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Setting boundaries when there's too much to do, with Amy Wilson

Published Jan 8, 2025, 8:00 AM

What Fresh Hell co-host Amy Wilson talks about people pleasing, and learning to live with discomfort

Welcome to Before Breakfast, a production of iHeartRadio.

Good Morning, This is Laura. Welcome to the Before Breakfast podcast. Today's episode is going to be a longer one part of the series where I interview fascinating people about how they take their days from great to awesome and any advice they might have for the rest of us. So today I am delighted to welcome Amy Wilson to the show. Amy is the co host of the excellent podcast What Fresh Hell. She is also an actor who's been on many shows, including the TV show Norms. She's appeared on Broadway. She is also the author of a brand new book of essays called Happy to Help Adventures of a People Pleaser. Amy, Welcome to the show.

Thank you, Laura, thank you for having me.

I'm excited to have you on this.

So maybe you could introduce yourself to our listeners. Just a little bit about your life, your work.

Okay, so yeah, I shouted out as a performer and a sketch comedian. As you said, always wrote my own things to perform. Always found that I got farther writing my own material in terms of playing the roles I wanted to play, and once I became a parent, moved into creating content for parenting, did a show called mother Love that toured around the country for a while. Out of that, got my book deal for a book called When Did I Get Like This? That came out in twenty ten, around the same time as your first book. I believe because that's how we first met.

I've been in this business for a very long That's.

Right, we've met. I've been on the road for book promotion, and since then my life took many personal turns that are certainly laid out in the book and started What Fresh Hell in twenty sixteen and found my way back to writing this second book after writing a novel that didn't work. A few different things that are all part of the journey. This book is finally coming out. I'm so excited.

Yeah, and What Fresh Hell? I mean launching in twenty sixteen, that was pretty early in the podcast day, correct it is.

Yeah. Margaret Abeles, my co host, was somebody that I was acquainted with. But really that was it again, like knew each other from the space and she said she took me out to lunch and said, so, I have an idea, what if we did a podcast together? At the time I mean I knew her, I didn't know how many.

Kids she had, how old they were.

People assumed that we were always best friends, and we have certainly become very close friends and work wives. But at the time we didn't know each other that well at all. We just kind of thought the other person was funny and started the podcast on a whim. Let's try this, let's do something fun together. I don't think we could ever have predicted we'd be doing it all these years later. But it's still fun, so we're still doing.

It, still doing it.

Yeah, what people who If you haven't listened to What Fresh Hell, you should everyone who's listening to this podcast. But one of the things that makes it so interesting is Amy and Margaret have slightly different personnel, lightly slightly. Margaret's a bit more of a free form sort of person. I think Amy, you have described yourself as very things, as a type a kind of person as you've used words such as recovering perfectionist. Maybe you can talk about how you came to write this book, Happy to Help Adventures of a People Pleaser, I mean, what it means to discover that one is a people pleaser in life.

Yeah, with me, I mean, I think I am and am not a people pleaser as I've looked into this more, but what I definitely am is an over deliverer. I've actually found a very old episode of the podcast where I said I was a sticker outer, and I'm like, well, that's it.

I wish I thought of that for the cover a sticker outer.

I stick with things. I see things through to a complete fault, and sometimes that is the right thing to do. It's certainly a good trait to have sometimes. But I have definitely stuck with relationships, jobs, you know, ideas that kept me stuck that I just thought, well, it was me and I just have to work harder, and I'm going to make this unfixable situation fixed. And I think that's where I got stuck. And I came up with the idea because I was actually talking to Ziby Owens about writing a book for Ziby Books, who was publishing this book, and she suggested that I sort of engage with the idea of slack in our lives and when we have to pick up the slack, when we have to give ourselves slack, other people slack. So I was sort of whiteboarding that out and the column that had nothing in it was times that I had to pick up the slack that I hadn't worked hard enough. And the longer that column stayed empty, the more I realized, Oh, that's what's the book is about that. I don't know. I don't know how to not give it my all, even when it was a terrible idea to do that.

Yeah, and so I know a lot of us are juggling many things in life as you are, you know, work, family, home, etc. I mean, one of the things you've written about is that a lot of the sort of traditional productivity advice like say no right, just say no more often isn't particularly helpful maybe for people who are.

Committed to seeing things through and all that.

Maybe you could talk a little bit about why is this productivity advice unhelpful?

