you need five minutes. I've got five minutes for you. Five minutes, all you need.

Speaker 2:

Wow, and what a gift that is to be that person and to be seen that way. Like you, seem like you need some help from your friend.

Speaker 1:

Yes, yeah, to be seen and show up. So let's talk about Happy to Help. Adventures of a People. Pleaser, take me to the moment when you knew that this was your next book, that this is something you had to write.

Speaker 2:

Well, it's a funny story because the original thing I was sort of working with Zibi Owens and I talked about ideas for what this book would be, because I'd written another book of funny essays and she said, okay, do a second book and maybe it could be something about slack that the times that you have to pick up the slack for other people, you give other people slack, you give yourself slack, you have to pick up the slack. Okay, so I was whiteboarding with those ideas as a starting place and the one column times when I needed to pick up the slack because I hadn't worked hard enough or put in enough effort, I couldn't think of anything to go in that column, right. But there was this other column in my head. I was just going to say hmm.

Speaker 2:

However, there have been 1100 times that I have over-delivered, stayed too long right, tried to make the boy love me or the boss appreciate me, thankless enterprises where I went down with the ship. That column is full of stories and then I thought, okay, so that's what I'm going to write about, and that's how the book sort of came to be.

Speaker 1:

I love it. I love it For somebody wanting to write a book or thinking about writing a book, or not even writing a writing about just thinking about starting something. You really have to commit to it, right? I mean, it's a full time job. I always say that when I wrote my book, I had to commit every day to writing something. I had to show up.

Speaker 2:

I find the same thing if you, because if you take two, three, four days off, then when you sit down to write again, the OK. So wait, where was I? And rereading what you already wrote takes the whole time up. You need to be touching it every day and to do that, I had to be ruthless. I got up, I did it.

Speaker 2:

I wrote the first draft of this book, which is sort of the hardest part to make something out of nothing. I did that in about 10 months and it was every, every day, except for Thanksgiving and Christmas. Every single day I got up and I worked from 6am to 8am, no matter what, because that was before my family was up and at them and I could hide, um, and I was lucky to have that time. But I stopped exercising, I stopped having lunch with friends. You know, I cut the fat from my own life in order to write this book and still have time to show up as as a mother and a partner and a professional partner and all those other things. So I really, you know, no baths for me for 10 months, no massages or walks outside, but I got the book done.

Speaker 1:

Yeah, and so I don't know if it's a good trade-off, but that's the trade-off I made.

Speaker 1:

That's the trade-off. I remember, and I know I've shared this on other episodes, but you know, my husband traveled about three, four nights a week and I was in the midst of writing and my son, I think, might have been a junior in high school and he, literally, I would get up too early in the morning and that's when I do my best work, to be honest. So before the sun rises, sipping my coffee, writing, and then my son leaves for school, and then, I think, he came home after soccer practice and hadn't moved Like I had not moved. I hadn't moved Like I had not moved, I hadn't eaten, I hadn't hydrated enough. I mean, you know, now we're hearing I mean, how much water can we possibly drink in a day?

Speaker 1:

But, you know, I mean it's hydrating. I didn't do any of that and and that was the the no-transcript, but still commit to it. But uh, you know it's. You have to give yourself grace once in a while.

Speaker 2:

It's a weird balance, cause it's putting yourself first to do this thing that's very important to you. In my case, like, okay, I have a contract, I'm going to fulfill this contract, but in order to like, put that first, it means putting the things that bring you joy at least for me very much aside for a while. And then I had catch up to do in my friendships and my relationship with my spouse and everything else Like, okay, I have neglected all of this I need a haircut.

Speaker 2:

I need a haircut, I need a date night. I really need to go back to all those things and I wouldn't change it, but I just want to underline that, like it isn't as easy as like 20 minutes a day. It was something I had to give a lot of effort to Right.

Speaker 1:

I want to ask you something and I hope I can articulate this properly. But you know there's a whole lot of there's a big spotlight on women over 50 right now. There really is. I mean, I'm, you know, I'm in the middle of that. I'm 55, just about 55. You know, there's a lot of hype, a lot of encouragement, and I love it and I live for that stuff because that that's what I do. I encourage women just to be their best self. At the same time, some women, I think and this is my own opinion are feeling almost like it's walking the middle school hallways again and they want to write a book or they want to start exercising, they want to start something, they want to rekindle friendships or whatever, and they just can't because they're so intimidated that they're not going to do it well enough. Yeah, have you heard what I'm saying?

Speaker 2:

Yes, there's something called socially prescribed perfectionism. Have you heard of this? I learned about this.

Speaker 1:

I have not Say it again, say it again. I have to close my eyes because I have to picture it.

Speaker 2:

Socially prescribed perfectionism. So, um, uh, he would. He would inflate. They are the um two, the two foremost sort of psychologists who talk about perfectionism, and they first started talking about it in the nineties and then they really underlined it in a study in 2022.

