#187: Is It Better to Heal While Single or in a Relationship?
Whether you’re single or partnered, you might find yourself wondering: Am I in the right place to do this work? There’s often an unspoken belief that there’s a “best” time to heal — and that if we’re not doing it in the ideal conditions, we’re doing it wrong.
One of the most common questions I hear from my community is this: Is it better to heal while I’m single, or should I be in a relationship to do the work?
It’s a question that makes sense—particularly for those of us with anxious attachment. We want to do it right. We want a plan. We want to make sure we’re not sabotaging our healing journey. And when we care deeply about something (especially something that’s caused us a lot of pain), that desire to get it “right” can become especially strong.
But as with so many things in life, the real answer is not so clear-cut. There is no single path, no universal blueprint, no perfect conditions for healing. What there is, however, is nuance.
Let’s explore that.
Why We Ask the Question in the First Place
Before diving into whether it’s “better” to heal while single or partnered, it’s worth examining where this question often comes from.
For many people—especially those with anxious attachment—it stems from a place of anxiety. The part of us that wants certainty, control, a plan we can follow step-by-step. But healing isn’t a tidy process. It’s not linear. And if we try to approach it as something we can optimise by “doing it right,” we risk feeding the very patterns we’re trying to heal.
Instead, we need to learn to sit with the discomfort of not knowing. To cultivate trust—not just in others, but in ourselves and the process.
The Gifts and Limitations of Healing While Single
Healing while single offers a spaciousness that can be incredibly valuable, particularly for anxiously attached folks who are often deeply other-focused. Being single gives us the opportunity to reorient our attention back toward ourselves. To ask:
What lights me up?
What do I want and need—separate from anyone else’s preferences or availability?
How can I become the centre of my own life in a nourishing, self-honouring way?
There’s a kind of selfishness that can be deeply reparative when you’re used to chronically abandoning yourself in relationships. Choosing to spend time with yourself—not in waiting, but in deep investment—can be a powerful foundation for healing.
That said, the absence of relational triggers can also be a limitation. You might feel great until you start dating again… and suddenly find yourself spiralling just because someone took a little too long to reply to a message. Healing in solitude doesn’t always prepare us for the vulnerability and unpredictability of real-life relationships. So it’s important to approach singlehood as a valuable season—not a protective bubble or avoidance strategy.
The Gifts and Limitations of Healing While in a Relationship
On the flip side, healing while in a relationship puts you right in the arena. You’re in the game, so to speak. Your wounds and patterns will likely surface quickly, which can be confronting—but also offers rich opportunities for growth.
This is where the idea of corrective experiences comes in. For example, if in the past you were punished or abandoned for expressing needs, and now your partner meets your vulnerability with care and responsiveness, that is healing in action. That lived experience is something no amount of journaling or insight can fully replicate.
But—this is a big caveat—it only works if the relationship is emotionally safe enough to support that growth. If your dynamic is highly triggering, full of conflict, or lacking repair, then you’re likely reinforcing your core wounds rather than healing them. Constant dysregulation is not a healing environment. And staying in a relationship that keeps you in a heightened state of stress might do more harm than good.
So, What’s the Answer?
Both paths offer gifts. Both come with limitations. The real question is not “Which is better?” but rather:
What do I need right now?
What feels most supportive and nourishing in this season?
Am I avoiding discomfort, or am I choosing growth?
Whether you’re single, dating, or in a relationship, the most important thing is to keep turning toward yourself. Healing anxious attachment is as much about the relationship you have with yourself as it is about anything else. It’s about building self-trust, emotional resilience, and the capacity to stay grounded even when things feel uncertain or vulnerable.
You don’t need to have it all figured out. There’s no perfect timeline or set of conditions. Just keep asking yourself, with compassion and curiosity: How can I best support myself today?
That’s where real healing lives.
If this post resonated with you and you’d like to go deeper, I’d love to invite you to my free training: How to Heal Anxious Attachment and Finally Feel Secure in Life & Love. In it, I walk you through my 3-part framework for healing, common obstacles to look out for, and how to know whether the real issue is your attachment patterns or something genuinely misaligned in your relationship. It's a rich and valuable 75 minutes, and I know you’ll get a lot out of it!
Questions for Discussion & Reflection
Do you find yourself believing there’s a “right way” to heal? Where do you notice a desire for control or certainty coming up in your healing journey?
When you consider whether to focus on healing while single or in a relationship, what are the hopes or fears driving your preference? Can you identify any underlying anxieties influencing your decision?
In what ways do you tend to orient towards others and their needs in your relationships? How does this impact your ability to focus on yourself and your own growth?
Have you ever had a “corrective experience” in a relationship, where voicing a need was met with care or understanding? What was that like, and how did it challenge or reinforce your previous beliefs?
How comfortable are you with making your life “all about you” for a season? What comes up emotionally when you consider turning your focus inward and prioritising your own joy, vitality, and nourishment?
Are there signs that you may be using “healing” as a reason to avoid new relational experiences or challenges? What are you most afraid might happen if you opened yourself up to being triggered again?
If you’re currently in a relationship, do you feel there’s enough emotional safety for you to be vulnerable, make mistakes, and repair? How does this environment support or hinder your healing?
Reflect on a time when you felt deeply dysregulated or in a constant state of conflict in a relationship. What did you learn about your capacity to reflect, learn, and integrate during that period?
Do you notice a tendency to swing between feeling “all healed” while single, and then doubting your growth as soon as you start dating or get triggered? How might you reframe your expectations around what healing actually looks like in practice?
