Guest episode- Jenna Baird

In this episode, we talk about the mindset challenges Jenna faced while building her dating business. As the first female entrepreneur in her family, she shares how she navigated self-doubt and limiting beliefs to get to where she is today.

With over 40K Instagram followers, Jenna is setting the dating world straight with honest, empowering advice for women navigating modern relationships.

We also dive into the identity shifts required to grow a business — and how becoming the woman who can hold visibility, impact, and growth has been key to her success.

Follow her on Insta/tiktok/youtube/facebook/linkedin - Jenna_mydatingpa

Transcript

SPEAKER_01 0:00

Hello everybody and welcome to a very special episode of Success Starts Within. Today I've got Jenna Baird with me who is going to be talking to me about coaching and dating and all things business. So Jenna is a dating coach and runs a high-end boutique dating service that's online, and she supports women that are in their 40s and 50s to change their previous dating patterns and to find the love of their life. So, welcome, Jenna.

SPEAKER_00 0:28

Thank you very much. Thank you. That was quite an intro.

unknown 0:31

Thank you.

SPEAKER_01 0:32

Well, thank you so much for joining me today, and I'm super excited about chatting to you because dating is something that is always on everybody's mind. And we're all trying to look for the love of their of our lives. But we just had a very uh interesting conversation about exactly who the love of our life is. So fill me in. What fill everybody in? What were we just talking about?

SPEAKER_00 0:54

Yeah, well, it's you know, people will come to me and go, you know, can you help me get the love of my life? And and I'm like, yeah, and confident I can say yes, because I truly actually believe the love of your life should be yourself. Um, because that that is where it all starts. That can lead you to find that external love of your life. But I truly believe it it comes from within. And you know, sometimes we even say, Of course I love myself, of course I, but do we? Do we really? You know, and and sometimes we try to outsource that to a partner, and it's sometimes people think they're coming to me with the result of having a partner, which absolutely I can help with, but the biggest turning point, you know, is when you realize, like, wow, I'm enough, you know, and that that makes you more attractive, so that will help you find a partner.

SPEAKER_01 1:44

So yeah, no, I completely agree with that. We always look for that external validation, and I find that a lot in in women, especially, like looking for that person to say, Well done, you know, you're doing really well. But actually, when you find that within yourself, you find the ability to start recognizing yourself, your achievements, who you are, you know, what you've done, then actually you don't need other people. But the result of that is that people then start to, I find like clients start to do all these amazing things in their business and get these awesome results just because they've connected with themselves.

SPEAKER_00 2:22

Absolutely, absolutely. And although we work, I know kind of the same age range and things like that, but although you focus on women like in business, and I'm dating, actually, what we do is not very dissimilar. Like we really, because that is the core of what you need to do to success in all areas of life. Yeah, you know, you you have to be okay with you for business, for families, you know, for the way you parent, for everything. I think it's really, you know, but some people focus on the love life, some people focus on the business side, but equally we're probably teaching the same thing, if I'm honest.

SPEAKER_01 3:00

Yeah, and I I I completely agree. I think the foundations are so similar, and the work that I do is, yeah, although it is business, as you say, it's connecting with you as well. You have to have that trust in yourself, and so many people don't have the self-trust, they don't have the self-belief, so they do things like sabotage, and I'm sure you probably find that in the dating world as well.

SPEAKER_00 3:21

Yeah, yeah, absolutely, absolutely. We all do it. I mean, I preach it all day and I do it myself, you know. I'm not perfect by any stretch of the imagination, you know. It's um by default, we go back to that, you know, because it's kind of how we've spent, well, when you I'm 43, by the time you reach like my age, you've been doing that consistently for so many years. You just naturally go to that. Um, but I think like with the work you do and I do, it's that recognizing and calling it out rather than acting on it, you know. I think that's the difference. When you reach our age, it's like it's more of an effort to no, that that's not me anymore. Like, it's a bit an effort where it's I really hope like we can give it to the next generation. They they can click to this a lot earlier than we did, and that's got to be one of the benefits of social media that we can put that out there.

