Handling Difficult Conversations Around Quitting
Ep. 259
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This week we’re diving deep into having difficult conversations around quitting.
We’re going to look at the people in your life—the ones who have lots of opinions on what you should or shouldn’t be doing. You know the type: spouses, friends, family, and even coworkers who always seem to have something to say.
The first and most crucial step is understanding whether these people should even have a say in your decisions.
Now, here’s the thing. Different people play different roles in your life. If it’s your spouse, for example, their opinion matters because it directly affects both of you. But for others, like your parents or that super opinionated friend, it’s important to figure out if they’re just giving their two cents or if you genuinely need their support or permission.
In this episode, we’ll also dive into how to clearly communicate what you need from these conversations.
Show Transcript
Hey, welcome to Lessons from a Quitter, where we believe that it is never too late to start over. No matter how much time or energy you've spent getting to where you are. If ultimately you are unfulfilled, then it is time to get out. Join me each week for both inspiration and actionable tips so that we can get you on the road to your dreams. Hello my friends. Welcome to another episode. I'm so excited you are here. We're gonna talk today around having difficult conversations with spouses, family members, people that you want to talk to. This has come up a lot in the conversation of quitting. So, so many people that I coach who want to quit their careers, but you know their family relies on their income and their spouse may not be on board or their parents, you know, are really upset that they wanna leave.

We talk around these difficult conversations. Now, what I talk about today obviously can be included or used in any type of difficult conversation you have to have. It doesn't have to be about quitting or your job, it's just a good framework to think about when you think about approaching these conversations. Last week we talked about how to handle guilt over quitting, the guilt of leaving coworkers, bosses, people that you believe are gonna be really upset. And this is another kind of part as people prepare to quit, there's kind of a lot of different things that make it difficult for them. One might be leaving the people at work and how they're gonna feel and one is dealing with the people in your life, in your interpersonal relationships. Like I said, spouses, friends, family, people that have a lot of opinions on what you should and shouldn't be doing and having those conversations or getting them quote unquote on board is a really big problem or deal or you know, block for people from moving forward.

So I wanted to talk about how you do that. Okay? The first thing that you have to do, I'm gonna give you a bunch of steps, but the first thing that I want you to understand is really whether this person should have a say in what you're doing and why you think they should. So you really want to explore why you're having this conversation with them and what the point of the conversation is about. Okay? So you wanna get clear on like what you want from them and why you're even going to them. Okay? What is the objective of this conversation? Now for some people like let's say your spouse, there is more of hey, this directly affects your life. If I'm bringing home this income and I'm gonna not be bringing it or I'm gonna be getting a lesser paying job or I'm gonna start a business or whatever, okay?

That is something where we have to actually like iron out the finances, how it affects us, how you feel about that, your risk tolerance, all of that stuff. That's a very different conversation than I see a lot of people who are just like informing people in their lives who are gonna have a lot of opinions. So if it's like my parents who I don't live with anymore, who don't support me but are just worried about me, or let's say, you know, maybe an a very opinionated friend or whatever, coworkers or whatnot, you wanna get really clear on like who am I going to for whether it's support versus permission and what is the point of this conversation? Because if they are not directly affected by your decision in the sense of like it's just their opinion, they want you to be safe, they're doing it from a place of good, okay, fine, that's a different conversation then.

Like, hey, we need to really figure out what we can and can't do here and like what we rely on me for and what we need to like move around. Okay? So its first is like really just getting an understanding of what the objective of the conversation is. Because the reason I say this is because for some people, if it's just support, let's say if they, if it's your parents, it's an opinionated friend, you have to really question like, do I need to have this conversation right now? Do they even need to know? Do they need to be privy to my decision making? For a lot of people, when you are in a very fragile place around your own decision, meaning you're not certain about it, right? You have a lot of doubts, you have a lot of fears for a lot of us when we're gonna quit, we don't know like is this the quote unquote right thing?