Well, I think it's from the point of view of people who aren't the people ask in the first place. You know, Like people were like, just say no, there's a complete sentence, and like nobody ever asked me to do stuff. Well, right, they don't, but they ask me to do stuff because I'm the person who over delivers and who doesn't say no, and who shows up every time, and so for people like me to rewrite the narrative. You know, I've had success over the last couple of years while I was writing this book living this out in my life. Why do I always say yes, are there places where I can hand things over? And then I'd try to and that wouldn't work either, and saying no didn't work either. Or I'd say no and nobody would say, oh, okay. In that case, I'll start doing it all, you know, I'll host Thanksgiving or something like that. Doesn't always happen. It's not as simple as you stop worrying about things and they magically resolve. You stop doing things, and somebody else picks up the slack. That doesn't happen often. And so what you really have to get comfortable with is the thing not happening at all, or people being disappointed in you, or things remaining uncertain, which I think getting comfortable with uncertainty is probably the key to everything. But I had to learn how to do that in order to be okay with stopping sooner.

Well, let's talk about that Thanksgiving one, because that strikes me as one that yes, the result is that you just don't have a big group Thanksgiving. But maybe that isn't the end of the world.

Right, Maybe that isn't the end of the world. I mean, there's some things that you really can't say no to. Right If your aunt breaks your hip and you're the only one who lives in the same town, you're probably going to be taking her to a few doctor's appointments, and you can say no and put yourself first and hold a boundary. But then you're kind of a jerk, right, And so then what are the other things that you can put down? Because that kind of feels like nothing. Maybe they're hosting Thanksgiving is something you can put down. But when I think you're somebody who's traditionally taken on a lot, been the capable one that people can count on, you look around at your too long list which of these things? I can you think? Which of these things am I going to put down? And the answer feels like nothing?

Well, it's part of that then that other people sort of feed into this relationship. Like if you have a relationship with a capable one and your family you or your spouse or your best friend or whatever it happens to be, does that tend to create some sort of less capability on the part of the other people.

Is that how that work?

I think so, And I don't think it's intentional, and I don't think it's malicious. It's just everybody around you is pretty disincentivized to do it. You've always done it before, and sometimes you've probably said you're not going to do it this year, and then you did it anyway, and so why wouldn't they keep going the way things were? It works pretty well for everybody else. So this redistributions. It's hard work and it can happen, but you have to ask and then ask again, and then say and then say again, and that the redistribution is a lot of work too, which is worth it. But I just think to the overwhelmed woman in particular, the world often says that it's your mindset. You know, you just need to relax. Things will get done, says the person who knows that you will do the things right. So it's just get a sense of humor about it. Stop liking to make things harder than they need to be. Are you doing that sometimes?

Probably?

Are you doing that all the time? No? But I feel like that's too often the only advice you get instead.

Of help yeah, absolutely, But we're going to take a quick ad break and then I will be back with more from Amy Wilson.

Well, I am back.

This is one of the longer episodes of Before Breakfast. I am interviewing Amy Wilson, who is the author of the brand new book of essays, Happy to Help Adventures of a People Pleaser. So, Amy, I mean, there's a lot of different short essays in this book, I mean kind of quick read for people. What would you say was your favorite one of this to write?

My favorite one was My eighth grade Diary, an exploration of my eighth grade diary, which is the only year I kept a diary in my whole life. And my friend Julie recently said that the eighth grade you is the most technicolor version of you of anyone. That it is you, right, and when you look back, why it's so cringey is because like there you were in highly you know, crystallized form, waiting to burst forth. And that was certainly true for me. And when I went back and looked at my eighth grade diary, I was constantly giving myself assignments. And the last thing I wrote in my eighth grade diary was that I had to do everything I could to make the people I really love happy. And I found that after I started writing this book, and then I went back and found that diary. I'm like, holy cow, I was telling myself that when I was thirteen that I had to do everything I could. And I think that that's that sort of hallmark sentiment is something a lot of us. I think it's kind of drilled into all young women. But for some reason I ran with it. For some reason, I was like, that's right, and I'm gonna do it too.

And You've talked a little bit about this maybe eldest daughter, so yeah, yeah, right, what is that?

