How I Learned to Live With, Manage, and Love (Sometimes) Being a People Pleaser.

Let me say here at the outset: I’m intimately familiar with the harm this personality trait can cause, both to oneself and others. It’s something I live with every day. I am a certified, diagnosed (literally—by my therapist), card-carrying people-pleaser, and I’ve been one for as long as I can remember. I’ve lived through its curses, but I’ve also come to appreciate its gifts.

I’m writing this blog post to remind myself and others who struggle with this particular issue that people-pleasing is not something to be purged. It’s something to be understood, not shamed; nurtured, not suppressed; and disciplined, not punished. Too often, I’ve watched friends convince themselves to shame, suppress, or punish personality traits baked into their nature because of the negative consequences resulting from them. This, I’ve found—without exception—does more harm than good. And I’m a firm believer that most of these personality traits have a beneficial side as well. Every gift is a curse, and every curse is a gift. And beyond all of that, it’s these imperfections that make us who we are, that make us human.

I’ve included in the post a photo that may seem unrelated to the subject matter. I assure you it is very much related. But I want people to read through the whole post first so that its significance really sinks in. So, I’ll explain at the end.

I’m going to talk a lot about business in this post, because that’s what I spend most of my time doing. But definitely, most of these impact my personal life as well. So, here are the five ways I’ve found, in my life, that being a people-pleaser is not only manageable but can actually be a superpower.

1. Trust

Being a people-pleaser means that you are constantly on high alert with regard to other people’s feelings. You often notice the smallest shifts in behavior or subtle changes in mood. This can be challenging because these interpretations aren’t always on point but usually are. And it can also be challenging because the feelings you’re picking up on may not be entirely relevant the moment you catch wind of them. The superpower here is that, in my experience, this ability makes people trust you very quickly. While that’s a huge responsibility, it’s also a major asset, especially in business.

When trying to build something new or innovative, the ability to establish trust quickly is invaluable and powerful. But of course, with great power comes great responsibility. The ability to gain someone’s trust so quickly must be handled with care. You have to balance it with a deep sense of integrity and a desire to benefit people who put their trust in you.

2. Everyone’s Opinion Counts

A people-pleaser’s sense around others’ feelings makes us want to make sure everyone feels heard. We’re incredibly open to feedback, willing to listen to criticism, and sincerely interested in everything everyone has to say. In business, this can be a huge advantage. While this may slow some things down, when you value making sure everyone feels heard, you become receptive to ideas from all corners. Anyone who’s run a successful business knows that some of the best ideas come from the least expected places.

This trait also helps foster a work environment where people feel empowered to share ideas, knowing they’ll be heard. While too much feedback can sometimes result in “too many cooks in the kitchen,” the fundamental trait of wanting to listen and learn from others is a major asset in both personal and professional relationships.

3. Spotting Evil-doers

One of the more challenging but powerful aspects of being a people-pleaser is a heightened ability to sense when someone isn’t being forthright or has ulterior motives. This is really, really hard in our personal relationships, as we end up trusting very, very few people—not realizing that most people aren’t pure in their motivations, and that’s just something to balance.

In business, however, this ability is a massive asset and can help you quickly weed out those who may negatively affect your organization. The challenge, similar to that with personal relationships, is understanding that everyone doesn’t need to be purely sincere in business; they just need to be committed. People can have mixed motives but still be a net positive for what you’re doing. It’s all about balancing this sensitivity without expecting perfect purity from everyone you work with.

4. Spotting Trends

Being highly attuned to others’ feelings has, on many occasions, allowed me to see trends developing in the marketplace long before others do. Colleagues have told me that my ability to predict these shifts and developments is remarkable. When you view the world through a lens of human behavior, emotion, and motivation, you tend to notice subtle but significant changes that can signal much larger trends.

It’s this deep focus on human behavior, rather than just data, that allows people-pleasers to spot opportunities and shifts in marketplaces before they become apparent to others. While others are focused on analytics (which are equally important), we often see the emotional undercurrents that indicate bigger developments on the horizon.

