Should I quit my job? Questions that tell you more than a list of pros and cons

“Every morning I sit in the car park for another five minutes before I go in.”

That is how someone once described their working day before it had even begun. Five minutes in which he doesn’t look at his phone or listen to the radio, but simply sits and gathers the strength to open the door. At home, on his computer, there is a document with two columns, “for” and “against”. He has opened it many times. The columns are almost the same length, and every time he closes it he is more tired than before.

If you recognise yourself in this, I am not writing to tell you whether to hand in your notice. I don’t know — and nobody who doesn’t know you can know. What I would like to show you is why a list of pros and cons so rarely helps with a decision like this, and which questions tell you more. I will look at it through the systemic lens I am training in: a workplace, much like a family, is a system with roles, alliances and unwritten rules. And the decision whether to leave it is never purely your private business — even if, in the end, you make it alone.

Why a list of pros and cons isn’t enough

A pros-and-cons list works well for decisions where things are comparable: two flats, two offers on a car. When you are deciding whether to resign, though, you cram things into the same column that have no common measure. “Good salary” and “every Sunday evening my chest tightens” are not two items on the same scale. One is a fact, the other is a message.

The second reason is that both columns are true. When you are in doubt, you want to leave and to stay at the same time — and both wishes are genuine. We call this state ambivalence. It is not a sign that you haven’t thought hard enough. It is a sign that you care about several things at once, which this time happen to stand against each other. A list doesn’t resolve ambivalence; it just tidies it neatly into two columns.

The third reason is less comfortable. When we think about a decision for a long time, the thinking itself can become a way of avoiding it. I wrote about this in Decision paralysis: when thinking it over becomes a way of avoiding. As long as you are writing the list, you don’t have to decide. And as long as you don’t decide, you don’t have to face the loss that any choice brings with it.

What a coin toss reveals

The economist Steven Levitt ran an unusual experiment. On a website, he invited people who had been agonising over a decision for a long time to flip a coin, which a computer tossed for them. The decisions varied, but among the important ones, “should I quit my job” and “should I end my relationship” came up often. Nobody forced people to follow the coin afterwards. But the coin nudged some of them in the direction it pointed.

The finding, published in 2021, was surprising. For important decisions, those whom the coin “told” to make a change, and who then did, were on average happier six months later than those who stayed with the status quo. Levitt cautiously concluded that we may be overly cautious when facing major life decisions.

Please don’t read this as advice that resigning always improves your life. The experiment wasn’t designed to prove that, and an average says nothing about you. It does say something else, though: that we are pulled towards the existing state of affairs by a force stronger than reason. Decision researchers call it status quo bias. What already exists feels safer simply because it is already here. And when the two columns seem equal, it is often because the “stay” column secretly carries a little extra weight.

Thomas Gilovich and Victoria Medvec showed another side of this. When people look back over a short period, they regret actions more — the things they did that didn’t work out. When they look back over a whole life, they regret more what they didn’t do. That is not an argument for leaving. But it is a reason to include in your thinking the question of how you will look back on this period in ten years — there is an entry on regret in the knowledge base.

A workplace is a system

In systemic therapy we see the family as a whole in which every member carries something — one is the peacemaker, another the rebel, a third the one everyone relies on. I wrote about how a change in one person moves everyone in The family as a system: why one member’s change moves the whole family. A workplace is not a family, but it works by surprisingly similar rules. There, too, there are roles that nobody handed out, alliances nobody talks about, and triangles in which the tension between two people spills over onto a third. That last pattern has a name: triangulation.

When you are thinking of resigning, it is therefore worth asking whether you are leaving a job or a role. Perhaps the work itself doesn’t bother you; you are tired of being the one who puts out fires, mediates between the boss and the team or listens to everyone’s complaints. A role like that can be waiting for you at the next workplace too, if you don’t recognise it — because you will bring it with you, and others will quickly sense it.

Systems have another characteristic: they resist change. When someone announces they are leaving, something odd often happens. The boss who had no time for a conversation for a whole year suddenly has it. Colleagues who took you for granted tell you how much they will miss you. This may be sincere — but it is often also the way a system keeps its balance. It’s no bad thing to know this in advance. Then you can tell whether something has really changed or whether the lights have simply come on for a moment.

