Updated on May 18th, 2019

Some decisions are only for you to make. Like whether you should stay in a job, a relationship or a group – or not. Often, these decisions are not so clear-cut. Staying might mean putting up with irritation, forever wondering if we don’t owe ourselves better. And leaving might mean losing what’s good about our situation, as well as hurting someone. So I’ve come up with 8 ways to get clear. Read on to learn about my best dilemma-busting questions…

Sometimes, I get an email from a reader or someone interested in coaching with me, in which they explain a dilemma and ask me what they should do:

  • “Should I stay in my job that pays me good money but makes me really angry / unhappy / lethargic?”
  • “Should I stay in my relationship where everything’s good but I’m not feeling met emotionally?”
  • “Should I stay with a group of people – an association, a choir, a club – that give me a sense of connection, but that I’ve outgrown?”

This kind of Should I stay or should I go? question is not only an iconic song by The Clash, but also one of the fundamental decisions we’re asked to make in life, again and again and again.

Tolerance for the greater good

Our life situation at any time is rarely ideal, even when we’re overall happy with where we are. Often, there are things we tolerate for the sake of a greater good, so we can maintain something that’s important to us:

Finding productive ways to work with a demanding boss, for example, allows us to keep a well-paid and otherwise satisfying job. Being generous towards our partner’s quirky habits when, over the years, they’ve gone from being endearing to being annoying, means that we can sustain our relationship longer, or enjoy its positive, loving aspects more. Tolerating a difficult family member lets us maintain a loving and secure greater family unit that we can feel part of.

When we’re mature and conscious enough to know that our own view of the world is not the only valid one, we can tolerate what’s not ideal for us with a spirit of generosity and love. And be grateful when we become aware that others are tolerating our less ideal aspects and love us regardless…

Sometimes I think it’s not money that makes the world go ’round, but our capacity to tolerate what’s not ideal, with kindness, and still make things work and enjoy what’s good about them!

(One important caveat to what I’ve said so far: It’s never ok to tolerate any behaviour from anyone that is violent, dangerous, cruel or malicious towards us, or makes us feel unsafe, powerless or worthless. Never. If you are experiencing something like this, please challenge it if you can, or take yourself away from the situation and seek help to protect yourself and anyone else affected!)

Should I stay or should I go can be a tough decision

But what if that less-than-ideal-thing becomes more than a niggle we choose to tolerate? What if we’ve tried to work it out with the person, group or organisation it concerns, to no avail? What if it now weighs on us to a point where we’re starting to think about whether we want to tolerate it any longer? Whether we should continue to stay, or whether we should go?

That can be a tough decision to make. Because we don’t want to hurt and offend others. Because we don’t want to feel the pain of leaving and losing the good stuff our situation also gives us – or losing a situation which, if not ideal, is at least familiar, and face the scariness of the unknown What next? And we don’t want to feel our fear of not finding another work / partner / group to be part of, and ending up alone, isolated, unloved.

So we stay – but the question keeps creeping up: Is it good for us to stay, or should we rather go?

We might be tempted to ask others what they would do if they were in our situation, or what they think we should do.  But ultimately, it’s a decision only we can make for ourselves.

We might tell ourselves that, if we just endure for long enough, the situation will eventually change or resolve itself. Yes – that sometimes happens, but rarely in the way we would want. So why not grab our own power and decide for ourselves, rather than giving it away to circumstance and hope for the best?

There might not be an easy or perfect answer – but what is right for you at this moment in your life is good enough. It’s all you need for now. In order to help you find that, here they are:

8 questions to clarify if you should to stay or go

A classic was of resolving dilemmas is to list your options and the pros and cons for each. Or asking yourself What’s in it for me if I stay or if I go. Yet good decisions don’t tend to get made rationally, or logically (at least not entirely). Gut feeling and intuition play a big role, too – and often, we’re not aware of it.

The questions below aim to help you inquire more deeply into yourself, so you can truly uncover what the right decision is for you at this stage!

1  What’s really important to you?

What’s important to you in work? In a partner? Or in a group you’re associated with? Or in whichever other situation you’re thinking of leaving? What is it you want from them?

Don’t think of YOUR partner, YOUR work, YOUR group – just tune into what’s important to you to have in A partner, A work, A group, generally speaking, because it contributes to your happiness, health and wellbeing in an intimate or working or group relationship.

Perhaps what’s important to you in a relationship is loyalty, fun, emotional or physical closeness, respect… Perhaps in work, you really need to feel a sense of meaning, the right level of challenge, harmonious and stimulating working relationships, flexibility… Perhaps in a group, you want to feel included, share a sense of pursuing a cause, feel mutual support, have fun together…

Write down ten things that are important to you, for the situation you’re thinking of leaving.

Then put them in order of priority – with the most important at number 1, and the least important at number 10.

Be honest with yourself and assign your true priorities. If you struggle to decide between two things you’ve written down, ask yourself: Which of the two would you mind less if you didn’t have it? That’s the lower priority one of the two.

