This Is Woman's Work with Nicole Kalil - How to Push Back: From People-Pleasing to Power with Tonya Lester | 369

Episode Date: December 10, 2025

If you’ve ever swallowed your needs, kept the peace, and then randomly lost your shit over something tiny (hi, dirty spoon in the sink), this episode is for you. Therapist and author Tonya Lester is here to talk about conflict, boundaries, and what it really means to be “difficult” in a world that still rewards women for being nice, accommodating, and endlessly available. Tonya is the therapist women call when they’re done being walked on. A Brooklyn-based psychotherapist with decades of clinical experience, she specializes in women’s emotional health, conflict skills, and relationships. We dig into why so many women default to do nothing → do nothing → do nothing → FREAK OUT, how to stop building silent resentment brick by brick, and what it looks like to push back early and often—in love, in work, and in every relationship that actually matters. This is real-talk conflict management for women who are done disappearing to keep everyone else comfortable. In this episode, we get into: Why “being difficult” is actually a compliment when it means being honest, boundaried, and real The subtle ways women suppress their needs in relationships, families, and at work (while telling themselves “it’s not a big deal”) The do-nothing-do-nothing-freak-out pattern—and how to catch yourself before you emotionally flip a table How to say hard things clearly and calmly: phrases you can steal for your next conflict at home or in the office The difference between healthy anger and full-on rage (and why anger is often a sign you still care) When ultimatums do have a place—and when they’re just emotional terrorism How to stop over-functioning in your relationships (aka rowing both oars while the other person “rests”) What to do when your partner, boss, or friend refuses to collaborate—and how to decide if it’s time to stay, shift, or go Tiny, doable ways to practice pushing back if you’re conflict-avoidant but deeply over people-pleasing If standing up for yourself has ever been labeled “too much,” this conversation will help you see that maybe the problem isn’t you—it’s the system that benefits from you staying small. Let’s fix that. Thank you to our sponsors! Get 20% off your first order at curehydration.com/WOMANSWORK with code WOMANSWORK — and if you get a post-purchase survey, mention you heard about Cure here to help support the show!  Sex is a skill. Beducated is where you learn it. Visit https://beducate.me/pd2550-womanswork and use code womanswork for 50% off the annual pass. Connect with Tonya: Website: http://www.TonyaLester.com Book: https://www.amazon.com/Push-Back-Others-Without-Yourself/dp/1608689468. FB: https://www.facebook.com/tonya.lester.58/ IG: https://www.instagram.com/tonyalesterpsychotherapy/ LI: https://www.linkedin.com/in/tonya-lester-b9a3ab14/  Related Podcast Episodes: How To Be Selfish with Naketa Ren Thigpen | 329 297 / Boundaries vs. Ultimatums with Jan Yuhas & Jillian Yuhas How To Find The Right Words When Creating Boundaries with Amy Green Smith | 201 Share the Love: If you found this episode insightful, please share it with a friend, tag us on social media, and leave a review on your favorite podcast platform! 🔗 Subscribe & Review:Apple Podcasts | Spotify | Amazon Music | YouTube Learn more about your ad choices. Visit megaphone.fm/adchoices

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I'm Nicole Khalil and you're listening to the This Is Woman's Work podcast. We're together. We're redefining what it means, what it looks and feels like to be doing women's work in the world today with you as the decider. Whatever feels true and real and right for you, that's how you do woman's work. And part of that work for all of that, us is learning how to live, to love, and to lead without losing ourselves in the process, which sounds kind of obvious and easy until you actually try it. Because the moment you start saying no, setting boundaries, or daring to challenge or disagree, someone inevitably accuses you of being a little difficult. And honestly, they're not wrong. You are being difficult,

at least in the way women are taught not to be. You're interrupting a system that rewards compliance, a relationship dynamic that depends on you overfunctioning and overgiving in a workplace that still labels ambitious women as aggressive while excusing or applauding men for the exact same behavior. I know all of this from personal experience. I've always been a little feisty. You can count on me for the occasional rant. I say fuck a lot. And yet, I still catch myself holding back regularly. I tell myself it's because I don't want to damage the relationship or lose the opportunity or hurt someone else's feelings. I've swallowed my needs. I've stayed quiet to keep the peace and then felt resentful when the people around me didn't meet those needs that I never actually

communicated. I've been called too much and too difficult. Hell, I've even said to Jay on more than one occasion that I know I'm not an easy person to be with. Though I'm not sure if that's actually true or something I've absorbed over time, like secondhand shame. Because maybe relationships aren't supposed to always be easy. And for the record, I don't think they're always supposed to be hard either. But maybe real connection in work, love, and life requires healthy, thoughtful conflict. Maybe pushing back isn't defiant. It's devotion.

