Ep. 40. Sales, Boundaries, and Fear: Why People-Pleasing is Sabotaging Your Sales

Hello, it’s Kari here and welcome to today’s episode. Listen, I have got a good one for you today. We’re gonna be talking all about sales boundaries and fear and why people pleasing is [00:01:00] sabotaging your sales in so many ways that you may not be aware of now. I spend my week talking to founders and troubleshooting marketing and sales and boundaries and fear and people pleasing, it comes up a lot. In fact, I just had two conversations with clients yesterday and today and experienced my own boundary crossing marketing collaboration issue, that I am gonna share with you today in order to teach you all about how having more firm boundaries will actually help you to create a bigger impact in the world and a way of selling that feels really aligned and good for you.

All right, so let’s dive into sales, boundaries, and fear, and the topic of people pleasing. Now as I mentioned, [00:02:00] this is a really timely conversation that we are having because I’m just fresh off of a couple of client conversations where I offered up this perspective to them, and I also just noticed myself getting triggered in one of my marketing collaborations that’s coming up in a couple of weeks where the collaborator has suddenly decided needed to change the plan. It didn’t feel very aligned for me, and I watched my brain do what brains do. I watched myself with a lot of curiosity, and then I used tools to work through it. So my hope for you today is that I can give you some new ways of viewing people pleasing in sales environments that’s really going to help you to understand the neuroscience behind what’s happening, and also tools to help you to navigate it when it happens. We’re gonna go through several different points today, and then I’m gonna give you some coaching [00:03:00] check-in questions that you can ask yourself in order to navigate this with more ease.

The first point I wanna make is that most of the time, when we go into a marketing collaboration. What I mean by a marketing collaboration is a relationship where someone or a certain platform is positioning you or presenting you in a way where you get to either pitch or talk about your company or get in front of prospects, and ultimately you wanna sail from it. That is a marketing collaboration. When you enter into a marketing collaboration, one of the main reasons, or really the only reason why people pleasing would ever be an issue is if something in that collaboration at some point or another just doesn’t actually work for you. That’s a really important first thing to talk about [00:04:00] because oftentimes when we go into a marketing or sales environment, we are very focused on the outcome of making money, on making the sale, and getting a yes from the other person. We’re stepping into a scenario where our sense of self can get lost really easily because we’re fixated on the other person’s response, what the other person thinks of us, what the other person will say. There can be fear around their potential response. There can be fear around what that response might actually mean. So, for example, if they say no, what does that mean for your business? What does that mean about you as a business person? What does that mean about the legitimacy of your work? What does that mean about your professionalism?

Our brain likes to story tell, and create a lot of [00:05:00] drama around what another person’s response will be. It is really easy for the brain to get triggered into this internal dialogue, which doesn’t feel very good and takes a lot of time, right When your brain starts to ruminate on why a particular person said no or doesn’t wanna work with you. But this type of triggering environment can actually be a window into our current mindset around sales and our current people pleasing patterns. So instead of viewing some of these moments where we do get frustrated, we do feel like, you know, I’m a little annoyed at this person, or this doesn’t quite work for me. We can use this as an opportunity to check in. To check in on who we are. What matters to us. Where our boundaries are. Where [00:06:00] our fears are. Where our triggers are. This is an invitation to do some self-reflection, to do some self-questioning. It is not an invitation to do whatever the other person says, just because we want to be easy to work with. Just because we wanna be easygoing, just because we wanna be flexible or just because we want the sale. It is also not a sign to slam the door in their face. Right?

I run into this all the time where sometimes my founders will just be like, yeah, they weren’t my person. Nah, they weren’t for me. Eh, they weren’t willing to invest. Without actually looking deeper into why this was so triggering for them and how they could have navigated it in a way that served both themselves and the other person on the other end who actually showed up to a sales conversation who actually needed help solving a problem. So there’s this middle ground here where [00:07:00] we wanna pause and just look at why we feel a sense of activation in our body, why we feel irritated, annoyed, frustrated, why our heart rate went up, why we can’t get this off our mind, why we are consumed with the best way of responding. All of these are signs of nervous system dysregulation caused by someone crossing over a boundary. We wanna start to get deeper under the surface around what that fear is and what that people pleasing tendency is and how to navigate it in the best way that works for us, and also works for the other person.