SPEAKER_01 4:19

And yeah, I totally agree. I always say that we are the generational chain breakers, we are creating a new world for these other men and these other women, and yeah, as you just kind of alluded there, about the identity. So it's working on like who we want to be rather than who we were, and kind of going through that process of changing. And no, it's not easy to change the person that we were because we're holding on to beliefs that we've had for yeah, like 40 years. So our our nervous system and our subconscious mind like that's all it knows. A nervous system feels safe with like these maybe these toxic relationships that people have had, but even though consciously they're like, I don't want to be shit on anymore, but they can't help but go for these relationships because that's subconsciously, that's what they're drawn to. So it's going through this big process of learning to learn another way, but also teaching the nervous system that it's safe for them to have this more kinder, nicer, loving relationship. And yeah, stepping is what I call into it the main character identity, someone that's like that next level version of you.

SPEAKER_00 5:28

I love that. I love main character energy, it's so good. Who wants to be an extra in your own life?

SPEAKER_01 5:34

You know what I mean? Exactly, exactly. So tell me what what got you into the online dating um coaching?

SPEAKER_00 5:42

Love to tell me the story. So I became a matchmaker completely by accident. It was something that found me I didn't even really know it was a job. So I was doing matchmaking and I loved it, and it was very exciting, and um, and I was trained really, really well. I was trained by um a couple and they had very traditional values, and and I loved it. And it's as I got well known and more experienced, I they were charging a premium for me, and I had hit a salary ceiling, and I was a bit like, oh, I I think I'm quite good at what I do, and they're charging more, so I must be good at what I do, but I I'm a single mum, I've got four children, and I was like, but do I think I'm good enough to do it? So I knew I was never gonna beat that salary ceiling, and I I wanted to continue with matchmaking and also the coaching side because I found that I enjoyed my conversations with men and women more than I enjoyed passing those numbers and you know, hearing feedback of the dates. They they were all well and good, but I loved it if like a woman kind of said to me, 'Oh, I don't, I don't know why. Um I just can't move forward, or I just can't, and I I found I enjoyed those conversations more. Um, but yeah, it took me uh battling my brain for many, many years of you're a single mum, play safe. You need that wage. It was a very small wage, let me put that out there. But it was safe, it was consistent, I knew it just about covered my bills. And so I thought, maybe when the kids are older. But I just strongly felt like I'm undervalued here. You won't up my salary, but each year, the more experience I get, I I don't know. It was so it was just so hard. I've come from generations and generations of being employed. You know, you just left job, you you sorry, left school, you got a job, you were employed. And that's just always the way it's been. I no one in my family has set up their own business, or you know, and I know people probably thought I was a bit crazy, but my hands took over one day a couple of hours about two, three years ago. I literally just found myself sitting there and I was like, type out my resignation with immediate effect. And I was like, something's happening. That it was honestly this overwhelming feeling inside me that I know, I know that I can do more, I know that I'm meant for more, and but it was that fear, it was the well, everyone in your family's employed. You you've got to feed your children at the end of the month. It's you must know what wage is coming in. And and don't get me wrong, being self-employed is the the bravest thing I've ever done. And it hasn't been uh skyrocketed straight away. It's the journey, um, and it definitely is the bravest thing I've ever ever done because I feel like like you just said, breaking a generational it's scary. It's scary. I will never any change is scary.

SPEAKER_01 9:01

Change is scary, but it sounds to me like you've been on such a journey of battling like all of these beliefs that you have been brought up to believe, these stories that you were telling yourself, this pressure of like having the family and but also knowing that you are making somebody else a shitload of money when you could be doing that for yourself, but you've been brought up in a family where it's like you finish school, you go to work, and that's it. So taking those steps to kind of get to where you are is like you say, really brave. But what was your yeah? I mean, also you've covered like the stories that you told yourself, but what was the point where you were like, I'm actually just gonna do this? And what were you telling yourself in terms of how, like, what beliefs were you deciding that you had to change in order to make it happen?