Looking at your current season—single, dating, or in a relationship—what unique gifts and limitations are present for your healing right now? How might you consciously make the most of this particular chapter?
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Episode Transcript
[00:00:04]:
In today's episode, I'm answering the question of whether it is better to heal while single or in a relationship. Now this is a question that I get all the time, and I get this question from people who are on all ends of the spectrum. So people who are single and wondering whether it would be more advantageous for them in their healing to be in a relationship. People who are in a relationship and wondering, 'Should I actually just take some time away from a relationship and be single so I can really focus on this away from the triggers of my relationship?' And also maybe people who are casually dating, so somewhere in the middle who are wondering whether they should tap out for a while and really allow themselves time and space to just do the healing work or whether they should be really focusing on putting themselves out there to do the healing work. Right? So I think everyone's looking for the right way to approach their healing, to maximize their results, to optimize the process, all of this stuff, right? And I understand that.
[00:01:31]:
I know that there can be this sense, particularly when it matters so much to us, to want to do it the right way and to not want to sabotage or compromise our ability to achieve the transformation that we're seeking. And at the same time, I think we do need to acknowledge where that question is coming from in us. And I'll talk a little bit more about that as we go on. You know, am I wanting to grip and control my way to this endpoint of being healed, and how realistic is that? And maybe the question is a function of my anxiety more than anything else. And while if you know me and you're familiar with my work, you can probably anticipate what the crux of my answer to this question is, which is there's no one right way, there's no black and white. This is the blueprint for healing that you must follow and it's going to be the same for everyone. Of course, that's not the case. But I will acknowledge that there are certain gifts and upsides and limitations or challenges that you will encounter in different seasons.
[00:02:35]:
So while single, I think there are gifts and limitations. While dating, I think there are gifts and limitations. While in a relationship, I think there are gifts and limitations. And I suppose being aware of what those might be and how they might apply to you and your particular past experience, the specific things that you struggle with and are wanting to work on. Having all of that context might aid you in making that assessment of what is going to be best for me, what is going to be most supportive for me, what do I need at this point in my life. So that's what we're going to be talking about today. Before we get into that, a reminder for anyone who missed it, I've created a brand new free training called how to Heal Anxious, Attachment and Finally Feel Secure in Life and Love'. It is really comprehensive, it's 75 or so minutes long.
[00:03:24]:
I apologize for that. I know everyone's very busy and time poor, but it's a very valuable seventy five minutes and has received amazing feedback from the people who have gone through it so far. We talk about my three step framework for healing anxious attachment to the role of the nervous system and somatics. We talk about core belief reprogramming and some of the core wounds of anxious attachment and how they infiltrate everything and act as a filter through which we perceive ourselves and others and relationships. And then we talk about secure relationship skills, so things like needs and communication and boundaries and conflict resolution and why a lot of people get that a bit backwards and it can actually backfire if you focus on that before you have the other pieces in place. We talk about common obstacles to healing. So, you know, if you're someone who's been doing this for a long time and you're still feeling stuck or you keep ending up in the same patterns, talking through exactly why that might be. And spoiler alert, it's not just because you are the exception to the rule and you are irreparably broken.
[00:04:26]:
And we also talk about a very big question which I get a lot, which is: How do I know if it's my anxious attachment that's the problem, that's causing all of these ruptures in my relationship, that's causing me to take issue with all of this stuff that my partner's doing, or are the things that my partner's doing actually not okay? Is it me or them, basically? And while that is, of course, not a black and white answer, I do go into some of the things that will make a secure relationship hard, AKA if they're doing all of these things then it's probably not just your anxious attachment. So go into all of that in this training. The link to sign up for that is in the show notes or you can come find me on Instagram at stephanierig and you can sign up for it there as well. I would love for you to check it out. It's super valuable. And as I said, has gotten amazing feedback from everyone who's gone through it so far. Okay. So let's get into this conversation around, is it better to heal while single or in a relationship? And as I said, this is not directed to the single people or the people in a relationship because I get the question from both sides.
[00:05:30]:
And so I am gonna give a balanced view and be speaking to everyone and anyone in between. So let's start first with why we ask this question. As I said in the introduction, I do think there's probably an aspect of the question reveals the anxiety because our anxiety wants to do things right. It wants there to be a formula. It wants information and structure and certainty. Right? And so it's like, if I just do these six things and control all the variables, does that mean I will be healed in x amount of time? And, you know, that's the the challenge for me, of course, in teaching this and distilling it down into frameworks and programs and all of the things, like, we can create these pillars, we can create a roadmap, and at the same time there's so much fluidity in that and everyone's journey is going to look a little different. And so being able to hold both of those things is so core to this work and so essential to not feeding that part of us that wants to believe that we're doing something wrong if it doesn't look a certain way. And so recognizing at the outset that there is no perfect solution, there are only trade offs, and that is true in every aspect of life.
[00:06:48]:
There's no one thing that solves every single problem. You just need to figure out what are the trade offs that make most sense for you. Now, when we're talking about relationships and healing relational wounds, you might have heard the saying be tossed around that, you know, we are hurt in relationship, or we are wounded in relationship, and so we must heal in relationship. And I think there can be truth to that for sure. You know, this concept of a corrective experience that's essentially meaning that if I have had an experience or many experiences in the past of, for example, speaking up about my needs and someone turning away from that. So whether they say, oh, do we have to talk about this again?' or, oh, give me a break. I can't believe.' You know, all of those things that feel really invalidating and dismissive and then lead me to reinforce this internal story of I'm not allowed to have needs because if and when I voice my needs or concerns, that leads to the loss of connection and that is not a price I'm willing to pay. That's a really deeply ingrained story and experience that I might have, and I can do so much work on that on my own, but until I have an experience that tells another story, that actually I voice a need and someone receives it with love and care, and that kind of ingrains in my system as an alternative possibility.
