How to Stop Living with Chronic Disappointment

If you feel like life keeps letting you down, like no matter what you do, it’s never enough, this episode is for you. Because you’re not broken and you’re not doomed to always feel this way. Chronic disappointment is a pattern, not a life sentence, and today I’m going to show you exactly how to shift it. Let’s go.

This show is for women who’ve been labeled, misdiagnosed, or misunderstood. Whether you have a diagnosis or just know deep down that you experience life differently, this is your space to stop fixing yourself and start trusting who you already are. My name is Amanda Hess. Let’s go.

Do you ever feel like life just keeps letting you down? Like no matter what you do, how hard you try, it’s never enough. Here’s the truth: chronic disappointment isn’t proof that you somehow haven’t got it figured out. It’s actually a pattern, and it’s a pattern that you can shift. And when you learn how, everything else changes.

Now, I want to start out with the understanding that most of us live with some level of disappointment in our work, in our relationships, and in ourselves. And it’s normal. But the problem I see is when it becomes chronic, when it feels like it’s the background music of your life.

Oftentimes, when I’m talking to someone, when I’m coaching someone, when I have somebody that comes on to a discovery call, they will tell me the story of their life. And we all tell the story of our life. And of course, if you come on to a call when you are trying to get something that isn’t working fixed, you’re going to tell me about the problems that are going on in your life. And that makes sense. And that’s of course, how you’re going to show up in doing that.

But what I find is that this is actually oftentimes the story that you’re also telling to yourself. And many times, there are results that are happening in our life that we don’t want. And we reach a point within ourselves where we realize, or we think we realize, I should say, that this is as good as it gets for us, that we don’t get to have better, that we don’t get to have more. Or I think even worse yet, that in order to have better or to have more, that what we would need to do is blow up our entire life. And we’re 100% not ready to do that.

And I, first of all, just want to honor this. That of course, there are things in your life that are working and there are people that you love, and there are things that are happening that you don’t want to change, that you don’t want to shift, that you don’t want to blow up. And that makes perfect sense to me.

But at the same time, we have to look at the results that we’re getting and be honest with ourselves whether or not they’re the results that we want. And too often, what I see is that women will be chronically disappointed, and they will just make the assumption or make the decision that this is as good as it’s going to get for them.

And when we do that, when we decide we can’t have more, it can’t be better, we can’t have the things we want to have. When we believe that that is the truth, then we stop trying to go get it. We stop setting that as being the thing that we’re working towards or we’re working on. And too often, what ends up happening is years go by. Years. Years go by. What will feel like all of a sudden is that you will wake up and you won’t know why you feel as terrible as you feel, but you feel terrible.

You will look at all of the components of your life and realize you don’t really love the relationship that you have with your partner. You don’t really love the relationship that you have with your kids. You don’t really love your job. You don’t really love your house. You don’t really love your friends. You don’t really love yourself.

And that is so heavy. It feels heavy, it feels draining. It feels like you’re carrying invisible weight. And that you kind of like some of the things that are going on, but there are a lot of pieces of it that you don’t like at all. And you feel very powerless in being able to change that.

When we carry a lot of disappointment and it becomes something that shows up in every area of our life, it will begin creating a lot of self-doubt, a lot of resentment, a lot of numbing out, and a lot of settling.

I have really seen over the years that I’ve coached, with the women that I’ve coached, that there is a station where we think we land. And I don’t know where that station necessarily comes from. It’s all made up inside of our own head.

But there is a station with respect to the kind of relationship that we think we can have. There’s a station with respect to the amount of money we think we can earn and own. There is a station with respect to what our kids will be like and our relationship with them. There’s a station when it comes to our career. And what I mean by a station is that there’s a ceiling and that that ceiling is lower than where we’d like it to be.

And so we will unknowingly end up believing that that ceiling is there and addressing and approaching our life from the standpoint of there is a ceiling. And because we do that, we don’t push for more. We don’t ask for more. We don’t go for more. And once we start having this experience in our life, emotionally, we become somewhat stunted. We find ourselves really just feeling a lot of low-level negative emotion. And that just rides. It rides over every part of our life.

I see this happening in so many clients and so many of them come up when I think about them. One client of mine went through a really painful separation and divorce. And when that happened, she took shelter and made it her life’s work to take care of her kids. And there were three of them. And she single parented these kids into college and adulthood.