Speaker 2:

So self-oriented is like my bangs aren't perfect and I have to start over and I'm going to be late for work. I mean stereotype, stereotype, but that's what it is. Others-oriented is you know, sit up straight and you know the Christmas lights don't look right. That's others-oriented. And then there's socially prescribed, which is a belief that the people and the systems around you are holding you to excessively high expectations that you can't meet. And when they first studied it in the 1990s, they were like, isn't that sad that some people, usually women, think that society is holding them to excessively high standards? Clearly they're not. And so these people and I thought, wait a minute, but it is.

Speaker 2:

So there's been a change and now, in 2022, those same psychologists studied again and said this is a thing, this is a. You know, this is like a public health issue that needs to be studied that socially prescribed perfectionism puts way too much pressure on people, and the people it puts pressure on is women, that you have to Women. You can be vital at 55, as long as you look like you're 35, right, that you have to women. You can be vital at 55, as long as you look like you're 35. Right, I mean, it's the. The expectations are so high and they're not just coming from inside the house, they are imposed on us and so I think, sort of recognizing that is a big, a big thing to be like. Yeah, a lot is expected of me and I'm not imagining it. So what am I going to accept and what am I going to reject?

Speaker 1:

Exactly. Wow, I just learned something new, see. That's why I love doing this. One thing I read about you is that doing your podcast actually kind of helped you or informed you to kind of write this book.

Speaker 2:

Yes, right. So I've been doing a podcast called what Fresh Hell, laughing in the Face of Motherhood. It's been around since 2016. My co-host, margaret Ables, and I we've done 800 episodes, and 400 just us and a couple hundred more with guests and experts and we've always pushed back. We've always tried from the very beginning that every episode is funny and a fun listen, but also has useful takeaways you can actually use.

Speaker 2:

And that, no matter what, the takeaway isn't yeah, mom, stop being like that, mom which I think we get a lot in society right that we both hover over our children incessantly and all we do is look at our phones because we're selfish parents, like, well, we can't be both at one time. Well, according to society, we are both right Two self-involved and two hovering. We're both Okay. So we really try. We're like that's not useful, that's not anything I can act upon. Let's give actionable, useful advice. So I really tried in this book. I came at it from that point of view. It should be a really funny, easy read that also walks you towards some wow, I never thought of it that way ideas that you can actually apply to your life.

Speaker 1:

Yeah, yeah, isn't it amazing? Every podcast I do, when I step away from the mic I always just take a moment just to exhale and just be like, wow, I just learned something. I love it I learn so much from my conversations, from my guests, from being present, from actually listening. Yeah, it's crazy cool.

Speaker 2:

I was just saying to my co-host yesterday that it really is. In a world where we always have our phone and we're always half paying attention, recording a podcast is one of the most concentrated activities that I do, besides writing, sitting and having a conversation like this. It is the most attention I pay to almost anything, and I'm glad I get to do it because I learned so much too.

Speaker 1:

I do. I learned so much, so I'm going to link everything your podcast, your book, all of that and I know we're giving away a copy too, yes, which is so cool. Thank you for that. Yeah, I just. This book is going to resonate with so many people. It's like the what to expect when you're expecting what to expect, the toddler years, all those years, but right now, as people pleasers, and mainly women, they're going to love this book and I love. I can't wait for your next book. Do you have another, one kind of, in the plan?

Speaker 2:

I have an idea. Yes, it's on a very low simmer, on a back burner, and as soon as the sort of as soon as the blitz of publicity that I'm doing for this is over, I'm going to get back in the chair and start on the next one.

Speaker 1:

Yeah, I love it, I love it. Writing for me is very therapeutic. It is just something I love to do too, and whether it's a book or whatever and that's why I encourage anybody I always say tell your story. You hold the pen to your autobiography, write it, edit it. It never has to be published, but tell your stories and write them if you want to.

Speaker 2:

It's so true.

Speaker 1:

It's so important.

Speaker 2:

You learn so much about yourself. I'm definitely a different person for having written this book. I learned so much about myself. Writing this book and being published is gravy. You're right. I still would have learned all those lessons.

Speaker 1:

Exactly. So, before we close today, I'm going to ask you a question. I ask everybody, and that is Amy if you were sitting on the couch and you looked over, and there you are, at 30, what advice would you give her?

Speaker 2:

When you have hard times in life and they're coming those times are going to be hard because they're hard, not because there's anything wrong with you. So just believe in yourself and do your best and don't worry about fixing yourself before you fix the situation.

Speaker 1:

Oh, I like that. I wish I had a little mic drop that I could. That's a good one.

Speaker 2:

I wish I could have heard that young me and maybe also that some things can't be fixed and it's time to head out. I wish I learned that at a younger age.

Speaker 1:

Thanks so much, Amy, for your time today. Everybody go out and buy a copy. You can buy it anywhere, right?

Speaker 2:

Anywhere and books are sold. You have to search. Happy to Help.

Speaker 1:

Happy to Help Adventures of a People. Pleaser Amy, thanks so much. Look forward to connecting again.