Should you Stay or Should you Go? (7 Questions)

Knowing whether to stay – in a job or a relationship – or to go, is hardly ever simple. We can feel so differently about the same thing from week-to-week and some weeks, from day-to-day! We can also never be sure that our apathy isn’t just grass-is-always-greener syndrome or a dry spell; a rough patch. A glitch. A bump.

On the other hand…

What if staying in this job (or relationship, or country) could swallow years of your life? Time you could have spent doing something else – with someone else.

The question of how much pain to endure before calling time on a thing is a very personal one. Which is why the advice from friends, no matter how well intentioned, only helps us so much.

What we all really need when faced with tough decisions is time and space to think. To figure out whether our reasons for staying or going are good ones. Whether we need to develop our courage.

Here are seven questions to ask yourself when navigating a ‘should I stay or should I go’ style scenario.

1. What are the practical considerations?

(The circumstances where this applies are often fewer than we think, but) leaving isn’t always a possibility to entertain.

Maybe you are bound to see through an employment contract because you have huge debt to pay. Maybe you are compelled to keep working at your marriage because there are very young children involved.

What harm will you cause by leaving? Is that suffering going to be worth your freedom in the long run?

Asking ourselves these questions helps us to know when to stay and accept a situation.

Alive time versus dead time

Even when we do stay ‘against our will’, we get to choose whether the time is alive time or dead time.

Dead time is when we are passive or waiting. Alive time is when we are learning and acting and using every second. Each situation that we do not choose deliberately presents this choice.

Psychologist Viktor Frankl used his experiences of living in three Nazi concentration camps to refine his definitions of meaning and suffering. Those definitions, which he wrote about in Man’s Search for Meaning, have helped thousands to come to terms with bleak periods of their lives.

Activist Malcolm X also took dead time and made it fruitful. During his long imprisonment, he taught himself how to read. He learned about religion. He transcended his confinement.

We can use every day of our experience in situations we wouldn’t choose to enrich our understanding of ourselves, and to improve our will and patience.

As they say, a single moment is not your life – it is a moment in your life.

How we use that is up to us.

2. What do you really value?

This is a question that we need to ask ourselves again and again. Being unclear about or out of touch with what we value is why we feel indecisive at all.

Staying in a relationship that is ‘just fine’ is more painful for some of us than others. For some people, it isn’t painful at all. They know themselves enough to know that it is enough. For others, something that is just fine when they can be by themselves is a huge burden and source of discontent.

The same applies to a work type scenario. Some people can withstand a lot of monotony at work because they are being driven by other values in life.

For an in-depth guide to figuring out your values, read this.

3. What is the nature of my dissatisfaction? Is it specific or pervasive?

In terms of how we interpret our experiences, in his book Learned Optimism, Martin Seligman shows us how some people are ‘pervasive pessimistic’ thinkers: they cannot isolate in their minds one dissatisfying aspect of a situation from the situation as a whole. Optimists on the other hand are far more likely to be able to not to let that self contained element affect their entire experience of the thing.

The upshot is that there might be something within our thinking to tweak, rather than an outside change to make.

4. Have you given it your best?

Going into something or staying in it with ‘one foot out of the door’ isn’t giving it your best try. Committing to something or someone, and choosing it every day until you know you have done your best is.

Another slightly different question you can ask yourself is: have I done everything in my power to change my experience of this? If it is a relationship, have I given the other person the opportunity to address my feelings? If it is a job, have I attempted to adapt the role so that it plays to my strengths more?

If not, why not?

5. How changeable are your feelings about it? (How volatile are your feelings in general?)

This is a really important one to pay attention to. We know whether we have the tendencies to find fault with things over time. That would indicate that the major challenge isn’t the situation. The major challenge to overcome is in your thinking – why do you appear to lose interest?

In relationships, this could be because you have an avoidant attachment style. In your work, maybe you just don’t like working for other people and you need to take the plunge in your own entrepreneurial or creative venture.

It is worth asking yourself the question – have we been here before? What’s underneath this?

6. How long have you been ignoring your feelings about this?

A lot of us put aside our personal feelings about something in order to get it done. It’s a fine line between emotional maturity and repression.

But ignoring our desires continually can only make us unhappy and dissatisfied in the long run.

If you think you have a habit of ignoring your feelings, read this.

7. Has this situation become unhealthy?

There isn’t anything in this life worth risking our health over. After all, without your health, you don’t have any life.


Hopefully you haven’t found these questions painfully obvious.

In the end, nobody can say what’s right for us, but us. And oftentimes, we know what we need to do, but we still defer and delay. I know I have done that few times. And even though I should have left the situation, staying didn’t do me so much harm in the long run. In fact, I have learned valuable lessons that way.

We perhaps owe it to ourselves at least to ask the questions. Be honest. And then whatever we decide, working on truly accepting the decision (not just fake accepting it).