SPEAKER_00 9:57

Um, well, I honestly don't know what made me just do that that day. I honestly, I don't know, divine intervention, I don't know. Like, I don't know what made me do it because I battled with it in my head for a long time. And I'm a very, very reactive person. Now that has its pros and its cons, you know. Um, if I just think, do you know what? Actually, I really trust my gut and know I'm worth more, and I'll react on it. Relationships, jobs, like that appears in different areas of my life. It also has a bad thing because you know, the first time I put a post out, no one watched it. I was like, oh well, failed, done, jack it in. You know, I'm so reactive with everything, and so and again, relationships. Oh well, that's it, gone. That date didn't go well, this is over. Like, so it was just recognising that reactive thing of being okay, you've done that as a positive. This isn't uh one of the bad cases of when you're reactive. So it was a bit of well, you've done it now, you have to make it work. Um, but trying to then control how reactive I was. So I I was taking at the beginning when I was setting up, I was taking everything as a oh well, there you go, doesn't work, jack it in, like just give up. You tried it and it hadn't even really tried it. I mean, I I'm talking like registering with company's house and then going, oh my god, they're asking me really hard questions. That's it, it fails. Like from the start, I was telling myself that it wasn't gonna work, yeah. Um, and it was really tuning into that gut. I think your gut instinct is so powerful. I really do.

SPEAKER_01 11:47

Yeah, 100%. And that's amazing that you you know that you're like your head is telling you one thing, it's telling you no, you can't, like, this is hard. And that's what happens when when like we come across, for example, like you said in Company's house, like a question's difficult. It's like, do you know what I can't do this? Because what's happened is that you've gone through like so far, like pushing yourself out of your comfort zone, and you've reached a limit. So just something so small will just pull you back and say no, we need to stop, but you've just kept pushing, and the fact that you've used your gut, are you in human design? About what? Sorry, into human design. Um, yeah, okay. Are you do you so I'm sacral, I make my decisions from my gut. Okay, um, I don't know whether you are, what your it's still called your authority. Um, maybe we'll look into that. But yeah, it's absolutely yeah, it's making those decisions from your gut and being like, okay, I know this is right, and really, really tuning into that and allowing your gut to be the thing that is supporting you. And again, it's it's it's also like what do I say to what I say to my clients is work with your nervous system the whole way through, any big change, your nervous system is going, fuck, I can't do this, which is why all these little small things are going to start become huge. But it's like teaching that safety and like in the moments like that, just you know, just like breathing through and allowing those thoughts and emotions to work through your body. Um, but at the same time, as you say, just like listening to that gut and going, I know this is right, um, yeah, yeah, and just working through it.

SPEAKER_00 13:31

Yeah.

SPEAKER_01 13:31

Oh, that's so you actually make your decisions from your gut. I do, yeah.

SPEAKER_00 13:38

Always, or did you have to teach yourself a little bit to do that?

SPEAKER_01 13:40

I had to teach myself, but I know that my gut is if it's not a hell yes in the moment, then it's a hell no. Okay. Sometimes I think, oh my god, this is gonna be a great opportunity. But if my gut's going, no, I can't, it this doesn't feel right, I have to honour it. And most of the time, nine times out of ten, it's been the right decision because it's opened up something else for me, or maybe what I was gonna do wasn't the right thing. Um, so yeah, I just I do follow my gut, I do. So I wanted to ask you a question about old Jenner versus current Jenner. So, the identity that you have had to take on in order to have this really successful dating business that you've got. So, tell me what what old versions of you have you had to get rid of and what have you replaced them with?