Cuz we don't know how it's gonna turn out. We're already scared. I would caution you to be careful with how many people you bring into your inner circle to talk about these things. Oftentimes when we are not ready, uh, when we have all of these doubts ourselves, bringing on other people's doubts can be really hard to handle, right? Can be because we already have that. So it's gonna trigger more. If you're gonna start a business, let's say maybe talking about it to your most critical friend might not be the best thing to do. You know, that might just be like, Hey, I know I talk about a lot of things with this person, but this might be something that I don't really wanna talk about until I'm in a place where I can handle this discussion more. Where I can handle their doubts or their criticisms or whatever it is that they're gonna do even with my parents, right?

Maybe I can, maybe I do need to inform them or I want to inform them, but do I need to keep running by every single decision I'm making? Do I need to keep bringing it up? Because the reason I say like we need to know the objective is like you have to understand what you're asking them for, why you're going to them, okay? If you're going to them to like flesh out an idea like hey I wanna start this business and I have these ideas for this business idea, again, you wanna ask like, is this the best person that I'm asking this for? Is this the person I wanna be fleshing this idea out? Do I have to go to them for everything? If you're asking for support, that's a different person. Again, can they give me the support than I need? Right? Am I asking for permission?

And this is a big one that we have to really understand is oftentimes we don't realize that's what we're asking. We don't realize that we're going into these conversations wanting people because we already have our doubts. We want them to tell us like, it's okay, you should quit, you should go after your dream. And then we get really triggered and emotional and upset when they don't do that. But maybe they're not in the place to be able to give you permission. Maybe that's not their role. And you have to really even ask yourself like do I need their permission? Like with, let's say as an example of parents, and I say this, I went through the same thing as an Iranian American. I understand the need for having family involved in everything and I talked to my parents about a lot of things and it's not as though I was just gonna quit without telling them.

But when I look back at it, it's like I was at an age where I didn't need their permission to quit my job, but I did feel like I needed it because that is just the way that our relationship had been up until that point. And so I wish I had these tools back then of just like really realizing that like does it feel good to have their permission? Of course, because it massages my own fears. Cuz if someone else is telling me like, oh you should do it, don't even worry about it. Like we'll make this work. This is the best thing for you. It feels so good. It's like a warm hug. You're like oh this is so great. You the right, I will be okay. And I think that's too often what the problem is, is that we are going to people addressing the conversation as of like, Hey, I just wanna tell you something, but secretly we want their permission and they don't know that we haven't like relayed that information.

We haven't said like I really want you to just like tell me it's gonna be okay and that I should do this. And so when we ask their opinion and then they give us their opinion, we get very upset cuz it's like, why can't you just support me? Why can't you just tell me this is gonna be good? And it's really because it's just triggering our own insecurity. So the first step is like really understanding what is the objective of this conversation I'm having with this person? Why am I going to this person right now? Right? Is it for fleshing out the idea? If it is, why am I getting defensive when they're fleshing out the idea, when they're giving me constructive feedback, when they're asking me questions, right? That might be like a little alarm to me that I wasn't actually going to flesh out the idea, I really wanted something else from them, right? I think for the most part, obviously you don't need most people's permission. Like we talked about maybe with a spouse, I don't, I honestly think you don't even need your spouse's permission. I'm gonna tell you what I mean by that. But that is a different like logistical conversation that you have to have. But I think for everybody else, like you have to get really clear on like am I asking for support or am I asking for permission?

Because if you ask for support, this is step two. So like step one is objective, step two is like communicate very clearly what you are going to them for and what you need. I think a lot of times we just expect them to understand that I want support. And part of me having these difficult conversations is being able to communicate what you need. So if you are going to your parents or to someone that's critical and you're having this conversation, you need to be very upfront about, I'm gonna tell you what I wanna do. I know that you love me, I know you're worried about me, but I really need you to just support me on this decision. I'm coming to you to tell you about this but I want your support. That puts the conversation in a much different light. Now they may still make some comments or ask questions or be concerned, but at least you have given the kind of indication of why you're coming.

