Stop Dickin’ Around with Your Messaging

If you're only relying on AI to write your stuff, it's going to kill your content, which is going to kill your marketing, which is going to kill your business, because people can smell it and they're looking for reasons to trust you.

Welcome to the next evolution of the podcast Entrepreneur School in the AI era. We are here to figure out how to integrate AI into the business you've worked so hard to build in a way that still feels like you. I'm your host Kelly Sinclair, award-winning marketer turned AI platform co-founder. AI has fundamentally changed how I thought about work, systems, and what's actually possible? This show is about navigating that new reality together. It's going to be a wild ride, my friend, but I truly believe there's a way to leverage AI in a way that's intentional, human-centered, and aligned. It's an ongoing evolution, so let's explore because AI may just be the unlock you need to achieve the life-first business you truly desire.

Welcome back to Entrepreneur School. I have a guest with the best bio that I've ever read on my show, so I'm just gonna go straight there because I was laughing so hard when I finally read this out loud. Jen Liddy helps course creators, coaches, and expertise-based entrepreneurs stop dicking around with their messaging so that they get it right, whether they're using AI to help them write it or not. I mean, I feel like you did not use AI to help you write that bio, Jen.

I did not. I spent hours being frustrated. I have had more generic that you know, I had generic bios that did the trick, but I got really pissed one day, and I was talking to my my brand voice mentor actually, and he's just kind of pushing me and pushing me and pushing me. He's like, "Well, what do you really just want to say to people? And I want to say, "Stop dicking around with your messaging. Like, stop going to ChatGPT. Stop going to Claude. Stop like asking a robot to like pull out of what your heart, what's in your heart, and what's in your brain, and what's in your soul, and stop dicking around with it, and just freaking put it out there. So that's that's how I came up with that. It does also. This is kind of funny. If you went to my website, which is jenliddy.com, so the website is me. It's a beautiful, lovely picture that my brand photographer took of me. Everything is like pink and soft, and I'm this like basic white lady who like wears Ann Taylor Loft clothing, and it says, "Stop dicking around with your messaging. And I just love the juxtaposition of it so much because every time somebody like I meet somebody new, I'll say something, and they'll be like, "Oh, I didn't expect to hear that out of your mouth. And like, I know I, I the way I look and the way I am are like kind of two different things. So,

oh, I know it's like a secret weapon that you can keep in your pocket. Like when you drop an f bomb, and people are like, "What do you wear?

They're pearls.

Yeah, I do that too. I'm like I save it. I save it for the impact, you know. I okay. I love I love that we're going to talk about messaging. Like my people on this podcast know that that is my journey as a brand strategist and marketing and PR and communications, and that just like evolved into an AI company for reasons we don't need to talk about today, but I think I first of all like let's just get your opinion like right off the bat. What is the soapbox that you like stand on with respect to how AI fits into the world of what you do?

with Laura Schoenfeld. She said, "If you didn't have 20 people working in your business before, why do you need 20 people working in your business now? And I was like, "Yeah, that's it. So at this point, the hill I will die on is, especially when it comes to messaging. Robots can help us, and they should help us. But I think that people expect them to help us in ways that are unreasonable, and that if you don't even know what your brand voice is, and you don't even know what your brand messaging is, and you can't say that from your own mouth and your own fingers and your own brain, then how on earth can you expect a robot to do a better job? Because the schlock that it's spitting out to you, it probably sounds pretty good, right? It's probably like, yeah, I'm not a good writer, so this sounds pretty good. But to everyone else who's reading it, it just sounds so tamped down and so flat. But you can't see that because you're just so kind of starstruck by it, and unless you can say and push back on your robot and say no, that is too choppy. No, I don't like that construction. No, I don't ever say those words. No, I don't talk about that. And you can push back on it, you're always going to be at its mercy, and so that's, I guess, the hill I would die on. You have to put your brain back on it, and you have to understand it. You have to understand what you want to say and how you want to say it at a fundamental level, or your robot's going to be running your content. And I think from here on in, people are literally reading your content, their first question is, "Did a robot write this?