Devotion to the truth, to the other person, to the relationship, and to yourself. Our guest today is Tonya Lester, a Brooklyn-based psychotherapist, writer and author of Pushback, Live, Love, and Work with Others without losing yourself. Her work has been featured in The New York Times, The Guardian Newsweek, Psychology Today, and more. And Tonya's here to help us unlearn our aversion to conflict, redefine what it means to be difficult, and to finally push back without losing ourselves in the process. So, Tonya, thank you for being here today. And one of the things that you said that I noticed when I was prepping is that women don't often even realize that they're suppressing their own needs or their desires in an effort to care for others. So can you start by talking to us about what that even looks like, what that means and how we are backing off far more than we are pushing back? Sure. Thanks so much for having me, Nicole, first of all. What I have noticed, certainly with clients, certainly with friends and certainly and myself, is that there is a tendency with small areas of disagreement or conflict or one person's needs, like whose needs moment to moment

are more important. And I think part of being in a relationship and adulthood is that sometimes your needs aren't the most important. But I think that women do a default that their needs are always the least important. And I think what raises to the level of where there should be conflict, for some women, it's just too low. It's just too many times of saying, it's not a big deal. Why even bring it up? We're only going to have a fight. Nothing's going to change anyways. I don't want to hurt his feelings. I don't want them to be mad. I don't want anyone to think I'm difficult. And that builds, right? So that's like a brick in a wall between us and the other. person, where pretty soon we might get to a place where we don't feel known at all. And we're so

used to suppressing what we want to say that we almost either, A, don't know what we want to say anymore, or it just feels like too heavy of a lift to kind of write the ship. And that's when I see a lot of women feeling very demotivated and hopeless, kind of collapsed around how much efficacy they have to make changes at that point. And then so that's when maybe you show up in my office and leaving feels, it just feels too late to put the work in. Leave it. You feel like, oh, I just have to start over. Right. But if you start over without learning the skills of speaking up often and early, then you're just going to recreate the same relationship again. Tony, while you were talking, I thought of so many moments where I've done this, and I can't imagine I'm the only one where I

you know, like you said, the threshold is too low. So I don't speak up or I keep the peace and resentment builds or feeling unseen or unheard or undervalued, all of that builds. And often I feel like we get to a breaking point or a point of no return or a point of like full explosion. And it's almost that where I actually feel I am being difficult as opposed to I wouldn't have been difficult if I would have addressed the small thing when it was small. 100%. And it may be potentially actually being difficult because I've collected a mountain of small things and turned it into this massive point of no return. So am I the only person who's doing this? I can't imagine. And is what you're trying to say is there's value in addressing the things

and raising our threshold. So we do address the things when they're a little bit smaller. Right. Yeah. You're not the only one. I call this the do nothing, do nothing, do nothing. freak out phenomenon of communication. And I think a lot of us fall into that pattern. Even as you say that, I have flashbacks of freaking out in an airport or, you know, where it just got to be built too much. And then what ends up happening is we might really lash out, be mean, name call, catastrophes, throw in everything, including the kitchen sink, and then end up apologizing. And then being the one who because our presentation was so difficult and maybe unfair, ignoring all the unfairness that, you know, built up to cause that moment, then I think, you know, we end up feeling

kind of sheepish and apologizing and trying to make a repair, but those underlying issues are still not resolved. Yeah. And so one thing I really encourage women to think about is sometimes we we have an idea that we either stay silent or are so extreme, are so kind of difficult or kind of hysterical in a way that we don't like in ourselves and we don't like, we have judgment about it in other women, which is its own topic, like our own internalized misogyny around that. But I really encourage people to think about, I can say something direct, simple, concise, without being mean or harsh, it's okay to state things clearly. And that's what I really encourage. I don't like this. We need to find a different way. This isn't working

for me anymore. That was very hurtful. You know, when you said this, I imagined this. Help me walk through how we can do this differently before. None of those sentences are meaner attacking. They're just clear. And saying things like, I am not happy, it feels like we'll destroy, maybe, depending on your relationship, like we might destroy the person across the table. That would be so hurtful to him. But if we don't say it out loud, we're destroying ourselves, right? And so we need to have relationships where we can say hard things. We have a part who hopefully can listen, which is helping our partners do that as a whole another piece, but also doable.