It will make them think twice from like tearing apart your idea. They may give you the thing that you need, right? And maybe if they don't, it becomes an easier way to set boundaries. Like I understand your concerns but I can't have these conversations with you because right now I'm in a really vulnerable place and I'm in a really place like that. I'm managing my own fears and so I really just need the support to like make this decision. I know it might not work out, I'm willing to handle that but like as someone that loves me, I just need your support right now. Right? If I go in with that conversation, like think about how different that conversation is, rather than just me being like, so what do you think of this idea of me quitting and writing a book? You know like if you're entering a conversation in that way and that person is just coming from their mindset where they've been taught their whole life that you always have a secure job and that you, you know, not having a job is the worst thing you could do.

Like what do you think their reaction is gonna be? It's not because they hate you and they want you to fail, it's simply because they've been taught to fear the scenario in every turn of their life. And when somebody they love comes and says like, oh by the way I'm just gonna quit the stable career I have that I've worked years and years to get and I'm gonna go out and I'm gonna become a life coach. Ask me how I know this. They may not be the most supportive and that's okay, but when I tell them like I'm having this conversation with you because I'm hoping to get your support, that's what I want outta this. I've already made the decision, I'm gonna do this. I don't need your permission to do it. I mean you don't have to communicate that like you can say it, but I've already made this decision and I need your support.

That conversation will go much different, more, more differently, much differently. I don't know what the word is, it will be different than just like launching into it, which is what we mostly do right now. Going back to permission. And this is why again, even with your spouse, I want you to be clear on what it is, is oftentimes again we are seeking permission because we're using it as a way to kind of calm our own fears about what we're doing. We're hoping that somebody else says like, oh you're totally right, you should do this, this is gonna be great and that makes us feel better. I say this from personal experience, this is exactly what I did and I didn't realize I was doing it and I did it multiple times with my husband, okay? And I realize now, like as an example, I talked about it on the episode that he was on, I had had a photo with business before I started my coaching business and I was done with that business.

I didn't wanna do it anymore. My passion was in building this platform and this podcast and launching this business. And I felt guilty about closing down the photo booth business because I had spent a lot of time and he had supported me a lot in building that business and it was going well and I had gotten to a place where I could scale it and I had to put in a lot of effort to do that. But I didn't realize at the time, like obviously from his point of view, he doesn't know anything about this online business. He doesn't really understand this world. It, it seems risky. I've already spent a couple of years building this other business, it's now doing well and it's in a place where I can scale. No rational person would be like, you know what, you should just give it up .

You should just shut it down and move on. Obviously not like thinking from a rational brain. And for him especially cuz he was an engineer and he understood the photo booth business and he understood where it could go. I realized every time I was having this conversation, I wanted his permission. I wanted him to say, you know what, if you wanna do this podcast, it's okay. You can just shut it down. And I realized that later when I basically just told him like, you know what? I've made the decision to shut it down and I understand that you don't get it and I understand that you think I should keep building that business, but I need you to just trust me on this and I need your support. And when I realized I didn't need his permission, and this is what I mean even with your spouse, I want you to like really consider do I need their permission?

Like am I asking because like financially it affects us or do I just think they need to support everything I do, even if it financially it affects you. I want you to think of it this way. Let's say you do need your income. Let's say you guys are uh, you know, you're relying on your income and you wanna quit the job to start a business and it, it's obviously gonna affect the finances and clearly your spouse is gonna have some doubts because of that, right? Like this is not like, they're not like a jerk or mean, it's like of course human fears, they want you to be safe, you have a safe job, they're gonna be reluctant in thinking of you starting a business. Okay? So if that's the scenario, and let's say you can't quit for the next year or two years. Let's say you need this income for the next year or two years.

