#186: When Life Hasn't Gone 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