Don’t let a job break your heart

Don’t let a job break your heart

Don’t let a job break your heart

Is bias sabotaging your work life?

This article was inspired by heartbreak. Except in this scenario my ex is an agency and the break-up happened in the form of a contract that wasn’t extended.

I started calling it a heartbreak when my compulsive stalking behaviour struck me as oddly familiar. You know how in a post break-up manner you might find yourself lurking on your ex’s social media accounts? That was me, systematically and shamelessly checking my ex employer’s website, blog and LinkedIn page during the first months that followed our separation.

I wanted to know what they’ve been up to. I wanted to see what cool projects I’ve been missing out on. Like a good masochist I wanted to add insult to my injury.

Clearly, I haven’t moved on. What I needed is closure. And my way of healing from any kind of break-up, professional or personal, is by turning pain into insight.

It’s not you, it’s me

Luckily there’s no “new girlfriend” to compare myself to. I have not been replaced and I don’t think I will be. But this didn’t ease my obsession, instead it only seemed to feed my “you were supposed to be the one” narrative.

We were a match made in heaven. On paper this position seemed to fit me like a glove. I remember reading about it and thinking: this is it. But for many reasons, which will not fit in one article, we were also a match made in hell.

Like the majority of challenging relationships we recreated the infamous trinity of bad communication, unmet needs and unrealistic expectations. And like with any dysfunctional dynamic, I had to step out of it to realise how much damage it had done to my self-esteem.

It takes distance to have a full perspective. And now that I’ve had time to reflect back I’m ready to own my part.

The truth is, I took this job against my own intuition. I had spent months planning and preparing for my next career move. I read article after article about company culture. I compiled lists on the kind of job I wanted and the kind of employer I wanted to work for. I did one hell of an expensive training to push my career forward. I developed an intricate plan for where I saw myself in the next couple of years. But it all went down the drain when I met my ‘bad boy’.

The irrational ex-girlfriend

So what went wrong? The answer now seems so simple: flawed design. Let me explain.

An interview is nothing more than a dance of seduction where everyone is on their very best behaviour. We desperately want to be liked, so we dress nice, smile a lot, and say things that are not necessarily true. It’s human nature.

And I knew this, because I’m interested in and have been trained in understanding human behaviour. So I designed my own process to sift through the bullshit. But my design was completely centred around my future employer.

Behaviour science had taught me that “The best predictor of future behaviour is past behaviour”. So in addition to the usual small talk, I asked my potential managers about how they handled certain situations in the past instead of buying into their aspirations and plans for the future. I also took note of their possible cognitive bias. My plan was to notice when they were sounding overly confident about something without providing any concrete proof, and then to challenge their self-assurance. I did everything by the book. Meanwhile, I failed to hold myself to the same standards.

The only way for me to ensure that I was making sound and rational decisions, in a realm that triggers so much false behaviour, was by designing a process that also takes my own irrationality into account.

In simple speak, what I needed was a mechanism to protect me from my own biases and faulty judgements, not just theirs.

Illustration by Fiamma Degl’Innocenti

Love at first sight

When we enter the domain of decision making we’re rarely prepared to see the truth. Instead most of the time we see what we want to see. Our brain is an association machine. In an attempt to be helpful it’s constantly trying to give us more of the information we already have. This is known as “confirmation bias”.

For example: Maybe you’ve looked up your future manager on LinkedIn before the interview, found out what kind of college they went to and it’s a school you admire. And you have this pre-existing belief that everyone who goes there is talented and hardworking. When you meet this person your confirmation bias will start doing its job to prove your hypothesis right.

For all you know, this person could have partied their way through school, barely graduated and then gotten this position through good connections. But instead you will fall into the false belief that they are hardworking and admirable because they went to that school. Maybe there were signs of their true nature at the interview, but your brain was too busy connecting the dots elsewhere. And you could get lucky, or you might end up working for someone incompetent.

Another bias that comes to life during interviews is the “halo effect”. Something as simple as a pair of glasses or the person’s bone structure could trigger a list of false assumptions about their leadership style. It could have you believe that they are more intelligent or empathetic than they truly are. And you don’t know why, but you might leave the meeting feeling like you could really trust that person, a judgement that is grounded in no real evidence.

My ‘bad boy’

When I stalked my ‘bad boy’ the night before my interview I noticed that he had been working for that company for a while. I figured that’s what dedication looked like (confirmation bias). And he did seem devoted, he had that passionate stare thing going on when he talked about serious topics. The details of which I don’t remember because I was too focused on his strong jawline, which reaffirmed that he must make a good leader (halo-effect).

But my ‘bad boy’ also made remarks that made me feel uneasy. He described my work as “quiet and clean” like it was a shortcoming. He also made condescending remarks about the culture of UX, even though I had told him that this is what I was headed towards in my career. But I wanted to be liked by him, because he worked for an agency that had the name of that one designer I admired since college (halo-effect).

Fast forward a couple of months later and I’m working for someone who can’t mentor me in the areas I want to grow in. Turns out we’re very different people who want very different things. And it was all right there in front of me, I just had no way to filter through my own bullshit.

These are just two unconscious bias that wreaked havoc on this particular career decision. And although it’s nearly impossible to be 100% unbiased, I do think it’s possible to catch yourself before you make a final judgement.

It’s what’s inside that matters

If you’re already familiar with the topic of cognitive bias then you probably know they’re there to ease the cognitive load of decision making. They’re shortcuts designed to drive behaviour by triggering an emotional response, which in turn masks itself as a rational thought worthy of driving a decision. So between every bias and decision there is also an emotional reaction. And that, if properly harnessed, can become your guiding light.

