People pleasing: the good and the bad
[P]eople pleasing [is] defined by Merriam-Webster as “having
an emotional need to please others often at the expense of his or her own needs or desires.”
By Meg McKeen, CIC
This edition of “Let’s Lead” was inspired by a recent conversation with a reader. Knowing I speak often about my own people-pleasing tendencies and knowing that their own people-pleasing tendencies are getting in their way right now, they asked me to share my thoughts—and my experience on the topic. As always, the ideas shared here aren’t intended to be mental health advice; and if it’s accessible for you, please seek the counsel of the appropriate professional(s) when navigating mental health challenges.
For many (ahem, me), people pleasing—defined by Merriam-Webster as “having an emotional need to please others often at the expense of his or her own needs or desires”—doesn’t begin at work. It’s a lifelong anxiety response.
As a young girl, I had a deep respect for authority figures: my parents (any parents), teachers, and nearly every other adult person I knew. They made the rules, and I followed them with above-average grades and a spot on the honor roll, free pizza rewards for perfect attendance, and impeccably good manners. When I dared to go against the grain, I wasn’t met with a celebration of my cleverness—just unpleasant consequences!
Early in my insurance career, this respect for authority looked like following the sales scripts provided for me by meeting the service deadlines set for me on time, or early, and doing more than was required, whatever “more” looked like on a given day.
Less than all 5s on my performance review, a less-than-everyone-else-got raise, and my bonus were on the line if I didn’t, right?
My career progressed and, as a leader, the authority figures in my life shifted to my direct reports (and my own boss) and, later as a producer, my clients and the carriers I represented.
We come by this honestly
In insurance sales, when a lead comes in, we are taught to be the first to respond. Drop everything and act on it. If you don’t, and even a second goes by, the moment will pass, and the prospect will move on.
In leadership, the [insert report name here] is due by the end of the week. No matter the myriad other aspects of the job you do that have consumed your energy and your time, the report must be done by the end of the week, and you must do whatever it takes to finish it.
The variable I could control every time? Well, that was me.
I could choose to skip a workout and stay late to perfect a proposal. I could choose to leave work last, feeling unsafe walking through a poorly lit parking garage. I could pick up that client call, even though I promised myself I’d stop talking and driving. And I could take a quick peek at the alert on my phone while my then-partner was telling me about his day— just this one time, of course.
I could do these things, and I did.
It’s not sustainable
For me, it wasn’t “the customer is always right.” It was “the customer’s needs are more important than mine.” I believed, just as I did as a child, that if I worked extra hard to keep those around me satisfied, no one would be disappointed in me, others would have no choice but to respect me, and no one would ever reject me.
These are tough words to share but, over time, those changed plans and disappointments became the roots of resentment that, like a weed, continued to grow.
The late nights at the office became the wonky sleep schedule that became brain fog, and the fires of burnout began to ignite.
And the pile of “just one more things?” As much as I thought I could prevent it, eventually it would topple.
After the stringing together of many seemingly mundane and a few quite significant life experiences, it became exceedingly difficult to sustain this misalignment in the way I was showing up in my work— and for myself.
It was true for me that the first step towards change was the hardest, and acting in a way, even if I didn’t yet believe it, that my needs were as important as anyone else’s felt selfish, irresponsible, even mean. And a people pleaser doesn’t want to be any of those things!

Baby steps still count
The notion of choosing yourself first is heavy and counter to what is fundamental for a people pleaser, but it’s when the journey toward change truly began for me.
Sharing below a few more ideas for you to consider as you explore your own experience as a people pleaser:
- Manage your inputs. I’m on what sometimes feels like a life-long journey, evaluating my relationship with social media. If you’re like me and find yourself “doom-scrolling” or comparing yourself, your life, or your career to others, maybe it’s time to take a pause. Even a 24-hour break from the apps can help you re-center.
- (Practice) say(ing) no. I say practice because this is hard! The reality is that authority structures still exist within our organizations and as employees, to a certain degree you are beholden to them. But can you be professionally rebellious as you set and then test your limits and establish new boundaries with those around you?
An impactful way to check in with yourself before you respond to an ask of your time or energy? Is this a decision that “future me” is going to be happy/proud/satisfied I made?
- Ask yourself ‘What can I do?’ If someone is asking for your attention seconds before you’re switching gears, instead of changing your plans to accommodate them, let them know what you can do instead. I’m headed out for the day, and I can have that report for you tomorrow before noon.
I suspect you’re thinking to yourself: Sure, but if I don’t do it now, I’ll just be thinking about it from now till then, so I might as well get it done now. A gentle reminder that this is the place where resentment grows—conceding your needs for another’s—and it can feel illogical, and even uncomfortable, as you learn this new behavior.
- Set realistic expectations. Gradual changes are more likely to stick, so now is not the time to overhaul all of your self-proclaimed “bad” habits. You may identify as a people pleaser for the rest of time, but you can make small, incremental shifts that over time help you to show up in a more aligned way.
- Watch for the doormat. My partner is good at, with affection, calling me on my people pleasing behavior, reminding me that my desire isn’t to be a doormat. Old habits die hard, and accountability is helpful in so many areas of our life, and it’s helpful here, too. Can you lock arms with someone who is also on their own journey to hold you accountable when your own doormat tendencies creep up? And can you offer the same support to them?
A note to leaders
In many ways, people-pleasing behavior benefits our organizations—and often you. More work output from an individual can shave dollars from your bottom line. But the hidden costs of resentment, overwhelm and burnout can be a hit to your bottom line, too.
If you are the leader of your team or organization, you are in a unique position to affect cultural change; and it’s worthwhile to identify those on your team who might identify as a people pleaser, offering support as they journey towards change.
The person to please is you
I believe you are a treasure in this industry and a treasure in this world; and though changing your people-pleasing tendencies can feel tedious and frustrating, it’s worth it. You are worth it.
If this topic resonates with you, I encourage you to revisit past “Let’s Lead” columns on delegation, anxious leadership, and boundaries.
The author
Once told “you’re someone I’d like to receive bad news from,” Meg McKeen, CIC, founded Adjunct Advisors LLC in 2018 with the simple belief that we can and must do more to support the individuals who choose a career in the insurance industry. Now in her 25th year, Meg’s experience working in underwriting, leadership, and sales within the industry informs her work as a consultant today, in which Meg now holds space, at the crossroads of personal and professional development, for insurance professionals as they navigate their shifting relationship with work and this current hard market. Meg’s work includes private and small group coaching, workshop facilitation, industry event speaking and planning engagements, and the podcast she hosts, Bound & Determinedsm. Learn more at www.adjunctadvisors.com.