And she had a lot of pain that she just didn’t address because she needed to be able to show up for these kids. That was her thoughts, right? That’s how she did it. And she was a spectacular mom. She took really great care of her kids and gave them everything they needed. But what she was finding as she became an empty nester and these kids were leaving and being on their own is that she felt empty inside.

And I feel that chronic disappointment is a creator of emptiness. What happened for her is she found herself numbing all the time. She was either working or she was numbing, or she was there for her kids. And I think this is a very common thing that happens to a lot of women where we end up in this scenario and we wonder where the happiness is, where the joy lives, where are the good emotions that people talk about, where’s the positive part of this 50/50 that’s supposed to exist, right?

And what I will say to you is that for her, what had happened was she had put a ceiling on herself without realizing that she had, and that she had to live where she lived and she wasn’t able to move. That she needed to over function for a child that had a health concern that was living still at home. That she had to accept the job that she was in and just grin and bear it.

That she had to hide pieces of herself from the world so that people didn’t see how maybe fucked up she is, possibly, her thoughts, okay? Maybe not her words exactly, but close. And she found herself trapped in a cage. So you have the ceiling and then you have the cage that comes next. And that’s what I really see with chronic disappointment is that first there’s the ceiling and then comes the cage and then we become trapped.

And this is just such a common experience when we are trying to survive all the time, when our life becomes about survival. And I want you to know that this isn’t because something is wrong with you. This isn’t because you did something wrong or because you are somehow not strong enough or not positive enough. I hear that a lot. It has nothing to do with that at all. The truth is is that it’s conditioning over time.

The truth is is that, first of all, society teaches women to people please, to actually turn their own needs off to be able to take care of other people, right?

So you see this a lot in parenting. You see this a lot in women and their kids, where they are no longer looking at their needs. They are always looking at their children’s needs, their husband’s needs, their partner’s needs, their wives’ needs. They are looking at the household’s needs, their parents’ needs, their siblings’ needs, the dog’s needs, the cat’s needs.

We are socialized to do this and to be this way. We are conditioned by society. And so we also, at the same time, are conditioned to expect disappointment.

And the first thing that comes to mind for me is my niece, okay? So my niece plays soccer. She is an elite soccer player. She is going into grade 11 this year. I am so proud of her. She works so freaking hard. She is always thinking about soccer. She goes to every camp she can. She doesn’t want to miss a single practice. She does her own practice at home for hours every day. She gets up extra early.

She is tuned in to how to become a better soccer player because she has goals. She wants to play for a national team. She wants to be drafted, I think that’s the right word, for an NCAA school. She wants soccer to become her career. And it’s amazing.

But I watch the adults around her that are saying things that I find fascinating and also hugely problematic, which is, “You better have a plan B. That’s probably not going to be what you’re going to be able to do for the rest of your life. I hope that you’re keeping your grades up because, you know, this is going to crush you. I hope that she knows that she should be tempering her expectations, that she should be wary of how crushed she will be if she doesn’t make it.”

And what I find is that as a society, as a whole, we start teaching our teenagers to have low-level chronic disappointment all the time. Before you even try to get the goal, you should believe that it’s probably not going to happen so that you don’t feel disappointed. But instead, what we do is we feel disappointed in advance. We’re teaching our children to feel disappointed ahead of time, which is crazy. And so what we’re saying to her is, don’t be too attached to this. Don’t put everything into this because it might not happen.

And that is when we start to quietly quit. And we are teaching her that what we think she should do is quietly quit. And I don’t believe in that at all for anyone.

And what I’m going to tell you is that this chronic disappointment that so many women are dealing with comes from this mindset. This idea that you must temper your expectations because you can’t have everything that you want. And when we think that, then we start believing it. And when we believe it, we start feeling that disappointment in advance. And then what happens? We stop trying. And when we stop trying, what happens? We don’t get it. And then what do we get in return? Disappointment. That is how that works. That is just how that always works.

The other thing that I see happening for women is this idea that we always have to be perfect. So on one hand, we can’t have anything we really, really deeply want because that’s unrealistic and we should temper our expectations. But on the other hand, we should always be perfect at everything we do. Now, what’s fascinating about this perfectionist drive is how we don’t actually know where the bar is. And if we do magically somehow reach it, we just raise it.