Yeah. Ah, couple things, many things there. I feel like, well, one one way that I like to phrase this is, it's about being able to validate the output of whatever AI gives you. Yes. So if you don't have the expertise of what you're trying to get AI to do for you, you probably will be like,

"Ooh, sounds good.

Okay, let's do it. Like, and and maybe maybe there's something else to what you just said that's like, "Oh, I'm just like impressed. I'm impressed by this is still new technology. I got something that was so much better than I would have ever been able to do, at least on a first draft. Like, and you have this like, you know, lovey lovey, like, oh my goodness, Claudia, my friend, you're so proud. Yeah, and I love it, and I, I feel it because, like, to your point, the conversation that I had with Laura Showenfeld on this show, I was like, I am so called out right now. Like I am, and I'm just, I love building. Yeah, I know what happened, but I just, I'm just obsessed with it, and it is distracting. And I have to tell myself, no, you are not allowed to do this shiny thing right now. You have to actually respond to the people who said that they wanted to work with you, or who are actually-I

heard you say that. You are like, oh, three people have asked me how do I give you money, and it's been weeks since I got back to them. I am like, I didn't even email them. Like that's a real thing that's happening because of the distraction of AI. Yes. Well, to go back to the like being starstruck by it, so I'm going to say visuals are by absolute kryptonite. I suck at anything visual, which is why when I had this new messaging of stop dicking around with your messaging, I'm like, oh god, do I need to change all of the visual branding? And I was, I was like, you don't know, like I'm kind of this weird person who looks one way but acts another, and I'm not going to change. I did not want to spend $12,000 on a rebrand. Is really what this came down to, because ah, the visuals are so hard for me. So when Chat started creating visuals, or what is the one, Nano Banana started creating visuals for people. I'm like, this is super fun, especially if you're not good at this, and then you start seeing like, oh my God, the ubiquity everywhere. It's all the same. And then I started watching brand designers and visual graphic graphic people bitching about the stuff they're seeing that AI creates. The way I bitch about the the words it creates, and I'm like, oh, but there was something that let me see the ubiquity of it in a way that I don't think I don't think people trust themselves with their words, and I think they might have writing trauma from college or high school or whatever. But like, there's a thing that people are afraid to trust their writing, afraid to. Trust their voice and afraid to say what they want to say in the way they want to say

it. Yeah, I was going to say there's something deeper underneath this. Yes, is not this is not just about throwing spaghetti at the wall.

That's right, because the people I work with are like they're. I mean, how many iterations of your own business have you had, Kelly? Like, how many degrees do you have? How many trainings have you taken? How many certifications? Right, and so my people, that it's like your people-they are experts. They have a lot of experience, and so they don't. You know, they-the messaging is frustrating to them because they're like, "Why is this so hard now? I've done all these other things. Why is this so hard? Yeah, because it is hard. It is hard, and so can robots help us make it easier? And I get, I get wanting that. I get it. So I guess that's the hill I would die on. Like, please put your freaking brain and your soul back on your writing before you just let the robots do it.

Yeah, I'm. I don't want to like say this is a contrarian opinion, but on one because I totally respect obviously everything

for a contrarian opinion.

Yeah, but I'm like I appreciate the work that you do because I tried to do that work for many years also, and here I am with a tech company now. So clearly, didn't work out for me that way. The contrarian opinion is like, if you're not going to say any words at all, if that's what you're battling with, right? That oh, I'm just I'm not showing up. I'm not doing any marketing. I don't have a what? Like you don't have any of those things because there's a blocking away.

Yes,

then 100% Like AI will give you what will help you to start making progress, but the caveat is probably you need to now look at that as an experiment and go, okay, did this land?

Yeah,

does this feel good? And now we go to the next level because I know that where you work is in the massaging and nuance and in the next layer of it, right? Like you're not working with someone who's like, "What is my business? You're working with people who are like, "Okay, I've had iterations, and I know that when I do this, I'm getting the wrong people, and I know who I don't like working with. And and like, so expand on that.