2  Are you getting enough of what’s important to you?

Got your list of what’s important to you, in order of priority from 1-10? Great!

Now go through your list and put a check-mark against those important items you currently are getting from your work / partner / group.

Are enough of the higher-importance ones – say your top 5 – currently being met?

As I’ve said before, perfect situations are rare. We might never get all of what’s important to us. But if a work / partner / group meets enough of what’s really important to us, we might just choose to tolerate what’s not being met, and stay. Only you can say how much is enough for you, so be honest with yourself.

Next, look at the important stuff you feel is not currently being met: How much of a priority is it to you? How much does it matter that it’s not being met in your current situation?

A former client of mine, an artist, once faced a dilemma of whether to keep producing repetitive work to be sold in an arts and craft shop (and have a relatively certain income), or leave the shop to show her work in art galleries, with greater uncertainty of income. She made a list of what was important to her in her art. Once she realised that her own artistic development mattered to her more than commercial success with repetitive pieces, she knew what she had to do: She left the shop – literally the next day – and started exhibiting her work in art galleries. Happily, she found three galleries that agreed to show here work almost immediately.

3  Have we done all we can?

Perhaps the above exercise has helped you clarify what it is exactly you’re missing in your work/ partnership / group – and why that matters to you.

Have you addressed this particular item with the person(s), group or organisation it concerns?

Have you been able to explain how you feel about it, what you are missing, and how you’d like things to be instead? If not: Is this something you could still discuss?

Sometimes we avoid conversations in which we honestly voice our needs and ask for them to be met, because we’re anticipating the other person to turn us down, or become awkward or hostile.

And yet, if we drop all intent of blaming or attacking the other person and start the conversation with a sense of openness, asking to work out an issue together, we might well find that we are heard and, together, able to change what was pushing us to go.

A friend of mine experienced this when she started talking to her long-term partner about their relationship, which had become stale, directionless and conflicted. She said that she loved him and wanted to stay with him, but also wanted them to move beyond their current way of relating to each other. That she was starting a process of envisioning the future she wanted and invited him to join her. That she would move forward, and would still love him, whether he decided to participate or not. She found that her partner heard her and stepped up to work on his part of their situation. They started talking about their future together. Within six months, her partner proposed to her, and they got married shortly afterwards. 🙂

My friend is a gutsy woman. Hers wasn’t a heartless ultimatum: She was prepared to put in the work to change the situation she was in and to give her partner time to do his work. She made it clear she wanted to stay together, albeit not in the way they were then. And she braved the risk of having to move forward on her own – which she would have done, had her partner not heard her plea.

So consider this – and be honest:

Is your isse an unchangeable given? Have you – and the other person(s) involved – done all you can to address, improve or fix it? Is the situation beyond repair? Or is there something you (both) could still do, perhaps with external help? If so, are you willing to do it?

4  What’s the impact of your situation?

No matter how strong we tell ourselves we’ll be in our situation, no matter how much we tell ourselves we’ll grit our teeth and endure it: If it goes on longer term, it will take its toll on us.

We might feel it as a general unease, unhappiness or dissatisfaction, or experience full-blown stress or anxiety symptoms that affect your health and wellbeing, making it difficult for us to function well. It might get our mood down and make us feel hopeless and despondent. It might affect our confidence. Or, on the other hand, perhaps it has no impact on us at all.

It doesn’t matter what you think or are being told that the impact should be, or what you believe you should be able to cope with. Ask yourself what the impact of your situation is on your happiness, health and wellbeing – and that of your family. And be honest.

Now how do you feel about that?

5  What are you resisting?

Sometimes what stops us from making an empowered decision and moving forward in our life is resistance – usually to a truth we don’t want to look in the eye or cannot accept.

This is a tricky one, as we can be unaware that this is going on within us. And come up with all kinds of good reasons why waiting a bit longer and seeing what happens is a good idea.

Waiting and seeing has its merits, of course. Sometimes a situation has to mature – or we have to mature the most helpful point of view on it within us – before it can be resolved. But if we’re using waiting and seeing as our excuse for not making a decision which is long overdue, it will not help us, and indeed will have an impact on us, too. (See point 4)

Ask yourself: What truth are you resisting or not accepting?

When I worked in corporate consulting, the Should I stay or should I go question was with me for a while, unresolved, after our small organisational change company got taken over by a large systems house.  As the new, post-merger organisation structure, processes and working conditions began to come through, I started feeling resistant to the changes. Resistance is of course a normal human reaction to any change. Mine stemmed from the fact that the new company values, management style and ways of doing things were very different and not very compatible with the ones I had totally embraced in my old company. I knew that, if I couldn’t find a way to reconcile this within myself, it would be better to leave.

Yet I stayed on. First I tried to hide from the changes in the organisation on projects abroad. Then I tried to fit in and make it work. I got more and more dissatisfied, disgruntled, even angry. Yet still I stayed on. I’m sure fear played a role in my staying – fear of being out in the unknown, not knowing What next? after ten years of an intensely scheduled, fast-paced, upward-moving career.

