Kelley Rowland On How to Recover From Being a People Pleaser

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Be What You Want from Others. While last on my personal list, this one might be the most powerful technique of all. It’s less of a technique and more of a model to live by. In my opinion, we should model the behavior that we expect from others. As a mom to twin boys, I don’t expect them to behave or do things that I don’t do. If I want them to be kind, I better be kind. If I want them to keep their room clean, I better keep the house clean. You get the point. We can start to break the cycle of people-pleasing by creating relationships built on trust, openness, and love. Don’t judge others. Say no to gossip. Be kind. Be supportive. Be open about it. Tell people how proud of them you are. Tell them that you have their back. Don’t speak negatively about ideas or career changes that you don’t understand. I don’t want anyone living their life to please me, and it’s partially on me to make sure they don’t feel like they have to

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 Kelley Rowland.

Kelley was born in Biloxi, Mississippi, and was raised in England, Florida, Japan, and finally Tennessee, where she graduated high school in 2008. She settled in the panhandle of Florida after graduating college in 2014 with her husband of 10 years. Together they have rambunctious twin boys, Cayson and Asher, and a house full of pets. Kelley is obsessed with her Peloton, a self-renowned home chef, and loves traveling with her family. Kelley has a background in corporate America, where she worked with utility, chemical, and aerospace companies serving as an expert in communications, strategy, and change management. However, over the years, she has been called to share her family’s testimony after giving birth to twin boys that were three months premature. She is an engaging and authentic speaker with experience speaking in many different settings. In 2019 she combined her passion for speaking and inspiring others and started her Brazen and Brave podcast. Her hope and prayer is that together we would be encouraged by God’s truths, boldly take faith-inspired action, and create a powerful movement where no one can deny the presence of our Father. Kelley’s own twin boys were born early and admitted to the NICU, where she and her husband Skyler journeyed through the ups and downs, praises and pain, and hopes and despairs. Kelley took her own painful journey and wrote it in a way to help others in her best-selling debut book REVEAL.

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 military family so, naturally, change has been a constant in my life. I was born in Biloxi, Mississippi and my family moved to England when I was very young. My parents were divorced by the time I was three and my dad moved to Florida, closer to family, with my infant sister and me. I started elementary school in a super small town and received the shock of the lifetime at the ripe age of eight that we were going to be moving to Japan. By that time, my dad had remarried and I had gained another sister. I was SHOOK. I distinctly remember running to my bedroom crying because I was so scared. I didn’t want to move and thought that Japan didn’t have toilet paper, so that somehow meant I’d have to wipe my behind with sand. As it turns out, moving to Okinawa, Japan for five years was one of the best things that could have ever happened. It opened my eyes to the world, to new people, cultures, and helped me adapt to the ever-changing world around me. When we first moved, the kids at school called me “cowboy girl” because of my thick southern accent. I went from being incredibly sheltered to playing taiko drums, eating eel from the Japanese mall, and snorkeling in beautiful 100-foot seas. I’m so grateful for our time there because it had a huge influence on shaping me into who I am today. We moved the summer going into my eighth-grade year and I was devastated. My dad retired from the military and found a job in middle Tennessee, which is where I graduated from high school. I graduated as valedictorian with a full-ride Air Force ROTC scholarship to any school I could get into. I was supposed to do “big things” with my life. Looking back, I was in a pressure cooker ready to burst from the pressure at any moment. Life didn’t exactly pan out the way I’d always expected. I ended up moving colleges for, you guessed it, a boy, and after two years of being in ROTC I decided that I wanted out. I took a semester off and two colleges later, I finally graduated with my Bachelors of Electrical Engineering, I met my now husband of 10 years while going to college, and now we have miracle identical twin boys that just turned eight. We have three dogs, a cat, and life is pure chaos, but we love it.

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

I graduated from college with my electrical engineering degree. As I stated in my origin story, I needed to do something big and cool, you know? So, my first major was physics, then math, then my uncle convinced me to do EE, and I’m super glad he did because it enabled me to get a great job. I worked for a utility company for ten years and I joke that I became a victim of a merger and acquisition. During that time, I landed a new role in Change Management and I absolutely loved it. Somehow the stars aligned and I started consulting. I decided to start consulting full-time a few years ago and it has been a game changer for our family. Before that, while doing engineering work, I started a podcast. It was the first time in my life that I had really done something for me, something that I alone wanted to do. I also started doing some online coaching on the side, creating courses and such. I figured out that wasn’t exactly for me, but I like throwing spaghetti at the wall to see what sticks. I believe it was the coaching that helped me open my eyes to consulting. I truly believe with each change, each opportunity, and even each redirection, we are getting closer to our ultimate purpose. So now I am a change management consultant and I still podcast AND I just released my first book. Life is such a roller coaster, but I am here for it.

