243. How to Stop Negotiating Against Yourself
Self-doubt often talks us out of asking before anyone else even answers, turning ordinary meetings into losses we hand ourselves. Our inner critic and inherited beliefs shape what we think we deserve, but both can be examined, questioned, and rewritten through deliberate self-talk. When we finally ask for what we want, the risk is small and the potential reward is large, so the real goal is simply to stay in the game.
You cannot successfully navigate a negotiation if you've already counted yourself out.
Are you talking yourself out of asking for a raise before you even walk into the room? Are you letting your inner critic or imposter syndrome convince you the risk isn’t worth it? Are you constantly giving to others, quietly carrying the heavier load and hoping your good work will speak for itself?
You’ll learn that the very first negotiation in any situation is the one you have with yourself, and that asking yourself honest, open-ended questions builds the self-knowledge you need before you ever sit down across from someone else.
WHAT YOU WILL DISCOVER
Why your inner critic isn’t your enemy
6 practical tips to ask for more at work
Why asking for more is one of the lowest-risk, highest-reward moves available to you, and what not negotiating can cost over a lifetime, especially for women
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TRANSCRIPT
Welcome to the Stop Sabotaging Your Success podcast, episode two hundred and forty-three. I'm your host, Cindy Esliger. This is the podcast focusing on what we can do today to take control of our careers and overcome the inevitable barriers to success that we encounter along the way.
You're sitting in the parking lot at your office. Your meeting to discuss the raise you want starts in a few minutes. You are already losing it because you've been overthinking things since you woke up this morning. They're going to say 'no'. You don't have the numbers to back this up, anyway. Someone more qualified already asked for this and got turned down. Maybe you should just see how the conversation goes and bring it up next time when you're more prepared, when you're more sure, when the moment seems right.
Now it's time to go in. You take a deep breath, walk in, sit down—and you chicken out. You get nothing, not because they refused you, but because you didn't even ask. Because you discounted your value before they even had a chance to.
In this episode, we're talking about the negotiation that happens before the negotiation—the one where you talk yourself out of asking for what you deserve before you've even made the case. We'll look at why the inner critic shows up so convincingly and tells us that it's not worth the risk, where our limiting beliefs actually come from, and why our belief in ourselves has so much to do with who gets ahead and who doesn't. We'll talk about the fact that the very first negotiation to have is the one with yourself, long before anyone else sits down across from you. And we'll spend some time on asking for more—why it's one of the lowest-risk, highest-reward moves available to you, and why so many of us, especially women, were never taught to do it, and what it actually costs us over a lifetime when we don't.
You cannot successfully navigate a negotiation if you've already counted yourself out. The best way to win is to at least stay in the game.
How much of your life have you negotiated away before anyone else had the chance to respond? Not because you made the case and got a 'no'. Because you assumed the 'no', built your whole case around being rejected, and then acted accordingly with a smaller risk, using a softer voice, or better yet, made no ask at all.
This is what negotiating against yourself looks like. It's the meeting where you had a real case for a raise and you left having asked for nothing, because somewhere between your desk and the conference room you already decided that the answer would be 'no'. It's the second-guessing that shows up as an email draft you rewrite over and over, softening every direct assertion with a suggestion. It's the constant, quiet audit running underneath every decision where you're constantly asking yourself, "Are you sure?".
If you walk into every high-stakes moment already convinced it won't go your way, and you shrink your ask to match that story—are you actually being rejected? Or are you just failing in advance? Because these are two very different things. It could be considered a failure when you try, and the answer is 'no'. But honestly, rejection isn't necessarily a failure in my books. Failing in advance happens when you never let anyone seriously consider your request. You rejected yourself, not even giving anyone a chance, and then considered that evidence that you can never have what you want.
The frustrating part is that this kind of self-doubt rarely announces itself as fear. It shows up as realism, humility, or just being practical. But practical and defeated can look identical from the inside. And the only way to tell them apart is to ask: did I make this decision based on facts or based simply on an assumption and a feeling? That distinction—facts versus fear—is going to come up again and again because almost every limiting belief we carry is fear disguising itself as fact.
