Questioning our thoughts and feelings on purpose is something we do a lot in the practice of thought work. With intention, self-questioning in this way feels open and comes from a place of true curiosity. Second-guessing yourself, on the other hand, feels wildly different. 

Second-guessing is something many of us do all the time. It’s so subtle and pervasive in ways we don’t even recognize, and it’s not just some minor mental tick we don’t have to worry about. Second-guessing becomes a way of life for people socialized as women, and the truth is it’s impacting more areas of your life than you might think. 

Tune in this week to hear why women tend to be in the habit of second-guessing themselves and why it’s such a problem. I’m sharing what happens when we chronically second-guess ourselves, the important distinction between useful and unhelpful self-questioning, and how second-guessing might be playing out in your life right now. 

Joining The Clutch is easier than ever and we are open right now! Click here or text your email address to 347-934-8861 to receive a link to all the information you need. Hope to see you inside The Clutch soon!

What You’ll Learn From This Episode:

  • How I define second guessing.
  • What happens when we second-guess ourselves, and why it’s such a problem.
  • The distinction between useful and not useful self-questioning. 
  • What second-guessing ourselves feels like in our bodies. 
  • 3 kinds of second guessing and how they play out in our lives.
  • Why people socialized as women tend to second-guess themselves. 

Listen to the Full Episode:

Featured on the Show:

Full Episode Transcript:

Welcome to UnF*ck Your Brain, the only podcast that teaches you how to use psychology, feminism, and coaching, to rewire your brain and get what you want in life. And now here’s your host, Harvard Law School grad, feminist rockstar, and master coach, Kara Loewentheil.

Hello my chickens. So if I sound a little strange I’m having really intense allergies and I can’t hear out of one of my ears. So it sounds very weird to hear myself talk. But I’m not going to second guess myself, I’m still going to record this podcast because I actually want to talk to you about second guessing. And I think that it’s such an important topic and it’s something that I see, God, happening around me all the time. So let’s talk about what happens when we second guess ourselves and why that’s such a problem.

And I think that some of you are second guessing yourselves all the time and not even realizing that that’s happening. It’s so subtle sometimes and pervasive in ways that we don’t even recognize. So we’ve got to define it first because I think that it’s a term that we use and we sort of even may intuitively identify with and not necessarily actually understand what we’re saying, or sort of not be able to define it. We totally understand what we’re saying, but not be able to define it.

So the way that I sort of define second guessing is it’s when you are questioning yourself in a not helpful way. And I want to preface this by saying that I’m going to talk about the distinction between kind of useful self-questioning and not useful self-questioning. So don’t worry, I’m aware of that concern. I am going to talk about that. But when I think about second guessing what I mean is this sort of tendency to constantly have second thoughts about things, about ourselves and what we’re doing.

So for instance, you have a thought and you immediately start to question that thought like, well, I don’t know if that thought is true and I don’t know if that thought is valid or I’m allowed to have that thought. Maybe that’s a thought I shouldn’t have or maybe that’s a dumb thought or maybe that’s a useless thought of maybe that’s a silly thought. We have a thought and then we immediately are questioning it. And, of course if you’ve been listening to this podcast you’ve been learning about thought work.

You know that questioning our thoughts is actually a thing we do a lot in thought work on purpose. We want to question many of our thoughts, but just like any other action that you can take, the thought and feeling behind it are very different. So good self-questioning is when you are truly coming from a place of curiosity. You’re like, “I wonder if this thought I’m having actually is true.” Let me really look at it. I’m okay with either outcome. It’s like you’re actually just curious.

When you are second guessing yourself and questioning yourself in a kind of socially programmed unhelpful way. It’s not neutral and curious. It’s undermining and negative. You’re coming from the presumption that probably your thought is not okay or not smart or not valid or not accurate, and that’s bad and a problem. It’s sort of like coming from this presumption of not enough-ness, of unworthiness, of kind of not trusting yourself. So those are two very different things.

