The Pleaser Tax
On the cost of keeping the peace and learning to trust yourself
For years, I thought one of my strengths in business was my ability to see the best in people. I could understand where someone was coming from. I could see their potential. I could find reasons to give them another chance, extend another deadline or have one more conversation before making a difficult decision.
I told myself it was empathy.
And sometimes it was. But sometimes it was people-pleasing dressed up in a more justifiable outfit.
I’ve been thinking about that a lot lately because a situation I thought was long behind me has found its way back to my doorstep. The details aren’t important and, if I’m honest, they’re not really the point. What it has done, though, is force me to revisit a pattern I’ve repeated more times than I’d care to admit.
A pattern where I knew something didn’t feel right.
That knot in your stomach that you’ve been trying very hard to explain away. The one that keeps showing up at inconvenient moments, usually when the rest of the world goes quiet and you’re left alone with your own thoughts.
Looking back, I rarely struggled to see the issue. What I struggled with was believing myself.
Instead of treating that discomfort as information, I’d immediately begin building a case against it. Maybe I was being unfair. Maybe I hadn’t understood properly. Maybe they were having a difficult time. Maybe I was expecting too much.
If someone else had come to me describing the exact same situation, I would have spotted the problem immediately. But when it’s your own situation, objectivity has a habit of packing its bags and disappearing.
So I’d look for more evidence. I’d ask for more opinions. I’d explain the behaviour from every possible angle until I could barely remember why it bothered me in the first place.
I’d give another chance.
Then another.
Then one more for good measure.
Because what if this time, I was wrong?
From where I sit now, I can see the fear was never really about getting the decision wrong. It was about disappointing someone, creating conflict or being seen as the bad guy.
There’s a discomfort that comes from accepting a reality you don’t want to be true. Especially when that reality involves another person. Because once you acknowledge what’s happening, you’re usually required to do something about it.
And doing something about it often means creating tension. You have a difficult conversation. You decide where a boundary sits and then you enforce it. Sometimes you have to say no.
I’ve realised over the years that I have a very strong preference for harmony. Most people probably do. Given the choice, I’d much rather have a pleasant conversation than a difficult one. I’d much rather leave everyone feeling understood than disappointed.
The problem is that reality doesn’t seem very interested in my preferences. I’ve noticed that every time I’ve avoided a difficult conversation, the conversation has eventually happened anyway. It just showed up later, with interest.
That’s the part nobody talks about enough.
The cost attached to postponing things we already know.
Not a financial cost, although sometimes resulting in that too. But initially it’s more like an emotional surcharge. The longer you spend explaining away your own concerns, the more energy it takes to untangle them later.
I’ve paid that tax in business.
I’ve paid it in relationships.
I’ve paid it in projects I should have abandoned sooner and opportunities I probably should have pursued earlier.
The common thread wasn’t that I lacked information. It was that I lacked trust in my own interpretation of the information. Somewhere along the way I developed the habit of assuming everyone else’s perspective deserved more weight than my own.
Which is strange when I think about it like that.
I’ve built businesses.
Raised children.
Managed teams.
Made decisions with consequences far larger than most of the situations that kept me awake at night. Yet somehow I could still find myself treating my own instincts like an unreliable witness. And I don’t think that’s uncommon.
The older I get, the more conversations I have with people who tell remarkably similar stories. Different circumstances, granted. Different industries. Different personalities.
But the same pattern.
They knew. They noticed something didn’t sit right. Then they spent months or years convincing themselves it wasn’t what it appeared to be.
Maybe that’s because instinct gets romanticised as some magical force when it’s often much more ordinary than that. Sometimes instinct is just pattern recognition. Your brain putting it all together before you’ve consciously assembled all the evidence.
That doesn’t mean instincts are always right. Mine certainly aren’t. But I’m beginning to suspect, and trust, they’re right more often than I gave them credit for.
Now that shift for me, thankfully, hasn’t been towards cynicism. I haven’t become someone who assumes the worst in people. I still believe most people are doing the best they can with whatever is going on in their world.
But what has changed is that I’m becoming less willing to explain away my own feelings and reactions in order to preserve someone else’s comfort. Those two things aren’t actually opposites.
You can be kind and still pay attention to what you’re seeing. You can be empathetic and still have boundaries. You can understand why someone behaves a certain way without accepting the consequences on their behalf.
That distinction has taken me an embarrassingly long time to understand. Over 30 years in fact. Or maybe I’ve understood it for years and am only now starting to practice it. I’m not entirely sure which is true.
What I do know is that I’ve spent a lot of time wondering why certain situations became so complicated, only to realise later that most of the complexity arrived after the moment I first recognised something wasn’t right.
The initial signal was usually pretty simple. It was everything I added afterwards that made it messy.
If this struck a chord, Richard and I explore these sorts of questions every week on the Richly Told podcast. Business, family, travel, leadership and all the complicated bits in between.
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