SPEAKER_00 14:35

Um wow. Um I well, with self-development's been a big, huge thing for me. Um, and just being aware. So, you know, when you when you really do that inner work, you go back to kind of childhood, don't you? So I realize for various reasons and another, uh, from a very young age, I've been a people pleaser, and that that is probably my my strongest um I'm gonna say bad trait, but I actually also think it can be good sometimes because I feel like I can adapt and work with anyone, and you know, and and I do genuinely just adapt, it's finding the boundary, but so I know from a younger age I've always people pleased, and so I I do that and I can I can adapt, but it's what I've had to realize is you can't really keep making other people happy. You you can't keep doing it because that's who they want you to be, because eventually I I can't live a lie. I can't live a lie, and I have to be true to who I am, and so it was turning that people pleasing into kind of a a positive of wow, I've I I know how to communicate with that person, I know how to communicate with that person, and you know, I've dealt with people that are struggling with food banks to people that are, you know, really, really high-end and you know, are struggling because their private jets had to wait two minutes. You know, I'm talking like different scales, and I'm like, okay, stop people pleasing where you're changing you, but just use that as a skill that wow, I'm I'm so lucky that I've got that skill within me because I can actually speak to people on all levels, and I I genuinely am interested, and I genuinely do want to relate. I don't know what it's like to go on a private jet, but like I will really put myself in and understand that. So it's taking those things that probably aren't really always your best trait and using them to your advantage and seeing kind of the positives. So, so just looking at people pleasing, where has it held me back and where can it move me forwards? That's that's probably something because I know you look back, and I'm not I'm not a fan of the whole, oh blame the parents, you know, but it's not our childhood is our childhood, you know, not blaming anyone, but that is what I brought out of my childhood, our people please. So do I let it hold me back or do I let it move me forwards? And I love that's that. I love that.

SPEAKER_01 17:17

I love that you've taken like that old part of you and actually taken the good parts of it, and you've been able to reframe it and you know, still have that label. I always talk about us having these labels as part of our our identity and like peeling the labels off and getting rid of them, replacing them with new ones. So, although you've kind of kept the people pleasing, you've reframed it, and you're like, actually, it just means that I can then go and speak to you know, people of like all different ilks, all different classes, you know, all different, etc., and use that to your advantage. So I I love that that's that's such a great way of reframing it because you're also not putting yourself down and saying, Oh, I'm such a people pleaser, and I put my you know, everyone else before me. And it's like, well, actually, I'm aware that that's what I was doing, but now I can now go out and I can talk to anybody and I can support anybody. So I love that and love to reframe that.

SPEAKER_00 18:12

It's like you said before, it's having that, but having boundaries. Boundaries are important, aren't they?

SPEAKER_01 18:18

Massively, and boundaries are something that a lot of people struggle with, and a lot of people they don't know what the boundaries are, boundaries get blurred, and it's like it's it's so important to work out what they are and then honour them as well. It's not always easy to honour them as well, is it?

SPEAKER_00 18:33

Absolutely, and again, that's in dating and business and everything. You've got to have those bloody boundaries, you have to exactly.

SPEAKER_01 18:43

So, what is one thing you would like the listener to know, or one thing that you would like them to try? I always think it's really good from your experience to share that with other people that people can think actually, that's something that I might start implementing in my life, or that's one change that I can do. Obviously, you've mentioned about the reframe uh with the people pleasing, but what's one bit of advice you would like to give the listeners?

SPEAKER_00 19:10

Oh, geez, the pressure, the pressure. Um I think it is really the more you speak to women, you're you're really not on your own. Like, you know, I went for coaching myself because I I felt like a bit I was being dishonest because I was saying all these things to women, and I truly believed they could do it. Like I in my soul, I was like, she can absolutely smash this, she can do this. I believe in her, and doing it, doing it, and then I would look at my own life and I'd be like, Yeah, but not you. Like, and there must have been another woman in the world that believed it in me, and it's I I think it's the more you talk to women, we're actually all a bit the same. You're not really on your own with your struggles. Like, we all most of us want well for other women, I certainly do, like, and I believe that any woman can achieve anything. People actually, not just women, but you know, for the context of this, I believe that any woman can do anything. But then I looked at me and I thought, but not you, not you, and I would play small and I would think, no, I love that for other people, but it's just not for me. And so I felt like a bit of a fraud saying it when I wasn't actually doing it in my own life. So I went for coaching and worked on myself, and I actually believe it for me now.

