Jen Guidry of Brilliantly Bold On How to Recover From Being a People Pleaser

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An Interview With Brooke Young & Yitzi Weiner

Practice strength and assertiveness. This ties everything together. It is a daily practice. I had to learn how to express my opinions (because they DID matter) and my boundaries (because I finally HAD some) in a manner that was respectful, but strong, to others. Take small steps and progress. Remember that people might not like what you have to say, but they will respect you for saying it.

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 would like 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 Jen Guidry Fassler.

Jen is a success and business coach. Her coaching style is marked by compassion, authenticity, and a deep understanding of the challenges faced by those striving for greatness. She owns Brilliantly Bold (, and is a partner with Dr. Robb Kelly in, where they encompass coaching people as a whole, including uncovering past childhood trauma in order to empower clients to reach their full potential. She is also a two-time award-winning author and motivational speaker.

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” a bit better. Can you tell us your “Origin Story”? Can you tell us the story of how you grew up?

I grew up in a middle-class family in Buffalo, NY. My childhood was tumultuous, to say the least. My father was an abusive alcoholic. I also endured molestation as a child (by another relative) and sexual assault as a teen. I lived a childhood filled with a lot of traumas, which is prime breeding ground for a future of people pleasing.

Determined not to be a victim of my childhood, I worked diligently to be the best at whatever I did, even when it was to my detriment.

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

I now coach entrepreneurs, business owners and teams using techniques in neuroplasticity and mindset coaching. I am also an author of 2 books (so far) — Grit & Gratitude and The Storm. I motivationally speak for businesses and Women’s Conferences.

My past incredible success in leadership, the mortgage industry and my traumatic past have prepared me for what I am doing now. It was a natural progression.

I want to help as many people as I can to rewire their brains for success. The path isn’t easy; but like all great things, it is always worth it. I chose this field to show people that their past doesn’t have to dictate their future and that they can achieve whatever they want to no matter who they are of where they came from.

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?

To me, a “people pleaser” is someone whose identity and value as an individual revolves around trying to accommodate needs of everyone around them while discarding their own needs as a person.

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?

There is a definite difference between being nice and being a people pleaser. Don’t get them confused. When someone is nice, they are choosing to show their big-heartedness by doing something for someone else. Their self-worth is not rooted in their kind act.

A people pleaser, on the other hand, does things out of fear.

Some challenges of people pleasing could include:

  • You are so busy taking care of everyone else, that you will tend to neglect yourself. Your health — both physical and mental — suffers.
  • You get taken advantage of by people. Some intentional (narcissists LOVE people pleasers) and some not (those who don’t know your past).
  • You look to everyone else but yourself for your worth.

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

I would say that they are “perceived” advantages. They look great on the outside until you do a little digging.

For example, one of the traits of people pleasers is that they will do anything to avoid conflict. They want to keep the peace and be in harmony at all times. Someone like this, on the surface, is great to have around because they can help with reconciliation. However, when you get down to the root cause of WHY they can’t stand to have conflict, the “advantage” goes away.

You also get a lot of praise and compliments because you are doing so much for other people. Sure, this temporarily boosts your self-esteem and makes you feel better, but you are getting your worth from what other people say versus how you actually feel about yourself.

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

As a recovering people pleaser, one of my worst habits was avoiding conflict at any cost. No matter what, I wanted to keep the peace. I prioritized keeping the peace over most other things when it came to my relationships. I never voiced my opinion or needs. I wanted to maintain a steady and normal relationship.

Then I wondered why every relationship that I had failed.

Eventually, I learned that in a relationship, conflict is going to come up and it is not my obligation to fix everything. Sometimes, people are just going to be mad. I learned to communicate my needs, wants and desires to those around me. I realized that the “stability” that I thought I got from always keeping the peace and not speaking up wasn’t real.

Once I got out of this cycle, my relationships with others became more meaningful and successful.

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

Two words: childhood trauma. Abandonment trauma, to be more specific. When you are abandoned as a child, you develop a fixed pattern of thought. You believe you will be alone because everyone close to you is going to leave you.

You also develop emotional “triggers” about your value as perceived by others. You become insecure and look to others for validation.

Abandonment trauma leaves people with the thought they are discarded, unwanted, and undesired. So, what happens? You become the one who no one can live without…the people pleaser.

How does people-pleasing behavior impact personal relationships?

When one person is constantly neglecting their own needs, the relationship is not balanced. A healthy relationship is mutually supported and both sides feel the benefit, not just one. Additionally, if you are the people pleaser, your actions often lead to resentment and dissatisfaction because you are the only one “doing the work” without reciprocation.