And you can really feel the difference in your body between when you are second guessing yourself. Second guessing yourself doesn’t feel open and interested and curious. Second guessing yourself feels anxious, ashamed, guilty, heavy, scared. When we’re second guessing ourselves, when we have a thought and then we immediately second guess it, we feel unsettled, we feel nervous, we might feel ashamed. It’s a very different feeling. So the energy behind it is totally different.

So that’s some examples of what can happen when you’re second guessing a thought. We also are taught and many of us second guess our feelings. You have a feeling and then you immediately tell yourself, I shouldn’t feel that way. That’s a bad feeling, having that feeling makes me a bad person. Maybe that feeling isn’t justified. Maybe that feeling is invalid. I don’t deserve to feel that way. I should feel some different way. I wish I felt differently. I want to feel differently. I shouldn’t feel this way.

So we can have our thought and second guess it, we can have a feeling and second guess it. And we second guess actions to high heaven. And we second guess actions we’re thinking about taking. We second guess actions we are taking. We second guess actions while we’re taking them. We second guess actions that we already took and are over. There’s so much second guessing and self-doubt around the things we do. When we’re thinking about doing something we’re second guessing, should I do that thing? Is that the right thing to do?

I don’t know if I should do that. Maybe that’s not right. We ask other people what’s their opinion about what we should do. We feel anxiety. Again, very different from being truly curious of here’s a problem, what are three potential solutions? That feels open and curious. When you are second guessing yourself and second guessing your actions you feel anxious, often you get analysis paralysis. You can’t decide what to do. You go back and forth and back and forth. You think about all the options over and over again.

You’re trying to think about it until you feel sure, but you’re never going to because of the way that your brain is operating. So we doubt ourselves, we second guess ourselves when we’re thinking about taking an action. Often then when we take the action we don’t have our own back. We’re not kind of confident in it because we’ve spent so much time second guessing it. And so then we’re second guessing it even as we’re doing it. That shows up in how we take the action.

And then we continue to second guess it afterwards or we take an action. Maybe we actually didn’t second guess it, but then if we don’t get the ideal outcome then we start second guessing ourselves. Then we sort of beat ourselves up endlessly for doing the wrong thing, having said the wrong thing, having done the wrong thing. We take responsibility for everything that comes from that action.

I just coached somebody on a Clutch call yesterday who had taken an action many years ago that she now regretted and that she’d been beating ourselves up the whole time. And she had been taking responsibility for everything that happened, even though everybody else involved in the situation had also made their own choices, that had contributed to the situation they were all now in. She was taking responsibility for all of that. So that is very intense second guessing, I shouldn’t have done that thing and now I’m responsible for everything that comes of it.

So second guessing is that sort of constant process of questioning yourself, not in an open curious way but in a judgmental and anxious way. Open minded questioning like thought work questioning doesn’t have a kind of presumption built in. It doesn’t assume that you’re probably wrong. It doesn’t assume you’re probably right. It sort of is not about right or wrong. It’s just being genuinely curious about what you’re thinking and how is that impacting you. And it’s kind of open to whatever transpires. It’s not trying to evaluate your worth or whether you’re okay. It doesn’t have that kind of judgmental quality.

Second guessing ourselves has that judgmental quality. Second guessing ourselves presumes that there was a right and wrong decision or a right and wrong thought to have or a right and wrong feeling to have or a right or wrong action to take. And that what we are second guessing is whether we picked the right one. That there was a right thing to think or feel or say or do. And we are trying to figure out, am I doing the right one? Did I do the right one? Did I do the wrong one? Is that a bad thought? Is that a bad feeling? It has this quality of evaluating and judging.

So second guessing is really self-judgment. And I think there are three kinds of second guessing in the way that I think about this and kind of try to separate them out to see how they play out in our lives. So the first one is kind of self-doubt. And that is when you second guess sort of your own characteristics or qualities or work or art or whatever. When we doubt ourselves we sort of doubt our own perception, we doubt our own ideas, we doubt the quality of what we’re producing or we doubt our own attractiveness or whatever.

We end up seeking external validation to make us feel better. So self-doubt is kind of second guessing, that produces insecurity and that makes you seek external validation. And then what I call worth doubt is when we are doubting our essential worthiness. We are doubting whether we are good enough to exist. I mean that sounds extreme but that is really what’s going on in our brain sometimes.