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?

My definition of people-pleasing…. Here we go, People-Pleasing: Living based on what you think others want. A complete disregard of self for the sake of anyone and everyone else. A crying shame. Okay I’m done, ha.

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?

I don’t believe wanting to please people is an innately bad thing. I think that most of us, if we are being honest with ourselves, desire to be liked and loved. With that desire comes the natural tendency to want to make people feel good, to be happy, especially to be happy with us. Somewhere along the way we got things mixed up. Making someone happy doesn’t mean that he or she is happy with everything that we do or say, or at least it shouldn’t. It starts from a place of love but can quickly get out of control. Another challenge is that often people-pleasing can feel rewarding at first. However, most of the time that rewarding feeling that we worked so hard for is fleeting, and once it’s gone you can end up feeling emptier than you did before. What’s worse is that the cycle of people-pleasing is never ending. You realize that you change yourself to please people, but that you can still end up short of the mark and feel like you will never be good enough. And you know what? You won’t. We can never be all things to all people, which is why it’s so important to acknowledge that within ourselves.

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

This is a tough one. My gut response is, potentially, if you are in politics. Otherwise, I don’t believe people-pleasing has any true advantages, just temporary falsified ones. I believe in being a peacekeeper, and I am working on myself to not just be a peacekeeper, but a peacemaker. The challenge is to not sacrifice on who you are for the sake of creating peace. There is a big difference in being a peacemaker vs a people-pleaser. Creating real peace in a situation means that you are staying true to who you are, therefore, keeping peace in your own heart and soul. People-pleasing does the opposite — it creates turmoil in your heart and soul and does more harm than good.

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

Absolutely. I distinctly remember a phase (and certain instances during that phase) that felt like a slap in the face. It was almost like I had a huge bucket of ice water dumped on my head, and I violently woke up from the people-pleasing path I was on. I had been working as an engineer for a few years, was married, and had two beautiful children. We were living the “American dream.” It was during that time that I started a podcast. I absolutely love speaking and inspiring people. It sounds a little cheesy, but I was so proud of myself and excited about doing something for me that I loved. I was going to continue working as an engineer, and it was just going to be something I did on the side. The reaction and lack of support I received from those close to me was shocking and, to be honest, super confusing. I couldn’t understand, I had made it! I had worked my tail off to make everyone proud, and I was going to continue to do those things, so I just didn’t understand why people couldn’t get behind the one thing that I wanted to do. I mean, my podcast was intended to help people, to put a smile on their face. It seemed like a good thing to me, but not to others. It almost seemed to embarrass them. This was a huge wake up call to me. I learned that you can do everything in the world to please people, but that it just takes one thing that goes against what people like, and then bam! You’re at the bottom of the people-pleasing pit clawing your way back up to the top. I clawed for a long time. I tried to explain myself away, desperately hoping to receive the support I longed for. The longer I went without it, the more it hurt. I have cried many tears and sat confused for many hours to try and understand why I couldn’t please people. Then one day I woke up. I realized that the things that God puts on my heart and the purpose He instills in my soul is mine alone. I can expect others to possibly feel the same way about those things that I do. I can hope for their support but must reconcile with my own feelings when I don’t receive it. Another thing I have learned is that it’s not fair to the people we are trying so desperately to please. I have made many assumptions in my life about what people want from me and what they think of me. Most of them are probably not true. That’s the saddest thing about people-pleasing, most of the people-pleasing that goes on is based off assumptions! We waste time being someone different based on information that is fabricated in our wild imaginations. There is nothing helpful about that.