Your “harmonious relationship” isn’t real. It isn’t authentic. Often, the people pleaser in the relationship conforms to their partner’s expectations and opinions versus expressing their own.

Let’s face it, people pleasers can also be very annoying. Dealing with the constant need for validation from others, saying “yes” to everyone and everything, low self-esteem and no boundaries is exhausting.

How does people-pleasing behavior impact professional relationships?

It is hard to grow professionally if you don’t assert yourself. People pleasers don’t speak up for fear of negative validation. Your ideas and perspectives are overlooked because you don’t express them.

Want that promotion? That raise? When you don’t have the self-confidence to ask for something, you probably aren’t going to get it.

Being the “yes” man or woman is pretty grueling. You are overcommitted and overwhelmed, which leads to sloppy work, struggle to meet deadlines, and burnout.

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

Constant people pleasing causes a lot of anxiety. Long-term anxiety is not healthy.

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

Just like most things, once you recognize WHY you do the things that you do, they are easier to stop. We like to say, “Uncover. Discover. Discard.” Once you find out what the root cause of your current tendencies are, you can take the necessary steps to overcoming and changing your behaviors.

In order to find the root cause, you have to do your inner child work, which can be delf-directed, through a therapist or a highly trained coach.

Here is the primary question of our discussion. 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”? If you can, please share a story or an example for each.

1 . Develop self-awareness. To me, this is Step 1. Why do you feel the need to people please? In my personal life, I had abandonment issues that developed from my childhood. I would do anything and everything to get someone to stay, even if it was an unhealthy relationship. I was so laser-focused on getting my worth from external sources, that I didn’t even know what made ME happy or what I needed. Once I took the time to reflect on my own needs, values and boundaries, my life changed. I realized my worth was not attached to anyone else’s opinions.

2 . Challenge negative beliefs. This launches off of Step 1. Whenever a negative thought pattern like, “I am only a good person if I make others happy” or “My needs aren’t as important as so-and-so’s” popped into my head, I replaced them with positive thoughts that were empowering of self-affirming.

3 . Set boundaries. Clearly define what you will and will not accept. Then, stick by those boundaries. I learned to communicate them to those around me. At first, people might be surprised that you are sticking up for yourself (for lack of better words), but they will respect you for it and abide by them. Boundaries are not just for work, you have to set them for work, personal life and relationships.

4 . Prioritize self-care. You have to nurture yourself physically, mentally and emotionally. Start to take time to do things that nurture yourself and stop saying “yes” to things that you don’t truly want to do. This one was tough for me…the saying, “no” part because I didn’t want to disappoint others. With practice, though, I was able to establish a routine for myself and I also started blocking out days that were just for me! Instead of having day after day of dread and resentment because I “had” to do something I had committed to, I found a more manageable and relaxing lifestyle where I was able to not only take care of myself, but still help others as well.

5. Practice strength and assertiveness. This ties everything together. It is a daily practice. I had to learn how to express my opinions (because they DID matter) and my boundaries (because I finally HAD some) in a manner that was respectful, but strong, to others. Take small steps and progress. Remember that people might not like what you have to say, but they will respect you for saying it.

What steps should people pleasers take to establish healthier boundaries?

Setting boundaries is a gradual process. Be patient and kind to yourself throughout this process. Here are my “Big 3.”

  1. Take the time to understand why you struggle with setting boundaries to begin with through self-reflection.
  2. Practice saying, “no.” It is always best to start with small requests of things that you don’t want to or don’t feel comfortable doing. After you get comfortable with that, you can move onto the bigger requests that might seem more uncomfortable to say, “no” to.
  3. Identify what your needs are. Have you ever sat and thought about what those actually are? It is OK to prioritize your own self-care and needs.

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

Empathy is identifying with or understanding the emotional state of another person. By communicating with empathy, you can still acknowledge another person’s perspective and feelings, while still expressing your boundaries and needs. You cannot help and please everyone, and that is okay. It is important to understand that you cannot be responsible for everyone’s happiness, but you can still be a good listening ear to others without feeling like you have to fix their problems.

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

  1. They always say, “yes.” So, when they finally say, “no” to something, the requestor might react in a negative way.
  2. They are weak. Just because you have a tendency towards people pleasing, doesn’t mean that they aren’t strong. It takes a lot of strength to do all of that extra work!

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

Counseling can help get to the root cause of the people pleasing behaviors.

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

Mine is simple: Just be kind and know that it is not all about you. We live in this world where everyone is so offended all of the time. We take everything personally when in reality, it is not about us one bit. If everyone was just kind, the world would be a better place.

How can our readers further follow your work online

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.

Jen Guidry of Brilliantly Bold 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.