So I am everybody knows about this eldest daughter syndrome. Everybody's talking about that. You're sort of a type a personality, but it's visited upon you by your circumstances, which I firmly agree with. In my case, I'm the oldest of six kids, my mother was the oldest of eight kids. I'm the oldest of twenty five first cousins, and so I think that, yeah, I'm sort of like a.

Super double triple eldest sister.

I mean, I really, I was really soaking in it during my formative years. And see, I grew up since I was in second grade. I was babysitting for free and changing diapers, and I liked it, and I was good at it. I wasn't a grade schooler who was seething with resentment. I got a lot of identity from it, from being a happy helper, And I think that couldn't help but shape me, not even necessarily for the worst, but it did shape me that I love to help other people and that's what I'm good at, and that's where I draw my self esteem.

So one of the things we like to do on this show is share practical tips, right, and so obviously there's many psychological things to unpack with what makes someone a people pleaser or maybe has difficulties broadly with setting boundaries. But let's say someone is, you know, resolving in the new year to set better boundaries. Are there some practical small things that you would suggest people start doing.

I think that for me, I had to learn that saying no was the first step the whole Like saying no is a complete sentence thing. Never I just sort of thought, like I know that, but when I say no, then nothing changes that Saying no What you really have to prepare yourself for is the silence that will follow, usually uncomfortable silence. Again not malicious, but when you say I'm going to need to step down from this committee. Some things have come up and I'm going to need to step down that there's this you know, there'll be a long, confused silence that will follow. And that's where I had to really learn to not say, I mean, I guess I could stick around till we find somebody else, or I mean I guess I could be the vice person on the committee.

Like that, you you are.

Everybody's a little uncomfortable.

Everybody else is like, wait, what, she's not going to do the committee. I don't want to do the committee either. Who's going to do the committee? While everybody's sort of cogitating on that, I think I would take it all back, or take some of it back, rush to fill the silence, and to me, like no is the easy part. The silence and sitting on my hands while nothing happens at first, that's the hard part. But if you can sit through that and that discomfort and that silence, like things are changing, things are changing slowly, and that uncertainty is something that I've spent a whole life trying to rescue other people from myself first and foremost, I suppose, And once I learned to live with that, I don't know what's going to happen next, but I can't do it, things started to really shift from me.

Yeah. Well, uncertainty is challenging for many people. I mean, it's also the nature of life, right, we just don't know what's going to happen. But I mean, certainly there is the advice who don't negotiate against yourself. Yes, yes, that it is in that silence where somebody is deciding what their counteroffer is going to be, but you don't need to make the counteroffer for them.

Very very well, said I wish I had heard that twenty years ago.

Exactly exactly.

So, I mean you've written people listening to this movie Beyonest Song, it sounds like Amy's are perfectionist. But you've said you don't really like that word perfectionist.

Let's talk about that.

So in the book, I go through all the different forms of advice that I have received that women tend to see when we say that we're overwhelmed, that we can't do it all, that we're we really need some help in the situation written. What we tend to get back is advice to fix ourselves, and I think a perfectionist is certainly one of those things. Stop being a perfectionist. You have too much to do because you're trying to make everything perfect. And I think I took that on for a long time, like, oh, that's right, I'm such a perfectionist, And then I really stopped and thought about it, and I thought, you know, that doesn't really resonate for me. A perfectionist, to me is somebody who is so caught. And also, perfectionism is something that is primarily applied to women. It's really hard to find men out there self identifying as perfectionists and talking about how they get in their own way. But I know I accomplish a lot, I get through a lot. It's just I have a lot on my plate, and I do know how to not sweat the small stuff. I don't care what my kitchen sink looks like. I don't care what my my hair looks like when I go to yoga, Like, I'm not that kind of person who is so overcome with having everything to be perfect that I can't get enough done. That's definitely not my problem. My problem is I simply have too much to do because I've taken too much on, which I think is a different problem. And when you're fed back, we'll stop being a perfectionist or get a sense of humor or these things that are about go change this failing in yourself and then the fact that you have too much to do will magically resolve. Well, it doesn't work, and I love an assignment. So I spend a lot of time trying each of these methods, right to lean in to care less, I mean, I did them all, and none of them resolved the situation. It's the situation that sometimes has to be really addressed.

Yeah, although when we do have too much to do, I mean, we still have to deal with what is right in front of us. Yes, So I'm curious what does your planning process look like? I mean, I know, for me, dealing with the entirely huge pile of stuff professionally and personally often at least partly a matter of figuring out what exactly is in the pile and then roughly when the things will be addressed in the pile.