And when we have that kind of worth doubt we doubt that we are good enough or okay the way we are. Then we end up people pleasing. That’s when worth doubt leads to believing that we aren’t worthy, we aren’t valuable, other people matter more than us. And so then we get into people pleasing and constantly trying to control what other people think and feel.

And then the third big category I see is decision doubt. And that’s when we second guess decisions, when we don’t trust ourselves to make decisions and we get either paralyzed and unable to make a decision or we make a decision but then we ruminate and second guess ourselves constantly afterwards. So this is sort of a broad schema obviously. There may be forms of second guessing that don’t neatly fit into one of these categories. But I think that they’re useful because it helps you see the broad range and impact of second guessing yourself.

Second guessing yourself is not just the sort of minor little mental tic that you have that you don’t need to worry about. Second guessing is actually a way of life for people socialized as women. We’re taught to do this and we do it in all these different areas of our lives and it impacts our self-worth, our beliefs about ourselves, our self-concept, our ability to make decisions. It impacts so many different areas of our lives. And the reason that we second guess ourselves in all of these ways is that we are taught to do that.

And women and people socialized as women get these very conflicting messages from society because we’re somehow both taught that we aren’t responsible enough to be leaders. We’re not authority figures. We are not as intellectual or as smart or as competent as men. But then also we’re somehow responsible for anything that ever happens to us. So it’s this very weird thing. It doesn’t really make sense together, but whoever said society was kind of consistent.

We are socialized to believe that we both can’t trust ourselves to make decisions, we can’t trust ourselves to be in charge of things. But we’re also responsible for anything that ever happens to us or anything that happens to anyone else, including their thoughts and feelings that is in any way connected to us. Women are taught that we’re irrational, that we’re emotional, that we can’t trust our own thoughts and feelings and perceptions.

And again, this is one of those things that used to be taught very explicitly, I mean historically in a lot of western societies, that belief was that women were like children. Women and children both didn’t have the mental faculties to participate in kind of civic and social and intellectual life at the level that men did. And so men should be running things in the public sphere and women and children were in the home. And women and children needed a man to shepherd and guide them through life.

This was the kind of prevailing ideology and parts of some of the bigger prevailing theologies like Christianity taught this for many hundreds, thousands of years in the west that the man is the head of the household. And he is the wise one who can help his dependents, the women and children who aren’t intellectually advanced enough to understand things on their own. He’s in charge of them and he should make their decisions. He should show them how they should behave. He should discipline them to make sure that they behave properly.

All of this was pretty explicit until fairly recently historically speaking. So you may not have heard this at school growing up explicitly, but it’s still part of our social fabric. And we still see the way that it comes up in daily life. Just look at how women are treated all around you. Why do we have a word for mansplaining? Because men tend to explain things to women that women don’t need explained to them. Men don’t really mansplain to each other quite as much.

There is a reason we have that term because this still happens because women are still presumed to be less educated in something, less expert in something, less intellectually capable, more irrational, more emotional. We still have jokes about women’s feelings, women’s PMS, women’s hormones. All of this is still part of society.

I mean just look at how we treat women who allege sexual assault. We know that such a small, tiny proportion of women even come forward. And then when they do, an even small, tiny proportion of those actually result in any kind of conviction because even though we want to think that we’ve evolved, there’s still a lot of the same old discourse of, well it’s he said, she said, or what was she wearing or how was she acting or did she lead him on? All of that is all in our heads.

So we are just taught at this very deep subconscious level not to trust ourselves, not to trust our own perceptions, not to trust our own understanding, to second guess ourselves, to doubt ourselves. And that allows people who take advantage of that or people who aren’t doubting themselves at all to kind of steamroll. Because we don’t speak up, we don’t say, “Hey, I’m uncomfortable, I don’t like that.” We don’t say “Hey, that was sexist or that was racist or that was fatphobic.” We don’t say “This is what I want to do. This is what I think.”