This can apply to, like I said, , a marketing collaboration where you have a partner and ultimately they’re the avenue for you to reach potential customers. It can also be when you’re speaking to the prospect themselves. For example, you’re on a free consultation call, or you’re going into a meeting into [00:08:00] someone’s office and you’re presenting your solution to them. We wanna understand any time we get an emotional response. That is around frustration, irritation, or annoyance. So I’ll give you some examples. It could be if you are about to be interviewed on a podcast and that podcast has a really great reach, you’re gonna reach tens of th thousands of people, and yet there’s something that the host is doing that doesn’t work for you, that’s making you feel uncomfortable or stressed out. It could be that you are already in a collaboration where there’s a contract and there’s agreement. Or you have a particular point person and suddenly that point person has changed and now you’re talking to a different individual and you don’t have a sense of trust and understanding yet, and they wanna change things on you halfway through. It can be if you are in a relationship where the understanding was that you would both [00:09:00] be positioned as equal parties and then you get into it and suddenly you’re pushed down. You’re positioned as the less than party, right? They take all the spotlight. They take all of the room and they give you a little shout out for your help. That’s totally happened to me. Can you tell?

It could be where the prospect is wanting you to change the way you do things with your package or your pricing or your product, or the way you deliver something. They’re wanting you to make all sorts of concessions in order for them to buy from you. You’re feeling that sense of oof, that’s gonna be difficult. Oof. I don’t wanna run my business like that. There are just so many ways that this could show up. Instead of staying in that frustration again, we wanna dive in. Here are some questions that are really good coaching questions for you to ask. Whenever you feel [00:10:00] any type of negative emotion coming up in a relationship where there is annoyance, frustration, or irritation.

The first question you always wanna ask is, what is the point of this relationship? Whenever we have a micro issue, right? The little alarm system going off or the red flag going like, something’s not working here. You always wanna zoom way out. This is sometimes called chunking up in psychology. You’ll learn this from any type of relationship, a therapist or a psychologist, or you’ll learn this in the counseling room where we’re working with, you know, a married couple, for example. We will chunk up until we find where we actually do agree. Where our values and our vision and the point of it all does align so that we can reconnect there and then we zoom back in. The same would apply here. We wanna chunk up and we wanna zoom as [00:11:00] far out as we can, and we wanna re-identify for ourselves what the original point was for our business.

Was it to reach a certain a number of people and to get that visibility and to bring in customers. If so, what kind of conversion rate? What kind of reach were you hoping with the resources you allocated to this, right? You might not be allocating actual money to it, but you’re allocating time and attention to it, which equals money. You could take that time and attention, and you could put it on a different marketing activity, a different relationship to get a better outcome, to get a better return on investment. It’s important to zoom out and to be honest with yourself around what am I actually needing to gain from this relationship in order for this to be worth my time? The other person in the relationship should be asking that as well. We don’t just do things for the fun of it, right? [00:12:00] We have businesses to grow, we have people to help. We have team members. We have family members. We don’t just do things for the fun of it in our business. We can have fun while doing strategic things, but we don’t wanna waste our time or waste anyone else’s time. We wanna zoom out to what did I specifically wanna gain outta this relationship, because that becomes the foundation for all of the other questions you then want to check in on. What am I willing to do in this relationship in order to get that result? There’s things that you are willing to do and there’s things that you are not willing to do. These two questions, what am I willing to do and what am I not willing to do, are really, really powerful. You wanna really get a sense of the structure and the dynamic that is going to make it worth your time and your resources and your budget. [00:13:00]

