
Therapist and author Tonya Lester joins Nicole to unpack how women can set boundaries, have hard conversations, and handle conflict in relationships and at work—without losing themselves or being swallowed by guilt. If you’re tired of people-pleasing, silent resentment, and being labeled “difficult” for simply having needs, this episode gives you practical language,
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Tonya Lester
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Nicole Kahlil
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Tonya Lester
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Nicole Kahlil
I'm Nicole Kahlil, and you're listening to the this Is Woman's Work podcast, where together we're redefining what it means, what it looks and feels like to be doing woman'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 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 over functioning and over giving 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 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?
Tonya Lester
Sure. Thanks so much for having me, Nicole. First of all, what I have noticed, certainly with clients, certainly with friends, and certainly in 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 right 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 gonna recreate the same relationship again.
Nicole Kahlil
Tonya, 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 the 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?
Tonya Lester
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 freaking out in an airport or, you know, where just. Just got to it built too much. And then what ends up happening is we might really lash out, be mean, name call, catastrophize, 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 being. Feeling kind of sheepish and apologizing and trying to make a repair, but those underlying issues are still not resolved.
Nicole Kahlil
Yeah.
Tonya Lester
And so one thing I really encourage women to think about is sometimes 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, you know, 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, are mean or 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 ourself. Right. And so we need to have relationships where we can say hard things. We have a partner who hopefully can listen, which is helping our partners do that is a whole nother 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 the thing. Yeah.
Nicole Kahlil
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 to 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.
Tonya Lester
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.
Nicole Kahlil
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 till we're 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 has 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?
Tonya Lester
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 disserviced men in 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 over function on keeping the relationships and. But men are sometimes not given the tools 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 counselor 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, that level of connection or just isn't going to invest in you if he can't or she can. But if, if the other person cannot say, you know, your happiness is as important to me as mine. You, you have a very, very, it's extremely important information and you have a big decision to make. Women often feel that if we work hard enough we can make any relationship work. And I think if we can work, work hard enough, we can stay married to someone who doesn't treat us like someone they love. But what kind of win is that?
Nicole Kahlil
Right?
Tonya Lester
Right? Yeah. At some point you have to make a hard decision.
Nicole Kahlil
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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 was many, many years ago. Of like, when I think of a woman over functioning in a relationship, it's like there are two ors. And over functioning 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 or longer or whatever, then at some point this person's gonna 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. They're taught 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 in sync, in the same direction at the same time.
Tonya Lester
Right.
Nicole Kahlil
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 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, over functioning 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 over functioning 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 in relationship where flipping tables or anger or ultimatums do make sense?
Tonya Lester
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 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.
Nicole Kahlil
It's.
Tonya Lester
We need that. That's. 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.
Nicole Kahlil
Yeah.
Tonya Lester
So I. I 100% believe that there's a place for that. And I think the idea that as women, we're supposed to be kind of Stepford 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. 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. I'm so sad, but I. 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. 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.
Nicole Kahlil
Yeah.
Tonya Lester
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. I think there's a place for it.
Nicole Kahlil
Yeah. It popped into my head, an argument that 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. So my point being the difference between healthy anger and rage 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 am never okay with having somebody talk to me like that. That will never happen in our relationship again. And I heard it. Like, I, I knew for sure. And I'd already. 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.
Tonya Lester
Yes.
Nicole Kahlil
And as is often the case in my relationship is, I learn a lot about dealing with healthy anger from him than the other way around.
Tonya Lester
So that's all the collaboration I'm talking about. For him to say this. I, 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.
Nicole Kahlil
A hundred percent. 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 be addressed.
Tonya Lester
Yes, 100%. I do this so often and it's embarrassing because this is my whole life's work is not doing this.
Nicole Kahlil
I get. I'm like, I know better.
Tonya Lester
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. 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, 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, 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 fact, six months after the fact. I want to bring something up. It happened a while ago, so I think it's going to feel odd too. 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 the first five minutes after it happened. Like, allow yourself to go back.
Nicole Kahlil
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.
Tonya Lester
Yes.
Nicole Kahlil
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 we're gonna give 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?
Tonya Lester
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, you will be disempowered.
Nicole Kahlil
Right.
Tonya Lester
If you're an intern, you aren't going to have the same power or leverage as the CEO and, 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, of 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, 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?
Nicole Kahlil
This is.
Tonya Lester
Most everyone always says that the great bosses, they learned from having a really terrible boss. And so then you're as you get more senior 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 in any situation.
Nicole Kahlil
A hundred percent. Well said. And I think there are small ways that we can stand up for ourselves or speak our 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 environments. But I still think a lot of what you shared when we were talking about romantic relationships applies here too.
Tonya Lester
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.
Nicole Kahlil
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.
Tonya Lester
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 gonna 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, 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.
Nicole Kahlil
Yeah. Well, that's a good example of how we get good at pushing back is how we get good at anything. And it's 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 tonialester.com we're going to put all the ways to find and follow Tonya in Show 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.
Tonya Lester
Thank you so much, Nicole.
Nicole Kahlil
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 then. And that is woman's work.
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This Is Woman's Work with Nicole Kalil, Episode 369 (December 10, 2025)
Guest: Tonya Lester, Brooklyn-based psychotherapist and author
Host: Nicole Kalil
This episode explores the art—and the necessity—of pushing back, particularly for women conditioned to prioritize harmony over honesty. Nicole Kalil and guest Tonya Lester dig into the “people-pleasing” trap and share practical strategies for advocating for your own needs in work, love, and life. Together, they challenge listeners to redefine what it means to be “difficult” and make space for healthy conflict as a sign of commitment, not rebellion.
Inviting Collaboration (12:49):
Tonya underscores that relationship health relies on mutual investment. Women often try to "row both oars" in relationships, doing all the emotional work while their partners coast.
Men and Emotional Labor:
The discussion touches on how men often haven’t been equipped with skills for empathy or collaboration, reinforcing unequal dynamics.
Knowing Your Own Patterns (27:02):
Both Nicole and Tonya admit to still struggling with advocating for their needs, despite their professional expertise.
Strategies:
Power Dynamics (30:08):
Addressing issues at work is more complex due to hierarchy and job security. If a workplace is toxic, it may require leaving rather than fighting.
Building Skills:
Use tough work environments to build skills (e.g., standing up for oneself, saying no, public speaking) that you can bring elsewhere.
Practical Example (34:30):
Tonya shares how a client challenged the expectation that she always take meeting notes by calmly suggesting a rotation, helping shift the team dynamic.
Nicole closes with an empowering call to redefine “difficult” as a badge of authenticity and self-respect, urging listeners to set boundaries, express their needs, and embrace constructive conflict as acts of care.