Why Asking for What You Want Feels So Hard for Highly Sensitive People and How to Do It Without Overthinking

 By the end of this episode, you’ll see why it can feel so uncomfortable to ask for what you want as a highly sensitive person, and how to move through that without second-guessing yourself. In this episode, you’ll discover what’s happening when it feels hard to ask for what you want, why overthinking shows up so quickly in these moments, and how to move forward without needing everything to feel completely right.

This is an edition of Strategy Fridays, where we think about specific things you can do to help manage stress as a highly sensitive person. So why is it so hard for us to ask for what I want, what we want as highly sensitive people? There’s a lot going on actually, and when we lo- slow it down, you can see that what happens is our awareness expands in that moment.

As HSPs, the moment you think about asking for something, your awareness widens, and it doesn’t just say, “Oh, I want this,” which is probably more common for others. Things like, how is this gonna land? Or how is the other person gonna feel? What does this imply? And what could happen next? And so the moment becomes bigger than just the simple ask itself.

It’s not … The problem is not getting the words out, it’s that there’s a lot more involved to it with it than what you might think at first. And so the mind will start managing impact and very quickly you’ll be thinking about, “How do I ask this in the right way?” Not just, what do I say? But more like, how do I say it?

How will it be received? How do I avoid discomfort? How do I prevent any negative reaction? And so now you’re not just asking, you’re trying to manage the entire emotional outcome of the interaction. And so the ask becomes loaded in a sense because the request starts to carry extra meaning like, “Oh my gosh, is this gonna be too much?

Will this inconvenience them? Will they think differently of me? What if they say no?” So even simple requests start to feel like they have weight. Am I going to impose myself on them? And this is how overthinking can begin and can get caught into kind of a loop. This overthinking isn’t random.

It’s really just an attempt to get it right and that is laudable and it is natural for us as highly sensitive people to try to do a good job at everything. It’s attempt, an attempt to find the right wording, to f- avoid missteps, to create a clean outcome and- To reduce risk, which is what we’re designed to do as HSPs.

But what can happen is the more you think, the more variables can appear, and it can start to feel stressful. Also, there can be a kind of pressure underneath all of this. Something like, “I need to ask in a way that doesn’t create any problem,” and that’s actually a very high bar. Not… It’s often even impossible to do in some situations.

So the system can hesitate because of that, and it’s not that you don’t know what you want, but you’re wanting to ask it in a perfect way that may not always be possible to find. So the discomfort comes from holding all of this at once, your desire, the potential reaction from the others, the need to say it well, and the wish to avoid any negative impact, and that’s a lot to carry in a single moment.

So what causes the actual overthinking to come in? Part of it is our natural depth of processing. As HSPs, we process everything deeply. We think about implications, and we plan. We think before we act. And so it’s natural for us to have that kind of thinking, which other people might label as overthinking.

I tend not to label that as overthinking because it’s just naturally how we process things. But naturally, you’re going to be paying attention to a lot of things going on. And so when you’re about to ask something, your mind will be taking in all kinds of details of where the other person is and what their state is, and you’ll be thinking about the wording to use and wondering how it might land, and you’ll consider different ways of saying it.

And this is not dysfunction. This is depth. This is natural depth of processing for highly sensitive people. It’s your system doing what it does, taking a moment and exploring it more fully. And in many cases, that leads to more thoughtful and attuned communication. So that’s the first thing. What some people label as overthinking is not really overthinking for HSPs.

However, that can shift when pressure enters the picture, and it can start actually being overthinking and feeling like overthinking when you start having pressure types of thoughts like, “I need to say this the right way. I don’t want this to create any discomfort. I should be able to do this easily.”

These kinds of thoughts prevent the mind from just exploring and trying something out. And put a lot of of weight on whether you get it right or not. And so if you even make one thing that causes some little kerfuffle, then you’re going to feel resentful or s- sad or disappointed or feel like you’ve failed in some way.

So this is trying to control the outcome, and that’s always stressful. And there’s a fine line between this too, because as HSPs, we are aware of implications more than others, and so we naturally can control outcomes more than others. But there are an infinite number of variables, and if you go too far with trying to set things up and do things well, you reach the limit of what you actually can control, and that’s when it gets stressful.

Whenever I’m trying to control something that I can’t actually control, that’s a formula for stress, and that’s what we can see can drive a kind of overthinking. So the mind starts trying to solve for certainty and tries to get this feeling that there is no risk anymore and be able to predict completely what will happen and say the very best thing that is needed.

And so that can run into a kind of looping where you’re rehearsing and revising and revising again and not fully knowing what the other person is going to say or where it’s gonna land. And so this can make for a lot of hesitation for asking. And so you think, then you adjust, and then you think again, and then you find something else that you need to consider, and then you adjust again.

And then it just can go round and around, and that’s where we can say it is overthinking, even for HSPs, which we tend to think clearly and deeply more than others. But when it starts looping, then we’ve gotten more into a stress pattern rather than just naturally exercising our depth of processing.

