Gayle Weill On How to Recover From Being a People Pleaser

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An Interview With Brooke Young & Yitzi Weiner

Practice, practice, practice! Sticking to your boundaries is difficult. It will take practice to master not giving in to every request. Know that there will be times when you do give in, and that’s okay. Don’t be judgemental of yourself and practice every win.

In today’s society, the tendency to prioritize others’ needs and expectations over one’s own can lead to significant emotional and psychological challenges. In this series, we would like to explore the complex dynamics of people-pleasing behavior and its impact on individual well-being and relationships. We want to discuss the root causes of people-pleasing behavior, its effects on personal and professional life, and practical steps for cultivating healthier relationships and self-esteem. We hope that this series can provide insights, strategies, and real-life experiences that can help individuals navigate and overcome the pitfalls of being a people pleaser. As part of this series, we had the pleasure of interviewing Gayle Weill.

Gayle Weill, LCSW, is a licensed psychotherapist who currently offers telehealth psychotherapy sessions for people in New York, Connecticut, and Florida. Having graduated from Yeshiva University’s MSW program, Ms. Weill received additional certifications and training in Child-Parent Psychotherapy, EMDR, and Hypnosis. She also has national accreditation as an Adoption-Competent therapist. She is a Circle of Security-Parenting facilitator, a program promoting the attachment bond between parents and their young children.

Thank you so much for your time! I know that you are a very busy person. Our readers would love to “get to know you” better. Can you tell us your “Origin Story”? Can you tell us the story of how you grew up?

Growing up in Cheshire, a quaint town nestled in Connecticut, I was raised alongside my parents and younger brother. Despite being only seven years older, my relationship with my brother carried a unique dynamic as he navigates life on the autistic spectrum. Our bond was one of understanding, patience, and unconditional support.

Adding another layer to my upbringing was the presence of my maternal grandfather. From the age of 9 to 17, I shared my home with him, witnessing the gradual progression of his dementia. It was during these formative years that I learned the value of empathy, compassion, and the importance of caring for others, especially those facing cognitive challenges.

These experiences profoundly influenced my aspirations and instilled within me a deep-seated desire to pursue a career in the helping profession. Initially drawn to nursing, I soon realized that while I wanted to make a difference in people’s lives, my passion lay in engaging with individuals on a personal level, understanding their struggles, and collaborating on solutions to overcome obstacles.

This realization led me to shift my focus towards a profession that allowed me to utilize my strengths in communication, empathy, and problem-solving. I found my calling in counseling, where I could engage in meaningful conversations, empower individuals to navigate life’s challenges, and facilitate their journey towards personal growth and fulfillment.

My upbringing in Cheshire, alongside my family members, especially my brother and grandfather, laid the foundation for the person I am today — someone driven by a profound sense of purpose to make a positive impact in the lives of others. It is through their influence and the lessons learned along the way that I continue to strive towards creating meaningful connections and fostering resilience in those I have the privilege to serve.

Can you tell us a bit about what you do professionally, and what brought you to this specific career path?

I am a licensed psychotherapist in private practice. I provide psychotherapy telehealth sessions to individuals in New York, Florida, and Connecticut. My primary focus is working with anxious, insightful mothers of small children (like me! ☺) who are struggling in their relationships — not just romantic relationships, but relationships include parenting, friendships, coworkers, or identifying and setting boundaries with extended family. I love being able to help people with these types of issues because I find it so empowering to get to the root of a problem and brainstorm ways to overcome it. Relationship dynamics are so interesting to me because, as human beings, that is what life is all about! We are social beings — who we interact with and how we interact with them is a massive factor in an easier or harder life. I like to help people facilitate making life easier. It fascinates me to work with incredibly insightful people who could know something logically, but struggle to determine how they feel and believe what they know to be inherently true. Anyway, with all that being said, this is a career I immensely enjoy!

Thank you for all that. Let’s now turn to the main focus of our discussion about People Pleasing. To make sure that we are all on the same page, let’s begin with a simple definition. What does “People Pleaser” mean to you?

People pleasing is when someone goes out of their way to accommodate another person, usually to the extent of their own needs and wants.

On the surface, it seems like being a person who wants to please others is a good thing. Can you help articulate a few of the challenges that come with being a people pleaser?

People pleasing means that you consider others’ needs. This in itself is an excellent thing. However, when it’s to the extent of your own needs, that is when it becomes problematic. There is a misconception among some people that putting one’s own needs first is “selfish.” The word selfish has a negative connotation. I see a difference between selfishness and having boundaries for one’s own emotional and physical well-being. The point is that it is not selfish to consider your own needs before deciding to help someone else.

Does being a people pleaser give you certain advantages? Can you explain?