SPEAKER_01 20:40

Yay, I love that. That is gonna resonate with so many people because you know, I think there is that that thought where, you know, I can see that in other people and I can support people to do that, and then they look at their lives, they're like, oh my god, I I like you say it's that I feel like a fraud, I'm not doing it. But as you said, getting that coaching support to allow that person to get you to that point. Um, but that is, yeah, that is a hundred percent gonna resonate with people because it resonates with me. Yeah, we're not on our own. Like, this is one of the reasons why I did the podcast, and I want to start having people on the podcast because when I was doing when I started, I had people messaging me saying, Oh, you know what? That episode, I felt exactly the same. And I was like, Yes, and it feels so validating in a way when you know that you're not on your own. And I just we all have the same thoughts, I feel as women. We all have the same worries, the same feelings, but a lot of people don't want to talk about it, so they keep it within, and then there's this kind of ripple effect where no one's really talking, and it's like, no, we need people to start saying it as it is. A lot of people go, Oh my god, I'm not on my own. Okay, well, she felt like this, but now she's doing this. So that's possible for me. So, really, you know, we're showing people what is possible for them if we do the self development and all of the inner work.

SPEAKER_00 22:00

Absolutely, absolutely. And we should mention here how you and I met, by the way. Um, because we both went for a coffee at the coffee station at the same time at a random event in London. Yeah. And I don't know how we spoke about it straight away, but we were both saying we were both being held back by the same thing at the same time, and that was putting ourselves out there on social media. And I I clicked with you straight away, and I thought, oh my god, I feel like that. I feel like that. And then we followed each other. I was so proud when you started putting yourself out there and actually post it, and you did it, oh my god, a good bloody year before I actually started doing it, and I thought, love that. And was I jealous? Absolutely. Because I was like, that was our struggle at the same time, and you've actioned it. How dare you? And then, but so just always remember that people are watching you, like, and and they are, and yeah, it took me a little bit longer, but I got there. But you what you do and show other people that they can also achieve is huge.

SPEAKER_01 23:02

So yeah, well done, you and we're that's what we're doing, you know. That's what we're doing. We're showing women that it's possible for them, and you know, both of us have been through our own journeys to get here, it's not been easy. God, tears have been shed. Like, I don't know how many journals I've got under my bed, and just doing the work, like going really deep. But once you do face the gremlins or the shitty comp committee, whatever we want to call it, and we start to release it and work through it, we're then able to come out and be on social media and support the people and could and just do all of the things that we want to do. And like you, I'm such a massive advocate and cheerleader for other women as well. Like this competition, there's enough, there's enough space for us all out there, and it's just realizing that as well. Um, so yes, thank you. Well, I've absolutely loved our conversation, and it's been amazing. And yes, so Jenna, where can people find you on on social media, online? Where can they find you? Tell me.

SPEAKER_00 24:05

Oh, I'm all over the place. I uh so I'm mainly more active on Instagram to be honest. Um, and it's just Jenna underscore my dating pa. Um, but yeah, I'm also on YouTube. Um, but yeah, uh LinkedIn, TikTok, Facebook, you name it, I'm on it. But um yeah, Jenna My Dating PA, and um, you'll you'll find me.

SPEAKER_01 24:30

Well, go and follow Jenna, and yeah, she is absolutely amazing. So thank you so much for listening to the episode today, and I will speak to you later. Bye. Bye.