That's the personal Kamband method that I learned about when I was researching this book. Jim Benson sort of took the Kamband method and adjusted it for personal use. And that's his sort of basic thing, that you have to engage with the entirety of all the things you could be doing. And he says write them on post it notes, which I do find really helps me get out the post it notes. Write each thing, the dry cleaners, and the draft of the chapter four, they each get a post it note, and you engage with them all. I use different color post it notes for different parts of my life. Then you pick three and you put them in your doing column, and you leave the other ones alone, and you do the three. And then when as you do each one of the three, you move it to the done column. And you can't move anything into the doing column until you've moved one of your three things to done. Now, my doing column always has like seven things in it, not three. But when I'm feeling like today is one of those days that I feel like I have seven hundred things to do and I need to have first engaged with. Yep, here's everything I have to do. I won't do it all. That's okay, Let's pick the three things that are jumping out at me right now as either the most urgent or just the most I feel like doing that right now, right, and do those three and don't engage with the entirety of my list while I'm doing those things, just engage with the next three things. It really helps me get more done and feel less panicked.

Less panic to get over that paralysis if I have one hundred things to day, so I'm going to score Instagram instead, right right, yeah, exactly, which can be fun, yes, but maybe a little.

Bit less productive than we might like.

All right, Well, We're gonna take one more quick ad break and then I will be back with more from Amy Wilson. Well, I am back interviewing Amy Wilson, who is the author of the brand new book Happy to Help Adventures of a People Pleaser, various essays on her life as attempting to deal with all that there is to do way too.

Much for many of us.

So, Amy, we always.

Like to hear about people's routines on this show. I understand that you have a morning routine.

I do.

Like most people.

I think my calendar lives on my laptop slash phone. But I really am sort of a paper person. So I've found a middle path, which as I get up and make my coffee, then I sit down and I actually have a remarkable tablet that I use now instead of paper because it saves paper, but also because I find I really like it and it keeps everything in one place. It's all in there somewhere. I sit down with my calendar for the day and I just sketch out. I have a a PDF of the day's calendar that I pull up and I just copy it over longhand onto my day, and doing that helps me engage with what I have to do that day. And then I see the blocks that I might have left, and then I pull the things from my to do list that seem either the most urgent or the most call to me the most for some reason, and I fill those in and I plan my day. And I don't beat myself up too much. If by two o'clock I didn't get that researched and I was supposed to do, I can adjust. But engaging with my day very carefully before I begin it really helps me. Not I don't have the panicle like what am I supposed to be? What am I supposed to be? Doing. I know because I kind of looked at it at the beginning of the day and I make enough room for what I need to do and leave the rest behind. That's really saved me.

Yeah, well, limited to do lists they are always always good. But what does the day actually look like then?

For you?

I mean, are you generally working like nine to five or is it more all over the map.

It's more all over the map because I'm either recording podcast episodes or researching podcast episodes, or you know, hopping on ten others zooms. But I try to block things out and if I have a chance to go to the library. I live right near Columbia University, so I belong to Columbia's libraries, and there's a special library that I go to when I want to write or really concentrate. And having that separate space where I can unplug and not look at my kitchen or whatever is really where I get my concentrated work done. When I'm in a writing season, I get up early and go do that first. I find that if I can write from seven to nine thirty or ten and get it done, and then I can go on and feel great about my day. Right now, I'm not writing, So I'm trying to get in some exercise or yoga first because I feel like I have too much. I wake up panicked, so I need to relax and do some exercise and then get to my day.

But I find that.

Early early part of the day is it's where I do my best work, no matter what it is, So I don't want to necessarily waste it on peloton if I have a writing deadline.

Yeah, I think a lot of us have found that our most product of time does tend to be that morning.

And maybe for some people it's like four am. Maybe for a lot of us it's more like eight am. Yeah, but you know, making sure that it is.

For what we want to give it to, right, right, and not giving that time away to something that is requires less folks, that's right, just sets the tone for the whole day.