[00:08:16]:
And I think certain things we need to learn through experience rather than through theory, that is super valuable. And so this idea that there are certain things that will only really land in our system in the context of a healing relationship container, I think that there is some wisdom to that and there is some truth to that. But then we can also look at other things that say you have to love yourself before someone else will love you, which is completely opposite, right? That's saying that you've got to basically deal with all of your self esteem and self worth stuff, and heal your inner relationship before you can get into a relationship with someone else that's going to be that way. And while I don't really subscribe to that view of you need to love yourself first because I think that's setting the bar pretty high, I do think that there is validity and value in the idea of focusing on our inner relationship, particularly as people who struggle with anxious attachment because the inner relationship tends to be very underdeveloped. We are so focused on the other person that we tend to not really know who we are and we tend not to have very high self esteem and we tend not to be very good at really grounded and embodied self advocacy. All of these things that allow us to go to relationships on a firm and level footing as our embodied adult self, and give and receive the kind of love that is conducive to those healing corrective experiences, I think there's truth in that as well. And so there's wisdom in this idea of focusing on the self first. So all of that to say, like, you're gonna hear people say one thing, you're gonna hear people say another, and it's not trying to figure out, like, who's right and who's wrong.
[00:09:57]:
It's what's the wisdom in each of these things, what's the nuance, and can I have the discernment to figure out what is it that I might need in light of where I'm at, or what is it that I can take from the season that I'm in, What's the most helpful and supportive thing for me to focus on? Rather than feeling like I need to fit my life and my relationship status into some sort of mold so that I can do the healing work. So with that being said, let's talk a little bit more about the gifts and the limitations of healing while single. So as I was just saying, for anxiously attached people in particular, that self piece tends to be the crux of the work. And so whether you are single or in a relationship, my advice will always be focus on yourself. And I think that when we are single, that has the advantage of there being more space. You know, you have the luxury of real selfishness when you're single. I was giving advice to someone in my Healing Anxious Attachment course the other day who'd just been out of a breakup and saying, what if this was an opportunity to go all in on yourself, even for three months, right? What's three months in the scheme of your life? What would it be like to be totally self centered in the best possible way? Like, really make your life all about you without the distraction of focusing on someone else and what they need and what they're thinking and when they're going to be available. What would it be like to not rush back onto the apps or feel like you need to be hunting for the next thing? Like, how can I make my life so totally about me and what feels nourishing to me, and to really go in on my vitality and my joy and my sense of aliveness? And I think that that is really, in my mind, the great gift of doing this work while single, particularly if you are someone who has historically tended to focus on the other person and what they think and want and need and prefer and what will suit them and their convenience.
[00:11:56]:
Like reorienting that back onto yourself might be uncomfortable. You might not be accustomed to receiving that much attention, even if it's just from yourself. But there's huge growth in creating a life that is so fulfilling and so nourishing, and totally about you. So I think that doing that in conjunction with doing some of that deeper and sometimes heavier work around understanding your wounds and the things that you've carried and the grief that might come with that and all of those layers of emotional unraveling that we have to do sometimes when we're turning towards this work. I think doing that when you have a lot of time and space, when you're not distracted and being pulled into your old patterns that tend to be relational in nature, when you're not coming into contact with day to day triggers in the way that you might be if you were casually dating or in a relationship, I think that can be really fruitful. And that can be, as I said, a beautiful season to devote to yourself. Some of the limitations of doing that work while single, it's kind of the other side of the coin. You're not gonna be triggered as much.
[00:13:11]:
And there can be real gifts in our triggers because they bring us into contact with things that still need our attention. And so while it's not necessarily helpful to be like triggered all day every day, and we'll come to that in a moment when we talk about the relationship piece, if we just create a little bubble that feels like cloud nine, while that can be really supportive for a period, it might allow us to skate over the surface and create this illusion of like, 'look at me, I'm all healed now'. And then what I will often hear from people who maybe fall into that pattern and get a little too comfy there, is that then they start dating and they're like, oh, I thought I was healed, but look at me. I've started chatting with someone on a hinge and I'm an absolute mess four days into chatting with them because I think they're pulling away. So I guess I'm not healed at all. And we swing back into this shaming thing of, 'I thought I was fixed. It turns out I'm still broken. I guess I'm never gonna be healed.' And that's not a very helpful loop to go into.
[00:14:12]:
I think we want to find the balance and have really honest and healthy expectations around it. Like, I'm devoting this season to my healing, to my growth, and allowing myself to really relish the the sweet selfishness that can come with being single, while not letting that be an echo chamber or wrapping ourselves in cotton wool and pushing away anything and everything that might disturb the pristine piece of our singleness. Assuming that you do eventually want to be in a relationship, I think knowing that there will be a time that will come when you will re enter that arena and it will challenge you. Having that not only as a possibility, but an expectation. Like, I expect that I will absolutely be triggered if and when I start dating again. I think that's a healthy way to approach it because that is reality. You will be. And it's not about never getting triggered again.