Had I asked myself this question, back then – Which truth am I resisting or refusing to accept? – I might have seen that my resistance was happening at a deeper level, too. What I was refusing to accept, really, was the death of our small, aspirational organisational change company with its people-friendly culture and values, which was completely disappearing the more the new, merged company conglomerate took shape.

That was a hard truth to accept and digest. I grieved for that fine, small, exceptional company I had grown up in, professionally speaking, for a long time after I eventually made my decision to leave. So did many of my former colleagues. As I write this today, I wonder whether, I could have left sooner, feeling more peaceful inside, if I’d known back then what I was truly resisting.

6  What if…?

This is where you come up with the options you have. But not just that: You then try them on for size.

Ask yourself:

What if I stay in my relationship / work / group? Imagine yourself staying, and picture what it would be like in vivid detail, with the environment you’d be in, with what your days would look like, and with all the things you and others would do, think, say…

What would happen?
What would not happen?
How does that feel to you?
Would you want to feel like this?

Now consider this:

What if you leave the relationship / work / group? Imagine yourself leaving, in vivid detail – saying good bye, leaving an environment, situation or person behind and closing the door. Imagine yourself moving on, doing nothing for a while, or finding a new, more satisfying and fulfilling situation. If you don’t know what that is, just imagine yourself having moved on and feeling satisfied and fulfilled.

What would happen?
What would not happen?
How does that feel to you?
Would you want to feel like this?

If other options  beyond staying or leaving now occur to you – staying connected in a relationship but not living together anymore, staying at work part time or as a freelancer etc. – consider them in the same way.

What do you find?

7  What are you prepared to do?

When we’re in a difficult situation, and it’s been going on for a while, we can start, without even being aware of it, perceiving it as our new, unchangeable reality. Our brain is wonderful in adjusting to any new situation and making it habitual, so it can handle it with the minimum effort.

This works out well when we’re learning a new skill. Like driving a car, for example. In the beginning we’ll struggle performing and co-ordinating all the necessary movements or executing the manoeuvres. But the more we do them, the easier they become, until they are near-automatic.

It’s the same when we’re adjusting to a change in a life situation. Only, if our situation has changed for the worse, and we’re going through the manoeuvres of living with it and coping with it day after day, we’ll start seeing this situation as our new normal – we’ll get used to it. This doesn’t mean that we’ll suffer less – but, instead, we’ll struggle more and more to see positive, affirming alternatives or ways of breaking out.

So this question is about testing out your boundaries – and becoming aware of them again. Noticing that you may choose to stay in this situation a bit longer or for good – but that you don’t have to stay. And realising that you get to decide, too!

Variations of the question above are:

  • How long are you prepared to wait out a bad situation, to see if it changes or improves on its own?
  • How long are you prepared to work on your current situation to see if you can improve it?
  • What are you prepared to do for your happiness, health and wellbeing?
  • What are you not prepared to do?

What does that tell you about what’s best for you to do in your current situation?

8  What do you not want anymore? What do you need next?

What we need when we’re in our twenties is not the same than what we need in our fifties. Whereas at one age we might enjoy a faster pace, greater level of challenge, or bigger amount of novelty or thrill, at another age we might prefer a quieter pace, a challenge that suits us, or looking deeper at the things we already know.

This is not necessarily dependent of lifetime or age: If we’ve been in a relationship with someone who was always late or never maintained their promises, we might long for a relationship with someone punctual and reliable. If we’ve worked in a closely regulated job with a controlling boss, we might have a desire to experience a next job in a role with more autonomy, freedom or decision power. If we’ve had an experience with a very tight-knit, closed group, we might want to try a more open one with looser ties.

The longing for a next and different experience – and we’re not talking about flippantly switching between one and the next for the sake of it – is a soul need. It shows that we’ve grown – and perhaps out-grown – our current situation. It indicates to us what we need next in our development as people, professionals and human beings. 

You can work on moving forward towards what your soul needs to learn and experience next, both by staying or leaving a situation you’re in. If you’re staying, you’ll have to work with your partner / organisation / group to make changes so you can experience what you need next. (See point 3) And if that’s not possible, and you decide to leave, then you’ll know what to look for next… 

So what’s it going to be?

I hope this has been helpful for you to clarify your Should I stay or should I leave question for yourself!

Having made some or all of the considerations above:

What’s it going to be then? What’s the right thing for you to do?

If you’re staying, that’s great. Make sure you’re doing it for the right reasons, creating the changes you need to move forward within where you are and stay happy and healthy.

And if you’re leaving, that’s great too. I wish you well for your next chapter away from your current situation! For further help in discovering what next in your life, and moving towards it, check out my Ultimate Guide to Changing Your Life.

Over to you

What are your experiences with deciding whether to stay or leave?

Which of the questions above did you find most helpful? What has it helped you realise? 

Which other questions have occurred to you that are helpful when deciding whether to stay or leave? 

I’d love to read your views! Why don’t you share them in the comments box below? 



Photos: Pixabay