Yeah, that's a really great point. Yesterday, I was working with a client who's a therapist, and therapists are in a special section of hell for marketing because they have the the themness has been beaten out of them, and so they're never supposed to talk about themselves, especially in sessions, right? So she's like, "How am I supposed to show up in marketing and suddenly be expressing my personality and talking about my opinions when I'm just like we we called her mr. Cellophane when she's in therapy sessions, right? Like she's just supposed to be part of the part of the landscape, and so this thing of like she's actually now afraid to write. She's afraid to write LinkedIn posts, and what she writes feels so blah and meh that it it makes her angry because she's like there's so much in me that I want to say but I don't trust it anymore, and I've had this beaten out of me by my industry and I don't trust that either, and so her first assignment really was we I pulled some you know some gems out of her and I'm like you're not really ready to say these publicly yet, but you do need to start practicing what it would sound like. And then it's a matter of like, I always like to say, there's like bumpers on the bowling alley. There's there's boundaries that we have when we're speaking, regardless of whether we're a therapist and it's been beaten out of us, or we're somebody who comes to the table with writing trauma, or we just don't really trust ourselves anymore because what we've said for so long hasn't worked, right? So you start practicing, and you're like, okay, well, what's what's too private? What don't I want to share? What's off the table? What are my non-negotiables? That's one of the bumpers, and then the other bumper is like, well, where am I so buttoned up? Where am I so invisible? Where have I tamped my down myself down so much that there's nothing? There's it's like it's like a nothing burger. Like there's just nothing there. When you,

it's just like it could be anybody. That may might be your AI stuff, right? And then you play in the middle of the lane where you're like, okay, I want to say this thing because I'm really either angry about it, or I have an opinion about it. I'd want to say something contrarian about it, and maybe you're not ready to publish it, but maybe you have to start practicing again. Nobody's coming for you with the red pen, even when you work with a messaging person. Like, I know that people are really afraid that I'm going to tear down their shit and make them burn it down. Nobody comes to me with stuff that I need to say, like we have to start from scratch. Everything has a kernel, at least a kernel in it, and then you just have to give attention to that and give some of your soul back to that and give some trust there and like let it have some air. And if you're not ready to publish, okay, but I guess I really want to convey. This episode, like if you're only relying on AI to write your stuff, it's going to kill your content, which is going to kill your marketing, which is going to kill your business, because people can smell it and they're looking for reasons to trust you.

Oh, I I have never heard that expressed the way that you just said that, and I'm like, now I know what my trauma is because I worked in corporate oil and gas for the first 10 years of my career, and it's always in PR. Excuse me, where literally everything was, what is the best way to say this so that it won't like so that is like platonic all the time. Like, is not going to ruffle any feathers, and we'll use words like, "Oh, I don't even know what I'm like. We're just going to use such blah where it's words that I'm trying to like remove from myself. Yes, truth is the real problem isn't writing; it's feeling feeling comfortable in the space of what you want to is knowing what you really want to say.

Yeah. So this is like the core of thought leadership that we are exploring right now. Where it's what is your opinion on this? Like, what do you care about? What everybody? I don't know. We need to make a permission slip here around what you get to say, what you want to say. Like, I'm gonna bring you. You, I think when you sent me an email about being on the show, you're like, I don't know if this is where you want to go. Yes, it is. Like, I want you to come on and say your version. Like, we can go toe to toe if we have different opinions. I am, I'm all about existing in a world where people have different opinions, and we're not trying to convince them of our own opinions. Right. To just stand in, and it's a hard place to be. Like that is culturally

sure, for God's sakes, yes,

really.