Educating yourself on cognitive bias is step one. Accepting that you are capable of irrational decision making, just like every other human on this planet, is step two. And flagging emotional triggers before they develop into decisions is the last and most crucial step.

This is why I developed an internal red-flag handbook for interviews. To keep things fun, but not any less serious, I will be using dating analogies. Since what we’re ultimately trying to avoid here is heartbreak.

Red flag 1: You want to impress them

Some persuasion masters might try to convince you that there is nothing wrong with a bit of smoke and mirrors. Others might even teach you how to use the halo-effect to your own advantage. I, however, am an advocate of authenticity. There is nothing more destructive than building a relationship based on illusion and the false promise of perfection.

Why? Because while you’re going about your seductive dance, your potential employer is falling in love with the fantasy version of you. Once they’ve committed to you, you’re going to have to spend the rest of your time together being the false self you presented at the beginning. And because being seen as perfect is a full time job on top of your full time job, this could get exhausting fast.

So if you notice that you’re being triggered into presenting a false-self, or wanting to be perceived as perfect, stop and reconsider before you set yourself up for failure and misery.

Maybe this is your confirmation bias reaffirming that you’re not good enough to protect you from failure. And your strategy/coping mechanism is to over impress and over deliver. I don’t know your demons personally, but this is definitely the case for me.

So you caught yourself getting triggered, good job. Now step away from the theatrics and try sharing something authentic instead, something real and vulnerable. Maybe share about how nervous the interview is making you. Or tell a story about a project that went sour from which you learned nothing but how to recover from failure. It’s terrifying to be real, but it will also foster real connection.

If they don’t respond to your vulnerability it could be that they’re driven by a culture of perfectionism, so you might have dodged a bullet. And if they do hire you or ask you out on a second interview, it will be because they liked you for who you are and not who they think you are. So in a sense, your authenticity can also challenge their bias about you.

Illustration by Fiamma Degl’Innocenti

Red flag 2: You can’t stop thinking about them

But surely this is a good thing? Doesn’t it simply imply that you’re excited? Or maybe this is a sign that the job is ideal for you, which in turn is making you nervous?

That’s what I thought too.

For a while I believed that I was simply passionate, and cared so deeply about my job that I just couldn’t get it out of my head. And generally speaking there is a thin line between passion and obsession. The difference between the two is that passion is about free will, you can have control over passion. Obsession, however, is about compulsion and the illusion of being in control.

So if you can’t stop thinking about your upcoming interview, or if when feeling anxious you catch yourself compulsively stalking future colleagues on LinkedIn, or lurking on the company’s website, or constantly checking your inbox for updates, there’s probably something unconscious at play.

It’s good to be informed and prepared for your interview, but there’s a limit to how much information you actually need. This emotional and behavioural response could be a sign of much more compulsion to come.

For me, compulsive and controlling behaviour is always rooted in some kind of false belief about myself. And confirmation bias feeds false beliefs. It will keep you looking for evidence to reinforce what you already believe in.

If you notice yourself falling into obsession and compulsion ask yourself: what am I trying to control here? And why?

Sometimes what I’m trying to control is the thought of a job being too good for me and how awful it’s making me feel. That’s why I no longer apply for positions that make me feel insecure about myself. I don’t see it as lack of ambition. What I’m trying to prevent is ending up at a job where I’m constantly trying to prove my worth. Been there, done with that.

Red flag 3: You’re always putting yourself second

Did you say yes to an interview even though it’s at an inconvenient time? Did you use money you don’t have to buy an outfit you can’t afford? Did they ask you if you could split your time between their two offices, and you know in your heart that this would wear you out in a couple of months, yet you’re still considering it?

A healthy and equal relationship is one where the comfort of both parties is taken into consideration. And I refuse to believe that professional relationships are any different. Here too your well-being starts with you setting your own boundaries and then not crossing them.

So if you are being triggered into putting yourself second, check your beliefs and bias about hierarchy and power dynamics.

Maybe you believe that you’re not in a position to say no to a future employer because they’re the ones with all the power. Or that it’s up to them to set the rules and for you to simply follow. Or maybe you think that you should never make the people in charge feel uncomfortable. Whatever you believe will set the tone for your future relationship dynamics. Remember, beliefs drive behaviour.

If for example you don’t want to make anyone in charge feel uncomfortable then you’re in for treat, because people get uncomfortable A LOT. You might make your employer uncomfortable by asking for a well deserved promotion for example. But at that point they’d already know that their discomfort could make you change your mind. They won’t even have to talk you out of it, all they’d need to do is sulk a little.

It’s good to be flexible, but having a spine can come in handy too.

So challenge yourself, try being assertive by setting boundaries early on. It will build the foundation for the kind of relationship you will end up having with the ones in charge. In the words of the iconic couples therapist turned workplace relationship expert Esther Perel: “As any parent of a 2-year-old knows, power can come from the weaker party”.

Illustration by Fiamma Degl’Innocenti


As long as we have human brains making human decisions for us, the process of finding a new job will never be completely rational.

I started working on this article in anticipation of my new job, and I have no idea where it will take me. During the interview process I did my best to learn from my past mistakes and to follow my own advice. I was honest, vulnerable, and I respected my boundaries. But you never know.

What I do know is that relationships of any kind require work. There’s inner work and then there’s the work you do as a team. I’m only one half of the puzzle.

I also know that getting my foot through the door is just the beginning. There will be more bias to challenge, and more unconscious and destructive patterns lurking in the background. So I will carry this internal red-flag handbook with me daily, because that’s my only safe bet against the biggest breaker of my heart: myself.