I had a client say to me yesterday, maybe it was today. It was today. It was earlier today. It’s been a day. And she said to me that the one thing that she wishes she could change is the belief that she’s just never going to be good enough, that that belief is so strong inside her. And I asked her on the call, how she’s going to know? How do you know when you’re good enough? How do you know? And she looked at me and she just said, “I don’t know. That’s a really interesting question. I don’t know.”

And the truth is, we don’t know. Because actually we’ve just believed that we are not good enough for so long that we don’t even realize where good enough lands. We don’t know where that is. We don’t know how to get there because guess what? There – there doesn’t even exist. It doesn’t exist.

So what I want to really say to you as I’m talking to you about this is if you live here inside of this, if this is happening for you, nothing has gone wrong. Your brain has just honestly learned through time and practice, not designed by you, that this is home base, that this is where we sit, this is where we live with ourselves.

But let’s really talk about what disappointment is really telling you. The first thing I want you to know is that disappointment is data. It’s information. In all honesty, all emotions are just informants. They’re informing us how we receive the world. They’re informing us how we see ourselves and how we see ourselves placed in the world.

Disappointment is often a sign. It’s a sign that you may be outsourcing your validation, that you might be looking to others to show and prove that you’re good enough instead of going inside and figuring out how to do that for yourself. Disappointment is often a sign that you’re ignoring your own needs, that you are not actually taking care of your mind, body, and soul.

Disappointment’s often a sign that you’ve set expectations for yourself without any real alignment at all, that you have beliefs like, I need to make my kids happy. I need to make sure I’m a good parent. I need to excel at work. I need everybody to like me. I need to ensure that I have a friend group. These are all interesting thoughts that don’t give you any guideposts. There’s no way to know whether or not you got there or not. And there’s no way to really understand how to do it or how to get there or how to know that you’ve arrived.

And what I will say to you is that knowing this is part of the battle. This thing that I’m experiencing, this chronic disappointment, it’s coming from inside me, not from outside of me. It’s not because I’ve reached a limit. It’s because something is going on internally with me that is problematic, that is not working.

When I coach someone, nine times out of 10, and maybe 10 times out of 10, when I ask someone what they like, they can’t answer it. When I ask someone what they want, they don’t know. And that can be really dysregulating. It can make you really feel sad and defeated and upset and maybe even disappointed. But to me, this is just the starting point. The reason why most of us don’t know what we want is because we’ve been taught how to be chronically disappointed. That’s the truth. And knowing that means we have a way to fix it.

So how do we get past being chronically disappointed? Number one, what you need to know is that you probably need to get better at experiencing, allowing, and processing emotion. I’d almost say there’s a 99% chance that that’s true for you. And most of us walk around really scared of emotion. And if you think about the examples that I gave you earlier in this episode, it makes sense. It makes sense because we were taught that we can’t handle emotion, that in fact, we shouldn’t go for it because the disappointment will be so crushing, we won’t be okay. So don’t go for it at all.

So number one, we need to start creating some awareness of the emotions that are coming up for us and the ones that we’re afraid of. What are you afraid to feel? I am not afraid to feel a lot of emotions that you might currently be afraid to feel. I am not afraid to feel embarrassed. I’ll give you an example. I may have talked about it on this podcast before.

So I waterski. I’ve waterskied for many years. I love waterskiing. I’ve slalom skied for so long. In fact, I had my son’s girlfriend on the boat and we were skiing and she got up on two on second try. It was so awesome. And she just said to me, I didn’t even know you could ski on one ski. And wow, how do you get so good at that?

And I just looked at her and I was like, you ski for 46 years. That’s how you do it for me, in my case. I have been skiing for so long. It’s like walking. I mean, I haven’t been skiing for 46 years. Maybe it’s like I started when I was six. So is that 43 years? It’s still a long freaking time, right? I’ve slalom skied for over 30 years. So of course, I’m good at slalom skiing for the sense of I can do it, okay? If you really want to get into the weeds, there are much better skiers than me, but that’s something totally different.

What I think you want to hear about though is me trying to wake surf. So wake surfing is arguably very easy. It’s supposed to be better on your body. It is supposed to be easy to get up. Both my kids can surf. My husband has surfed. Every person I’ve ever watched can surf. However, I have tried to surf many, many, many times. I mean, over 20, over 30, probably over 40 times over the span of, let’s say, five years – longer actually, more like seven years, although not always trying.