Well, and so while I was anti AI and angry about AI, I'm not like a fool. I'm not anti. I'm not even AI agnostic, and I will use AI in my writing to help me break my bad habits. So, like I said, I used to be an English teacher, and my whole thing was like I have to meet 27 people at every single class on the standard deviation, make sure everybody gets what they need, right? So, in my writing, I was doing the same thing. I'm hitting a point three different ways, three different times. I'm tying everything up in a nice bow, which makes me a really good teacher, but it doesn't make me a good marketer. And so I use AI to like push back on my bad hat, my bad writing habits. And so that's how I need to use it. Somebody else might need to use it. Like, hey, I have this story, and here's my here are my messaging pillars. Here's the shit I talk about all the time. I have this story I want to tell. Can you help me find which messaging pillar it fits into and help me make a bridge? Like for that person, that's going to be a really great use of AI. Or you put all of your stories into AI and you have it remember for you, so that you're like, hey, this week I'm selling this thing, which really hits on this messaging pillar. Can you help me pull one of my stories and like help me design something? So I am not here pretending like we're not using AI. I am really just asking people to put their freaking brains and fingers back on it, and I can't tell you how many email lists, email lists of my friends and colleagues that I have unsubscribed from, and not because I'm like fundamentally opposed to the fact that they used AI, but just that their shit is so boring to read. Like, there's just no soul in it. There's nothing. There's nothing there for me. So I'm not here. Just and I actually don't think our audiences are just here for information anymore.

No, no,

which AI is great at, right? So if all of your if you're like churning out emails, and you even said this on another podcast appears, like it makes a lot of content for content marketers. It does that, but does it make good content? And what is that doing? Like, how are your unsubscribes? How are you? How is your engagement? And it really just might be that you like need to put your soul back into it. And what I do think people struggle with at this point is like that lack of trust in themselves that we talked about before. Yeah, and also the habit of like, oh, I can have Claude do this for me, and I can actually have Claude do this for me, while I have Claude do something else for me, and Claude do another thing for me, right? And while I sleep, right, right, like I'm, I'm multitasking, so I feel like we just forget that, like we have to put ourselves back on it because our audience is desperately craving that.

Yeah, and isn't that just the way that you're actually going to stand out in social media where volume is increased because it's easy now to make 17 social media posts and four emails and a podcast and a YouTube and everything in one week from the same piece of content. And I'm like, I'm all for the repurposing and putting your stuff all over the loop. But like, how is it going to stand out? So, have you thought about how to define what that litmus test is? Like, how do you tell your clients to, like you say, put your soul back into your writing?

It seems like it's different for each person because they come with different traumas and dramas. From and I, I some of them it's big T trauma, some of them it's little T trauma from whatever has happened to them in their business life, but also in their writing life and in their school life. So it's different for everybody. The the client I was telling you about, the therapist, she was really just excited to have that permission slip, as you said before, of like, hey, here's some stuff I pulled out of your brain that you didn't realize was in there. There's some stuff that you feel and you know you want to share that you don't feel safe yet to talk about in your content. Let's start by creating some of those things, and like you don't have to put them anywhere yet. You just have to practice, and that like made her that made her feel excited about writing again because she felt like there was hope and possibility. For some people, what it looks like is, oh, like they'll bring me a sales page, and these are smart people who have sales pages that they worked in other times in their business, right? But they're not working now because we all know everything has changed, and so again, it's not about like taking a match and torching it, but it's like let me show you the gold here. You've usually buried the gold, or you've said something in a way that just needs a little bit of tweaking for a modern audience, and those are the kinds of nuances that a robot really can't do for you. But like, I'm just like I'm just happen to be. That's my thing. That's that's the one thing I'm really good at in business, and that's what I do, right? So sometimes you just need another human brain to reflect it back to you. So for those people who've been like, I've been working with Claude on this for four hours, and I'm not getting anywhere. I'm like, maybe you just need 30 minutes with a human, and that can change everything for you. So it's always different

for each person depending on like what they're presenting with.

see it anymore. So I completely changed my business model to be diagnostics, where I go in and it's either like I'm looking at one piece, or I'm looking at your entire brand, and I'm like, this is why it's not working, and this is how you change it, and I can help you, or you can do it yourself. But once people see why it's not working, generally they can fix it on their own, but they're always missing that. It's like that whole of like I'm just lost because everything seems like it should be working because it always did work, and I can't see it clearly because I'm too much of an expert.

And you're diagnosing the root cause, which is what we're always missing. I know, which is like why is the thing creating the symptom that I have? Right. I one time heard a really great expression of this. It was like, okay, so the symptom somebody has is they get headaches all the time. Well, what's the cause of those headaches? It could be any number of things. Luckily, sleep. Blah blah blah. What if it was blue light, right? Because you watch, you're on screens all day, and you're watching TV later. You're on your phone in your bed, or whatever. So then, I've identified that the cause of your headaches is blue light, and therefore the solution is these blue light glasses. Do you want them? Oh my God!