Another really great question is how do I expect to be marketed, presented, or positioned? I think that this is one of the main triggers that can happen that I’ve seen with my clients, where they thought that they were going to be positioned in a certain way, and then in the end they didn’t have as much control over how they were positioned and how it was structured and it didn’t work for them, and they felt insecure speaking up and saying no, I need to be positioned this way. This needs to be marketed and talked about this way. The other really great question is what do I expect the other person to do? What are the tasks? What are the things that I want this other party to do? What’s their end of this relationship so that I feel like we are both giving to this in a fair way. Now, this does not have to be completely equal sometimes. You will be the underdog, right? You will be going on [00:14:00] a show or going on a stage or being featured in a large publication where you know you’re just lucky and excited to be in that room. And so you don’t necessarily need to be the top dog and presented as, you know, some massive expert, but. You wanna really make sure that you feel like you got what you wanted out of the relationship, and that feels aligned and good for you so that there’s no resentment underneath it. I have a really good rule of thumb for myself that I don’t just keep going. If I feel resentment, I really check in on that and I either realign with what I want out of the relationship and I let the rest go. Or I restate my boundaries for what I do expect from the relationship and what I would like to happen. So after these questions, it’s really good to ask yourself, how can I communicate these expectations so we first get clear [00:15:00] on them and that it’s important to communicate them? This is probably one of the main issues in relationships, right, is communication.

Oftentimes we have a lot of un spoken uncommunicated expectations where we have like a manual for the other person and we have this list of things we want them to do and what we don’t want them to do and what we want them to say about us and how we want them to organize things. We want them to be instructured. We want them to be, and we have this long, long list of criteria and yet we’ve not spoken it to them or asked them to do it. I know I do this to my husband all the time. I catch myself, you know, being resentful when I actually haven’t even asked him. You can’t ask someone for something if you’re not clear on it first. That’s why we really need to investigate all of these questions first, to tap back into what do I want, what works for me, where are my [00:16:00] boundaries?

Lastly, we want to ask some questions around what will help us to feel safe communicating it. A lot of us don’t have a lot of practice with communicating our wants, needs and desires, and it feels a bit sticky and it feels a bit awkward, and we can have a lot of anxiety going into those kind of conversations. What do you need to create more safety for yourself? Safety is so important in relationship. It’s so important in selling, right? We need to feel safe presenting and we need to make the other people feel safe that we’re selling to. So maybe you need to talk to a coach and go through your points and get clear on what you do and don’t want, and you need to get clear on how you’re gonna say it. Maybe you just need to say, hey, can we have a quick phone conversation? To schedule that three or four days from now so you can just process what happens. You are always in the driver’s seat to create more safety for yourself. There’s [00:17:00] always a way to create more safety for you to be able to communicate your wants, needs and desires while keeping in mind the ultimate goal and what you’re willing and not willing to do.

That is step one to not lose sense of yourself in sales and marketing collaborations and in sales and marketing scenarios. There’s always a place for you to check in with what works for you and what you’re willing to do and not willing to do. And remember, communication is key. The next step is to step into their shoes. Activation. These emotions like frustration and irritation and annoyance, this is the fight or flight stress response. This is where adrenaline and cortisol are in the system. We feel more protective. We feel more defensive. We wanna write that email really fast. We wanna complain, right? We wanna vent to someone in our [00:18:00] world. It is really helpful to label this as nervous system activation and to notice that you’re actually triggered into the protective response. Now, the interesting thing about the sympathetic nervous system and what happens neurologically is that we put up walls, we put up defenses, right? We’re literally in fight or flight, meaning we’re self-protecting instead of leaning into intimacy, vulnerability, connection and communication with other people. It’s the opposite of that safe social engagement that we really need to collaborate and also to sell. So when our nervous system is in these emotions, we are biologically wired to go against to fight or flight.