If you get really clear about the fact that like you don't need a permission, this is what you want to do, you can get really clear about figuring out the finances or you can go to them to talk about that, right? You can say like, listen, I want to do this thing in my life. I would like to start this business and I would like your support on it and I would like you to help me figure out how we can make this work. I know that maybe I can't do it this year or next year. Maybe we're gonna need to save more, but I would like us to be a team on this. I would love your support in figuring out how can we do this in two years? Can we save in other ways? Can we cut our costs in different things so we can start like ramping up our savings so that in two years I can quit my job?

Can we, you know, start, I don't know, some kind of side hustle or can you change your job and get a more higher paying job? Or what whatever it is that you're willing to have these conversations with, you are setting a different stage when you go in asking simply for their support instead of their permission. Instead of saying like, I just need you to somehow agree with me and think this is the best idea. They get to be afraid. They get to not think it's a good idea. And you get to say that like I get that like I might fail at this and I know you love me and you don't want me to fail and you want me to not be unsafe and you don't want the ramifications. I totally understand that. I'd probably be scared too if you wanted to quit and go start a business, I can get that and I still wanna do this and this is still the dream that I want you to support for me.

Notice how different that conversation is rather than like, well what do you think of me if I just quit my job next year? It's like, of course that person is gonna have a reaction you don't want them to have and then that's gonna trigger your own not only like insecurities but then resentments and angers and like why can't you just support me? And it kind of snowballs into this really unproductive conversation. So I think one of the biggest things that like takeaways I would want you to take from this podcast is simply that you don't need other people's permission. Now you may need to figure out a plan. You, you may need to decide like, hey, how long would you, how much of a savings do we need for you to feel safe for me to leave? How much do I need to be making?

Maybe you're gonna start it as a side hustle. Maybe the permission, I mean the support is, hey, I want to get outta this job so I'm gonna need some of the nights and weekends to work on this. So I need more help with the kids or I'm not gonna be able to hang out as much, but I just need you to support me through this because I need to get out of this nine to five. When you come more with like an ask of for support rather than like, can you please give me permission to do this? Where that person feels the pressure of like this is now on my decision and I have to make sure they're making the right decision. It changes the dynamic of the conversation. And again, you can then communicate very clearly what you need and then you can figure out how you guys can make it work together, right?

Again, it may not happen in the timeline that you want, it may take longer, you might have to do other things, okay? But at least we know what we're working towards. And then I'll say the third thing for really being able to have these difficult conversations is be willing to listen to them and actually hear them and their concerns without making a story about it, without making it mean something about you. So I think what happens too often is that like we ask them, like we say we wanna have a conversation, we don't really, we just want them to agree with us, but we say we wanna have it and then we go in and then as soon as they're telling us what they actually think and feel, we get super defensive because it triggers our own thoughts, right? When they say something, when they say like, well I don't know, like what are we gonna do without the health benefits or what, you know, we can't really sustain that long without you making this much or what's gonna really affect our quality of life?

Whatever it is that triggers your own thought, your own insecurity, you're already worried about that. Like, yeah, we do rely on my income and this does mean that we may not be able to take vacations and this does mean that we might have to downsize and the kids might think that that sucks, that they can't go to summer camp or whatever. However it will affect you. And because you're already feeling insecure about those things or you already feel maybe even guilty like, oh, am I being selfish for doing this? Should I just stay? You have all these things when someone else brings it up, we get super defensive because we want them to convince us, we want them to give us permission. We want them to say like, no, you should go after your dreams, dream big, we'll make it work, don't even worry about it.

