The Real Reason Selling Feels Icky w/ Lauren Najar

Selling feels icky when you’re trying to rush to the pitch instead of actually getting to know someone.

If you’ve ever found yourself overthinking when to pitch, how to transition a conversation, or why selling feels unnatural, this episode breaks down what’s actually going on. I’m sharing why that “icky” feeling shows up and how it usually comes from trying to sell before you’ve taken the time to truly understand the person you’re talking to and whether they’re actually a fit.

I walk through what selling actually looks like in real life like recommending something you love, making plans with friends, or sharing a tool you actually use. None of that feels weird because there’s already trust there. That’s the part most people skip in their business. This episode brings it back to that and shows why forcing the sale is usually the problem.

So, if selling has been feeling harder than it should, this will help you see what’s actually going wrong and how to make it feel a lot more natural.

Chapters:

00:30 Why selling feels uncomfortable

02:30 The real reason sales feel icky

04:30 Why easy sales don’t feel like selling

05:30 The friendship example that explains everything

06:30 Everyday examples of natural selling

07:30 How recommendations turn into sales

08:30 Understanding the problem before you sell

09:30 Why timing in sales is not fixed

10:30 Relationship building vs cold outreach

11:30 Why I avoid high-volume sales calls

12:30 Letting sales feel effortless

13:30 Why forcing sales creates resistance 

Let’s Stay Connected:
→ Follow Lauren on Instagram: www.instagram.com/laurennajar
→ Learn more or work with me: www.laurennajar.com
→ Follow Business Over Cocktails on IG: www.instagram.com/businessovercocktails
→ Attend Growth & Connect retreats & events: www.instagram.com/growthandconnect

🎧 Subscribe & Review:
Love the episode? Don’t forget to subscribe, leave a review, and share with a friend who needs a business boost and a good chat over a cocktail.