It can also dip over into the fond state, which is where we are people pleasing with a lot of that resentment like I [00:19:00] just talked about. This second step is about building upon the foundation, which we just talked about, of checking in with your sense of self and what you want out of the relationship, and then giving the other person some airtime. Now people who are stuck in, a lot of people pleasing, they miss step one. Oftentimes they are so patterned and so wired to just jump into step two about, well, what are they feeling? What’s gonna work for them? How can I accommodate them? But it’s fear-based, and again, it has a lot of resentment tied to it. I’m going to share what I would do for step two and what I suggest that all of the founders I work with do when really empathizing and getting into the other person’s world. I don’t want you to ever jump to step two before you first check in with your sense of self. It has to go [00:20:00] in that order, in order for this to work really well. It’s important once you’ve done that first step, to notice your activation and to notice yourself getting protective and to lean in so that you can establish clear boundaries and to establish good communication while also really seeing the other person’s true heart. True desires, true intentions, because boundaries should actually never have a really hard emotional charge to it. It shouldn’t be filled with a lot of drama. If you have a lot of internal turmoil when setting a boundary and you’re kind of ruminating on it after you’ve set the boundary, you know that you did it from fight, flight [00:21:00] or fawn and you didn’t do it from a strong, grounded place of just, these are my boundaries. And moving on, right? It should feel quite powerful and strong, but it should also feel very calm and in love and in service of the other person as well.

That’s the goal of where we wanna get to when we’re communicating with other people in this step two of really empathizing and going into their emotional world can help to remove the emotional charge. Here are some check-in questions that I suggest, especially for marketing collaborations where you’re partnering with someone in order to get in front of your audience.

First, what do they want out of this relationship? Remember, we need to chunk up or zoom out, and we wanna really ask ourselves what’s important to them? What do they need to get out of this relationship in order for them to [00:22:00] feel like it works for them, in order to feel like they aren’t people pleasing for their boundaries to stay solid. It’s really important that you know that for the other person. What is the heart behind this collaboration? What are their desires? What were the good intentions here? You want to really look at the humanness and the raw good intentions that ultimately caused the two of you to talk in the first place, because a lot of that can get lost. Just think back to the last time you got in a fight with, you know, your significant other. Oftentimes we don’t zoom out and we lose sight of the heart, the desires, and the good intention behind that behavior. Now, the behavior might not be the best form of action, but there’s always a need underneath the behavior. [00:23:00] There’s always just someone who was trying to accomplish something and just didn’t do it quite in, in a way that you would prefer them to do. And so we do need to zoom out far enough to get to those good intentions. We also want to know how did they expect to be marketed, presented, and positioned? ’cause sometimes this is just a major area of misalignment. Transparent communication around this can solve a lot of issues.

Another great question is, what did they expect from me? All these questions will spark a more curious conversation with yourself, where the person becomes softer. It just will soften everything so that you can come back into that safe social engagement and more emotional connection with this person. You also wanna be on the lookout if you’re putting this person up on a pedestal or believing anything that would make [00:24:00] them feel like they’re not on the same playing field with you.

I think I mentioned this in another episode. I was talking to a potential collaboration here in Norway, a pretty big one like that would give me a lot of visibility and then suddenly things changed and the original agreement or the original conversation turned to where it would look differently than I had been told, and that I hoped it would be right. It was kind of turning from a really good opportunity to kind of like not such a great opportunity for me, and I saw myself going on the defense. Did step one to really zoom out, to say, okay, what is the point? What do I want? What am I willing and not willing to do? And then I stepped into the other person’s shoes. When I noted that anger, when I noticed that anger and activation, and I really sat to look at what I was thinking about this other person, and I was focused on poor intentions, I was really assuming that they didn’t have my best interest [00:25:00] in mind. So I was getting overprotective and as soon as I kind of softened and I really looked at, well, maybe they do want my best intentions here. Maybe they do want me to succeed. Maybe they are trying to help me and maybe they are just a normal person like me with kids and spouse and a to-do list and hobbies and fears. Then it started to soften it so that I could engage and communicate more clearly. This is what you want. You wanna feel a softening, not a softening of what you’re willing and not willing to do. So we’re not changing the boundaries, we’re changing the emotional charge to it so that you can be more powerful and calm and meet the other person’s boundaries with respect as well by creating space for all of it. Questions for sales prospects, meaning the actual customer can be a little bit [00:26:00] different.

