#269: Stay or Go: How to Know When It's Time to Walk Away
One of the hardest questions we can face in relationships isn't how to find love—it's how to know when it's time to let go of it.
Should I keep trying? Or is it time to walk away?
If you've ever found yourself stuck in that painful limbo, you're not alone. It's one of the questions I'm asked more than almost any other, and it's one I've wrestled with personally.
For many people—particularly those with anxious attachment patterns—walking away can feel almost impossible. We become deeply invested in making the relationship work, convincing ourselves that if we just try harder, communicate better, heal more, or love more patiently, things will eventually change.
Layer onto that a fear of regret, uncertainty about the future, and a tendency to doubt your own judgment, and it's easy to stay far longer than your heart knows you should.
The truth is that no one else can make this decision for you. But there are questions that can help you see your situation more clearly and make a decision that feels grounded in honesty rather than fear.
Hope Isn't the Problem
Before diving into those questions, I want to say something about hope.
Many people are incredibly hard on themselves for feeling hopeful. They tell me they "just can't stop hoping" their partner will change or that an ex will come back, as though hope is something shameful they need to eliminate.
I don't see it that way.
Hope is deeply human.
It speaks to our capacity for love, forgiveness, optimism, and emotional investment. Of course you hope things could work out. Of course part of you wants the story to have a happy ending.
The problem isn't hope itself.
The problem comes when hope becomes more influential than reality.
When we're so focused on what could be, we stop seeing what is. We magnify the occasional glimmers while overlooking persistent patterns that are causing us pain.
You don't need to extinguish hope.
You simply need to hold it alongside an honest assessment of your present reality.
1. Is This a Difficult Season—or Has It Always Been Difficult?
Every relationship goes through challenging seasons.
Stress, illness, grief, parenting, financial pressure, career transitions—all of these can place enormous strain on even the healthiest partnerships.
So it's worth asking:
Has this relationship generally felt safe, loving and dependable, and we're simply navigating a difficult chapter?
Or...
Has it always felt like an uphill battle?
If you've built a strong foundation of trust, teamwork and mutual respect, it may be worth persevering through a hard season.
But if you're constantly waiting for your relationship to become something it has never actually been, you may be chasing potential rather than reality.
Remember: the honeymoon phase doesn't count. Almost every relationship feels effortless when very little is being asked of either person.
2. Have I Cleaned Up My Side of the Street?
When relationships become painful, it's natural to focus on everything our partner is doing wrong.
If only they communicated better.
If only they were more affectionate.
If only they stopped shutting down or becoming defensive.
While those things may absolutely be true, relationships are systems. We are always one part of that system.
That doesn't mean taking responsibility for someone else's behaviour.
It means honestly asking:
Have I owned my own patterns?
Perhaps your work isn't learning to communicate more perfectly.
Perhaps it's noticing how much energy you're spending trying to change another person instead of tending to yourself.
One of the greatest gifts you can give yourself is knowing that, whatever decision you make, you leave with clean hands—knowing you took responsibility for your part without carrying responsibility for theirs.
3. Have I Been Caring for Myself Within This Relationship?
When relationships become all-consuming, everything else often falls away.
Friendships become neglected.
Creative pursuits disappear.
Exercise, hobbies and joy slowly fade into the background.
Before long, the relationship has become your entire world.
Ironically, this makes the relationship feel even more important because it begins carrying the weight of your entire wellbeing.
If you have anxious attachment patterns, this will probably feel familiar.
The more depleted you become outside the relationship, the more desperately you need the relationship to work.
Reinvesting in your own life won't magically solve your relationship problems.
But it will help you remember something incredibly important:
You are more than this relationship.
And from that place, you'll make far clearer decisions.
4. Are We Aligned on the Things That Truly Matter?
Differences aren't the problem.
Healthy couples can have completely different personalities, interests and emotional styles.
But compatibility goes much deeper than personality.
Ask yourself:
Do we want the same kind of life?
Are our core values aligned?
Are we moving toward the same future?
If one person wants children and the other doesn't...
If one dreams of travel while the other wants to settle permanently...
If your visions for life fundamentally diverge...
No amount of communication skills can resolve that incompatibility.
Compromise is healthy.
Sacrificing your deepest vision for your life often isn't.
5. Are We Both Doing the Work?
Relationships only grow when both people participate.
That doesn't mean both people need to love therapy or personal development equally.
But it does mean both people need to acknowledge what's not working and take ownership of creating change.
If the relationship improvement plan sounds something like:
"Here's everything you need to fix..."
...while the other person resists, withdraws or simply complies under pressure, meaningful change is unlikely.