And one more question people rarely ask out loud: who will you leave behind? If you go, someone else will take over your work, perhaps your battles as well. Feeling guilty towards colleagues is common and understandable. But it isn’t your job to pay for poor organisation with your health. Where the line between the system and the individual lies is the subject of System or individual: who is responsible for burnout.

What your family tells you about work

Each of us grew up in a family that had its own sayings about work. Sometimes they were spoken; more often they were simply seen. “You don’t walk out of a job.” “Be grateful you have one.” “Work isn’t meant to be enjoyed.” “In our family we don’t give up.” Or exactly the opposite: “Life is too short to do something you hate.”

These sayings didn’t come from nowhere. Many parents and grandparents lived through times when a job was all that stood between the family and poverty. In Slovenia, many families watched in the 1990s as the factories where parents and neighbours had worked closed down. If you grew up in that kind of environment, it is understandable that the idea of leaving voluntarily feels almost indecent — as if you were throwing away something others fought for.

The question is not whether these messages are right or wrong. The question is whether they are yours. In relational family therapy we often see that a person is not deciding only for themselves, but also on behalf of parents who never dared to leave — or against them. Both are a kind of tie. I wrote about how a person’s worth gradually becomes equal to their productivity in Worth only as much as you get done: self-image and productivity.

This is how it sometimes sounds in a conversation between partners (a composite, not a real person):

“I almost wrote my resignation again today.”
“And what stopped you?”
“I saw how my dad would look at me. He was in the same place for thirty years.”
“Did you ever ask him whether he was happy there?”
“No. That wasn’t something we asked at home.”

Sometimes the biggest shift is exactly this: recognising your father’s look as his, not yours. Only then can you ask what you want.

Fear or signal?

When you think about resigning, you will feel fear. That is to be expected, and in itself it doesn’t tell you whether the decision is right. Fear speaks up with every major change, even a good one — that is the subject of Why change knocks us off balance, even when it is good change. What matters more is telling the fear of change apart from the signals your present situation is giving you.

Fear of change points to the future: “what if I can’t find anything”, “what if the new job is even worse”, “what will people say”. Signals from the present are here and now: sleeplessness before the working week, headaches that ease on holiday, a cynicism you didn’t know before, the feeling that you have become someone you don’t like. The first calls for courage and a plan. The second calls for being taken seriously — whatever you decide.

One caution here. If you are exhausted, deciding is harder. In burnout the world narrows and every option seems equally bad. So if at all possible, try to give yourself at least a little space before a big decision — holiday, sick leave if your doctor suggests it, a few weeks with a lighter load. Not to postpone the decision indefinitely, but so that you make it, and not your exhaustion. Sometimes, though, leaving is exactly what opens up that space in the first place. That can be true as well.

Exit, voice and loyalty

In 1970 the economist Albert Hirschman wrote a book about how people respond when an organisation they belong to starts to decline. He described three paths: exit (you leave), voice (you speak up and try to change things) and loyalty (you stay because you care or because you have a reason). The book was written about companies and states, but it reads like a description of everyday struggles at work.

His observation is useful for you too: exit and voice are connected. Someone who never tries voice often leaves feeling there was no other option — and takes that feeling of helplessness with them. Someone who has tried voice and wasn’t heard can leave more calmly, knowing they did what was in their power.

Loyalty, however, is not the same as staying out of habit. Conscious loyalty means you know why you are staying — because you need a stable income for another two years, because you are fond of the team, because the work feels meaningful despite everything. And that you set a moment when you will ask yourself again. The dangerous one is a fourth path that Hirschman didn’t have on his list, but which we all know well: your body stays while your mind leaves. You do less, believe in nothing and don’t decide. It is the most tiring path of all, because it has neither an end nor a meaning.

Exercise: questions that tell you more than a list

Instead of opening the two-column document once more, take half an hour and a sheet of paper. You can also use the questions before a big decision tool in the knowledge base.