I like to talk about this a little bit separately than maybe a collaborator or a partner because oftentimes we are triggered in conversations directly with a prospect because of our own shit. Sorry for my language, but oftentimes we get defensive, resentful, or impatient with prospects. If this is the case, you’re not gonna sell well because we can’t go into marketing and sales conversations on the defense. We can’t build trust and understanding. We can’t serve people well when our nervous systems are activated in this way, and there’s nothing wrong with you if this happens.

So that’s the first thing that I want you to understand about this conversation today is that there’s nothing wrong with you if you do feel frustrated, angry, annoyed, or like you’re having to say yes to things that you wish you didn’t have to say yes to. This is all [00:27:00] just normal human stuff, but we want to support our nervous system here instead of just to keep going, just a bulldoze pass, which is what we are sort of conditioned and trained to do. So in this case, when you notice that you are on the defensive or resentful or kind of impatient with an actual potential customer or a customer, we need to drop it because if we keep going with resentment, if we keep going with that sense of impatience, we’re not gonna ultimately be successful anyways. We need to support ourselves circumstantially by removing the trigger, and then once the trigger of that actual person is removed, then we can actually do the deeper self inquiry and self-work to look at what was going on with me there, because no one can make [00:28:00] you feel defensive, resentful, and impatient. Unless there’s something on your end as, as well, right? There’s two charges, positive and negative, that create this electrical spark. We really wanna look into what is my side of the story, and oftentimes we just need to remove this, this person short term from the environment in order to just have some space in order to reflect.

You never have to say yes to a customer who wants to work with you. If you’re feeling triggered by their requests for you to customize or to, you know, change the structure or bend over backwards to accommodate them. If you’re feeling that resentment and that frustration or irritation, just say, you know what? I don’t think this is the right fit and then let’s dive deeper into investigating your own boundaries and investigating why you actually felt so defensive. [00:29:00] The same is for these marketing collaborations. I do think that step one and step two will soften a lot of this, and so you won’t ever get to this point where you need to actually just say, you know what? This marketing collaboration is not working. I would just politely like to decline at this time. You probably won’t get here as often, but if all that other mindset work has not created a softening and a transparency and good open communication where you feel like the relationship is working for you again, then we must remove the triggering circumstance. Otherwise, you’re spending way too much bandwidth and time and energy on this relationship where you could be using it elsewhere to make a bigger impact in the world. When you decide, you know what, I’m just going to drop this for the time being. I always want you to do the, the self work afterwards to really [00:30:00] investigate what was happening here that triggered this response in me.

You know, I’ll tell you a recent story. I have a recent client who kept on feeling really angry at potential prospects on consultation calls. Now, you might be kind of like, well, that’s strange, right? But actually you’d be surprised at how often this happens. Whenever this happens, when you’re feeling really impatient or you’re feeling kind of angry, like, Ugh, this person just wants something free from me and they’re not willing to invest and they’re just not my kind of person, and kind of just this slamming the door in their face, writing them off kind of energy. It’s always because there’s something under the surface in you that actually needs to be addressed and to looked at. So this client continued to try to resolve this with the way she communicated and the, [00:31:00] and the sort of the business strategy of selling on consults for a pretty long period of time and ultimately remain unsuccessful. That’s the reason I’m sharing this story with you is because you can try any method, any strategy, or take any masterclass on sales and if you’ve got your own stuff going on, it’s always going to end up as the thing that blocks you. That’s why it needs to be resolved if you’ve got a lot of negative emotion in sales and marketing scenarios going on. Because once you get that out of the way, then you’re able to come to your selling from this clean space. You won’t be expecting your customers to take a particular action or to give you a yes or to be on a certain timeline in order for you to feel confident and for you to feel okay. That’s one of the major things that shifted for me early on in my entrepreneurial journey, is that we cannot expect for our [00:32:00] business to meet our emotional needs. That was mind blowing when I first heard that. It hit me to my core because I was noticing that I was having a lot of negative emotion when, nobody showed up to my webinar or I didn’t make the number of sales that I wanted, or that particular strategy didn’t work or someone said no to me when I pitched them. I was really feeling that sense of failure and rejection really heavily. And yes, of course, it comes with practice. As you first become an entrepreneur, you need to practice receiving more nos and receiving more, rejection and getting your nervous system used to it. But I think one of the major issues with new founders especially, is there’s so much self worth relying on the business. The business needs to fill their emotional needs for them to feel successful. For them to feel good enough for them to feel smart enough for [00:33:00] them to feel legitimate, for them to feel important, for them to feel impactful. So that’s why when we don’t get the results that we’d want, we don’t get the responses that we want. That’s why it’s so painful. So we can get really needy and impatient, and it can cause us to step into scenarios where we are crossing our boundaries over and over and over again, and we are people pleasing simply because we just need that dopamine hit and that sense of self-worth these circumstantial things to give us that security. But what happens is that this is very short-lived and it doesn’t fill the hole, and it gets harder and harder to fill our self-worth needs using goal achievement, business growth, getting yeses, getting applause, getting visibility, getting pats on the back, [00:34:00] getting attention from the business. It gets impossible to keep using the business in this way because we ultimately cannot stay grounded and objective. We cannot stay consistent when we are using the business to do this. We are too irritated, too frustrated, too activated, and too impatient and too full of the emotional roller coaster when this is the founder.