And then when they start being like, they have seems like really scary, I don't know, I don't know about this, what if it doesn't work? We get super defensive, those insecurities come up and it's like, oh, why can't you just support me? I'll figure it out. I know you don't think I've thought about that. You know, whatever it becomes. And it's only because of that same insecurity. So you have to be willing to actually listen to them to understand that like of course they love me and they want me to be safe and they are gonna project their fears onto me. Whether it's my spouse, whether it's my parents, whether it's that coworker who's just constantly like, what you're gonna quit? Are you insane? How are you gonna do this? This person is not doing it to try to be vindictive and mean. I mean maybe some people are, and if they are, then you definitely should not be sharing your hopes and dreams with them.

And those are not the conversations for those people. But if you truly understand from this place of like they don't mean anything bad about it, they love me and they want me to be safe, and they were programmed in a society that told them anything outside the status quo is unsafe. And we have seen evidence of people who have maybe failed at businesses and they have all of these examples of like people losing their life savings or whatever and they're freaked out. And so they are trying to protect me and they may not be doing it in the best way and they may not be saying it in the best way, but that is where it's coming from. And if I cannot take that on, if I can make that mean anything about me, if I cannot make it mean they're right, I am gonna fail, right?

This is a bigger risk or whatever it is, then I can hear what they're actually saying I can. One of the, the best questions to ask yourself is how could they be right? How could they be right in what they're saying? Just so I can explore it, not because I have to take it on. How could my parents be right that this could be a colossal mistake? Maybe they are, maybe they are right? Maybe it is a colossal mistake. How would I handle that? What would I do? How would I take care of myself? Am I willing to do that just to see, to give myself the opportunity to explore in this world, to like try that business, right? If I can hear their fears and take it on and know how I'm gonna respond, it loses so much of its power, right? I don't have to then convince them, I don't have to fight them.

I don't have to get them to change their thoughts. I could totally even respect it and they might even help me. I might be like, yeah, you're totally right. I need to think about a plan B and a plan C. You're right. Like we should save even more because I didn't think about this than that. So maybe I won't quit for three years or maybe I will get my side hustle to completely replace my salary before we leave. Thank you for wanting to protect me, right? You can hear so much more when what's on the line isn't like they don't love me, they don't support me, they hate me, they don't understand me, all this other drama. So that's how I want you to approach these decisions. Okay? So we're gonna go through it again. Number one, know what the objective of the conversation is.

Why are you going to them? Get clear on what you want from them and why. And do you need that? Okay? This is the biggest step. Step two, communicate what you need very clearly from them at the outset. Don't just let this be kind of, let's, um, so what do you think about this? Like tell them why you're having this conversation. This is the thing, it's like amazing how much this open communication can solve things, but you can even express how you're feeling. I'm feeling really nervous about having this conversation and I'm really scared that you're gonna hate it and that's gonna like trigger a lot in me. So I just want you to know that like this is where I'm coming from and I don't need you to agree with me, but I just want you to know that I have a lot of like fear that like I just don't want you to shoot this down.

So like what I'm asking for you is just hear me out, right? Think about how that sets up the conversation differently for the person listening. So communicate what you need very clearly. And then three, be willing to actually hear them and their concerns. For a lot of people, if they feel like their concerns are being heard, they are gonna be more supportive. They're willing to then be like, okay, as long as you know like these are some of the possibilities and I can see that you're clearly hearing me, then yeah, go for it. Right? Maybe take the risk if you're okay with that. I'm just worried that like if this doesn't work out, you're gonna feel super bummed or whatever. And if they see like, no, I took this in and I get it, it can create such a better conversation. So don't fear having these difficult conversations.

You're gonna have to have them. You don't need everyone to agree with you. You don't need everyone to even support you to be honest. Like I know you can ask for that support, but you don't need that support. There's a lot of people, even within spouses, there's so many people I know who their spouses didn't support their business because they couldn't see how it was gonna work. And like I said, like with my husband, I was asking that permission. And it's not to say I did tell him when I decided to shut down the photo with business, I told him very clearly, I just need your support. And he was very supportive on that, you know, outside. But I know deep down he still had concerns of like, what are you doing? Why are you shutting this down? Right? Of, I'm sure he had thought like, you just built this other business.