Instead, ask:
Do we both understand what needs to change?
Are we both genuinely invested in making those changes?
Growth requires two willing participants.
6. Despite Everything, Do I Feel Loved, Valued and Respected?
This may be the most important question of all.
Conflict is normal.
Differences are normal.
Periods of distance happen.
But beneath all of that...
Do you know you're loved?
Do you feel emotionally safe?
Do you feel respected?
I've worked with many people who have stayed in relationships where warmth has been replaced by indifference, where repair never follows conflict, and where emotional needs are consistently dismissed.
When that's the case, it's worth asking yourself a difficult question:
What am I actually fighting for?
And...
Is it worth what it's costing me?
7. What Would I Tell the Version of Me Who First Entered This Relationship?
Imagine you could travel back in time.
You meet yourself on the day you first met your partner.
Knowing everything you know now...
What would you say?
If your immediate response is:
"Don't do it."
...it's worth paying attention to that.
8. Am I Staying Because I Truly Want This Relationship—or Because I'm Afraid of Leaving?
Leaving brings enormous uncertainty.
Grief.
Loneliness.
Financial stress.
Logistical upheaval.
Fear of making the wrong decision.
Fear of regret.
Sometimes we stay simply because the known pain feels more manageable than the unknown.
But every year spent staying out of fear makes leaving feel even harder.
The investment becomes greater.
The logistics become more complicated.
The story becomes more difficult to rewrite.
There will probably never be a perfect time.
Only an honest one.
9. If I Could Skip Ahead One Year, Would I?
Imagine you could wave a magic wand.
You're already one year beyond the breakup.
You've rebuilt your routines.
You're settled.
You're healing.
You're no longer in the immediate storm.
Would you choose that reality?
For many people, the answer is immediately yes.
If that's true for you, it suggests that you're not afraid of life after the relationship.
You're afraid of the transition.
And while transitions are painful, they're temporary.
The unknown often contains possibilities far greater than our anxious minds allow us to imagine.
10. Am I Looking for Permission to Stay—or Permission to Leave?
Finally, ask yourself this:
What answer was I secretly hoping for?
Were you hoping someone would tell you to keep trying?
Or were you hoping someone would finally say:
"It's okay to leave."
The truth is, you don't need anyone else's permission.
You don't need an irrefutable reason to end a relationship.
Nor do you need certainty that things will improve before deciding to stay.
Every relationship exists within its own unique context.
Your values.
Your capacity.
Your history.
Your desires.
Only you can weigh those factors.
There Isn't a Perfect Decision
One of the biggest mistakes we make is believing there's one perfect decision that guarantees future happiness.
There isn't.
Every path comes with uncertainty.
Every choice asks something of us.
Rather than trying to predict which option will eliminate all future regret, focus instead on making your decision from a place of honesty, self-respect and integrity.
Because whether you ultimately choose to stay or to leave, you'll carry something incredibly valuable with you:
The knowledge that you trusted yourself enough to make the decision consciously.
And that's a foundation you can build any future upon.
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[00:01:26]:
Hey everybody, welcome back to another episode of On Attachment. In today's episode we are going to be diving into the very delicate, very tricky subject of how to know when to stay in a relationship and keep trying and when to walk away. So it is that age old question of do I stay or do I go? And in unpacking this I want to actually read out for you a recent long form article that I wrote on Substack. You may have heard me share recently that I have joined Substack and I'm really enjoying doing doing some longer form writing, particularly off the back of just having finished writing a book. I'm very much in writing mode and enjoying sharing there. So I wanted to share with you this article that I wrote that seemed to really resonate with a lot of people over on Substack and I'm not surprised because it is one of those topics that I think needs a deep dive. Obviously it's very nuanced and subjective so I'm going to be reading that out today. Before I get into that, a quick reminder that I am running a free workshop next week on 9 July, although it will be late in the day on 8 July. For those of you in the northern hemisphere, it's all about understanding anxious attachment, protest behaviours.
[00:02:34]:
So all of those little things that we can do when it comes to conflict and communication that can get in the way of us actually getting our needs met, even though they are oftentimes a desperate attempt at getting our needs met. So whether it's sending a million texts in a row, pushing someone for a response, pressuring them to have a conversation, sulking, brooding, trying to get someone's attention, escalating in our attempts at being heard, threatening to end the relationship, all of these things that we know on the inside are frantic attempts at eliciting reassurance from someone or restoring the connection or testing to see if someone's really there. But because they're coming from this self protective, oftentimes reactive place, rather than being from our most mature and grounded, centred self, they can actually backfire. And they can. Rather than eliciting, you know, loving reassurance from a partner, they can actually bring out a partner's reactive, defensive protective parts. And that can so often be, you know, the start of a downward spiral into really unhealthy and unsatisfying dynamics. So I'm going to be talking all about the why beneath those patterns, why we do it, what we're really hoping to achieve, and how we can actually start to shift towards something healthier, what that looks like. And just as a bit of a spoiler, it goes a lot deeper than just say this instead of that.