So a simple way to recognize the difference is when it’s natural processing, there’s a sense of, “Okay, I see it,” and it comes from a natural place. You There’s a limit to it, and y- and you see the possible implication of something, and it’s now in your awareness, and it’s good. It affects what you do or what you say.

But if it’s stress-based, then it just keeps going, and it doesn’t land, and it feels like you’re trying to get somewhere where you can’t quite reach because this is what it feels like when you’re trying to control something that you can’t actually control And see, that’s the funny thing. As HSPs, we have so much insight and so much ability to see into things and see implications, see the future in a way, that we almost start to assume that we can control everything.

And that’s not actually true. No matter how sensitive you are, there’s always a limit to how far you can see and how many implications you can see and how much you can actually control. So getting in touch with where that limit is and finding that little fine boundary between what I actually can see and control and should be thinking about and what is beyond my scope as even a highly sensitive person, that– if you can be aware of that, then you can let go of the parts that you can’t control and just focus on the ones that you can.

So how do you move forward without needing everything to feel right? In these moments, it often feels like I just don’t feel ready yet. Like I’m not ready to ask. It’s too much. And you wonder “Is it gonna go badly? Will I regret this? Will this affect how they see me? Will it affect our relationship?”

And I need to be sure before I do this. And these are not neutral thoughts. They’re activating thoughts. They put your system into a kind of low-level survival mode where you’re like, “There’s something at risk. I could lose here. I could have a problem.” So the first thing to do is to recognize these as protective but not accurate.

These thoughts are trying to help to reduce risk and prevent discomfort and protect your image or your relationships, but they also come with an assumption that something bad needs to be avoided or controlled. And that’s what creates that feeling that you can’t move yet. “I can’t make even one tiny mistake.”

That’s what freezes us. If that assumption is loosened or let go of or questioned, then you may find that your relationship will still be fine even if you ask and even if they say no. Or that the discomfort that you’re projecting may be there, but it’s– may not be as major as what you’re thinking. And so the risk may actually be less than what you’re imagining.

What happens with the, with fear or any stressful thought is it exaggerates risk. It exaggerates what the implications will be, the negative reper- imp- implications will be. And so that’s what freezes us. It creates a kind of drama, and then we res– we recoil out of thinking, “Oh my gosh, it’s gonna be terrible.”

Yes, someone might not be thrilled, but that’s a lot different from them being really reactive. And of course, that can happen too, but oftentimes we imagine it’s gonna happen more often than it actually does. So just being aware of these thoughts, that these are thoughts and they’re not necessarily reality, can create some space because everything, everything that you think is not necessarily true.

And so it’s really great to even have that in your awareness that let me take a look and be sure that this is really as bad as I think it is before I hesitate as much as I’m hesitating. And of course, you can do this more formally, actually question the thoughts. This is what I do with my clients, and it’s what I’ve been doing for myself for almost twenty years of noticing what is the thought, the fearful thought, the stressful thought, the thought connected to that negative, tight emotion.

What is that? And question that thought. Is it true that I need to be completely sure? Is it true they’re gonna reject me if I ask this? Is it true I’m gonna ru- ruin the relationship if I ask this? So this is how to work with this part of the mind that, that is fearful or that is stressed in a way, is to give it some space and but gently challenge it to see if that’s really the whole picture and look at it objectively.

And if that can be done, there can be a lot more space coming in so that your reactions, the stressful part of your interaction becomes much less. You will always be an HSP. You will always think twice and three times about everything, and that’s a good thing. But it doesn’t have to go into a infinite loop which prevents you from taking any action at all.

So the feeling I’m left with today is that the difficulty asking for what we want comes from both our nature as HSPs to hold a high bar where it’s always a win-win for everyone. And this doesn’t necessarily need to change. We may always have some healthy hesitation because of this. But it also, this difficulty of asking for what we want also comes from the other part, which is fear-based stress that worries about doing it wrong, worries about making a mistake.

And if the fears can be questioned and loosened a bit there can be a lot more room for asking as highly sensitive people. In this episode, we looked at what happens when it feels hard to ask for what you want. And we saw that it’s not just about what do I want, which is, would be so simple. It’s about what are the implications of asking for what I want?

How is it going to affect everything, the relationship, the other person, all of that? And that’s a good thing to have that kind of hesitation because it means that we are aware of the context in which we’re asking. We also looked at why overthinking shows up so quickly in these moments. And that is for two reasons.

First, our nature, which is as HSPs to have a kind of depth of processing that allows us to think through things and see more of what could be happening when we ask for something. And the other is a stress reaction, a fear-based kind of thinking that actually is not our nature, but is piled on top of our sensitivity and can grind things to a complete halt.

And finally, we looked at how to move forward without needing everything to feel completely right. And the basic idea is to notice the fearful thoughts and take them with a grain of salt. You may be able to do that in the moment. You may not. You may need to come away and do some actual inner work and question those thoughts and see if you can find some space without them.

So thanks for listening. It’s always great to explore with you. This program comes out three times a week on Mondays, Wednesdays, and Fridays. Join me next time for Breakthrough Mondays, where I share success stories and helpful insights for highly sensitive people on the path towards inner freedom.