And, yeah, to say the hard thing before it becomes an explosion, before you have to throw a hand grenade, just say, say the thing. Yeah, I know for myself, if I'm at the point of wanting to flip tables, that I've let something build or go on for too long. And I have a responsibility in that. So what I'm hearing you say is we're not trying to pick fights here. This is not about ultimatums. This is about responsible communication, clear, direct, and addressing things when they come up.

The example you gave, I'm not happy. I think every human I know has had a moment of that in their, if they're married or long-term relationships. You are not going to be happy every moment of every day. No. And I've had that. like I'm not happy and I want to be happy in our relationship and I want to be happy with you. So how do we, this isn't, you know, I'm not happy and it's your fault. You fix it.

This is, I'm addressing something that I'm feeling. I'm being clear about it. And I want to work together because the desired outcome is for us to both be happy. Yes. I loved what you said in the introduction about that it's actually investing in relationships to, speak up where our needs aren't being met, you know, it's, the relationship is really over when we stop trying to communicate, right? And we're like, whatever, it doesn't matter anyways. I think we're always looking for collaboration. And one thing I end up saying to clients all the time, and I think about a lot in my own marriage, is if you don't win, I don't win. And if both parties feel that way, you're going to invest a lot in the happiness of the other person. Of course,

if you don't win, I don't win. If that's not reciprocated, you're never going to have healthy parity in that relationship. But anytime someone says, I'm not happy, I need this to change, can we please talk about this? It's an invitation to collaborate. Right. And collaboration and hearing your partner's needs is the bedrock of emotional intimacy. And you simply don't have it unless you're doing that level of communication. Okay, so what if you're in relationship, whether it's romantic or friendship or family member or somebody you work with, what if you're in relationship with somebody who isn't interested or hasn't been taught to collaborate?

I think we can tell people to wear blue in the face about responsible communication or about being collaborative or about addressing small things before they get big. But this is a two-way street, like you said. Jay and I made the agreement early in our relationship as similar as like, my job is to take care of you, which works as long as your job is to take care of me. And it is evolved into it's our job to take care of each other and ourselves. But it's a mutual agreement. If you don't have that or you didn't start your relationship in that way, what do we do? This is the tough part, right? This is where the hard decisions come in. I think there's a few ways we can invite people to be more collaborative. And I think sometimes it's as simple

as saying, you know, I love you and your happiness means as much to me as mine. It doesn't mean more and it doesn't mean less. And I don't always feel the same from you. So I want this to be an invitation to talk about that more deeply. I think very often we've disserviceed men. and not teaching them well enough to be collaborative, right? In the same way that we teach women to say nothing, men often sometimes don't even really know how to collaborate. Like, that is just a completely different frame. Women are the keepers of the relationship.

And so we overfunction on keeping the relationships. But men are sometimes not given the tools. And not sometimes. So to say, I need to feel like. you are as invested in me as I am in you, and this is what I would need to see. Sometimes if a partner can let their defensiveness settle and really take that in, in the context that I wouldn't be even inviting this discussion if I didn't care, sometimes people can learn to do that, right, or to say often, but can you see where I'm coming

from. Like, how would you feel if you were me, right? That's the basis of empathy. And this is, of course, also where a couple's concert can come in. You know, I often will say to one partner and then another, what is she getting right? Like, go through everything she just said. And what do you agree with? And what is he getting right? And that can help build empathy. All that said, if someone will not collaborate with you, at some point, there has to be acceptance of that and a decision. of how you're going to operate then in that relationship and whether it makes sense to stay. And I really believe that we have one life to live. We should make it great. I definitely don't think relationships should always be hard, but I do think relationships take a level of

care and attention all the time that sometimes we don't invest sort of consistently enough of trying to be attuned to the other person and making sure that, you know, that you're being transparent enough that they can be attuned to you. If you have someone who's very, very self-centered or not interested in that level of connection or just isn't going to invest in you, if he can't or she can't, but if the other person cannot say, you know, your happiness is as important to me as mine, you have a very, very, it's extremely important information and you have a big decision to make. And I think women often feel that if we work hard enough, we can make any relationship work. And I think if we can work hard enough, we can stay

