How to stop self sabotaging

This article was originally written for The Startup.

Street art near Brick Lane.

Street art near Brick Lane.

Self-sabotage is a confusing, seductive act.

For some of us, it’s overt.

We go sober for months, then binge drink every night for a week. We save up for a holiday, then blow it all on pointless crap. We meet wonderful, stable people, then push them away with an explosion of unwarranted vitriol. We skip town the night before an opportunity or don’t answer the phone when an important answer comes.

We extinguish opportunities and stamp out possibilities. We stand there, faces smudged with the ashes of what could have been, and secretly delight in the destruction.

For some of us, it’s subtle yet just as insidious.

We stay up a little too late, without any real reason to do so, then float, raw eyed, through the next day. We downplay achievements and leave details off our resumes. We don’t ask for help, then shoulder the consequences that leave us looking inept. We snap at friends, just often enough for them to drift away.

We backtrack on the little things and maybe we don’t know quite where the smoke is coming from, why we wake up choking in the night.

We blame ourselves. And we are to blame. But not in the way we think.


A few days before I met my partner, when we were still at the texting stage, he sent me an innocuous picture of a smiling cat wreathed in rainbows, accompanied by a message wishing me good luck with the day’s writing.

And my immediate response was to feel an overwhelming urge to delete his number and ignore him if he contacted me again.

The problem was not the text. The problem was that it made me suddenly realise I was going to like him. A lot. I knew going on that date would open up a Pandora’s box of emotions which someone who was genuinely caring. All of which would make it hard to follow my usual rules.

You see, I had all these rules about dating, carefully honed to maintain a distance from people. After my first serious relationship ended in a messy fashion, I detached for a long time. Even after that, I was determined not to ever put myself in a position where it could happen again.

Hence all the rules. Like not letting people I dated know my full name or read my writing, so they couldn’t learn anything about me I hadn’t told them. Or not staying over at anyone’s house if it were possible and frequently slipping out in the middle of the night. Or trying not to let them know where I lived or ever stay with me. I avoided kissing because it is the one type of physical contact that can never be devoid of emotion. The same was true of any sort of public display of affection. I didn’t talk about work in concrete terms. I was wary of sharing things I love, like Harold & Maude and Bright Eyes.

It wasn’t about trying to be mysterious or aloof. It was self-protection, which cost me dearly even if I didn’t realise it.

I didn’t want to change any of that. And then I happened to stumble upon someone who threatened all of it.


I nearly didn’t make it to our first date for the same reason. I was late, having spent a solid hour pacing around my room arguing with myself (and my mother and a friend) about whether I should go.

Ultimately, I decided to be polite and go for one drink. Even then, I was tense for the first couple of hours, a backwards flight instinct exacerbating my usual shyness.

When a coked-up multi-millionaire slammed his solid gold Rolex down on the table between us and commandeered the conversation for the next half an hour, I was relieved for the buffer, for the distraction that made it easier to hide my shaking hands.

Somehow, I kept pushing through despite the urge to ruin things on purpose.

For the first month, as we learned more about each other in increments, I awaited the moment when it would click, when he would realise I wasn’t who he thought, when he would uncover something unsavoury and vanish. The honesty was agonising.

At each vulnerability milestone — when he saw me without make-up for the first time, when I cried in front of him for the first time, when we talked about family and exes, when I shared my favourite music, when I started leaving odds and ends at his place, when I got us tickets to see Conor Oberst live — I braced myself for the backlash.

For whatever reason, I decided to let things play out, just this once, and I’m glad for that decision.

And we broke just about every rule in the first 24 hours.


I wrote in a previous post that I like to imagine each of us has a baseline level of self-esteem.

The actions we choose can bring us above or below that baseline. If we drop too low, we do things that make us feel better. I read somewhere that alcoholics consume more green tea than any other group which might not be verifiable but totally makes sense. Or how some billionaires give large chunks of their fortunes to charity.

If it rises too high, we get uncomfortable and self-sabotage. Only when we manage to sit with that discomfort for long enough can we raise our baseline.

We all know that discomfort. When things are going too well. When we achieve more than we could have hoped. When something seems too good to be ours.

Or as Adam Smith writes in chapter II of The Theory of Moral Sentimentsthe lesser known of his two books:

“Man naturally desires, not only to be loved, but to be lovely; or to be that thing which is the natural and proper object of love.

He naturally dreads, not only to be hated, but to be hateful; or to be that thing which is the natural and proper object of hatred.

He desires, not only praise, but praiseworthiness; or to be that thing which, though it should be praised by nobody, is, however, the natural and proper object of praise. He dreads, not only blame, but blame-worthiness; or to be that thing which, though it should be blamed by nobody, is, however, the natural and proper object of blame.”

Smith’s use of the word ‘lovely’ is different from our modern interpretation of the word; in the most basic terms, it means being deserving of love. Self-sabotage happens because we don’t just want good things in our lives. We also want to feel worthy of them.

When Smith writes that “Man naturally desires, not only to be loved, but to be lovely”, we can replace being loved with any number of good things; being happy, being healthy, being fulfilled.

We want these things, but only if we deserve them. Hence why those of us who struggle with self-acceptance can have such a hard time accepting any sort of praise or compliments.

Getting what we feel we don’t deserve is excruciating.

We panic and self-sabotage to assuage the accompanying guilt. Chasing what we want is an empty exercise if we won’t be able to live with ourselves if we get it.

I used to compulsively sabotage relationships (and still have to temper that instinct non-stop) because I couldn’t accept the possibility of another person feeling anything positive about me. The cat-and-rainbows text stung because it was a simple expression of kindness without any agenda. It was something beyond the usual perfunctory exchange of information and scheduling.


When we find ourselves self-sabotaging again and again, when we look backwards and spot the burnt-out matches scattered around the things that didn’t work out, we have two choices.

We can keep pursuing what we want and keep destroying it. We can ignore our own role in that and blame the world.

Or we can recognise that we don’t just desire these things, we also need to feel deserving of them. We can understand that we, as individuals, are not magically flawed and undeserving. In the end, we get what we think we deserve and the easiest way to improve things is to change our self-perception.

And when that discomfort hits, we can keep sitting with it. We can recognise our destructive impulses and focus on breaking the cycle.

So maybe it won’t work the first time. Maybe we’ll have to keep trying, keep spotting new discrete ways we get in our own way, keep looking at our lives from above to search for the self-inflicted obstacles.


That’s what I’ve been focused on lately: ending the cycle of self-sabotage.

It’s working. Bit by bit. I am happier right now than I have been for years. I have, in my biased view, the best job in the world; I learn interesting things, then write about them. I have a smart, stable, funny partner and I go on dates with cute people in various permutations. I live in a wacky old house in my favourite city in the world with ~24 people (plus miscellaneous animals) which is chaotic but never boring. (That’s not a typo.) I am in reasonable health, on good terms with my family, and financially stable. I have two exciting trips abroad and two concerts planned for the next few months.

It’s not all perfect. Yet there are moments when it’s hard to believe it’s real and that I feel very little guilt about it. An evening when my partner and I sat side by side writing Medium posts and drinking espresso martinis. A morning when everyone in my house was hungover and scraping together breakfasts and sharing coffee. Rampaging around Covent Garden with two people I’d just met one night, hugging strangers. Getting completely stuck into research in a beautiful library and waking up every morning looking forward to work.

So maybe the fear of it all collapsing and the slight struggle to keep it all in balance is scary. But I’m more aware than ever of the control I have over both what happens and how I react to it.


This post is a response to a question (‘how do I stop self-sabotaging?’) I’ve received via email and comments a few times lately.