If I really have something, oh I don't know, taxes or something, you know, a presentation that I'm really dreading, I often use cave Day, which is group accountability. Sign up for it and you join. They have all kinds of caves that are scheduled, say once starts at twelve thirty. You log on. It's a group zoom. You can unmute yourself or not. You say, hey, I'm Amy and today I'm working at my taxes, and then that you start and it's just group accountability. And you sort of promised these strangers on the internet that you weren't going to look up from your taxes for fifty minutes. You're not going to look at your phone. You're not going to walk away. And I love it. And when I and again, I'll go through seasons of using it and not using it when my list gets so long again, it's like, okay, one thing at a time, and then commit to that one thing at a time. And sometimes strangers in the internet are very helpful.

I love that.

What was it called again, cave day, caveday dot org day.

Yeah, okay, all.

Right, so anyone's looking for some external accountability and I don't know, your friends are busy.

Yeah, this is something you can do.

It helps, It really helps.

So I'm very curious.

You know, we always like to talk about ways we have made our days better. It sounds like maybe cave day is helping you with that too. But is there anything you've done recently to take a day from great to awesome?

Yes?

There is I live in New York City, where you can do you know, three hundred things on a Friday night, and so you do none of them, so you sit home and watch Netflix. And I've sort of resolved recently that if I am going to keep living here, I need to take advantage of things or else live somewhere that's a little easier to live. So my spouse and I went and heard zydeco music near Time Square. Zydeco is like Cajun New Orleans sort of music, with lots of accordion and washboard and stuff. I can't tell you why. It is the happiest music there is. And I love this music. It puts me in such a good mood. So we went with another couple and had burgers and beers and learned how to zoda go dance, and we did zada go dancing, and it just was one of those things where you realize, like, wow, there are people out there who are really good zoa go dancers in this band on stage were absolutely incredible Louisiana's and half of them had ever been in New York City before, and it just just like this little corner of the world that people are that you barely even knew about that. People are huge experts and huge artists, and it just made me so happy to try something new and hear this happy music and not have to get anything out of it, you know what I mean. I learned how to Cajun dance. I'm terrible, whatever, it doesn't matter. And to be in community like that, it was so much better than staying home and watching Netflix. I was so glad I did it. Yeah, So how do you find things like that? I mean this is always the problem. I mean, you know, there's a million things going on. You know some of them, you don't know some of them. Yeah, where do you look for adventures? I this one I knew because there are just those like really cool women out there that start these newsletters, right, and so this one is a real estate agent I know, and she sends out this newsletter every couple of months, like, here are these these fun things that are going on in New York that you should know about, and she listed it. There's there's a Zodago thing and they have dance lessons. And I saw it probably two months ago, and I put it on my calendar and not actually think good, I'd actually go and then that night I actually went. And I feel like I am not the great connector and the great like extravert that brings people together, but I've learned to attach, you know, hitch my wagon to those stars because they know where the fun is and then you just show up and you're part of the group.

That's true. Well, always better to have an adventure than a not advice.

That's kind of my full, lush life. So Amy, what are you looking forward to these days?

You know, I'm honestly really looking forward to this book being out in the world because I really first through the podcast and then through this book. I really like connecting with women and getting them to kind of think about their lives, but also getting them to feel better about themselves, because I just think we get so much. We're just told to fix ourselves every time we pick up our phones, and I just think some of us, all of us, take some of it on, some of us take all of it on. And I just want to get to like one reader at a time and say, you know what, there's nothing wrong with you. Your life is just hard right now, so take a deep breath and then start engaging with how you're going to fix it. And I feel like that message is really going to help the person who really needs to hear it, and so I'm just really looking forward to that.

Excellent. Excellent.

Well, you guys can all pick up a copy of Happy to Help And where else can people find you?

What Fresh hel podcast is at whatfreshellpodcast dot com or wherever you listen to this podcast, and you can find me my events and things like that at Amy Wilson dot com.

Excellent, Well, Amy, thank you so much for joining us. Thanks to everyone for listening to one of these longer episodes. If you have feedback for me about this or any other episode, you are welcome to reach out to me at Laura at Laura vandercam dot com.

In the meantime, this.

Is Laura, Thanks for listening, and here's to making the most of our time. Thanks for listening to Before Breakfast. If you've got questions, ideas, or feedback, you can reach me at Laura at Laura vandercam dot com. Before Breakfast is a production of iHeartMedia. For more podcasts from iHeartMedia, please visit the iHeartRadio app, Apple Podcasts, or wherever you listen to your favorite shows.

Before Breakfast

In each bite-sized, daily episode of Before Breakfast, host Laura Vanderkam shares a time management 
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