Most of us have that inner critic that shows up right before something matters and starts listing the reasons why it will never work. For a lot of people, that voice can take on a life of its own as imposter syndrome—that sense that you've somehow fooled everyone into believing you're capable, and it's only a matter of time before you're found out.
Honestly, I don't think the goal is to silence that voice permanently. Because frankly, I don't think that's even possible. Your inner critic isn't a defect. It's a protector that's working from an old job description. At some point, probably a long time ago, that voice kept you safe. It kept you from embarrassing yourself, from getting disappointed, or from taking a risk that didn't seem survivable, at the time. The problem isn't that your inner critic exists. The problem is that it's still applying an outdated risk assessment to a present day decision.
So, instead of trying to silence that voice, which rarely works for very long, try reassigning it. Give it a new job. Its old job might have been to keep us from ever making a fool of ourselves. Its new job could be making sure we're actually prepared. Same energy, redirected. When it pipes up before a big meeting, you don't have to argue it into silence—you can thank it for flagging this, and suggest that its energy is better spent strengthening your case in favor of your request instead of talking you out of making the ask at all.
This is where rewriting your self-talk script becomes a real practical skill rather than just a nice idea. Start by noticing your own worst-case narratives—the specific sentences you tell yourself in the moments right before you do something hard. Not the general feeling of dread, the actual words. They might sound like, "I'm going to freeze" or "They're going to see right through me" or "This is going to end badly". Write them down, because it's always easier to disarm them when you see them on paper in front of you, rather than spinning around in your head.
Once you can see the sentence, you can replace it—not with empty positivity, but with something more accurate and more useful. For example:
"I'm going to freeze" becomes "I'm prepared for this and if I stumble I can recover"
"They're going to see right through me" becomes "I know this material better than almost anyone in that room"
"This is going to end badly" becomes "What do I really have to lose?"
Notice these replacements aren't lies. You're not trying to convince yourself that everything will be perfect. They're just more honest than the catastrophe your inner critic was originally selling you, because that worst-case scenario was never based on any real evidence—it was based on fear, pretending it was fact. I invite you to try this exercise by catching the worst-case narrative in real time and swapping it for language that's more true and actually on your side.
Let's zoom out from any single moment of self-doubt and talk about the belief systems underneath it. This is where the real leverage is.
The major distinction between people who go on to achieve extraordinary things and people who don't isn't simply a matter of talent or intelligence, but rather it's belief. They achieve it because they think they can. That sounds almost too simple to be useful, but stay with me here, because the implications are more significant than they first appear.
Most of our belief systems are inherited, not chosen. They're a product of upbringing, absorbed early, often before we had any ability to evaluate them critically. And in most cases, those early belief systems are limiting—not because the people who gave them to us didn't trust us, but because those beliefs came from people who themselves believed they were limited.
We inherit a set of beliefs built for survival, not for success. Beliefs engineered to avoid pain at all costs, which quietly reinforce a "playing not to lose" mentality instead of one where we are "playing to win". That's not a character flaw. That's just what gets handed down when the people raising us were taught themselves to keep their heads down and avoid disappointment.
The good news is that some of us learn somewhere along the way to question those early belief systems. And when we do, we get to develop more empowering beliefs—but that development takes real, sustained investment, mostly through self-talk. This is not a one-time realization. It's monitoring the actual words you use about yourself, day after day, week after week, and understanding that reprogramming is never really finished. It's a never-ending activity. The same way improving your physical fitness is never really finished. You don't reprogram a belief once and move on. You must do more to maintain it.
It is possible to reprogram any belief you want into yourself through repetitious, ongoing self-talk. You can build that belief into an actual foundation for how you see yourself, brick by brick, through repetition—the same mechanism that installed the limiting belief in the first place can be used to solidify a better one. Which means a more empowering belief system can be built from scratch, no matter your age, no matter your upbringing, no matter your current circumstances. While our level of intelligence may play a small part in our outcomes, it is belief that is the real game-changer.