We don’t say, “That idea makes no sense.” We question ourselves. I talk about this all the time, the example of women and people socialized as women and always kind of qualifying what they say even as they say it, saying things like, “Does that make sense or I hope that makes sense, or maybe this is stupid but or maybe this is silly but, probably someone already said this but.” Even when we just try to talk and express ourselves we’re constantly undermining and second guessing what we’re saying.

And that’s only the things that we feel sure enough to let out of our mouths. think about all the things we second guess ourselves about that we never even mention. So we are socialized and taught to do this, which is really important to understand because if you second guess yourself a lot, that’s not because you are actually untrustworthy and having a lot of dumb ideas, or that you are having a lot of wrong feelings, whatever that would mean. You’re not doing it because the sort of quality of your experience is actually second rate and you should second guess yourself.

You are doing that because you’ve been taught to do that, where you’ve literally been taught to think that way. But we have to learn to stop doing this, you all. We have to learn to trust ourselves. And whenever I teach this, one of the first things I hear is, “Well, but what about when I am wrong?” On one level that’s an important question and I have an answer to it.

But I think it’s such a powerful indication of the way we’re socialized that we’re so worried about the 1% of the time that we might be wrong and we’re not at all worried about the 99% of times that we might be right but talking ourselves out of it. That’s just an example of how much we’re socialized to second guess ourselves, that when we hear about the concept of trusting ourselves we don’t think about the majority of time that probably our feelings are totally valid.

I mean I don’t believe feelings are valid. Obviously you can always have any feeling. But we don’t think about the majority of the time that the thought we have might be useful or helpful or our perception of something might be accurate or we made the best decision that we could at the time. We don’t think about all of the cost of questioning ourselves all the time, which is the vast majority of it. We just think about the smaller minority of the time that we might actually have something wrong and we’re fixated on that.

We have been socialized to care more about that little bit than all the rest of it. So we have to overcome this social conditioning. We have to learn how to trust ourselves. And that is a complicated process in the sense that we have to learn how to trust ourselves, but it’s not exactly trusting ourselves to always know the right answer. It’s not about learning how to trust yourself to always make the right decision. That doesn’t really work because your brain knows that often we can’t know what will happen from a decision until it happens.

So if we try to figure out ahead of time what’s the right decision or if we try to figure out ahead of time what is the right thought or the right feeling to be having as if there was one, we’re going to get stuck. So it’s not really about learning how to trust ourselves to get it right. It’s about learning to build a relationship with ourselves that allows for getting it wrong and that being okay. We have to let go. It’s almost like there’s this perfectionist fantasy of if we think about it enough and we doubt and second guess ourselves enough, we’ll figure out the right answer in any situation.

What’s the right thought to have? What’s the right feeling to have? What’s the right thing to say? What’s the right thing to do? And then we can control it all and then we don’t have to feel guilty and bad. But that’s not an option, there’s no right thought and feeling. And actions can have unpredictable consequences that you can’t control. So it’s not about learning to trust ourselves to make the right decision.

It’s about learning to trust ourselves to have a relationship with ourselves where we can have space for good ideas and bad ideals, awesome decisions and ones that we later wish we’d done differently. Creating that relationship with ourselves where we talk to ourselves in a different way. And that means overcoming all of that socialized conditioning that has us super worried about ever being wrong and has us not worried at all.

And just discounting all the times that we might be right or have a good idea or have an important thought to offer or have an exciting decision to make or whatever and we talk ourselves out of it. We don’t count any of that as a cost and we should. A woman who trusts herself can take decisive action, can set good boundaries, can create so much value for herself and for the world, can be emotionally open and vulnerable but won’t be codependent. Won’t be vulnerable in the way of constantly doubting yourself and therefore kind of resonating with other people who doubt you too.

We have to be able to identify second guessing when it happens and then learn to stop it. There’s just so much work here and there’s so many pieces of it. It’s more than I can even teach on a podcast which is why when I started thinking about this I realized that I really wanted an opportunity to work more deeply on this content, this topic, this issue with those of you who really resonate with this. So if you’ve been listening to this and you’ve been feeling like, yeah, okay, that’s me, why are you in my head, how did you know I did that?