Yes. Yeah. Yeah. So doing the diagnostic work well. Number one, it's more fun for me. I'm enjoying the work a lot more because the client then doesn't have to guess at how to implement. They're like, "This is what I was doing, and this is what I can I can stop doing that, and now I can just start doing this. So it's more fun to see them implement, and then they send me. I love this. They'll send me like, hey, this is I changed my website and this. I'm like, oh my god, it's so much better. It's so it's like then they can go to Claude, right? Because they know how to push back on it, and they have my diagnosis, and they're like, hey, no, don't like stop doing that because Jen said not to do that. It's like then they can use Claude more effectively.

I love that, and also yeah. So you're giving them the skills, and they're and also like just kudos to you for actually caring and giving a shit about what how your clients implement what you spend time with. You care about what you do, and you're like, oh, but you like this is how this is how I got into AI in the first place because I would write these great strategies, and then they'd be like, "He thinks nothing would never hear anything again. I know implement your strategy, right? I was like, "Oh my gosh, AI can help you implement the strategy. AI can help you implement and take action, and and like not get stuck in the things that are in your way, which always, like as we've even uncovered here, are much further deep. There's that deep, yeah. And you're so like in the weeds of a thing, and you're like, I'm smart. I I have done a lot of things. Why is this so hard? Why isn't this working? You know. So there is that. You just like you get that fatigue. Yeah. Oh my gosh. Yeah. Ugh. So okay, one more question on like the logistics. Just because if somebody's listening to this and going, okay, how do I know if I have a messaging problem?

I totally get this question all the time,

right? Because like, what is the thing that? Because most people are like, and I had this conversation with somebody else on the show recently, where it was like people don't really know the difference between tactics and strategy. That's right. That's right. So we're and we're always searching for tactics because we can see like they just make more sense.

Yeah, and they are like easily to implement.

I do this. This will happen or could happen, but like if. I start creating podcasts and social media content, but my messaging is shit, and it's not landing. No amount

of tactics will help you. That's right. That's right. That's so right. Yeah. So there's some questions. Let me tell you what some people do when their messaging is really the problem. They're like, I need a new logo. I need some new offers. I need because my offers aren't working. Oh, maybe my pricing is the problem. I'm either going to lower my pricing or I'm going to raise my pricing because nobody's buying. I keep tweaking this fill in the blank sales page, home page, about page, description page, whatever it is, like they keep tweaking it, feeling like it's just like the one word difference is going to make the difference. The messaging is your. I would start with messaging if you're thinking like I need to invest in a $12,000 rebrand. Well, what's at the foundation here? Like that because messaging is foundations, and nobody wants to do foundations because they're all like I'm too experienced for this. I've been in business a long time. I know messaging is. I've already done that work. Yes, but we're moving at such a faster pace that people aren't talking to their audience as frequently anymore. So maybe the last time you talked to your audience was a year, maybe two years ago. So your audience has changed. You have a messaging problem if you're you do sales calls and the wrong people show up on the sales calls, and you probably have a messaging problem, or I would look at a messaging problem if you have had a a program that you know you know people are asking for and people need, but the sales page isn't working anymore, and those are like some really top level things that. And you also have a messaging problem if you're not sending people to your website, and you're embarrassed by your website. And that's probably not like, oh, I just need it to be prettier. It's probably like it says things on there that I don't believe anymore or haven't caught up to who I am, and it's not expressing where my business is now or what my audience needs

to hear now. And one last thing I would say, and this is a very tactical thing for your listeners: audiences need specifics in a way that they almost never have needed them like this before. It's not enough to talk about their feelings about a thing. It's not enough to say I understand that you're busy or that you're overwhelmed or that you're stressed. It's like talking about feelings. You have to reflect with specifics what their lived experience looks like, and many people just don't think to do that because to them it's so obvious. Like, oh, that's just a boundaries problem. No, no, no, no. You need to unpack it for them, not because they're stupid, just because they need to see how it applies to them very specifically at this point.