Make a list of your most closely held beliefs about yourself and what you're capable of. Then, go through that list one at a time and ask: is this serving me or holding me back? Is it even still relevant or is it out of date? Is it a belief that made sense for a version of you that doesn't exist anymore? Question its validity. Where did it come from? And here's the reason this matters so much because our behavior follows our beliefs. If you want different behavior—like bolder asks or fewer negotiations you talk yourself out of—you have to give yourself permission to discard or upgrade the belief sitting underneath it.
When it comes to negotiation, I think the word itself is part of the problem. Say the word "negotiation" out loud and notice what comes up for you. For most people, it's something with a slightly negative charge—a back-and-forth to reach an agreement that's most certainly wrapped up in ideas like compromise, concession, or giving something up to get something else. We tend to think of it as something you only do when you want a specific result, and something that costs you in order to get it. We've also been taught culturally that negotiation is a specialized activity, something that happens around money, or something politicians and executives do—not something that shows up on an ordinary Tuesday conversation with your partner, your kid, or a coworker.
That framing causes real damage because it teaches us to wait. We wait for the once-a-year performance review to have the salary conversation. We wait until we're in a full-blown crisis with a client or a partner before we say anything real. But you don't have to wait until the performance review to negotiate your compensation with your boss. And you don't have to wait until a relationship feels like it's cracking to have an honest conversation about what you both might be missing.
The better approach is to treat every conversation as part of an ongoing negotiation of that relationship—continuously steering it rather than yanking the wheel only in emergencies. Approached that way, you show up with better information, more consistency, and—when the big money conversation does come around—a much stronger position because you've been building the relationship with good information all along, so your ask is not coming out of nowhere.
And yet, we all tend to miss the first step which is that the first negotiation in any situation is the one you have with yourself. Before you sit down across from anyone else, you need to spend real time asking yourself a few questions. Most of us were taught that negotiating means coming on strong—making arguments, controlling the conversation, having all the answers, and getting your way so the other person doesn't get theirs.
We were taught, essentially, that a good negotiator walks in with a script. But rehearsing all your arguments in advance isn't a negotiation; it's more like public speaking. And when you lead with a prepared argument instead of genuine curiosity, the other person is less likely to actually hear you, and less likely to give real weight to what you're saying, because they can feel that you walked in to perform rather than to understand.
Expert negotiators know their greatest strength isn't making the perfect argument. It's gathering knowledge—a real understanding of themselves and the other person—that produces an outcome that creates value for both sides, not just a win for one. Most people never ask themselves the right questions to build that self-knowledge in the first place, so they miss the chance to create real understanding with the other person they are negotiating with.
So, what does asking yourself the right questions actually look like? This is where the distinction between a closed question and an open question really matters.
A closed question invites a 'yes' or 'no' or one-word answer—it's efficient, but it shuts the door on any real dialogue.
An open question invites a broad answer across a number of topics—it prompts the sharing of factual information, which might provide insights into feelings, reasoning for what someone's actually doing, and a deeper understanding of how they see themselves.
If all you want is to knock out a simple task quickly, a closed question is fine. But if you're trying to solve something complicated, connect with someone honestly, or unlock your own creativity, you need an open-ended question. And the most useful question available to you, whether you're asking yourself or someone else, is not really a question at all, but rather a request for them to "tell you more" about that, whatever 'that' might be in your case.
This is a form of a courageous question, not a safe one, and that's exactly the point. Safe questions confirm what you already know to be true. Courageous questions uncover things you didn't expect to find.
When we talk about negotiation, we tend to obsess over tactics—who makes the first offer, how you frame your demand, and how you read the other side's strategy. But every negotiation actually begins with you, by asking yourself honest questions before anyone else is even part of the process. That's a form of self-discovery. It's how you get clarity on who you actually are and what you're actually trying to achieve. And that kind of self-knowledge turns out to be critical, not just for making deals, but for resolving conflicts, finding your purpose, and being genuinely happy in your life. Once you understand what's actually driving your side of a dispute, it tends to explain a lot about the conflict itself.
Only after that groundwork is set should you pose those same open, courageous questions to the person across from you—to gain real perspective on someone whose vantage point is different from your own. A lot of conflict persists simply because people lack the tools or the courage to have the conversation that goes past their own point of view.