[00:15:08]:
It's realizing that I am going to arrive at those moments of trigger as a new version of myself with different skills and tools and awareness and capacity. And that is my opportunity to put all of this work that I've been doing while single into practice. So it's not like I'm doing the work while single so that in my next relationship, I never have to feel triggered again. That's not realistic, and you're gonna feel defeated and confused if that's your expectation. But realizing I'm using this time to practice and to upskill and build my capacity, so that I can take a different version of me to that next chapter. Okay. So let's shift now to talking about doing this work while in a relationship. Now, I think the advantages of doing this work in a relationship are that that's real life.
[00:16:02]:
If you're someone who desires long term partnership and you're doing this work while in long term partnership or even medium short term partnership, That's the arena, right? That's what we're doing it for. It's all well and good to practice, to train, but I always say to my students and my clients, like, relationships, that's real life, that's game day, right? That's what we're doing it for. And so not holding ourselves back from real life, from getting messy, and allowing ourselves to be vulnerable, to take risks, and to hopefully have new experiences as a result of the work that we're doing, that's gold, right? And it's not always going to be comfortable. It's not always going to be easy or seamless. But that is so much of what we're doing it for is so that we can ebb and flow in real life relationships because that's not all within our control, right? It's nice to think of it all in terms of a video or a worksheet or a podcast or whatever, a nice script of how it's gonna go, But there's nothing really vulnerable about that and it's only when we actually show up. Face to face with a person who we love and care about and the stakes are high and it's real life, that is a huge opportunity. And it might scare the shit out of you, and that makes sense if it does, because it is real and the stakes are high. But that's that's what it's all about, right? That's where we put ourselves on the line for that because we care and we love, and that's what we're all doing it for.
[00:17:35]:
So I think that the reality factor, the mess of it all, the vulnerability, is a huge opportunity to build deep intimacy, because being really seen and attuned to and feeling understood, When we reveal parts of ourselves that maybe we've never shown anyone or we're afraid or unlovable, those experiences can be very deeply healing. And I think oftentimes it's only through the process of rupture and repair and speaking our needs and voicing fears or concerns or setting boundaries. These bumps in the road are very fruitful in terms of deepening our relationships. And so I think when you're doing this work and you're showing up to your relationship differently and showing up to those hard moments with more capacity to have those corrective experiences that that show your system another way is possible, that can be incredibly valuable and really catapult your growth and the evolution of your relationship into something deeper and more connected. Now I think the flip side of that is that if the relationship lacks the emotional safety that is needed to have those positive experiences, then there's every chance that you will just continue to trigger the hell out of each other. And maybe one or both of you lack the tools, awareness, capacity to engage in meaningful repair such that you're just getting triggered all the time and nothing's actually being done to tend to those wounds. So if you're just in the arena all the time getting pummeled, obviously not literally, but always being triggered, always on edge, always in hyper vigilance and high conflict, like, I don't think that that's a healing container. And I think we have to be really honest and discerning about is there anything about this dynamic or environment that is actually conducive to the building of trust and emotional safety.
[00:19:44]:
And if that's not the case, then you may be compromising your ability to grow and to build more security within yourself if you're in a relational dynamic that is reinforcing all of those wounds. And you're still collecting evidence every day that relationships are unsafe, that people don't care about me, that I'm always trying hard. Like, we wanna be doing the opposite of that. We wanna be collecting new evidence for new stories. And so if your relationship is providing evidence for the old stories, old every day, and you're always on edge and always stressed, then I don't know that that's going to be supportive of your growth and it might actually be keeping you stuck in the cycles and the patterns that you're trying to shift away from. I guess the other thing that I'll just add on to that is we don't tend to grow or learn or reflect or integrate when we're in a constant state of stress and dysregulation. That's just not really how it works. And so we do need that baseline level of safety.
[00:20:47]:
It doesn't have to be perfect, but if you are, like, seriously dysregulated all the time, walking on eggshells, fighting. You're not really gonna be in a reflective mode. You're not gonna have the bandwidth or the capacity to take those risks, to be vulnerable, to be open hearted because you're so locked in patterns of threat detection and self protection that, again, are not really conducive to that loving, connected, open heartedness that's really gonna take you to that secure relationship place. Okay. So with all of that being said, I suppose I just want to emphasize that healing, and healing anxious attachment in particular, there's a big self piece, there's a big relational piece. And really finding a way to weave those together is what is going to allow you to integrate everything that you're learning, the self awareness that you're developing, the new skills that you're building, the nervous system capacity, all of those pieces come together and it's being woven together in this tapestry. So it's not like I need to do one thing and not the other, or I need to do this and not that. There will be different parts of the work in different seasons, and I think that no matter where you are in life, there are opportunities for you to turn inward, to reflect, to grow, to get curious, to be compassionate.
[00:22:15]:
There's no perfect formula for healing, because it's not a neat linear journey with a start and an end point, and that you're somehow behind or on the wrong track if you are where you are instead of somewhere else. Okay? So it's really so much less about your relationship status and more about your inner orientation to the work and the place that you're approaching it and yourself from. So if you're avoiding relationships to stay comfortable and from this place of 'I don't trust myself to date again because I'm going to go back into all of my old patterns and I've been feeling so good so I can't start dating again' well that's that's not security, right? That's fear. Or from the other place going I can't leave my relationship even though it's driving me crazy and I'm so unhappy all the time because I don't know what I'd do without it. We've gotta ask, where am I asking the question from? What's going on within me? What am I afraid of? And can I build enough self trust that it's okay, I can release the grip, I can just surrender a little to the unfolding of things and keep turning towards myself at every step of the way and asking these fundamental questions of what's going on for me, how am I feeling, what do I need, how could I best support myself? That's really the crux of it, it's not rigid, it's not formulaic, it's all about that inner relationship and how we relate to ourselves, to others and to life as a whole. So I hope that's been helpful no matter where you are on that spectrum and as I said at the start, definitely check out my new free training. If what I've shared today has resonated with you, I promise you'll get a lot out of it and I'd really love for you to check it out. Otherwise, thank you so much for joining me, and I look forward to seeing you again next week.
