Amy Wilson’s, “Happy to Help: Adventures of a People Pleaser”— How to Say ‘No’ and Feel Comfortable Doing it

Amy Wilson is a wife, a mom, a writer, a co-host of the What Fresh Hell: Laughing in the Face of Motherhood podcast who can do it all. Correction: Wilson used to do it all. The word ‘no’ made a scarce appearance in her vocabulary, until she began her retrospective journey in understanding exactly why ‘yes’ was, sometimes, not the best answer. Her newest book, Happy to Help: Adventures of a People Pleaser, is a collection of personal essays exploring her thoughts and reasonings behind people pleasing in multiple areas of her life, including in the office or as a mother. Her can-do attitude for every task, even the ones that aren’t her responsibility, is the reason behind her title.

Between the 254 pages of narration, Wilson intentionally speaks on the pressure of people pleasing, imposed on not solely herself, but on women, as a whole, in society. She weighs out the positives and the negatives of people pleasing and explores a more balanced approach to be a woman that can do it all, but doesn’t need to. Just N Life had the opportunity to chat with Wilson about Happy to Help‘s relatability and vulnerability in exploring the power of the word, “no.” 

Just N Life: Was there a defining moment when you internalized, ‘This is what people pleasing is?’ Take us back to that moment.

Amy Wilson: I have been a helper all my life… a person who helped and was happy to help, honestly. I think it’s born and made, especially for women. Some examples: I’m the oldest sibling of a big family, I was a Girl Scout, I was a class president, valedictorian, student council kind of kid, you know. I loved the challenge, and I loved doing my best, and I was told I was good at it… Taking care of the people around me was just in the groundwater for me… I was told that I was somebody who was happy to help and I very much folded that into my sense of self without really examining it. It was, like, the most me thing about me. And it was really only writing this book that I came think, “Was that true?” 

I think the term, ‘people pleaser,’ is a fraught term. I mean, it’s in the title of my book, it’s not a word that I identify with personally. When I really went back to look at the definition of a people pleaser, the most general accepted definition is that you put other people’s wants and needs ahead of your own, which I think kind of women are supposed to do that and mothers are definitely supposed to do that. To then be told that’s a flaw of your personality, that you put other people’s wants and needs in front of your own, it’s like, “Wasn’t that the assignment? I thought you wanted me to do that.” It gets complicated. 

JNL: To stop people pleasing, what do you feel like is the most important boundary to set to and how to do get comfortable setting those boundaries?

AW: It’s all about getting comfortable setting these boundaries… When you start to say, “Look, I need to do things differently, I need to set boundaries,” you won’t be immediately hoisted into the air with this puffy cloud of support; people aren’t going to be like “No way I hate you,” but they also won’t be like, “Exactly. I know exactly what to do and you’ll never need to do this again.” They’ll be pretty confused, usually, that you’re saying it. What I’ve done in the past [when people would stare blankly after explaining she needed to take a step back] is say, “Or maybe I could find time, or maybe I could just do some of it…” you know, you start to fill the silence. There’s going to be this, not even pushback, this, “Wait a minute… what?” thing that happens when you start to do things differently. What I have had to learn is to sit in the silence, even if it starts to get a little uncomfortable for you and everyone else and not rush to fill it and put things back the way they were. That’s the hard part. 

One of the reasons I wrote this book is, to sort of, you always hope someone is going to learn from your mistakes. I spent a lot of my 20s chasing relationships that weren’t right for me and jobs that weren’t the right fit for me, thinking, “I’m gonna make this thing work. They’ll see.” Sometimes things worked out and usually I should’ve quit long before I did. 

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JNL: Was there ever a point where you reflected and recognized that [people pleasing] could actually be a strength instead of a weakness?

AW: There have certainly been times in my life where I’ve been like, “This isn’t working, and I’m not going to give up, and I’m going to stick to it until does work.” There’s time when that, stick-to-itiveness, is really beneficial… Sometimes that has not served me and other times it really hasn’t, so it’s not that it’s always a bad thing to be this person, this, “I think I can do it, I think I can try harder,” it’s just that I have over-applied that tendency throughout my life. 

Happy to Help: Adventures of a People Pleaser is now available and listed as a Top New Release on Amazon for your reading (and learning) pleasure.