Oh, I really like that last one particularly

because it's a tactic and it's doable.

Yeah, well, it's the whole concept of. I sent an email out about this the other day. It was like you, you know how you can't unsee something once you see it finally the first time. So it's like your brain also goes, oh, I know this, so therefore everybody knows this.

Nobody's exactly right, exactly. Yes, so like on on your on your in your messaging, that might sound like you know your boundaries are constantly being pushed against, and you're like, I don't even really know what that means anymore. Show me what that means, so that's another place where messaging is is the problem for you.

Oh, okay, great. I feel like I fired you, Kelly. You know, it's just kind of like funny other layer of this conversation because, like, I to do this work, and I can never like articulate it. Like, here's why you need this, right?

Right.

Because because you just knew it. Yeah, it was like, but this is the problem. But like, how do you like reverse into why this is the problem for you? So I just want to like come in and be like, yes, of course, it it is the problem. Like the thing you have to work on, it's almost always messaging. It really is,

yeah.

Like and then like the experiment, like message adjust, try things.

Yes, yes.

Information adjust, try things, get information. Like that's the loop, right? It's not maybe maybe there's overwhelm a little bit in people thinking, oh my god, I have to work on my messaging. Like that is like a reinvention. That's like that's like you know getting to my soul. I'm not in a space where I can do that. Like, what do you say to that? I say start with the header on your website. Just start there. Start with or go down, scroll down to your offers. Are your offers your offers, and are they clear about the problem, and the solution, and the outcomes that people get? People are talking in their offers about like they're talking in like just like diffuseness, like they're just talking in generalities. Like no, no, no, your offer has to express this is what your problem is.

when they are thinking about the messaging for their audiences that are going to pay them money someday. Oh yeah, yep. Who is receiving this? That's exactly right. And what do they need to hear, and how do they need to hear it? And not in a manipulative way, but in I'm going to meet you where you are kind of way.

Such a great way to express all of that. Thank you for this great conversation, Jen.

I'm so glad we had it. I love talking about this stuff. It's so nerdy, but I really love it. The opportunity

nerd out on all of like this. What the show is for? Please tell every. Well, first of all, did you have any final words? Oh, did it?

No, I think we have fire hose people plenty about messaging.

So, so tell everyone where they can find you, connect with you, get more of you. Get your diagnostics too.

Yep, yep. If you go to my website JenLiddy.com, everything is there. You can get on my email list if you want to. But I know that the people who are listening to this program, like they they don't need another quiz. They don't need another PDF. If you want something really effective, I actually have a private podcast that's 10 minutes, that's less than 20 minutes, and it's called "Why You're Getting Seen But Not Chosen. And if you go to genliddy.com/evolve, it talks about how you need to evolve your messaging so that you can all that visibility stuff that we're all doing, like how to make it actually land and why your messaging is keeping you from that. And it's kind of like very quick, under 20 minute. You can implement it. It also comes, and this your your people will love this. It comes with a self audit of your own messaging patterns and an AI writing checklist, so you can throw that into your favorite robot and have that robot push back on you when you do something and like, oh, you're doing that pattern again. Oh, you're doing that pattern again. So it's a under 20 minute private podcast, and then those two resources at genletty.com/evolve. And I think that would be like a really impactful thing for your listeners, rather than like taking my quiz or downloading anything else. It's just like if you're listening to a podcast, you like podcasts, and this is in your ear. I think there's a video version too, but I can't remember. But it's like get it into your head and then start putting it into practice.

I love it. Thank you so much, Jen.

You're welcome. My pleasure.

Thank you for listening. If this episode got you thinking about how AI is impacting your business and what it might look like to integrate it in a way that actually fits. I'd love to help you think that through. You can book an AI strategy chat using the link in the show notes. It's a space to talk about where you are, what's shifting, and how to move forward with intention. And if this episode was helpful, please share it with another business owner who's navigating this evolution too, and make sure you're subscribed so you don't miss what's coming next.