And the reason why I’m telling this story is because it’s embarrassing for me to not be able to get up when everybody else in the boat can get up. It’s embarrassing that I can slalom ski, but I can’t seem to figure out how to surf. So I go and I try. And you know what? I’ve had some success. My 18-year-old helped me the one day, and I was able to get behind the boat at least with my board turned and be up and surfing, but not really surfing because there was no chance I was letting go of the rope because I wasn’t actually surfing. I was just getting pulled behind the boat.

But the second time I went to do it, he wasn’t there, and I got up, but I couldn’t get the board turned and couldn’t make that happen. And six tries later, after drinking a whole lake, I was done. And I felt deeply embarrassed. It’s embarrassing for me. I want to be good at something, or at least be able to do it at all, but I could not.

Why do I tell you this story? I tell you this story because I need you to know I’m just not afraid to be embarrassed. I still think there could be value in me learning how to surf. I think I can figure it out. I just haven’t yet, but I’m willing to feel embarrassed. This is how I started skating again. This is how I ask for what I want and what I need in my marriage. This is how I make new friends. I do this because I’m willing to feel embarrassed.

So when you’re chronically disappointed, what happens is you are probably afraid of feeling embarrassed. And this is something that we need to grow capacity for. I’m not afraid to feel embarrassed. I’m not afraid to feel vulnerable. I’m not afraid to feel rejected.

And these are some of the big things that I see that create chronic disappointment because if we’re afraid of rejection, or if we’re afraid of vulnerability, if we’re afraid of feeling embarrassed, or whatever it is for you, but those are the big ones I find, then what happens is we shut ourselves down and we don’t go for it. And that is what we’ve been conditioned to do.

However, the path forward is learning how to experience those emotions without flipping out and without shutting down and without beating the shit out of yourself. And that is a process.

I always offer you the Love Yourself No Matter What method, which is one, we learn how to regulate your nervous system every single day and multiple times a day through quick and simple practices, right? Things that a five-year-old could do.

We do this and it allows us to grow our capacity to feel so that those emotions don’t feel heavy, so they don’t feel like a big shackle, so that they don’t feel this thing that’s crushing you. Without doing anything with thought work, without doing anything with even emotional allowing, we can do so much through nervous system regulation. So it’s what I offer you first.

The second thing is we learn how to process and allow emotion and to be safe with emotion. Emotions are just vibrations in your body, and there are simple and doable ways to be able to allow and process that. It does not require you to go on some transcendent meditation, I promise. It doesn’t need to take a long time. It takes seconds, but you need to learn how to find emotion in your body and know what to do with it.

And then the last thing is then we look at the thoughts, the beliefs, and we start to break apart the ones that aren’t serving you, that aren’t working for you, that are blocking you from trying new things, from really going for things that you care about.

Now, this isn’t just about goal setting. This is also about addressing your relationship. One of the biggest things that I coach on in somebody’s marriage is understanding how to get what you need in the marriage. And that isn’t about being directive. That isn’t about making your partner different. That isn’t about you being a doormat. That’s about you being able to show up and be embarrassed and vulnerable and willing to feel rejected and then go again and then go again.

We have to go all the way. When we don’t go all the way, then we don’t know if we did it. And yes, you might feel disappointed if it doesn’t get all the way there, but it’s a hell of a lot better than being chronically disappointed for the rest of your fucking life. I promise.

This is true in your career. This is true when it comes to money. This is true when it comes to parenting your kids. You’ve got to learn how to go for it. Now, that doesn’t mean you have to grin and bear it. That doesn’t mean that I’m going to teach you how to just really try and just hope that you make it. Not like that at all.

This is about you learning how to do it in a way that’s sustainable, that you can do it with complete confidence in yourself. This is something that you do with practice over time. So if you are the person that is feeling chronically disappointed, know that the path forward to experience real joy, real happiness, real excitement, real connection is going to be through changing this for yourself, learning how to not be afraid of emotion, learning how to navigate your brain. This is how you change it.

So this is what I’ve got for you today. As always, I want to offer you the opportunity to book a discovery call. You can just go to amandahess.ca/bookacall to set that up. Whatever you decide to do here, I want you to know that you being chronically disappointed doesn’t need to be the way you stay. All right, my friend? That’s what I’ve got. I’ll see you here next time. Bye.

Thanks so much for listening today. If this podcast is helping you, please follow wherever you listen and consider leaving a review. It truly helps this community grow and allows me to support more women like you. I’m excited to see you back here next week with a brand new episode. Until then, take care, friend.