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

I believe people-pleasing behavior begins when we are young. We desperately desire to make our loved ones and friends proud. We want to be understood, supported, and loved. If we don’t get those things, we try harder. We change. We do things we think would garner those oh so desired feelings of support. One root cause, I believe, is when we feel judged, or misjudged, I should say. When I worked in corporate America I was hit with a landslide when I learned that three separate people had reported me to Human Resources for attending a Public Relations event on my lunch break — an event I had asked my boss’s permission to attend, an event that even my boss wanted to attend but couldn’t. I was dumbfounded. It literally shook me to my core. What bothered me so much was that being reported to HR meant my character was being questioned. I hated it, it made me feel sick. This was a huge turning point in my life. I learned that no matter what, there are going to be enemies, people who don’t support you and throw you under the bus just because they can. If we are not careful, we can spend our life trying to prevent something like this from happening, but the truth is we can’t because we can’t control other people. So, I believe a major core cause of people-pleasing comes from us wanting others to see the good in us. We don’t want to be miscalculated or misjudged; we want to be represented fairly and as we see ourselves. I’m a proud “Swiftie” and I was obsessed with her New York Times article. There are so many amazing one-liners, and this is one of my favorites. Taylor Swift says, “I’ve also learned there is no point in actively trying to ‘defeat your enemies’.” It’s pointless — just like people-pleasing. The positive is that we can start to expose the root causes and chop away at them one at a time.

How does people-pleasing behavior impact personal relationships?

It creates a false environment and weak foundation for relationships. I love the movie The Ugly Truth. You know, where the girl pretends to be what the guy wants to get the guy. It works initially but it’s not sustainable. It’s not fair to ourselves to become something we are not, but it’s also not fair to the people we are trying to please. It creates unrealistic expectations and is simply fake. If we spend all our time trying to please someone it can also create major resentment. I don’t believe we can have healthy relationships that are built from people-pleasing.

How does people-pleasing behavior impact professional relationships?

I believe this is very similar to personal relationships. All strong relationships are built on mutual trust. Because people-pleasing often results in being someone we are not or doing something that goes against what we believe, it creates the opposite effect of trust. If I am leading a team, I want my team to have full trust in me. That means they can come to me if they disagree or have an idea that’s different than mine. People-pleasing is a rat race. It’s a vicious cycle that doesn’t create any real value or growth. I have been on a team where people were more focused on pleasing a leader than doing what they knew was right for the project. It creates friction, dysfunction, and ultimately unhappy employees and poor results.

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

I’m going to keep this simple. It hurts, and it hurts a lot. There is nothing worse than feeling like you will never be enough. Over time that is what people-pleasing does. It’s devastating to our self-esteem, self-worth, and to the relationships that matter most. It can lead to anxiety, depression, and isolation. We begin to believe whatever lies that the failure of our people-pleasing has created. When we don’t get the results we want we feel like we never will be enough. That is why it is so important to learn to disconnect other’s feelings about us from the ones that we have about ourselves. It’s not easy to do, but it’s very important for us to be able to live fulfilled lives.

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

It is everything! So often we know deep down that we are people-pleasing, but we want so badly to be liked or understood that we keep on doing it. We think, “If I accomplish this one thing then they will be proud of me,” or, “If I can just change this one thing about myself then they will love me.” It’s also one thing to be self-aware but another thing to make changes. So yes, self-awareness is important, but creating behaviors and habits to break the cycle of people-pleasing is crucial.

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. Ditch the Proverbial Box. Society loves the saying “Think Outside the Box”. A few years ago, I started to wonder why the heck does the box exist to begin with? So, my mantra is, “forget the box!” Throw it out. Never speak of it again. It was when I started living outside the nice box people wanted for me that I started to ruffle feathers and, in turn, my people-pleasing really kicked in. This doesn’t mean that we forget our values and morals, what it means is that we can become limitless in a society that wants us to fit into their own cozy and comfortable limits. Once we Ditch the Box it will make us less inclined to try and people-please and fit into the nice pretty box that everyone wants us to fit into.

2. Cherish those who Support You. This one is important. It’s vital to be taking care of the relationships in our life. People-pleasing not only hurts us and those we are trying to please, but it also hurts those in our life who already support us fully. I have seen this in my own life. I have spent many times and tears in my life trying to please others, while having the full support of my husband. He used to ask me, “Is my support not enough? Why do you need their approval?” At the time I would try and justify it, but over time I learned that he is right. I have so much support, so many people rooting for me and loving me just as I am. That is enough. Cherish those around you and express how much they mean to you.

