Could "Doing the Right Thing" Actually Be Self-Sabotage?

Why the choices that feel most right can do the most damage.

Part I of IV

Some of the most damaging choices we make in relationships are the ones we’re absolutely convinced are right.

We make sacrifices. We keep our promises. We protect people from painful truths. We stay because leaving would hurt someone. We leave because staying might hurt us.

And sometimes those are exactly the right choices.

Other times, we’re sabotaging the very things we’re trying to protect. And the worst part is that we may have no idea we’re even doing it.

I’ve been on all sides of self-sabotage. I’ve been the person doing it, hurting myself and others despite never intending to cause harm. I’ve watched people I love do it and seen the damage they brought on themselves. I’ve also been on the receiving end of others’ self-sabotage and been profoundly hurt by it. I’ve been changed in ways I did not want to be changed.

There’s a particular kind of heartbreak in watching people damage the things that matter most to them while trying so desperately not to. There’s a powerlessness in it that can drive you mad. The fact that our broader Comfort Culture so often encourages the very choices doing the damage makes it even worse, but that’s another book entirely. (Coming soon!)

I’ve spent more than ten years studying fear, shame, attachment, trauma, and their impact on our relationships, including my own. And one thing has become increasingly clear: we’re not nearly as good at recognizing self-sabotage as we think we are.

This is because it doesn’t look or feel the way we expect it to. What’s worse is that we think we’d know it when we see it, making it easy to dismiss anything that doesn’t fit that image.

Ask most people what self-sabotage looks like and you’ll get a familiar list. Picking fights. Pushing people away. Ghosting. Blowing up something good. But some of the most damaging versions don’t look like sabotage at all. They look like loyalty. Being supportive. Keeping the peace. Being the strong one. Making the responsible choice. And everyone involved can usually explain exactly why they’re doing it, and the explanation makes sense.

When we do notice, we tend to reach for a label. Toxic. Avoidant. Selfish. Needy. Dramatic. Labels feel like understanding, but they’re usually where understanding stops. They tell us what someone did, and maybe what kind of person we’ve decided they are. They don’t tell us why perfectly intelligent, loving, decent people keep doing things that ultimately wreck what they care about most.

Much of the time, though, we don’t even see anything that needs explaining. We see someone making what looks like a perfectly reasonable decision, and we accept it. Why wouldn’t we? Nothing appears to be wrong. It doesn’t even occur to us that there might be something to question.

But someone else may be living with the consequences while nobody around them sees anything wrong. Their attempts to make sense of what’s happening can be dismissed as overthinking or reading too much into things. And when no one looks any deeper, the self-sabotage goes unrecognized and the damage continues.

That’s why I’m writing this book. We need to look deeper than the visible behavior and think about what might be driving it. That’s not overthinking, it’s critical thinking, and we need to do more of it.

Look underneath the behavior. Underneath the explanation. Underneath the label. Underneath the certainty.

Then ask yourself: what is this person, or what am I, trying to protect?

If you’re willing to look that closely, behavior that seems irrational starts to make a terrible kind of sense. That isn’t the same as excusing it. Understanding why someone did something doesn’t make it okay, and it doesn’t mean anyone has to keep absorbing the cost. But you can’t interrupt a pattern you can’t see.

And recognizing these patterns isn’t about judging people, either. Most of us have made choices that seemed perfectly reasonable at the time and later realized we got something terribly wrong. The point isn’t to shame anyone for what they didn’t understand. It’s to help us understand it before we do it again.

No one can make their past unhappen, but understanding how this all works might help us find our way out of our own shit, or perhaps never get into it in the first place.

We’re not going to stop sabotaging the things that matter to us by getting better at identifying red flags. We have to get better at recognizing the behaviors that hide in plain sight.

What you’ve just read is a glimpse into Part I of my upcoming book, A Human Guide to Being Human: Self-Sabotage. It’s where we challenge what we think self-sabotage looks like and why we so often fail to recognize it.

But recognizing it is only the beginning. Understanding why we do it, who ends up paying for it, and what we can actually do about it is where the book gets interesting.

Over the next few weeks, I’ll be sharing a preview of the remaining three parts:

• Part II: It Made Sense at the Time | Why we believe in our choices even while they’re hurting us.

• Part III: Someone’s Gotta Pay for This | Who ends up paying, and why the price keeps going up.

• Part IV: Now What the Hell Do I Do? | How to recognize when you’re doing it and why repair still matters even when it can’t change anything.

My hope is that by the end of this series, you’ll start noticing things you might never have thought to question before. Not just in other people’s behavior, but in your own. Because some of the choices worth examining most closely are the ones we’re most convinced we got right.