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Agreed across the board, we're talking about marriage or a romantic relationship here, but I would say the same applies in a working relationship or a friendship. If you're doing all of the heavy lifting, the analogy kept popping in my head. I don't remember when I read this, but it's many, many years ago of, like when I think of a woman overfunctioning in a relationship, it's like there are two oars and an overfunctioning woman is rowing both. And I think your thing of like women think if they just work hard enough, it's like if I just row faster, harder, longer, or whatever, then at some point this person's going to want to row, as opposed to the fact that it's like, why would they ever want

to? You're doing all of the work. And to the other point, too, is a lot of men aren't taught the skill of collaboration and empathy. Those are more, and I put in air quotes, feminine skills, right? And so there is an element, I think, if you're listening as parents of sons,

of teaching this skill of both people rowing, and it always works best if we're both rowing together and sync in the same direction at the same time, right? And sometimes people need a break or sometimes somebody

might need to row a little bit. Like, this isn't a, I don't know, know why this popped in my head, but when people go to talk about going to marriage counseling, I often hear from women, like, they're just going to tell me that I'm right. They're just going to be on my side. And I'm like, no, overfunctioning is something that any good therapist or counselor is going to address. Just because you're doing all the work and it doesn't mean that you're right. It means that you're overfunctioning or overdoing or in relationship with somebody who isn't

rowing with you. Okay, I'm all over the place. I guess my question is, you said this, we have decisions to make. Are there any places in conflict and relationship where flipping tables or anger or ultimatums do make sense? Yes, for sure. I don't know, but I guess metaphorically flipping the table. If you feel like someone is ignoring you or just not hearing it, because I do think we have a tendency to, to minimize things we don't want to hear, you know, and to avoid. And so if you feel like your more measured attempts at communication are falling flat, I think showing anger and showing sadness is appropriate because it fuels, it amplifies the

message and it fuels the need to change. I often think that there's, you know, we don't want to hurt other people and we don't want to hurt their feelings. But real change really never happens without someone's feelings being hurt. Like, why would anything change if nobody felt badly, right? It's, we need that. That's the fuel to change. So the metaphorical flipping tables and really saying, and again, I don't ever condone like abusive language or name calling, but to say with feeling, I am so unhappy, I cannot live like this. This has to change. You are not hearing me. I absolutely advise that. I don't think you should go in like that. I think if that's how you always communicate, that will not be effective

either. But I think if you are not being heard and you are, I think anger also or deep sadness is also a way we show we care deeply about the relationship. Again, constructive, not destructive, not rage, but healthy anger. Yeah. So I 100% believe that there's a place for that. And I think the idea that as women were supposed to be kind of steppered wives and be flattened out all the time is both not effective at all, but also not realistic. We're human beings. We're not robots. And then in terms of ultimatums, you know, if you say, if we don't have a baby, I'm leaving, and you drag someone into doing what they want when they do not want it, that's going to be an unhappy, resentful situation.

If you say, I love you, I wish we could make this work. Having a baby is so deeply important to me that I need to walk away from this relationship. because I need to be with someone who wants the same things, even though I love you so much and I'm so sad. But I don't think I'd ever recover from not having a baby. He can either decide, we'll keep talking about this. We'll stay not forever, biological clock, but that there will be like collaborative conversation.

And he might decide, I can do this. We can move forward together. But I think there's a difference there. And I, you know, there are some things that are worth leaving relationships for. There are some things that are impossible to compromise on. And in that case, I do think you owe it to yourself and your partner to at least be clear about what those things are. Yeah. Or to say if there's some kind of, you know, often when someone's recovering like from infidelity, it can be very useful if they have decided to forgive and want to move forward to say this is a dead stop.

though, this would, if this ever happens again. And I think that's, that's useful because it gives us a sense of control. It's, it's expressing a clear boundary. And I think there's a place for it. Yeah. It popped into my head an argument the Jay and I had a decade or more ago. And it was one of those situations where I didn't speak up, I didn't meet. And then it came to a head and I, I raged out on him. And so my point being the difference between healthy anger and enrage and knowing what that is for yourself and how you want to communicate. And the next day he came to me and he basically said, I'm okay with conflict. I'm okay with talking about mistakes that I'm making, but I'm never okay with having somebody talk to me like that. That will never happen in our relationship again.