1. What exactly would you like to leave? Write it down concretely: people, tasks, the rhythm, the company’s values, the role you have. You may notice there are some things you wouldn’t want to leave behind.
2. Whose voice do you hear when you think about resigning? Write down the sentences that come up, and next to each one note who you know it from. Your mother, your father, your grandfather, yourself at twenty?
3. What have you already said — and to whom? Have you talked about what is weighing on you with someone who could change something? If not, what stopped you?
4. Imagine a year has passed and you stayed. What had to change for that to be a good decision? Then the same for leaving: what had to happen for leaving to have been good?
5. What would you like to say about this period in ten years? Not what would be sensible, but what story you would like to tell about how you made your decision.

The exercise won’t give you an answer. But it will show you whether your decision revolves around the job or around something bigger than it — values, fear, or messages you carry from home.

When this approach isn’t enough

I want to be honest here, because everything I have written can also be read the wrong way — as if every wish to leave were first and foremost a psychological puzzle to be solved.

When safety is at stake, there is nothing to weigh up. If you are exposed to violence, humiliation, sexual harassment or dangerous conditions at work, the question isn’t what your family history says about it. The question is how to protect yourself. How to tell bullying apart from a difficult relationship is the subject of Workplace bullying or just a difficult relationship? How to tell them apart and what you can do about each If you are experiencing violence, you can call the police on 113 in Slovenia, or 112 in an emergency.

When the questions are legal, you need a lawyer, not a therapist. Notice periods, your rights when you resign of your own accord, possible unemployment benefit, termination by mutual agreement — these are questions on which I mustn’t advise you. Before you sign anything, check your contract and talk to a trade union, a lawyer or, in Slovenia, the Employment Service (Zavod RS za zaposlovanje). A decision made without this information isn’t brave; it is needlessly risky.

When you can’t afford to leave financially, that isn’t cowardice. Staying because you need to support yourself and others is a responsible decision. But you can turn it from “I’m trapped” into “I’m staying until I’ve prepared my way out”. The same situation, but a different relationship to it.

When an illness is behind the decision, depression for example, every decision feels either impossible or urgent. If for weeks you haven’t been sleeping, haven’t felt any joy, or have been thinking everyone would be better off without you, turn to your GP first. If thoughts of death are strong, in Slovenia you can call the crisis line Klic v duševni stiski on 01 520 99 00 (every day from 7 pm to 7 am) or the Samaritans helpline (Samarijan) on 116 123 (24 hours a day). Your resignation can wait; you can’t.

Once the decision is made

Whether you stay or leave, you will probably feel for a while that you may have chosen wrongly. That is normal. Every choice closes off another option, and that option is worth grieving a little, even if the choice was right.

If you leave, it’s worth leaving in a way you will be proud of — even if your relationship with your boss or the team was bad. Not for their sake, but for yours. Systems remember how people left, and so will you. And if you look at it from a distance, the system you are leaving may turn out to resemble, in many ways, the one you once came from. Then it is good to know what you are carrying with you, so that you don’t repeat it in the next place.

If you stay, it’s worth making one small change that shows it was a decision and not a surrender: a conversation you have been putting off, a limit on overtime, one day a week you protect. And if you are wondering whether to change not just your job but your profession, you may find Changing careers at forty: what is real risk and what is only fear helpful.

How therapy can help

In therapy nobody will tell you whether to resign. My job isn’t to decide for you, but to help you tell apart which voices inside you are your own and which found a place there from other times and other relationships. It often turns out that distress at work opens questions older than the job — about who you are allowed to be, how much you are allowed to ask for, and whether you are allowed to leave when somewhere isn’t good for you.

As a therapist in training under supervision in marriage and family therapy, I work in person in Ljubljana, and I also work with English-speaking clients. For decisions in which family messages speak up loudly, a longer session with a genogram, such as A Look into the Past, can be useful — together we draw your family tree and look at how the people before you made decisions about work, what they risked and what they regretted. Sometimes the answer to your question was written a few generations back.

What to remember

• A list of pros and cons weighs the items, not their meaning — when resigning, questions about values, fear, family messages and your role are more useful.
• We are pulled towards the status quo by a force stronger than reason; in Levitt’s experiment, those who chose change were on average happier six months later.
• A workplace is a system — ask yourself whether you are leaving the job or a role you might carry on into the next one.
• Try voice before exit; loyalty can be a conscious decision, but quiet withdrawal is no decision at all.
• When safety, health or legal questions are involved, seek the right help first — psychological reflection comes after.