5. The Urge to Say Yes… to Everyone

There’s a Mike Tyson quote that I love about this: “If you say yes to everyone, you’re saying no to yourself.” This couldn’t be more true, and this aspect of being a people-pleaser is perhaps the most dangerous and difficult to manage. We really, really, really just want to say “yes” to everyone. No matter who asks, no matter the request, there’s always that nagging need to agree, to help, to get on that advisory call, to catch up over coffee (big problem for me), to attend the wedding, the anniversary, the birthday, the baby shower—the list goes on and on. It’s a recipe for disaster. Saying “yes” to everyone means you’re bound to burn out yourself and bum out your friends/colleagues.

And yet, this very trait is also a massive, huge, unbelievable, magical asset that I really cannot overstate.

Many of the relationships—maybe most or all—that have driven my career forward started with a favor I offered without expecting anything in return. Some of those relationships later turned into pivotal connections that I was able to rely on when I needed help. But just as often—actually, definitely more so—nothing ever comes of them, and you have to be happy with that. You got the opportunity to help someone, and that’s amazing.

All of that said, it’s important to balance this urge. Don’t let the fear of burnout stop you from extending a hand when you genuinely want to, and don’t be so afraid of disappointing someone you don’t know well that you end up hurting the people around you who matter most. The key here, like the rest, is learning to manage this impulse rather than suppressing it altogether.

The Big Picture

So now, about the photo. Let me tell the story. I had a flight not so long ago to the 2023 World Arabic Coffee Competition in Abu Dhabi, courtesy of the Ministry of Tourism, who flew me out in business class. Most of the passengers were asleep, but I was awake, having slept earlier to adjust my sleep schedule to UAE time—something I always do when traveling internationally. To pass the time, I wandered over to the bar area (yes, the business class had a bar area fully equipped with a bartender) and struck up a conversation with the flight staff. One was from Egypt, the other from Russia, and they started sharing bits of their lives and stories with me.

I love talking with people in service because I spent a lot of my life in that industry myself. I know how easy it is for people to overlook you, treating you as part of the background rather than engaging with you as a person. I always try to make a point to connect with them, as I would have wanted when I was in their place. As we were chatting, one of the passengers overheard our conversation and recognized me—turns out, he was a Port of Mokha subscriber. What started as a casual conversation quickly turned into an impromptu coffee brewing session at 30,000 feet.

Luckily, I travel with my coffee gear (of course). So, I pulled out my hand grinder, my V60 pour-over kit, and a little scale I always carry with me. But there was one problem—I didn’t have filters; they were in my checked baggage. We got creative and used a napkin as a makeshift filter. The crew, the passenger, and I all worked together to make it happen.

Soon enough, we had brewed a fresh cup of Yemeni coffee right there in the sky, and once the coffee was ready, we all shared it together. They all said it was the best coffee they’ve ever had. All of us, laughing, sharing our stories, and drinking coffee, inaugurated the Port of Mokha Mile-High Club.

So, this is the point I want to make. I love this part of myself. It actually might be my favorite part of the person I am. People-pleasing in some ways means you love to please people. You love to make people happy. In this instance, it wasn’t about seeking approval or avoiding conflict; it was about creating connection and sharing something meaningful. Despite the challenges, being a people-pleaser comes with its own deep rewards—joy, connection, and the ability to bring people together, even in the most unexpected places.

I’m not a psychologist and certainly don’t pretend to be. I’ve actually never even read a book on people-pleasing (maybe I should); these are just observations from my own life. I hope that those observations resonate with those of you who share this trait. If people-pleasing has had a significant negative impact on your well-being, I encourage you to seek professional help. Counseling has been a godsend for me, and I couldn’t recommend it more. Many of these traits stem from childhood trauma (definitely the case with me), and a good therapist can help you uncover and understand that. Just identifying it—shining a spotlight on it under the care of a professional—can have a profound effect.

I believe this advice applies to many of the tendencies we struggle with. When being critical of yourself and trying to improve, always ask: “What aspect of this quality do I love about myself? What’s the other side of the coin?” If we do that, I think we’ll be healthier and happier in the long run.

I’d love to hear your thoughts—but please, don’t ask me for a phone call, because I’ll say yes! (Maybe).