[00:24:05]:
Thanks for joining me for this episode of On Attachment. If you wanna go deeper on all things attachment, love, and relationships, you can find me on Instagram @stephanie__rigg or at stephanierigg.com. And if you enjoyed this episode, I'd be so grateful if you could leave a review and a 5 star rating. It really does help so much. Thanks again for being here, and I hope to see you again soon.
Keywords from Podcast Episode
healing anxious attachment, attachment styles, relationships, single vs in a relationship, personal growth, self-awareness, romantic triggers, emotional safety, inner relationship, self-esteem, corrective experiences, core wounds, nervous system, somatic healing, belief reprogramming, communication skills, setting boundaries, conflict resolution, relationship patterns, vulnerability, intimacy, self-advocacy, relationship breakups, dating, transformation, personal development, emotional regulation, being triggered, relational wounds, decision making in healing
#186: When Life Hasn't Gone to Plan
We all have visions for how we thought life would unfold — timelines we hoped to follow, milestones we expected to reach. So what happens when life doesn't go to plan?
Most of us, at some point, find ourselves standing in a version of our life we didn’t expect.
A job that once felt promising has worn thin. A relationship ends that we thought would last. The timeline we quietly clung to — for love, children, a sense of purpose — slips out of reach. It can feel disorienting, even surreal, to look around and realise: This isn’t how it was meant to go.
There’s a particular kind of grief that comes with unmet expectations. Not necessarily for what was, but for what was meant to be. And often, that grief is laced with shame — as though the fact that life hasn’t matched the vision means we’ve failed in some way.
You’re not alone in this. Far from it.
In fact, part of what makes this experience so painful is how rarely it’s spoken about. Most of us are surrounded by highlight reels — people who seem to have stayed the course, followed the steps, ticked the boxes. It can feel like you’re the only one who’s lost the plot, as though everyone else got a map you somehow missed.
But the truth is, very few people live the life they imagined in their early twenties. Not because they gave up, but because life is more complex than any script we could have written back then.
The grief, and the gap
There’s real heartbreak in letting go of a hoped-for future. And it’s important to give that space. This isn’t about telling yourself to look on the bright side or be grateful for what you have. It’s about making room for the quiet ache of things not turning out the way you’d hoped.
Maybe you thought you’d be married with children by now, and you’re still single. Maybe you poured yourself into a career that no longer fits. Maybe you thought you’d feel more secure, more connected, more settled than you do.
And in that gap — between the life you imagined and the life you’re living — it’s easy for unhelpful stories to rush in.
There must be something wrong with me.
I’m too late.
Everyone else has it figured out.
But those stories aren’t the truth. They’re the brain’s attempt to make sense of uncertainty — to find a culprit for a reality that doesn’t line up with the plan.
Trade-offs and turning points
There’s a quiet power in acknowledging that every path has its trade-offs. Being partnered has its comforts — and its compromises. So does being single. So does having children. So does not. There’s no perfect version of a life. There’s just the one you’re living now — and the one you’re still able to shape.
And that’s perhaps the most important piece: you’re still in it. However stuck or lost you might feel, this isn’t the end of your story.
That doesn’t mean you need to make radical changes tomorrow, or overhaul your life in search of something shinier. Sometimes, it’s enough to begin by asking small but honest questions:
What matters to me now?
What have I been postponing or avoiding?
What am I holding onto that’s no longer serving me?
Where could I choose something different?
We don’t need to know the whole path to take the next step. And we don’t need to feel confident to move forward. Often it’s the act of moving — of gently shifting something — that helps loosen the knot.
A different kind of hope
Hope, when life hasn’t gone to plan, isn’t about clinging to a new vision with white-knuckled optimism. It’s softer than that. It’s choosing to stay engaged with life, even when it’s messy. It’s allowing for the possibility that something unexpected — something meaningful — could still be ahead, even if you don’t yet know what that is.
It’s also remembering that you’re allowed to begin again. Or start over. Or try something you never thought you would. There’s no deadline on becoming the person you want to be, or creating a life that feels more aligned with who you are now.
So if you’re in a season that feels like a detour, or a breakdown, or just a long stretch of not-knowing — I hope you can hold space for the grief and the possibility. I hope you can be kind to yourself, even as you reflect honestly.
And I hope you can trust, even a little, that this chapter isn’t the whole story.
Questions for Discussion & Reflection
Have there been moments in your life where things haven’t gone to plan? How did you respond emotionally, and what beliefs about yourself emerged as a result?
When you reflect on your “life plan,” where do you notice your vision was shaped more by social ideals (like movies or social media), rather than your true values or desires?
Do you catch yourself comparing your timeline to those around you? If so, how does this impact your sense of self-worth or satisfaction with your current life stage?
In moments when you’ve felt lost or “behind,” have you tended to check out, deny reality, or try to force things back to how you thought they should be? Which of these patterns do you relate to most?
What grief or disappointment might you be carrying about a version of your life that hasn’t come to pass? How could you allow yourself to honour and feel these emotions, rather than bypass them?