Transcript

SPEAKER_00 0:01

Welcome to the Business Chaser, your quick pour of strategy, clarity, and momentum. We skip the small talk and get straight to the strategy here in these bite-sized episodes. We're here to help you grow smarter, market better, and chase what matters all in 15 minutes or less. I'm your host, Lauren Najar. Tune in and let's chat. Hello, hello. I'm excited to be back with you again today. If we don't know each other, I am Lauren Najar. I am the host of this podcast. I am a business coach, a marketing agency owner. And for the last year and a half, I've been hosting in-person dinners and retreats across the country. And I'm excited to be here with you today. We launched Business Over Cocktails in August of 2025, and we are quickly approaching 75 episodes. So, I mean, we are over 75 episodes at this point. We do two a week. And so right now you are listening to the Business Chaser segment. These come out every Friday, and Mondays are a little bit of storytelling aspects of people's journeys. If I interview guests, we're learning about why they started their business. If it's me, I'm sharing a story or something that it can you can probably relate to and resonate with. Okay, so here we go. We're gonna talk about selling today. And I don't know if I can cram this in into 15 minutes because I can talk about sales all day long. So if you think that selling or sales feels icky, you are probably in the majority of a lot of people. And unfortunately, a lot of you who are listening to this own a business or run a business, or you work in a business, or you have aspirations to grow your business and be an entrepreneur. So I say unfortunately because you have to sell and you have to get really comfortable with selling. So I think when we immediately think of selling, we think about not being ourselves. And I know I can't see you raise your hand, but raise your hand if you feel like that, right? You have to tune into like this part of you that doesn't feel natural. And that's what I hear a lot. I hear a lot about when people are like, well, this doesn't feel natural to me. This feels very icky. Like, when do I pivot the conversation? When should I feel better about this? How do I, you know, start to pitch somebody? So I'm going to talk about why you're probably feeling icky. And let's let's just start there. You're feeling icky because you just A, don't know how to sell, but B, you are if you're thinking about like pivoting the conversation, or if you are thinking about, you know, sending like five DMs and you know, every if okay, I sent five DMs and now I gotta pivot the conversation into like selling with me because this shouldn't be taking this long. It feels icky because you don't know if you're actually going to help this person or if you've actually built a relationship with them, right? AKA, you have no idea if this is a lead of yours, you have no idea if this is someone that's going to benefit from your work, anything of that sort. So that's what I really want you to think about is when you sell, and if you've made a sale before, especially in a service-based business, especially a high-ticket item, when you have made sales or you've closed clients, I want you to think about those times that you've done that. They probably weren't that hard. And right now, selling might feel hard for you if you're feeling this way. And I really want you to think about why those moments where you did make those sales, why it wasn't hard. And so when things don't feel easy, there's a lot of resistance. And why do we have resistance? We feel icky. Well, why do we feel icky about it? We're not gaining any knowledge as to whether or not we should be selling to this person. That is the beauty of having a conversation with that person, getting to know them over time. There is not a set time to get to know somebody. Everyone, you know, goes on dates and there's not a set number of dates before you marry someone, right? There's not a set number of conversation back and forth before you go out on a date. There's not a set conversation of when someone becomes your best friend. It just happens over time, right? That's what selling is. So I want you to think about some real life scenarios here, right? I just kind of named some. You know, selling can be like dating, but let's think about, let's really think about this. I've used this example many years in my business. I remember even in my Facebook group days, this is the example I would need. So back when I wasn't a mom and none of my friends were moms yet. You know, I was living in Chicago with my husband. We pretty much did something every weekend. And none of my friends actually lived in Chicago, but you know, they all lived in the suburbs of Chicago and would come visit me on the weekends. And I knew them so well that I knew what I needed to plan or what events I was looking at. And I'm like, oh, cool. Like these are things that they like to do. I'm going to plan this. And I would immediately just say, you know, to my friends, like, hey, friends, this is the event I found. Like, are you guys free? You know, April 23rd. And they would be like, Yes. Like, it was just a matter of if they were available or not. I knew that they were gonna send me money, I was gonna buy their ticket. I knew them so well that I knew that they would say yes, because these are the types of events we always go to. They're my best friends. So it has taken time. And when I think of my two best friends in particular, I've had one longer than the other. They're both, they're actually both really different relationships. They're both really different people. But us collectively, we do events like this all of the time. So for me to just be like, oh, cool, I see this event on this day, are they free? Yes, cool. Now we're going. So there was like little to no resistance. It wasn't like, you know, it was a very easy transaction. They sent me their money and then I bought their ticket. Another example could be where you show up at an event and someone compliments you on your outfit, and you're gonna be like, oh yeah, I just got this at HM in the mall. And, you know, this top was only$25 and these pans were only$50. And I feel these are really comfortable, and it's their new line, and I just got it at this, you know, at the HM down the street at the mall. That person is gonna go buy that if they like it so much, right? And they're like, okay, cool. Like I'm gonna go to HM at the mall and I'm gonna go buy this because it looked really cool on you. All of this is selling. Or the fact of like, think about even when I maybe some of you who are listening have done this, but I talk about Flow Desk a lot. And yes, I get affiliate income from it. However, I've been a user of it since they had like a beta, like they were in beta when I started using it. And so they pretty much just had basic workflows and and forms and things like that. And I've been using them since day one, and I've really grown my business with them. But I will talk about it because I really like them. I don't really talk about from the stance of like, ooh, I'm gonna make money, I will just refer them and I forget to include my link a lot of times. However, that's another version of selling is hey, like