[00:04:01]:
I'm not such a huge proponent of just memorising scripts or trying to say the thing in the perfect way so that they respond exactly how I want them to. I think that's actually an extension of our pattern rather than a shift away from it. So I'm going to be talking about what it really takes to stand on our own two feet, to be really deeply embodied in what we're saying, to really trust in our own judgement, to validate ourselves and to bring that version of ourselves to a relationship so that we can get through some of those impasses and not just repeat the same patterns over and over again that leave everyone feeling worse off. So if all of that sounds like something that you need, and I think it's something that a lot of people need, if you struggle with anxious attachment patterns, please do register for this free workshop. There are already over 400 people registered, so I don't know if a going to have to impose an upper limit on registrants. Hopefully not, but I'll just have to look into all of the software logistics of it. But in any case, definitely sign up ASAP just in case we do have to do that. I would love to see you there.
[00:05:07]:
There will be a recording, but as always it's great if you can join live because the energy is always better and I get to connect with you in person. So do that. The link is in the show notes okay, so without further ado, actually going to grab a sip of my coffee. Without further ado, let's get into reading this article that I wrote recently for my substack all about stay or go, how to know when it's time to walk away and I should have said at the start. Sorry, I will start reading it in a moment. I should have said at the start. I would be deeply appreciative if you could come over and join me on substack and subscribe to me there. It is currently free.
[00:05:45]:
I will be introducing a paid tier in the near ish future, but for now everything is free and accessible there okay, when is a relationship worth fighting for? How do you know if things are ever going to get better? How bad do things need to be before you walk away? How to balance being patient and compassionate against ensuring that you don't abandon or delude yourself? How long should you stick around hoping for something that may never come to fruition? How can you make sure you don't regret leaving or staying? These are questions I receive all the time. They're also questions I've wrestled with myself more than once. For many of us who struggle with letting go and tend towards relationship fixing at all costs, walking away can feel like a measure of absolute last resort. Like almost nothing would justify the immense and all consuming pain of having to let go of someone you love. And when you layer in self doubt and a deep fear of regret, it can feel next to impossible. Sadly, it's not a decision anyone but you can make. But there are absolutely ways to make the decision a clearer one. One that you trust in the rightness of and can confidently stand behind.
[00:06:54]:
Even if it doesn't make it any easier. I'm going to give you 10 questions which will reveal to you the truth of the situation and point you towards your next right step. This is true whether you choose to stay and keep trying or decide that it's time to walk away. A Note on Hope Most people are really hard on themselves when it comes to hope. We put hope in the bucket of feelings I should not feel along with things like jealousy and shame and assume it's misguided and unhelpful something that will inevitably lead us astray. Personally, I don't think of hope in that way. In fact, I think hope is a beautiful, tender, very human experience. Whenever someone tells me with a pained look that they can't stop hoping their ex comes back, my response is, well, of course.
[00:07:43]:
Of course you want them to come back. Of course you want them to realise the grave mistake they made in letting you go and tell you that actually they can't live without you. Of course. How very human of you. Hope speaks to our emotional investment, our deep care, our ability to forgive, and our optimistic spirit. There is a sweet innocence to hope. It's the part of us that longs for a happily ever after, that believes the future might bring brighter days. But when hope is at odds with reality, and when we let it be the primary driver of our decisions, we can find ourselves holding on in ways that don't support our well being.
[00:08:20]:
We can get so lost in the storey of what could be that we neglect to look honestly at what is. Hope can distort our vision, somewhat, magnifying the glimmers and looking past the glaring deficiencies. This doesn't mean hope is the villain and we need to get rid of it. It just means it's not always the best barometer when it comes to making decisions. We can acknowledge that the hope is there because of course it is, while also confronting the reality of whatever else we're dealing with in the here and now. With that being said, let's dive into these 10 questions to help you find clarity around whether to stay or go. 1. Does this feel like a hard season in an otherwise solid partnership? Or has it always felt hard? When we're feeling overwhelmed, exhausted and disconnected, our brains zoom in on the threat.