Are you gonna do the same thing with this one? Like I'm sure there was tons of thoughts there, but one of the things I was realizing too is like I don't need him to understand. I understand it's my dream. I'm the one that has this vision. He doesn't, I can either spend all of my time trying to convince him or I can just tell him what I need and move on and I don't need to keep bringing it up, right? And so I want you to even understand like, yes, does it feel good if everybody's on board and everybody pats you on the head and everybody tells you like you're doing the right thing and it's great and follow your dreams. I'm sure that feels lovely and it's a warm hug, but you don't need it. You just need to believe in it. You need to believe that it's the right thing for you.

And then you have to ask other people what you need from them. And you have to be willing to let them think what they want. You have to be willing to hear them out. And then let's just let them, let them be upset about it. Let them not think it's gonna work. I've talked about this a lot. It's, it's funny to me now, it wasn't as funny then when I quit the law, I had a lot of family members who were rightfully concerned, right? Like they had never done something like this. They hadn't seen somebody do something like this. I had spent my whole life working to get that degree and get that job. And so when I was gonna leave, they, um, had a lot of thoughts about it. And in the beginning, like I said, it would trigger my own insecurities when they kept telling me, are you sure?

Like, you shouldn't spend too much time. There shouldn't be like a gap on your resume. You gotta make sure, maybe you could do it on part-time. Maybe you could freelance all these things. And I used to get really mad about it. Like, oh, why can't you just like support me? Why can't you understand? Fast forward to the fact that like I now have a business that is something that lights me up. I'm, you know, financially successful at it. I'm emotionally successful at it. I love it. I love all parts of it. I still have family members that ask me this is like, what are we like, you're 9, 8, 9 that I've left the law now, still ask me if I'm gonna go back. Or like, are you sh what You sure you don't wanna try it again? And it's funny to me now cause I'm like, why do you care?

Like it doesn't affect you in any ways. And I have a business I love and I'm doing well. So like now it's so obvious to me that it's just these like programmed beliefs of what's successful and what's not and what people should do. But when I say that is that like I realize like I don't need them to understand. I don't need to like convince them that my business is successful and that they should be on board. I get to let them have whatever thoughts they wanna have. They can think that I made the wrong decision. They can think leaving law was the dumbest thing I've ever done. I don't care at this point, right? It doesn't matter to me because this was my life and I, they don't have to live my life. They didn't have to do the work as a lawyer. They didn't have to go into work every day and bill at six minute increments.

Still have PTSD from that. And so they get to think what they want and I don't have to change it. And that is the most liberating, freeing feeling. Like you could totally not think I'm doing the right thing. That's okay. I'm allowed to make mistakes in my life. I'm allowed to take, make decisions other people don't understand. I'm allowed to do things that not everybody agrees with. And when I can let them have those thoughts and I can listen to their concerns and I cannot take them on, I can decide what I'm gonna take on. I cannot make it a story about it. It makes having those conversations much easier. So go out and have that conversation, get really clear on these three things and watch how different it is and how, uh, much more manageable and not scary it is than just going in kind of hoping that this person says and does all the right things that they're not gonna do.

It's way too much pressure. All right, my friends, I hope this was helpful. I'll be back next week with another one in this series of how to get prepped for quitting. Have a wonderful weekend. Hey, if you are looking for more in-depth help with your career, whether that's dealing with all of the stress, worry, and anxiety that's leading to burnout in your current career or figuring out what your dream career is and actually going after it, I want you to join me in the Quitter Club. It is where we quit what is no longer working like perfectionism, people pleasing imposter syndrome, and we start working on what does and we start taking action towards the career and the life that you actually want. We will take the concepts that we talk about on the podcast and apply them to your life and you will get the coaching tools and support that you need to actually make some real change. So go to lessons from a quitter.com/quitter club and get on the wait list. Doors are closed right now, but they will be open soon.