if you are looking for this solution for your email marketing, it's super easy to use, it's super colorful or minimalistic, templates are pretty, does your workflows, does automations, the pricing is really great. Do you hear me how I'm selling this, right? Like I'm selling this to you. And I'm saying the things to you that matter to you, right? You might be looking for an email platform that's less expensive. Cool, Flowdesk fits that. I've had people all the time like, I'm looking for an email platform that's like more intuitive, like pretty designs, easy to use, a little bit more feminine. You know, I don't need all the bells and whistles, I don't need all these conversions and trip wires and funnels. I need something that's cost effective. All of those things, FlowDust checks those boxes. And so whenever I present that, I know that those are the most common pain points that people are looking for in an email marketing system. So when I do promote FlowDusk, I'm going to say, man, this is one of the best. And I truly believe this too. Like I truly believe this. It is one of the cheapest ones out there for what you get. It's really crazy for how much value you get based on the money that they charge. They're very responsive. So, like if you have a feature that you want, or you have a question, like you're going to talk to a real human being, their designs and their workflows are just so simple to use. So I definitely feel like that's how I sell. And then usually sometimes people will sign up. And a lot of my clients have signed up and you know, they utilize Flow Desk. So all of that to say is like these are all examples of selling. And we do it so effortlessly when for whatever reason it's not us. But I want you to think about one more thing is like, you know what you help with, you know the audience that you serve, you know the problem that you solve. So if you know that without a doubt, and you know exactly how to solve that problem, that's all you need to focus on when you're selling. So when you are talking to somebody who may or may not be a potential lead, your goal is to find out if they have the problem that you can solve. And if you have any doubts whatsoever, if whether or not they do have this problem or not, you're not doing a good enough job to understand what their problem is and to get them to open up. And again, I'm not gonna sit here and tell you it takes five days. It might take a year, it might take two years. I've had clients come back to me time and time again over the course of a five-year span. I've had clients that, like when we first connected, it took them a year to then invest in me. I've had people find me out of nowhere and just see all of my recent content and literally buy an intensive from me or listen to my podcast and buy an audit from me. So, like, there's so many things that you can be doing to put yourself out there and to have those conversations. But if you're not having those conversations, then none of this is gonna happen. So, like, chances are talking to people is gonna help you convert a little bit better. But again, if you're gonna pitch somebody, make sure that you're finding the need first. And the flip side of this is like, sure, you can go ahead and cold DM all the people that you want and play the numbers game. Chances are if you send a hundred DMs a day, you're going to get a bunch of yeses. Cool. You can do that. I don't personally build my business that way. That's not sustainable for me. Doesn't seem fun. I enjoy talking to people. I enjoy building relationships with them. It is paid off time and time again, where I get referrals from people who just know who I am and what I do. So I think that both can work. Both aren't like not, one's not worse than the other. I just personally don't like the cold DM route. I care about talking to people. I care about finding the need, and I care about giving them the solution that they need because I'm getting to know them. And then that also, that process allows me to not need to go on sales calls 50 times a week. That's not something I will ever coach to. I don't believe in, you know, oh, you need to fill your calendar with sales calls. No, you don't. You can have conversations with people and you can close a lot faster if you're having more and more conversations. So I guess again, this is another thing to each their own is would you have an inbox to manage with a bunch of messages and tracking? Yes, I love doing that. I don't want my calendar filled with 75 sales calls a week or even seven sales calls a week, and then like having to think about closing them on my own. No, I don't want to do that. That's also like exhausting and tiring for me to do. And some people coach that, and that is also successful. But again, I don't personally coach like that. I like the idea of getting to know somebody, seeing if they have a problem, and then letting the sales process be so effortless to where I'm inviting them and there's no friction whatsoever. And even if they say no, they are not gonna like our relationship's not gonna go away. I'm not burning a bridge. Everything's okay. It's just a no, not right now. And then they'll end up joining eventually, or not, or they'll just refer me, or they'll still engage in my stuff. But because I built a relationship with them, because I actually cared, then they're not gonna go away anytime soon. There are some people that in the past I've even like let go of as clients because they just weren't a right fit for me. Maybe down the road they might be, and I'll explore taking them back. But we still have a good relationship because I am in integrity of what I'm trying to do here. So again, I think the best way to sell, and the reason why you feel icky, right, is because of you're resorting to maybe some tactics that you don't feel comfortable in. And it's not because you don't necessarily like not necessarily uncomfortable selling, it's how you're selling. And you have a reason to feel icky. It's because it's going against maybe how you are, and you just want to serve and you want to help people and you want to provide a solution, you can totally do that, but you have to talk to people and you have to like vet them. And that's when your marketing comes into play, and that's why good marketing and selling also comes into play as well. So I hope this was helpful for you. If you have any questions whatsoever about selling, I talk about selling in the DMs a lot. There are some episodes previously that talk about all of those things. You can go ahead and listen to those. And a lot of my content talks about this. So make sure you're following me at Lauren Najar on Instagram, and we can go over that. That's your quick hit of clarity and momentum for the week. If it sparks something, share it with a friend or tag us in your stories at Business Over Cocktails and or at Lauren Najar. We love seeing what resonates. Don't forget, Mondays are for full-length episodes with rich conversations, and Fridays are the Business Chaser episodes. These are bite sized insights pulled from our guests to keep you inspired and aligned throughout the week. Do you have a question or takeaway? DM us at Business Over Cocktails. We just might feature it in a future episode. Cheers.