And I heard it. Like I knew for sure. And I knew that I'd crossed a line. I wasn't feeling proud of myself on the other side of that. And I don't know if it was an ultimatum, but it was a clearly communicated boundary that I heard and respected. And it was distinguishing from the, like, we don't have to agree. We can have conflict. But there was a line that was crossed and I'm not okay with that.

Yes. And as often the case in my relationship, as I learn a lot about dealing. with healthy anger from him than the other way around. So that's all the collaboration I'm talking about for him to say this, I can't be on the other side of that. It's too much for me. So we can have ways that that doesn't happen where I am still hearing you, right? He's not shutting you down at all.

Like that was beautifully articulated. Yeah. And it sounds like your relationship leveled up after that. 100%. And it's never happened. it's never, I've never, like, since it has made us better, it's made me better. And like I said in the intro, I know these things, we practice these things, and I still catch myself falling into the trap of, should I say something? No, it's not that big of a deal. I'm probably overreacting.

This is a me thing, right? Like, do you find that we as women do that? We oversimplify or over justify or talk ourselves out of addressing something when it needs to. to be addressed. Yes, 100%. I do this so often. And it's embarrassing because this is my whole life's work is not doing this. I get it. I'm like, I know better. Yeah. I know better. I know better. And sometimes, you know, I'll be sitting with a client and she'll be describing how she handled something. And I'll be like, wow, that's really good. I would not have been that forthright. So there's an aspect of this of kind of knowing which one you are, I like to say, like, where are you on the spectrum? And if you know, you tend not to speak up enough. And the reason you know this is

you feel like you're being walked all over or you feel so scared of conflict or you're feeling in your relationships. Again, it doesn't have to be romantic. Any relationships like I'm not really known. Then believe that about yourself and push yourself, right? If you are in a kind of regularly withdraw, what would it be like for a couple of weeks just to say everything? See, what would happen to your relationships? Are there some people who go too far and cannot let anything go and are constantly like after people? Yeah.

I mean, there's people like that. And I think you'll know, too, if you fall on that level of the spectrum. And in which case, I think it makes sense to write these things down in a journal, Give them 48 hours to breathe. See if you want to revisit it. And we can always say three days after the fact, three weeks after the fax, six months after the faxed, I want to bring something up. It happened a while ago. So I think it's going to feel odd to. I'm bringing it up. But it's really turning in my mind. And so I need to say it. And then say it. It's not like we only get five, the first five minutes after it happened. Like allow yourself to go back. Yeah. It makes me think of like a

pendulum. On one side, you have the person who says everything and is nitpicking and is constantly and then you have the other side of the pendulum when somebody says nothing at all. And our opportunity, our goal is to land somewhere in the middle. But sometimes the way we figure out landing in the middle for ourselves is pushing ourselves a little further in either direction than we think we could or should. There is a testing element of this. And being in relationship with somebody, committing to somebody long term, loving somebody, I think involves some space and the opportunity to fix and apologize for and give grace to that testing phase where we might push too far or not enough. And there's a repairing that gets to happen over time. Now, when you're in a

work relationship, sometimes there isn't that same level of love or commitment or agreement of like Oregon gives space for that. Is there any advice or any things that are different or more problematic when it comes to having conflict in a work relationship? Yes, it's harder, right? If you are kind of lower on the totem pole and don't have as much power in the workplace or organization,

you will be disempowered. If you're an intern, you aren't going to have the same power or leverage as the CEO. And that's fine. That's appropriate. We work our way up and that's how we learn. What I would say the corollary to being loved is in the workplace is being valued, valued because of what you bring to the table and because it's a place that's respectful of who you are, being just a human, right, believing that everyone's deserving of fair treatment. If you aren't being valued in your workplace, or it's a very toxic environment,

you're probably just going to have to leave. It's very hard for one person to change a toxic environment. What I encourage people to do in that situation is to really look at, here I am, I can't leave until this time or until I find something else or I finish this internship or whatever. What are the skills that I would like to leave with that nobody can take away from me.