It's easy to talk to people who already agree with you. What actually moves negotiations, relationships, and conflicts forward is the harder work of genuinely trying to understand someone else's perspective—their needs, their fears, and what actually makes them tick. That kind of perspective is rare precisely because it's uncomfortable to reach for. But it has the power to unlock deals, strengthen relationships, and transform even the most entrenched conflicts. Because better questions produce better answers. And better answers expand your view of the world, the people in it, and your own place among them.
Which brings us to the underlying theme, and that is asking for more.
An asymmetrical risk is one where the potential reward is far bigger than the potential loss. If you want to live more intentionally, your job is to go looking for those—to actively identify disproportionate opportunities instead of waiting for them to find you. And one of the easiest asymmetrical risks available to any of us, every single day, is simply asking for what we want.
Think about the actual math of what I'm suggesting. If you ask for something and you don't get it, what happens? You're exactly where you started. That's it. That's what's at stake for you. But if you ask and you do get it, you've just gained something you wouldn't have had otherwise. It costs you almost nothing to make it known what you want. If you get it, it could change your career trajectory in ways you might not have even imagined, yet.
If you don't ask, you will never receive. That's just a fact about how the world works. So, the practice is straightforward, even if it doesn't feel easy. Try asking for what you actually want and treat a 'no' as simply data, not a rejection of you as a person, not a verdict of your self-worth. If you're asking for things regularly and you never once hear the word 'no', that might be a sign you're not asking for enough.
Now, here's where I want to be honest about why this is so much harder for some of us than others. Women in particular are often taught from a very young age that negotiating isn't really an option—or that it needs to look a certain way if it is.
Popular culture aimed at girls tends to emphasize appearance over ambition. Girls are taught to be caring, agreeable, easy to be around. We're not taught to ask for what we want, and often we're actively taught to avoid being seen as confrontational. Meanwhile, boys are far more often nurtured toward assertiveness and self-advocacy, which are exactly the negotiation skills that get rewarded later in their careers. The result shows up in measurable numbers where the average starting salary gap between male and female graduates exists before either of them has completed a single day at that first job, often because one negotiated and the other didn't, but that's not always the case. Some estimates put the lifetime cost of consistently not negotiating far more at up to two million dollars. That is not a small rounding error in my books.
And it's not just about salary conversations. Women are frequently penalized in ways men aren't for the exact same behavior. Asking directly can read as "aggressive" to the same manager who'd call it "confident" coming from someone else. So, women often learn to get what they need by negotiating in a way that's warm, accommodating, and concerned with everyone else's comfort before their own. And I have to admit, that's definitely a real skill. But it shouldn't be the only mode available.
There's also a leadership identity piece here, because in most cultures, leadership still gets coded as masculine, while women are expected to be soft-spoken and accommodating. And this mismatch is a huge part of why so many capable women struggle to fully believe in themselves as leaders, even after they're already doing the job, and doing it well.
There's another pattern I want to look at, because I think a lot of people will recognize themselves in it, and that is the "giver who never asks". Maybe that's you. You define yourself by how much you give—to your team, your family, your friends. And you've built real pride around being the one who gets things done, who carries the heavier load because you trust yourself to handle it, or because some part of you believes other people need the help more than you do. Meanwhile, you're collapsing under the weight of it, but you never say so.
So tell me, if you enjoy the feeling of giving to others, why wouldn't you let other people have that same feeling by giving to you? Sometimes the instinct to always be the giver isn't pure generosity—sometimes it's a way of avoiding vulnerability, of making sure nobody ever gets to see you as needing something, because needing something might be perceived as weakness. But you don't have to be drowning before you're allowed to raise your hand and ask for some help. You can receive assistance without then owing anyone, and without it threatening the strength you're trying to project. Refusing to ask, or refusing to receive help when it's offered, isn't strength. It's often just fear.