It can, to a certain extent! Being a people pleaser can mean that people know they can depend on you. They know that you’re someone reliable who can help them. People often like people pleasers for these reasons. People pleasers are less likely to argue when someone asks them to do something and are generally attuned to others’ feelings. People pleasers are more likely to live a life of less conflict. People pleasing is also a protective strategy; going against that is to go against your nervous system. So, in that sense, people-pleasing is undoubtedly an advantage!

Can you describe a moment in your life when you realized that your own people-pleasing behavior was more harmful than helpful?

I realized it when I worked for an agency and had many tasks on my to-do list. My supervisor came to my office and asked me if I could take on another client task to lighten the load of my other coworkers. I said yes. A part of me said yes because I wanted to help out. I also wanted to show my supervisor that I was more than capable of taking on as many tasks as was asked of me. However, this added some stress, as I already needed more time with my other tasks. My supervisor was not telling me to take on this task; she asked me if my schedule allowed it. After I had said yes, I realized that people-pleasing could be more harmful than helpful at times.

In your opinion, what are the common root causes of people-pleasing behavior?

Common root causes of people-pleasing behavior include not wanting to upset others, not wanting to hurt someone else’s feelings, and not being honest with ourselves about what we are capable of handling.

How does people-pleasing behavior impact personal relationships?

I’d like to illustrate my response with an example. Let’s consider Person A, who enjoys hosting friends for weekly meals. However, she struggles with communicating when it’s time for her guests to leave. She fears hurting their feelings by implying she wants them to depart. Despite having young children and needing to maintain a reasonable bedtime routine, she refrains from setting clear boundaries. Consequently, her friends unknowingly overstay, assuming it’s acceptable because Person A hasn’t indicated otherwise. This miscommunication led to resentment on Person A’s part, as she expected her friends to intuit when it was appropriate to leave, while her friends believed they would be informed if their presence was no longer welcome. The above scenario illustrates boundary-setting issues, communication misunderstandings, stress, and resentment.

How can long-term people-pleasing behavior impact an individual’s mental health?

In your experience, what is the role of self-awareness in overcoming people-pleasing tendencies, and how can individuals cultivate it?

If you want to stop people-pleasing, self-awareness is critical. Here are some things to be self-aware of: when you people-please, with whom, cues in your body that you’re feeling unsafe, what you want to do instead, and how people-pleasing has protected you. These will help you know the when, where, and how so that you can prepare and act differently.

Based on your experience or research, what are the “Five Strategies Or Techniques That Can Help Individuals Break Free From The Cycle Of People-Pleasing”?

1. As previously stated, self-awareness is critical! Notice when you people-please, without being judgmental of yourself. For example, Person X may have agreed to do something for Person Y without even giving thought that she was people-pleasing. She cannot change her behavior until she is aware of the behavior and why she responded the way she did.

2. Once you have awareness, the next step is to figure out the “Why?” What is causing the people-pleasing behaviors? For example, are you worried that you will hurt someone’s feelings?

3. The next step is to challenge that “why” you came up with in step 2. For example, if you’re worried that you will hurt someone’s feelings by enforcing a boundary, question yourself as to whether there is a way to implement your boundary while still being kind.

4. Learn strategies for managing anxiety that comes along with enforcing a boundary. For example, your natural inclination is to say yes when Person X asks you to do something. However, because you know that it’s not something you can realistically accommodate, you feel really nervous, but you know you will have to enforce your boundary and say no to Person X. Saying no, rather than giving in can feel really uncomfortable and anxiety-provoking. Strategies to calm anxiety include taking a few deep breaths, practicing mindfulness by grounding yourself to the present moment, reminding yourself that all will be okay, etc.

5. Practice, practice, practice! Sticking to your boundaries is difficult. It will take practice to master not giving in to every request. Know that there will be times when you do give in, and that’s okay. Don’t be judgemental of yourself and practice every win.

What steps should people pleasers take to establish healthier boundaries?

Practice makes perfect, especially if you have a formula to go by. Practice the following:

1. First, ask yourself, and be honest with yourself, about what it is you really want. Do you actually want to help this person right now, or will it be a hardship in any way? Reflect on the feelings that come up with that.

2. After you realize that you don’t want to give in to the request, then it’s time to tell the person what you are feeling when that request is given (i.e., “I feel angry when you ask me to get this extra task done.”)

3. Next, give the person the benefit of the doubt so that they don’t feel and become defensive (i.e., “I understand that you want me to get this extra task done because it will make the rest of the work week easier and flow more smoothly.”)

4. Then it’s time to state the boundary, using the word “and” instead of “but” because using the word “but” is devaluing to the other person. (i.e., “I need you to please understand that when I have many things on my to-do list, I cannot take on another task).

– So, putting steps 2–4 together, using the above examples: “I feel angry when you ask me to complete this extra task. I understand that you want me to get this extra task done because it will make the rest of the work week easier and flow more smoothly, and I need you to please understand that when I have many things on my to-do list, I cannot take on another task.”