[00:09:11]:
Our nervous system has a knack for convincing us that things will forever be this bad or worse. In some situations, that alarm is an appropriate response to a relationship that isn't working. In others, it can be helpful to zoom out and take in more of the scene. Perspective often brings clarity. If your relationship is fundamentally solid, if you've built a life together, if you know how to work as a team, if you have a baseline of trust and commitment, then perhaps this is a hard season that's worth persisting through, rather than a sign that things have run their course. On the contrary, if your relationship has never had that quality of mutual respect, joint vision and dependability, then it may be that you are reaching for a mirage, a version of your partner that is more fantasy than reality. To be clear, the initial honeymoon stage doesn't count here. It's easy to be hopelessly in love when nothing much is at stake.
[00:10:06]:
2. Have I cleaned up my side of the street? Tempting as it is to point the finger at our partner and insist that if they were only more affectionate, a better communicator, less defensive, everything would be fine. The truth is not so one dimensional in actuality, relationships are a system and we are one input to that system. That means we wield more power to influence the dynamic than perhaps we realise. Indeed, oftentimes the feeling of powerlessness and exasperation comes from directing our change making efforts at our partner rather than looking in the mirror. To be clear, I'm not excusing anyone's poor behaviour or shifting blame. To recognise our contribution to the pattern is simply to acknowledge reality. If anything, we should feel encouraged by the invitation to own what's ours and reorient our focus from trying to force change upon them to cleaning up our own mess.
[00:11:00]:
Indeed, for many of us, me included, hyper fixating on a partner and what we think they should be doing can be part of our stuff and is something that we must keep in cheque if we want to create a relational environment that is actually conducive to growth. This is not to say that you must show up perfectly or do endless work on yourself before deciding to leave a relationship, but it can grant you significant peace if you feel you're walking away with clean hands and the knowledge that you did your best, owned your stuff and didn't leave anything on the table. 3. Have I been nourishing my well being, self worth and vitality as an individual within this relationship? Speaking of hyper fixating on a partner, often when our relationship feels hard, it occupies our entire field of vision. We can become so preoccupied with what's not working, our unmet needs and our disappointments that we drop all the other balls, including the ones that support our well being. We pour so much into our relationship that we neglect our friendships, our health, our creativity and many other things that bring us joy and remind us of who we are, only to then blame our partner for how lonely and empty we feel. If you have anxious attachment patterns, compartmentalization is likely not your strong suit. If your relationship is on the rocks, it really can feel like nothing else matters.
[00:12:21]:
But this feeds a vicious cycle of dependency and self abandonment that leaves you feeling ever more helpless, needy and desperate, like you need your relationship to work because it's all you have left. Nurturing your vitality and wellbeing won't necessarily fix your relationship troubles, but it will allow you to 1 feel better and more confident in yourself 2 see the goodness in your life outside of your relationship and 3 trust that no matter what happens, you will be okay. This is a far better place to make big decisions from than if you're feeling isolated and insecure. 4. Are my partner and I aligned on the Things that matter? It is completely fine and normal for you and your partner to have different personalities, temperaments, interests, needs and preferences. None of those things mean that you can't build a healthy, loving partnership. But there's a difference between being different to people and being fundamentally misaligned when it comes to values and vision. Put simply, it's important that you've both bought tickets for the same train headed to the same destination.
[00:13:25]:
If you want fundamentally different things from life and relationships, particularly when it comes to big ticket issues like marriage marriage, kids, location or lifestyle, you might be forcing a square peg into a round hole by trying to make it work. And while relationships will always involve compromise, you don't actually want your partner to sacrifice their vision for a life well lived to accommodate yours because that will only lead to resentment and the same goes in the other direction. 5. Are we both clear on the changes that need to be made or is the work one sided? If there are changes that need to be made in order for the relationship to feel workable and viable long term, it's critical that you're both fully opted in and aligned on what those changes are and what the plan is to make them happen. To be clear, it's entirely normal for one person to be more enthusiastic. Let's say, when it comes to growth, personal development and so on. That's not a deal breaker or a red flag in and of itself. But there's a difference between one person leading the way and one person imposing their agenda on the other.
[00:14:29]:
So if it feels like the work is entirely one sided and largely comprises you telling them what they need to change and them being resistant or capitulating out of pressure, I wouldn't be holding my breath waiting for those changes to materialise. It's also worth noting here that if you're broadly aligned on the things you want to work on, it's good to be specific. Setting an intention of being more connected is vague and will mean different things to different people. Get granular about how you want it to look, make sure you're both contributing to the conversation and have clear ways to gauge progress. 6. Despite our challenges, do I know that I'm loved, cared for and respected? This one's important. Perhaps it sounds obvious, but I can't tell you how many people I've supported over the years who have been holding on to relationships where they feel chronically neglected, unimportant and disrespected. Relationships that are largely devoid of warmth and goodwill, that involve near constant rupture without repair, and where needs are not only unmet but outright dismissed and discounted.