Now, I think it’s really important to just note here that like this happens to a certain extent to every human, including me. If you’ve ever found yourself really wanting that visibility or that attention, or that high five or that thumbs up of look what you did. I’m so proud of you from the business or from a mentor or another human being. In order to feed your self-worth, I think that it happens to everyone and it’s part of the [00:35:00] human condition. We can drop into this accidentally all of the time, so you’re not a bad person or you’re not too weak, or you’re not broken if this is you, but it isn’t important to just look at. You know when you do feel a lot of drama or when you are triggered by a person in your business, whether that’s a prospect or a partner, to look at maybe some of your own sense of self-worth and how that might be relying on a particular goal being achieved or a particular thing inside the business.

I have never, in my business felt so calm and grounded as now. To be honest with you, I’ve had several iterations of business, right? Several different areas where I’ve pivoted to different offers and different niches and different products like every single company. It’s been interesting because I [00:36:00] feel really passionate about the work that I’m doing in the world right now and really drawn and compelled to what these tools mean for founders and getting these tools into the hands of founders. I’m really emotionally connected to the work that I’m doing. I think that these tools are needed in the entrepreneurial space, and I have a passion for them, but I could throw away this business tomorrow. I can’t necessarily say that for the past iterations of my entrepreneurial journey, especially when I think back to my first business, I remember thinking, oh my gosh, I could not imagine not having this magazine. I could not imagine my life without it and that is a red flag. You wanna have a very loose grip on the business. It cannot be who you are. It cannot be your baby. You have to be your baby. Your sense of identity and who [00:37:00] you are as an individual outside of anything you do, any task you accomplish for the day. Any type of way you position yourself as an expert or as a founder, yes, that can be part of your identity and something you enjoy doing, but it really needs to be something that you can hold loosely and you need to have a sense of self underneath that. Because that will allow you to not only grow the business faster because of how objective and how curious and open and strategic you can be when you are not emotionally so needy to the business. It makes you way more strategic. It helps you to make better decisions. It helps you to show up in a more magnetic way to your customers because you’re just there for service. You’re not there for the gold star. But it also helps you to get a lot more fulfillment out of the work because there’s less of that, you know, emotional roller coaster. [00:38:00] So there’s this sense of self work that needs to happen whenever you find people pleasing or a lot of emotional dysregulation happening in your business. Again, everyone will have some part of this. I think that everyone needs to unwind this a bit, right? I’m still unwinding my attachment to accomplishment. But the work is to constantly build up our sense of self outside of the business in who we are and what we stand for, so that we don’t feel so emotionally needy on the prospect or on anything necessarily going our way. That will make you so much more powerful in any room you step into. It will help you to have less fear. It will allow you to go bigger and bolder. It will allow you to make a bigger impact in the world. It will also help you to protect your boundaries and to protect your sense of wellbeing in your personal life [00:39:00] because there is a clear differentiation between yourself and your business. This is deep stuff. This is not stuff you will hear on a typical, you know, business podcast, but it is so important.