Are there hidden gifts, opportunities, or lessons in your current season of life—even if it looks different to what you’d planned? How might you shift your perspective to find richness in where you are now?
Where do you notice a tendency to feel powerless or “defeated” about your circumstances? How might you reclaim a sense of agency or choice, even if it feels small?
How have beliefs like “it’s all over for me” or “there’s something wrong with me” influenced the actions (or inaction) you’ve taken in your life or relationships?
What would change if you saw yourself as the “hero” or main character in your story, open to what’s next on your journey? What possibilities or excitement does that open up for you?
How can you practise both self-compassion and self-responsibility as you navigate life’s detours—making space for tender feelings, while also taking steps towards what you want next?
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Episode Transcript
[00:00:29]:
In today's episode, we are talking about what to do when life hasn't gone to plan. So how to navigate the immense, confusing, conflicting emotions that can come with a life that is unfolding, that has unfolded, in a way that's maybe really different to what you had imagined for, what you had hoped for. I think this is incredibly common and maybe not talked about enough, because for a lot of us, for most of us probably, the vision that we have for our lives when we are young, so maybe as a child in our teenage years, when we're in our early twenties, I think we can have these really idealistic notions of what our life path is going to look like, and that it's all going to be quite linear and smooth sailing and picture perfect. And then when life throws its inevitable curveballs our way, when we come up against challenges in our work, or in our relationships, when relationships break down that we thought were going to be for the rest of our lives, or maybe we struggled to find a partner altogether when we thought that we'd be settled down with a couple of kids. All of these things can leave us feeling really confused, disoriented, and broken. I think the sense of failure and unworthiness that these experiences can touch into is really really profound.
[00:01:57]:
And so I want to talk today a little about some reflections on when life hasn't gone to plan, and it's a deliberately broad framing of the conversation because I don't want it to be only about if you are still single in your mid thirties, for example, which is, I think, a common expression of this, and a lot of people listening I think will fall into that category. But equally, it can be if you're newly single in your fifties, and that was completely unexpected and not part of what you'd planned for or hoped for. Or it can be that you're thinking of leaving a relationship at a period in life when you thought you'd be settled down, or it can be unrelated to relationships. Maybe it can be something to do with work and purpose, and feeling like you've invested so much in one path only to realize that it's not right for you, and you want to change directions. All of these experiences are, I think, branches off the same tree, and they require us to reflect on similar questions and come back to our power, because it's really easy to feel powerless when we're in that situation, when we feel like this isn't how it was meant to be, and we feel kind of out of control. So I'm hoping to share some insights for people in all of those situations and and everything in between in today's episode that will allow you to feel a little more grounded, a little more trusting, a little more surrendered to the flow of life and the unfolding of of whatever may be, and how you can simultaneously grieve and honour the realness of whatever emotions are there for you around where you're at and where you've come from and, you know, what might lie ahead or not, but also so that you can remember your agency and not kind of lay down in defeat and feel like well it's all over for me now', really reminding you that there's still so much richness and beauty to be had no matter where you're at and where you find yourself. So that's what we're going to be talking about today. Before we get into today's conversation, a reminder, if you listened to my most recent episode, you would have heard me share about my brand new free training, how to heal anxious attachment and finally feel secure in life and love.
[00:04:11]:
I announced this new training less than a week ago, and already I think 1,200, 13 hundred people have registered and signed up, and it's been getting beautiful feedback. So I would love for you to check it out. If you're someone who struggles with anxious attachment, no matter where you're at on that journey, whether you're brand new to it, whether you're in a relationship or not, this free training goes into the core pillars of healing that I've taught to thousands of people. I also talk about why you might feel stuck even though you've been doing the work, so to speak, so some common blocks to healing and how you can overcome them, and how to discern whether the challenges you're experiencing in your relationship are quote unquote just your anxious attachment, or whether there's some genuine misalignment or incompatibility in the relationship that needs addressing. In other words, is it me, or is there something really wrong here? So I go into all of that in this free training. I would love for you to check it out if any of that sounds like something that is up your alley. The link to register for that free training is in the show notes. It's also on my website and my Instagram.
[00:05:19]:
So definitely check it out if you're interested. Okay. So let's talk about this, when life hasn't gone to plan. Now as I said in the introduction, this is so common. It's so rare that life goes exactly to plan. Right? And yet, we cling to our visions of how it was meant to go, and we can feel so vulnerable without those visions. When things start to deviate from the course that we had charted, all of a sudden we feel kind of lost and naked, and this isn't how it was meant to be. We can be in such resistance to the reality that we find ourselves in.
[00:05:54]:
And I think depending on who you are and how you operate, you can respond to that in different ways. Some people maybe give up and check out altogether. Some people live in denial of it. Some people try to reverse it, so kind of cling to something that just clearly isn't meant to be, just because you have these ideas like, no, this can't be over, I can't be getting a divorce, or I can't be a single parent, or whatever the thing might be. Now, as I started to say in the introduction, I think this can take lots of different forms. I think some really common ones are things around success, achievement, career, so whether you've not had the success that you were hoping for in the line of work that you have pursued, and so you've had to pivot, or losing a job, or maybe you took longer than expected to get through your studies, struggling to find a sense of meaning or purpose in your work, feeling really unfulfilled, wondering, like, is this meant to be enough? It doesn't feel like enough. All of those things, I think, in the career, work, purpose bucket can be really real that could fall under this category of, like, this isn't how it was meant to look. This is not as neat and linear and clean as maybe I expected it to be.