3. Set Boundaries. We all know boundaries are important and in the world of people-pleasing it is no different. Often, people-pleasing comes from someone saying something about you behind your back or maybe gossip in your family or crowd. This goes back to being a peacemaker versus a peacekeeper. Sometimes it’s better to say nothing, but sometimes silence isn’t the best answer. In the past I have gone to people in my life and set very important boundaries. I have told people that while they might not agree with everything I do, I respectfully ask that they keep their opinions to themselves and not talk behind my back. This was NOT easy, and I wouldn’t want to do it again, but I haven’t had to because it worked. Another example could be going to your parents and expressing what you want to do with your life and asking that they support you even if it’s not what they had planned or expected. This creates the mutual trust that we discussed earlier. It’s so much better to get these things out in the open rather than harbor them inside, which often creates false narratives. End the cycle, be the brave one, and have the tough conversations that will make everyone’s lives so much better.

4. Be Confident in Who You Are. To care less about what people think, we must be deeply rooted and confident in who we are. So, we were misjudged, so what? So, they don’t agree with our decisions, so what? As I mentioned earlier, we are the only ones with direct access to our own hearts and souls. We must take responsibility for how we feel about ourselves and our actions and reactions. It’s a journey, it takes practice. When we are confident of who we are we can love others more easily. Even when people disagree with us. I believe this is a blessing to others. When we have grace for ourselves, we can have more grace for others. I am okay with people not agreeing with me or my decisions all the time. I didn’t always think this way, it has been a journey of self-awareness and building better habits. We should expect that people won’t always agree with us. Accept it, keep moving, and don’t explain yourself away to change it. This comes from confidence.

5. Be What You Want from Others. While last on my personal list, this one might be the most powerful technique of all. It’s less of a technique and more of a model to live by. In my opinion, we should model the behavior that we expect from others. As a mom to twin boys, I don’t expect them to behave or do things that I don’t do. If I want them to be kind, I better be kind. If I want them to keep their room clean, I better keep the house clean. You get the point. We can start to break the cycle of people-pleasing by creating relationships built on trust, openness, and love. Don’t judge others. Say no to gossip. Be kind. Be supportive. Be open about it. Tell people how proud of them you are. Tell them that you have their back. Don’t speak negatively about ideas or career changes that you don’t understand. I don’t want anyone living their life to please me, and it’s partially on me to make sure they don’t feel like they have to.

What steps should people pleasers take to establish healthier boundaries?

Love this question. I would recommend what I discussed in Step 3.

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

I think the first thing is to recognize that you aren’t a bad person if you are okay with not doing things that make everyone happy. To an empath who really longs to make everyone happy, this can sound counterintuitive. I believe we can go against what people want us to do but still lead with love and compassion. To me this is the key. Don’t be spiteful, don’t throw things in people’s faces, and don’t treat people differently. If someone disagrees with you be okay with it. Do not treat them any differently. Love them the same. If they treat you differently, it’s hard. Give yourself space, set those healthy boundaries, and give everyone time. Time is most often what stands between people not understanding and having their support. People-pleasing does not equate to loving someone. Once we start erasing this from our minds, we can move forward with compassion and be assertive when we need to be.

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

A common misconception, and one that I have experienced, is that people assume that we just want everyone to like us. While that sometimes may be true, most of the time it’s way more complicated than that. In my opinion, it doesn’t matter. What matters is that we acknowledge it, discover our own personal root causes, and take action to eliminate it. We must get rid of the stigma that surrounds people-pleasing, because if we are being honest, everyone has been there before. It also goes back to Step 5. We need to stop judging people-pleasers, it only makes it worse. Love, support, and kindness over judgement, always.

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

Therapy and counseling are so important! I believe therapy helps us to be more self-aware and it helps us see the scenarios wherein which we tend to people-please. Therapy can also provide tips and tricks on how to tangibly beat the cycle of people-pleasing by exploring the root cause. To truly beat the cycle of people-pleasing we must be willing to apply what we learn in therapy.

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. 🙂

This is going to sound cheesy, but it goes along with Step 5: Be What You Want from Others. How cool would it be if an “I Believe in You” campaign existed? Every single person on the planet has incredible strengths, talents, and ideas. What if the world was the kind of place that was safe for all of us to share ideas? What if we supported those ideas? With words of affirmation and encouragement, funds, and sharing connections, that could make the idea possible. People crave love and support. What if we gave it and gave it freely? It costs nothing to be kind, but the benefits are endless.

How can our readers further follow your work online?

You can find all the things at There are links to my new book, podcast, and other social links!

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

Thank you so much for the opportunity! These were great questions and made me go deeper on people-pleasing and the effects of it. Wishing you good health and continued success as well!

Kelley Rowland 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.