So I invite you to maybe ask some of these questions, especially if you’re finding a lot of irritation, frustration, or negative emotion in the business. A great question to ask is how much is riding on this company to succeed? Is there a lot of pressure here that I reach a certain milestone in a certain, you know, amount of time? And if so, why? What would it mean about me if I don’t reach this goal? What if I don’t reach this milestone? Am I tying any ounce of my self worth to this? Because the truth is it shouldn’t mean anything about you. Oftentimes we’ve got [00:40:00] these sneaky little ties to our self-worth underneath the surface that we don’t shine a light on and that’s what we wanna uncover with these questions.

Another great question is what would it mean about me if this fails, if this next strategy fails, if this business meeting fails, if this presentation fails, if this company fails, what would it mean about me? The last one I like to ask is, do I have a sense of playfulness and fun with this? If not, why? There should always be a sense of playfulness and fun when we’re doing something that actually doesn’t matter for our self-worth at the end of the day, because it is play, it’s not make or break, it’s not do or die. It’s not time to anything deeper other than just having fun serving the world with something we find interesting. That is all we’re doing, and the more we can remind ourselves of that and not be the savior [00:41:00] of the world. Then we can loosen the grips and become so much more strategic.

I wanna tell you one last story as we wrap up, and this is probably not a story you would expect me to tell, but I was working with a founder for several years. So I got to watch her whole entire startup journey and into, I think, year four or five of the business. It was a really fun client relationship because I got to be a part of her first crowdfunding campaign and bringing on a celebrity as a first main investor and helping her to get a major national prestigious award and helping her through, I think three, three rounds of capital raises, building the team dealing with all sorts of crazy scenarios like being kicked off Facebook and, you know, dealing with how that affected the business model. All sorts of twists and turns like any startup [00:42:00] business would have. This was a quite visible business, so she had a lot of success in the beginning. So she was always front and center. Part of her business was using PR and publicity in order to drive visibility in sales. She was on the daily TV shows and she was in newspapers and being interviewed all the time, her picture was everywhere. This was a very visible founder. When we first started working together, as I got to know this founder, it was very clear that this founder’s self-worth was tied to this business. In fact, this founder was using her business as a way of finding herself of healing, a past wound of figuring out who she was and what she standard for, and getting kind of revenge on a past painful experience, a past wound. I think that a lot of founders would fall into this category, including me.

One of the reasons why I started my [00:43:00] first company rank and file magazine is because I was so pissed off at my last corporate company with how bad the leadership was. I was so mad at how they were like the opposite of values driven and they were not taking care of the people that I wanted to start a magazine about social impact businesses, businesses who were serving the world and doing good. It was like a direct counteractive in your face of move to heal that wound and to figure out who I was. I think a lot of founders would fall into this category and it’s not necessarily a bad thing. I think that a lot of the most impactful businesses are coming from maybe a painful experience or a challenge that the founder had. Where they didn’t have the tools or support they needed, and therefore they’re stepping into this business saying, I’m gonna right a wrong. I’m gonna help a vulnerable group of people here. What I experienced, was it correct and I’m gonna do something about it. That can be very impactful for the world. [00:44:00] But it can also be depleting and draining on the founder. And really hurt the ultimate success of the business. The reason I’m telling you this story is because we worked on this with the founder and we really, really went a long ways on this with her. She grew in so many different ways to develop her identity, to find her sense of self. To figure out who she was without the business, but there was always something that was there that was causing her to overcompensate, overwork and to use a lot more emotional energy than she needed to in the business. Ultimately, they weren’t able to raise their last round of funds and she closed on the business, and I remember having a very particular coaching call with her in the very end. Asked her to paint the picture of what her life would be [00:45:00] without the business. Now, this was before everything went down and she decided to actually close. This was maybe four or five coaching calls before that actually happened where I said, Hey, you’re having a lot of activation here, a lot of anxiety. We really need to go to worst case scenario so that you can be okay with the outcome. You’re too tied to the succeeding, to the point that it’s now a weakness of yours, and it was really eye-opening and healthy and hard. For her to look at who she would be without this baby of hers without this project that had completely consumed her for the last four or five years, and we started to paint a picture of what she wanted and what she could do and what she would be able to make more space for without this project and how [00:46:00] her journey was meant to be what it was. How this version of her, the current company that she had, was actually just a stepping stone to something greater in an ever evolving evolution of who she was supposed to become and what she was supposed to learn, and the joy and fulfillment and connection she was ultimately able to experience rather than, I failed at this accomplishment. It means I’m not strong enough to do it, and now I have to settle. It became, I’m so grateful for what just happened because it was for me, and now this exit, now this failure, quote unquote, is for me too, because it’s calling me into the next version of who I’m supposed to be, because this business is not who I’m supposed to be. It was just a part of my journey for this season, and we had a beautiful last couple of [00:47:00] coaching calls where we really stepped her into her next life with so much gratitude, so much self love, so much positivity at a time when she really at first, just wanted to curl up and hide and never be seen again.