[00:15:32]:
I've been in this situation before, so I get it. So easy to lose sight of the forest from the trees and feel so hurt and ashamed that you double down on your mission to get them to be different. We can convince ourselves that the only way to salvage our bruised self worth is to manufacture a happy ending to the storey. If this feels familiar, the question I'll gently put to you is what am I actually fighting for and is it worth what it's costing me? 7. If I could go back in time to when I first met my partner, what would I tell that version of me? If your immediate answer is don't do it, well that's pretty telling. 8. Am I holding on out of fear or a genuine desire to be in this relationship? Walking away is an unknown that brings many fears to the surface. The uncertainty of what comes next, the dismantling and rebuilding of our day to day life.
[00:16:30]:
The logistical overwhelm. The fear of regret, the self doubt, the guilt. There's a lot there. Sometimes it's easy to keep holding on even when things feel so hard, because the alternative, at least in the short term, feels even harder. It's a classic case of better the devil you know. Most of us know how to get by in our current reality because we've been living it for a long time. So waiting a bit longer to see if things improve feels like the more manageable decision. But here's the tricky thing.
[00:17:01]:
The longer you hold on out of fear, the farther you end up walking down a path that you don't really want to be on. And that can make leaving even more daunting and overwhelming for future you because you've got even more of that sunk cost rationale justifying your decision. There's no perfect time to turn your life on its head and you will always be able to find a reason to postpone the decision until a better time. After my birthday, when we get back from vacation, once this busy period at work is up, etc. But if you know deep down that your relationship is over, staying in it out of fear eats away at you and erodes your self trust. Sometimes we just have to make a plan, rip the band aid off and trust that we'll get through the initial shitty period of grief and logistical overwhelm that these transitions bring. 9 if I could wave a magic wand and be 12 months post breakup settled in a new normal, would I take that option? This question follows from the last and illuminates where our confusion is actually fear or anxiety about the in between. In my previous relationship, I knew I needed to end things for a long time, but I felt so overwhelmed at the thought of what that would entail that I held on for far longer than I should have.
[00:18:19]:
Personally, I would have leapt at the opportunity to wave a magic wand and be transported a year into the future to a point where I'd close the door on my relationship and re establish myself in a new life. If that resonates at all. It's a good sign that your resistance is less about leaving your relationship and more about stepping into the unknown. But guess what? The unknown might be magical. It might be so much better than you can imagine right now, with your brain heavily skewed towards all the things that could go wrong, and you have full agency and authorship to make it so. That's not to say there won't be moments of doubt, wobble and uncertainty as you navigate the change. There probably will be. But you are more capable than you know, and holding yourself through those hard moments is a powerful way to build or rebuild your self worth.
[00:19:10]:
10. Am I looking for permission to stay or permission to go? I'll end with a simple but revealing question. Are you looking for someone to validate your desire to stay and keep trying, or your decision to walk away? Did you listen to this, hoping it would give you permission one way or the other? If so, know that you don't need me or anyone else to grant you the right to stay or go, no matter your circumstances. You don't need a really concrete, irrefutable reason to walk away, and you don't need a guarantee that things will improve in order to stay and keep trying. We all have wildly different desires, capacities, values and circumstances, and these all factor into the decision that means there's no objective right decision, only the right decision for you right now. So focus less on determining which path will guarantee your future happiness and a life free from regret. You'll never find one. And instead make a decision from a place of honesty, self respect and integrity.
[00:20:11]:
Because no matter what happens next, a decision made from the right place within you is something to be proud of. Okay guys, so that was my article on substack stay or go. How to know when it's time to walk away. I really hope that if you're in that situation of trying to make a big decision that that shed some light for you or gave you something to think about. And of course if you would like to revisit that and read it yourself, you can do so over on Substack. And again, I'd be so, so grateful if you could subscribe and support my work there so that I can keep doing more writing for you because it is something that I've been really enjoying. Okay, I'm going to leave it there guys. Thank you so much for joining me today and I look forward to seeing you again next time.
Keywords from Podcast Episode
anxious attachment, protest behaviours, relationship conflict, relationship communication, self-protection in relationships, walking away from relationships, knowing when to leave, relationship decision-making, hope in relationships, self-worth in relationships, relationship alignment, relationship values, relationship growth, relationship compromises, one-sided relationships, feeling loved in relationships, relationship regret, fear of leaving, self-trust, making empowered relationship choices