[00:07:12]:
Maybe I'm looking over my shoulder at the people around me, and it seems like everyone else is not struggling in the way that I am. The relationship bucket is obviously another really big one. So relationships that you thought were gonna be the one, and whether that was that you then broke up, or you even got married and then got divorced, All of those sorts of things may be unexpected betrayals that were a total spanner in the works, and threw your life very suddenly in a direction that you didn't expect it to go. And of course, the other big one here is struggling to find a partner. So if you've been single for a long time and you really want a partner but you're starting to doubt whether that's even possible for you, or maybe you've had a string of short, dysfunctional, unhealthy, disappointing relationships, and so you've collected a lot of evidence that there must just be something wrong with me, or I must just be bad at relationships, even though there's a part of you that really, really longs for committed partnership. Some other things that might fall into this category of life not going to plan is maybe you're just struggling with feeling loneliness or disconnection, and again that can be from a sense of purpose or it can be as friendships and social circles shift over time, that you can feel like maybe you've been left behind, or you feel a bit isolated. Maybe as other people's timelines or trajectories have taken them to a particular place, into a season of life that you're not in, and that has taken you down different roads, and feeling the sense of grief and loss that can go along with the loss of friendships, or the drifting apart, and the sense of isolation that can maybe go with that. So there are really so many forms that this can take, and obviously what I've just shared is very much non exhaustive.
[00:09:02]:
But the point being that it's so rare that our life unfolds exactly as we thought it would because usually what we think is going to happen when we're young and bright eyed and thinking about our future, it's this beautifully innocent romantic ideal that maybe isn't fully grounded in the challenges of life and the inevitable setbacks and detours and struggles that we all face in different forms. I think that whether it's like Disney movies or rom coms or social media, we're always being presented with this really shiny version of what other people's lives look like, and whether we realize it or not, that's incredibly powerful in shaping our own perception and expectation around what things are meant to look like. So to the extent that our own experience is deviating from that or differing from that, we assume that, well, there must just be something wrong with me. The fact that I can't have that, or that I'm having a hard time when everyone else seems to be smooth sailing on this really linear path to happiness and meaning, and I'm here struggling and treading water and feeling lost and confused, and the weeks, months, years are rolling by, and I don't feel like I'm making progress. All of that can really become big and overwhelming, and I think we can carry a lot of shame and a sense of brokenness and inadequacy and unworthiness around that. So I think what's really important to honor in any of these conversations around when life hasn't gone to plan, apart from the fact that the plan was probably not a realistic one to begin with, because it's very unlikely that in our plan we accounted for all of those inevitable curve balls that life throws, and it was probably a very storybook life that we had mapped out for ourselves. I think that the thing that we really need to honor is being able to hold both the realness of those feelings, so like holding the grief and honoring the grief. I'm not going to tell you to just look on the bright side and skip past it, right? I don't think that's honest, I don't think that's being really true to the complexity of the emotions that come with these experiences.
[00:11:19]:
And I think that when we just try to white knuckle it and tell ourselves that it's not that bad and we should just be grateful or whatever we might do to try and bypass the bigness of that grief, I don't think that tends to work very well. I actually think we need to turn towards whatever's there and feel into it. Feel that sense of like, brokenness, and the pain and the sorrow and the despair and the fear, and that sense of scarcity, all of those things, and that sense of scarcity, all of those things that can come along with it. Because I think until we turn towards that and really see what's there and feel what's there, we're almost certainly not doing anything to address that core wound and all of the subconscious beliefs that go along with it. There's something wrong with me, no one's ever gonna choose me, or why can't I just be happy, or why is it so easy for everyone else? All of these things are grounded in a lack of self worth. And so until we really turn the light on, so to speak, and see what's there, we're not going to be able to address those underlying things. At the same time as acknowledging the grief and the loss and the fear and the sadness, I guess the reframe that I do want to offer is that every path in life has trade offs. Being in a relationship has trade offs.
[00:12:35]:
Being single has trade offs. Having kids has trade offs. Not having kids has trade offs. Quitting your job and starting your own business has trade offs, and staying in a job that's secure but maybe unfulfilling has trade offs. There's no perfect life. There's no perfect solution. There's no perfect partner. Everything is going to come with its upsides and downsides, its gifts and its challenges.
[00:13:00]:
So while we want to honor the grief, we also want to try and anchor into what is the opportunity that this season of life is gifting to me? And I think that when we can see that for what it is, like what is the richness that is here for me? Rather than just wishing it away or being in resistance to it, I think that allows us to find more joy and more vitality, and more life in the moment, which in turn I think energizes us to go after what we really want. When we kind of collapse down into this sense of scarcity, into this sense of almost like a hopelessness, like it's all over for me because of the way my life has unfolded. I might as well give up. When we kind of give up on ourselves and on our future, then obviously that becomes a self fulfilling prophecy pretty quickly. If we believe that there's no point in going after what we really desire for ourselves, what we long for, then we're never going to go after that, we're never going to bring that to fruition because we've kind of resigned ourselves to the fact that it's all over for us. So it's really juggling all of these things. It's holding all of them. It's holding, like, yes, I can feel so much grief for the fact that I'm not where I wanted to be, or that things feel confusing and hard, And I can see that this season of life has gifts and opportunities, and that there's joy to be found here, and that there are lessons to be learned here.