There was just so much being said about her and the company online. It could have been a very painful experience. Fast forward a couple of months later and she go and she reached back out to me and she sent me randomly a Christmas gift in the mail that was just thanking me for everything that I had done for her personally and how impactful it was to go on that journey with me and. She reached back out to me right after I received that Christmas gift and she said, you know what? I just got headhunted for that dream job and I want your help preparing for the interview. So of course I said, yes. We jumped on a call and it was so [00:48:00] just, you know, a full circle moment to listen to how happy she was and how the space of actually being unemployed brought out who she was and brought out her sense of self and reconnected her to what was important and her priorities and how she ultimately wanted to live. Now that she had this amazing journey, this four year journey that taught her so much, she was able to start envisioning the next thing, and then right when she felt emotionally ready for it, she got headhunted for her dream job in the same industry.

I am telling you this kind of random story to wrap up because this founder could have been destroyed emotionally, right? I don’t think we’re ever destroyed by closing up a business, but she could have been emotionally destroyed. Her sense of self, her sense of confidence could have been destroyed with that very [00:49:00] visible shutdown of the business. What it did instead because she connected back to her sense of self outside of the company, is that it was fueling, it was strengthening, and it ultimately led to her purpose, her new purpose. For the next stage, the business that you have now, it might just be a blip. Of your life, right When you zoom out, when you’re 85 years old and you zoom out on your life, it’s going to be this small period of time or this larger period of time where you got to grow and evolve and learn who you were. It’s going to be a season where you heal the wound, where you learn to lean in to more self-compassion, to lean into boundaries, to learn how to communicate, to learn how to lead, to learn how to stick up for yourself. This journey is about what you learn. It’s not about who you are. It is about [00:50:00] being proud of yourself and enjoying the crazy ride. How you evolve over time and the more you can just loosen the grip on knowing exactly how this turns out and reaching that particular metric or that goal for the month, and the more you can just settle into I’m exactly where I’m supposed to be and I don’t need this business, the more you will actually grow it. It’s as crazy as that.

So my last final words today is we wrap up this conversation about boundaries and fear and people pleasing, is that. In order to stop sabotaging yourself in this way, we need to always lean into our self sense of self outside of the business. That doesn’t mean being on the defense. That doesn’t mean slamming the door in people’s faces and being really in like unflexible. That also doesn’t mean rolling over and doing things that don’t feel aligned and that don’t work for us. But [00:51:00] it is about finding out who we are, what we need, how we need to operate, and doing that so inside the business, but also outside the business so that we don’t have so much pressure relying on the company.

I promise that if you take these three steps really to heart, take them seriously. Practice these, check-in questions often, and you will see your sales and marketing grow. Your sales and marketing will feel so much better. That’s what we want. We want your business growing while also working for you on all fronts. All right. Have a beautiful rest of your week and join me next week again because we are diving into more sales and marketing conversations on this 30 days of Sustainable Selling series. So I will see you again back here next week. Take [00:52:00] care.

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