This connects directly to self-promotion, which is its own uncomfortable frontier for a lot of people. Many of us were raised to believe that good work should speak for itself. I hate to tell you, but it doesn't. If you've done excellent work and accomplished great things, but you've never made it known to the powers that be, it may all be for nothing. You can't simply wait around to be noticed or assume they know. They can't read your mind. If your work, your voice, or your contributions are being undervalued, some of that starts with whether you're valuing them enough to make them known—because it's genuinely hard for other people to value what they know nothing about.
Realistically, you may not get everything you ask for, but you will almost certainly get less than you deserve if you never ask at all. The fear of disappointment keeps a lot of people stuck choosing "oh well" over "what if?". And choosing not to ask, in order to avoid a possible rejection, is still a choice. It's choosing the 'no' in advance, to protect yourself from a 'no' that might never come. That's the self-fulfilling prophecy at the center of failing in advance. The 'no' will not kill you, but the 'yes' just might change your life.
So, if you're preparing to ask for more at work, here are four steps worth considering:
Do the legwork. Come to the table fully briefed—talk to mentors, research what people in comparable roles and industries are actually earning, and write down the specific facts that support your case. Don't be vague about what you want, and don't leave it open for them to decide for you.
Think beyond salary. Negotiation doesn't have to only be about money—flexibility, schedule, remote days, and professional development can all be on the table, and sometimes those things can be accommodated more easily than a bigger raise.
Be realistic. Choose requests that make sense for your role and your organization's actual culture and calendar that will make it easier for them to approve.
Keep it professional. When you make your case, root it entirely in your expertise, your results, and your track record—not in your personal circumstances. They will not care that the cost of your rent just increased as much as they can be persuaded, when you make the case, that your professional value has gone up. Present your metrics with pride, not apology.
And here are two more tools worth carrying with you:
Anchoring. People tend to value things by finding a starting point and adjusting from there, which means where you begin the conversation genuinely shapes where it will end. If you can reasonably estimate the range of realistic outcomes, you should generally be the one to make the first offer. And you should ask for more than you actually expect to get—within reason—because a wildly unreasonable anchor just shuts the conversation down instead of opening it.
How you craft your message. Once you've done the listening and asked the right questions, how you deliver your ask matters almost as much as the ask itself—which includes what you say, the tone you say it in, and how you carry yourself while you're saying it. Frame your case in terms of what matters to the other person, not just to you. Say what benefits them, phrase it positively, and don't be afraid to say your core point more than once, in different ways—tell them what you're going to say, say it, and then remind them what you said.
And one last practical note: if you have several things you need, you're generally better off asking for them one at a time, rather than bundling every request into a single high-stakes ask. Piece-by-piece tends to get approved far more often than an all-or-nothing ask does.
If I had to guess, at some point soon, there's a hard conversation that's going to present itself. And you're going to feel that old, familiar pull to negotiate yourself out of it, before anyone else gets a vote. When that happens, I want you to remember a few things we talked about today.
Your inner critic isn't your enemy—it's just working based on outdated information and you're allowed to reassign it to a more productive job.
Your limiting beliefs aren't facts—they tend to be inherited and you're allowed to question them.
The first negotiation is the one you have with yourself—so ask yourself the honest, open-ended questions before you ever sit down across from someone else.
Asking for more costs you almost nothing if the answer ends up being 'no', but it could change everything when the answer you get is 'yes'.
So, ask the question. Take the meeting. Stop negotiating against yourself. And, be sure to stay in the game long enough to find out what happens next for you.
And that's it for this episode of Stop Sabotaging Your Success. Remember to download your Guide to Winning the Negotiation With Yourself at cindyesliger.com/podcast, episode two hundred and forty-three.
Thank you to our producer, Alex Hochhausen and everyone at Astronomic Audio. Get in touch, I'm on Instagram @cindyesliger. My email address is info@cindyesliger.com.
If you enjoy listening to this podcast, you have to come check out The Confidence Collective. It's my monthly coaching program where we dig a little deeper into what's holding you back in your career and we find the workarounds. We help you overcome the barriers and create the career you want. Join me over at cindyesliger.com/join. I'd love to have you join me in The Confidence Collective.
Until next week, I'm Cindy Esliger. Thanks for listening.