How can someone who is naturally empathetic maintain their compassion while becoming more assertive?

I often share with my clients a crucial insight: It’s not just what you say, but how you say it that matters. Enforcing boundaries doesn’t mean being harsh or uncaring; in fact, it’s quite the opposite. Assertiveness, when done with empathy and kindness, builds trust and fosters genuine communication.

By expressing your boundaries clearly, you provide others with the assurance that you’re being authentic and honest. They no longer have to second-guess your intentions or wonder if you’re simply being polite by saying yes when you mean no. Remember, assertiveness is not about being selfish or unkind; it’s about being true to yourself while respecting the needs and feelings of others.

For instance, while it may seem assertive to say, “No is a complete sentence,” a more compassionate approach could be, “I’m sorry, but I can’t do that right now. However, I’d be happy to help you when I have more time.” Both responses convey assertiveness, yet the latter emphasizes empathy and understanding, making a world of difference in how it’s received.

What are the most common misconceptions about people pleasers, and how do these misconceptions affect their journey toward recovery?

There’s a common misconception that people-pleasers always give in because they fear upsetting others. However, this isn’t always the case. Some people-pleasers genuinely find joy in making others happy and being helpful. For them, saying no isn’t about avoiding conflict but rather about prioritizing their own well-being.

Another misconception is the belief that once someone falls into the pattern of people-pleasing, they’re stuck there indefinitely. This misconception can be particularly damaging, as it can cause individuals a great deal of anxiety when trying to say no or establish boundaries. However, it’s important to recognize that feeling anxious about setting boundaries doesn’t mean one is destined to always give in.

Internalizing these misconceptions can lead individuals to harshly judge themselves for their inability to say no. This self-criticism only exacerbates anxiety, making it even more challenging to break free from unhealthy patterns. Furthermore, if individuals believe they’re unable to change their behavior, they may be hesitant to seek support from others who could offer guidance and assistance in their journey towards creating healthier patterns.

What role can therapy or counseling play in helping individuals overcome people-pleasing behavior?

Therapy can help people gain insight into their people-pleasing behaviors. Some may not even be consciously aware that they are people-pleasers. Therapy can help the person gain awareness, find out the root causes contributing to the behaviors, and provide skills to help people-pleasers still be kind but learn better boundaries for themselves.

You are a person of great influence. If you could start a movement that would bring the most good to the most people, what would that be? You never know what your idea can trigger. 🙂

Honestly, a simple smile can work wonders in brightening someone’s day. If I were to initiate a movement aimed at maximizing good for the greatest number of people, I would advocate for the simple act of smiling more during our daily routines. It’s such a small gesture but has the potential to significantly enhance a stranger’s mood. After all, you never know; a smile directed at someone could truly make all the difference.

How can our readers further follow your work online?

Please visit my website at https://gayleweilllcsw.com/, or you can find me on Instagram at https://www.instagram.com/gayleweilltherapy

Thank you so much for sharing these important insights. We wish you continued success and good health!

About the Interviewers:

Brooke Young is a multipassionate publicist, public speaking mentor, and communication consulting. She works with a wide range of clients across the globe, and across a diverse range of industries, to help them create, develop, and promote powerful messages through heart-centered storytelling. She has formerly worked On-Air with FOX Sports, competed in the Miss America Organization, and is the Author of a Children’s Book. She frequently works with children as a professional speaker where she educates on Volunteering and Therapy Dogs. She has over a decade of professional performing background and finds joy in sparking creative passions for her clients.

Yitzi Weiner is a journalist, author, and the founder of Authority Magazine, one of Medium’s largest publications. Authority Magazine is devoted to sharing in depth “thought leadership interview series” featuring people who are authorities in Business, Tech, Entertainment, Wellness, and Social Impact.

At Authority Magazine, Yitzi has conducted or coordinated thousands of empowering interviews with prominent Authorities like Shaquille O’Neal, Peyton Manning, Floyd Mayweather, Paris Hilton, Baron Davis, Jewel, Flo Rida, Kelly Rowland, Kerry Washington, Bobbi Brown, Daymond John, Seth Godin, Guy Kawasaki, Lori Greiner, Robert Herjavec, Alicia Silverstone, Lindsay Lohan, Cal Ripkin Jr., David Wells, Jillian Michaels, Jenny Craig, John Sculley, Matt Sorum, Derek Hough, Mika Brzezinski, Blac Chyna, Perez Hilton, Joseph Abboud, Rachel Hollis, Daniel Pink, and Kevin Harrington

Yitzi is also the CEO of Authority Magazine’s Thought Leader Incubator which helps business leaders to become known as an authority in their field, by interviewing prominent CEOs, writing a daily syndicated column, writing a book, booking high level leaders on their podcast, and attending exclusive events.


Gayle Weill On How to Recover From Being a People Pleaser was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.