[00:14:26]:
And I can continue to anchor into the truth of my desires and my longings, and trust in my ability to take steps towards that, and really remind myself of the agency that I do have to give effect to my future, and to take steps towards creating the future that I want. Because for so long as we really believe that something is not possible, of course, we're never going to take steps towards it. Right? If you believe that, like, well, I'm just never going to have a healthy relationship, guess what? You're not going to put effort into finding and building a healthy relationship. Maybe you just stop dating altogether and become kind of reclusive, or you accept something that is way short of what a healthy relationship is and what you truly desire in partnership, because that's all you think that you can get. And this is true for every area of life again. If you think the very concept of finding work that is fulfilling and purposeful is an impossibility, then you're going to accept the jobs that you hate. And so it really is like almost auditing, like what are these subconscious scripts that I'm running about what I believe is possible for my life, and is that really true, and what would be possible if I swapped out that script for something that was more expansive, more grounded in my agency, my choice, what is possible. And I think that that really brings us back to center, and allows us to go like, well okay, I'm not dead yet.
[00:15:48]:
I've still got my life ahead of me, so what am I gonna make of it? I think another really fun way to play with this can be to think of ourselves as the main character in in a great story. There's a book by Donald Miller called Hero on a Mission that came out a few years ago, and he's a very famous, like, business author, marketer, copywriter, but he talks about, in this book, Hero on a Mission, relating to yourself and your own life story as if you are the hero of the story, and you're going to come up against villains, and you're going to come up against trials and tribulations, and relating to yourself in that way allows you to almost get excited about like, 'wow, how am I going to triumph over this?' If this was my dark night of the soul, if this was my really, really challenging chapter, I wonder what comes next. And leaning into that sense of excitement and possibility and curiosity, and this sense of, like, I'm open to being surprised by the universe. What miracles are waiting around the corner for me? I think the more that we are open to and engaging with life, rather than hiding from it or turning away from it, that's when we can really change our whole energy in terms of how we're relating to our own lives and the world around us, and I think that can be a really powerful shift. And it can actually make it kind of fun because you're approaching it with like, oh, I wonder what happens next in this grand story that is my life. The other thing that I'll say before I wrap up is I've worked with people who are like in their early twenties all the way up to people in their seventies, and I can guarantee you that people experience this sense of like, I'm out of time', or it's all over for me because of the way things have gone'. People experience that at every step along the way, and I can guarantee you if you are in your thirties and you feel like you're running out of time, people who are in their forties would kill to be in their thirties again and have that time back. And same for people in their forties, and their fifties, and their sixties.
[00:17:51]:
Right? You get the point. It's so easy for us to focus on, like, what we lack, or what's already gone, or what feels impossible, but I promise you there are people out there who would kill to be in your position, and to have the time that you have and to be at the life stage that you are at with everything that is still in front of you. So before you resign yourself to a life of unhappiness or loneliness or whatever else you're kind of in at the moment that you feel is too big to move through, please know that there is so much more for you than what you're experiencing. If you're not feeling inspired by what you're living, just know that it doesn't always have to be this way, but that does require you to get uncomfortable and to get honest, and to look at how you are participating in your circumstances. If you want things to change, then that's gonna require you to make changes. I think when we can get into that kind of defeated mode, we create so much evidence for the story because we don't actually take action to change our lives, and then we say, well, what was I meant to do? I couldn't change anything. And that just becomes true. Right? So having so much self compassion at the same time as having self responsibility, as always, that is an absolute core value in all of my work, balancing both self compassion and self responsibility.
[00:19:15]:
Recognising the humanness of everything that we're struggling with and having so much love for the parts of us that are having a hard time or that carry those fears and those negative beliefs about ourselves, while also anchoring into, okay what are my choices? What can I do today that is going to support me to bring myself into alignment with my values, to become the person that I really really want to be, to show up in the world the way that I really want to, that feels like an expression of my true self, my authentic self, that allows me to feel a sense of purpose and momentum and aliveness? All of those things are possible for all of us, I really deeply believe that. Okay, so I'm gonna leave it there. I just wanna wrap up by saying the life that you plan is not the only life worth living. It doesn't mean anything about you if life has unfolded differently. As I said, it unfolds differently for all of us, and so reminding yourself that like there's so much life to be lived, there are so many gifts and opportunities in every season of life, and being able to hold that while also honoring all of the emotions that come with the curveballs and the challenges, I think that sets you up to really make the most of wherever you're at, and take really deliberate and intentional steps towards whatever comes next. So sending you so much love. I know that this can be really challenging and tender, but I have every faith in your hero's journey and what's coming next. And I hope that this has given you some comfort and reassurance and inspiration.
[00:20:52]:
So sending so much love, and I look forward to seeing you again next week. Thanks, guys.
[00:20:59]:
Thanks for joining me for this episode of On Attachment. If you wanna go deeper on all things attachment, love, and relationships, you can find me on Instagram @stephanie__rigg or at stephanierigg.com. And if you enjoyed this episode, I'd be so grateful if you could leave a review and a 5 star rating. It really does help so much. Thanks again for being here, and I hope to see you again soon.
Keywords from Podcast Episode
life not going to plan, overcoming insecurity, attachment styles, healing anxious attachment, building healthy relationships, relationship breakdowns, navigating emotions, sense of failure, self-worth, changing life direction, relationship grief, feeling unworthy, agency in life, embracing change, single in thirties, single in fifties, career dissatisfaction, finding purpose, life transitions, loneliness, friendship loss, societal expectations, perfectionism, resistance to reality, self-compassion, self-responsibility, personal growth, relationship coaching, romantic longing, authentic self