Like, if I treat this now like I'm in business school, is it learning to stand up for myself in conflict? Is it learning to say no? Is it learning some coding program? You know, it can be much more concrete. Is it getting better at my public speaking? With this idea of all my learning, I get to take with me and I can leave this toxicity behind.

And this is how I'm going to stay in my integrity here and kind of take something with me from this very hard environment and then ultimately try and find something better and then when you're the boss, right? This is most, everyone always says that the great bosses they learn from having a really terrible boss. And so then you're, as you get more senior,

you're going to pay it forward and really take that learning to create a better environment going forward. But when you think you might lose your income, I never want to pretend that any of this is easy or a no-brainer or if that you're not doing it your week or to blame for your situation. I think there's a lot of work environments that are very, very tough. And if you're paying the rent and supporting the kids, you might not be able to leave right away. But I think stepping back, being really grounded in who you are, what you can learn and what steps need to be taken to remove yourself and what's realistic, I think you can always do that.

a situation. A hundred percent. Well said. And I think there are small ways that we can stand up for ourselves or speak or truth or push back in work environments to both test and develop the skill. Like there are some environments where it's never going to be allowed and then it's your decision whether or not to leave that environment. Back to some of this is teaching other people how we work together, how we get the best out of each other. Back to my example with Jay, it's like, listen, I am open to feedback and I want to be great at my job and I want to be good at this role and I want us to work well together. And it doesn't work if you speak to me that way. So there are opportunities to test out and to push back in small, responsible communication

ways that don't involve walking out of the door or flipping tables, at least not right away. That might be the ultimate decision in some environment, but as still think a lot of what you shared when we were talking about romantic relationships applies here, too. Yeah, I do too. And again, it's back to if you are valued, your feedback will be heard more easily. And sometimes you can just be really creative with the pushing back. I had a client a long time ago who was in this kind of classic gendered situation where she was the only woman in the room and so was always asked to take the notes, right? Which is like, I can't believe that still happens in 2025. Not only can I not believe that it happened, I used to do it. I used to

take the notes. I can't believe I did it. Like, don't even get, anyways, keep going. Sorry. Well, what she did, you know, we had talked a lot about ways to problem solve this. And she at the beginning of the next meeting said, why don't we take turns doing this? So I'll do today. But then it's going to have to go around the table before it gets back to me. And it was just very calm. It was setting a boundary and there was kind of a shoulder shrug and okay, you know, and then at the beginning of the next meeting, of course, yeah, she had to say, you know what, it's not my turn. It's everybody's turn. She felt really, really good. Just having said it, just having approached it and the leadership, they got on board, you know, no, no, no, we're going to take turns. That's a good idea. Yeah. Well, that's a good example of how we get good at pushing back is how we get good at anything. by practice, right? So the book is called push back. I know myself and those of you listening are probably running to go order it right now. You can also find out more about Tonya and her work. Her website is tonia lester.com. We're going to put all the ways to find and follow Tonya in show

notes. All the links will be there. But again, the book is push back, buy it for yourself and all the women you love. Tonya, thank you for being here today and for an incredible conversation. Thank you so much, Nicole. My pleasure. All right. Friend, here's where I land. If standing up for yourself, if communicating your needs or refusing to carry more than your share makes you difficult, then go ahead, call me difficult. Because I've done the other thing. I've swallowed my words, softened my tone, and said, it's fine when it wasn't. And I've smiled through the situations that made me want to scream. And guess what? I got no medals and there were no prizes. There's no reward for being the easiest, quietest, most accommodating woman in the room. Only the slow erosion of your confidence and self-respect. Pushing back doesn't make you a problem. It means you give enough of a damn about yourself and the people around you to speak your truth. It means you care more about your relationship than you do your comfort, that you value connection over compliance. That might mean setting a boundary. It could be a clear and simple no thank you. And sometimes it's a well-deserved you

can fuck all the way off. So be difficult, not for the sake of being difficult, but for the sake of being you. Be bold. Engage in a little conflict. Push back instead of backing off. That's not rebellion, that's respect. And that is woman's work.