I want to be able to stop doing this. I can see how this is impacting my life. Then I want to invite you to sign up for the Stop Second Guessing Yourself Challenge. So this is a brand new five day challenge that I’m doing, which I am super excited about because as I have been thinking about the second guessing phenomenon and I’ve been seeing it all around me, I’ve just been realizing how deep it goes and how much it impacts our lives in ways that go really to the core of what it means to show up in the world as an empowered person.

So in the Stop Second Guessing Yourself Challenge, we’re going to spend five days together and I’m going to teach you in depth the three different kinds of second guessing that I talked about, self-doubt, worth doubt, decision doubt. We’re going to really dig into what’s happening in your brain when those happen and how you can change your thoughts to stop doing that. I’m even going to give you some examples of thoughts you can use, but I’m also going to teach you how to create your own.

We’re going to have opportunities for life coaching. So you’ll be able to raise your hand and maybe get coached on what kind of second guessing you’re doing, what’s an area of your life where you’re stuck in second guessing yourself. I can kind of guarantee that if you’re stuck in an area, you’re second guessing yourself there. We’re going to have time for questions and answers live. And we’re also going to talk about what are the subconscious blocks that make it hard to stop second guessing.

So I can teach you what second guessing is and how it shows up. I can teach you how to change your thoughts about it, but I also need to talk to you about what are the subconscious blocks you have that will get in the way when you try to make those changes and how do we solve those. I’ll be teaching all of that in the Stop Second Guessing Yourself Masterclass which is part of this challenge, that’s what we do on Friday.

So it’s April 17th to 21st. On Monday the 17th we talk about self-doubt and insecurity and how that leads to seeking validation. So how to create your own validation. On day two, the 18th we’re talking about worth doubt, how we second guess and doubt our value and worth and how that leads to people pleasing and how to stop trying to people please, create your own feeling of security there.

On day three, which is the 19th, we will be talking about decision doubt, how to make strong decisions, how to get unstuck, how to deal with fear of making the wrong decision and regret. On April 20th, we’re going to be doing live coaching on all of this. So you can really see how it plays out, see it in action. And on the 21st we’ll be doing the masterclass where we go through the bird’s eye view of everything again. And then we go deep into what are the subconscious blocks that are getting in your way so that you can solve those.

So April 17th, we kick off the Stop Second Guessing Yourself Challenge. I really think that if you second guess yourself 10% less, if you join and you second guess yourself 10% less afterwards, just that will change your life. You can’t imagine how much it changes your life to stop constantly doubting yourself. That is our biggest hobby and our biggest time and energy suck in the world.

So that whole week, all of that teaching, the coaching, Q&As, the masterclass, we have a popup Facebook group for you so you can talk to other people doing the challenge, how that amazing community get great examples of new thoughts people are trying, ask questions. My Clutch coaches will be in there in the Facebook group, I’ll be there. I’ll be on all the live calls of course. All of that is $37. For some of you that is an amount that you drop on a new lipstick without thinking about it. And this is way more valuable than a new lipstick.

For some of you that might be a stretch, but I want you to think about what would your life be like if you second guessed yourself less or if you stopped doing it at all. What would you be able create in your life financially or otherwise if you weren’t draining all of your energy constantly with this? I think about it as like a hole in the boat. It’s our time and energy and attention are just pouring out of this hole in the bottom of the boat because we’re constantly second guessing ourselves. If you plug that hole, think about what kind of resources you have.

And if that truly is financially inaccessible for you no matter what then I still want you to go check out this page I’m going to give you the address for because we do have financial support available if that’s the case for you. And if it is accessible for you, you are helping to make it possible for us to teach it for people it’s not accessible for, for free.

Okay, so here is how you can get more information, text your email address to +1347 997 1784. That’s +1347 997 1784, and we will ask you for the codeword and the codeword is trust. Or go to or text your email to +1347 997 1784 and the codeword is trust. I’m so excited to teach you this work in a deeper way. And I really just can’t wait to see what amazing things those of you who join are going to do with your lives when you stop second guessing yourself all the time. It’s going to blow this place up. Alright you all, I’ll see you there.

Enjoy the Show?