The Hilary Silver Podcast - How to Stop Sabotaging Your Love Life
Episode Date: November 14, 2025Think you’re “too much,” “too independent,” or “too intimidating” for love? You’re not. You’re just done playing small! In this episode, Hilary Silver sits down with Ready for Lov...e grad Kara Judd, a powerhouse executive who finally got honest about what was really holding her back in relationships. Kara opens up about how she stopped blaming her success, her height, and her “strong personality,” and started doing the deeper work, rewriting the stories that kept her settling for less. Now she’s in a healthy, equal relationship built on respect, communication, and growth. This isn’t a fairy tale, it’s what happens when you heal your patterns and show up as your real self. Episode Highlights: Why accomplished women still feel insecure in love How subconscious beliefs shape attraction and dating patterns Kara’s process for rewriting old stories and showing up differently What a truly equal relationship looks like after doing the work Why being “too much” is actually your greatest strength The difference between being chosen and choosing yourself Episode Breakdown: 00:00 Kara’s Love Story and Dating Breakthrough 03:10 How Childhood Beliefs Sabotage Love 05:26 The Wake-Up Moment That Changed Everything 08:45 Attracting a High-Quality Man After Healing 12:30 Boundaries, Space, and Real Connection 15:22 From Self-Sabotage to Self-Worth 18:44 How Confidence Changes Love 21:10 Real Love Starts with Self-Honesty Tune in and find out what really changes when you stop settling and start showing up fully. ✨ I’m Hilary Silver, LCSW, former psychotherapist turned master coach and founder of Ready for Love. I help high-achieving women show up in love as confidently as they do in their careers. 💡 Through this podcast, I share my WOMAN-centered, SELF-centered approach—time-tested methods that blend psychology, brain science, relationship skills, and no-BS dating advice. 🎙️ Since 2017, we’ve helped over 10,000 women with a 98% success rate, making Ready for Love the #1 program in the world for women who’ve tried everything else. ✨ Ready to stop repeating the same patterns and finally create the love you deserve? 🎯 Watch my free masterclass to learn the proven 4-step Ready for Love Method: https://readyforloveinc.com/masterclass 💬 Apply for a free Love Breakthrough Call with my team: https://readyforloveinc.com/apply Connect With Kara Judd: LinkedIn: https://www.linkedin.com/in/kara-judd-4477a01/ Cozy Earth: Luxurious Bedding Up to 40% Off + 100-Night Sleep Trial Use Promo Code: READYFORLOVE AirDoctor: The Trusted Air Purifier for a Healthier Home Use Promo Code: READY Up to $300 off + Free 3-Year Warranty Exclusive Podcast Offer
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He's like, I wish I had met you 20 years ago, 25 years ago.
And I was like, well, I wish that too.
But I'm not sure we were ready for each other then.
Hi, it's Hillary.
Welcome to the Ready for Love podcast.
Thanks for tuning into the conversation today.
If you haven't already, it would mean so much to me.
If you'd take a minute to just click that five-star rating on your podcast app,
leave a review, and subscribe so you never miss one of my episodes.
And if you're enjoying this podcast, please consider sharing it with a friend because if you like
it, they will probably like it too.
Hey, everybody, welcome to the Ready for Love podcast.
I'm so excited to have you here today.
We are doing another one of our amazing Ready for Love graduates interviews today.
And I love doing these because it really helps give me an opportunity.
It just gives me an opportunity to be my real self with you guys.
I'm not, you know, teaching.
I'm just being who I am with my amazing clients.
I get to share my amazing clients with you
and to lift them up and celebrate them and highlight them
because it really is truly amazing
when a woman steps up for herself,
signs up for something like this.
Not everybody is willing to, A, invest in themselves,
but also look at themselves really critically and do the work.
So today we're talking with Kara Judd.
She has been with KPMG,
for 31 years. That is astounding. So in that time, she's really proven herself as a dynamic and
critical leader right now. She is currently the senior director and head of U.S. account
management and operations. And also, she has a huge heart. She sits on the board for Habitat for
Humanity Charlotte and sustained Charlotte. And even since 2014, she's been actively serving with
women's executives and is a total complete, like me, champion for empowering women in leadership
roles. So let's welcome to Kara to the show. Hello. Thank you so much. I'm very excited to be here.
Well, thank you so much for being willing to share your story. Again, it's not like you're just
coming on and talking about business. This is especially vulnerable when you share your personal life
and your private life with anybody who's listening. So I always really appreciate that. And we learn
from story. You know, we hear stories and something will stick. And sometimes it's just one thing that you
might say that resonates with somebody and it clicks and they get it. So, you know,
our listeners are blessed to get to have you here today. So what we're going to start off with
is if you could just please tell everybody where you were at in your love life, what you
were struggling with, what was going on that was not working for you when you reached out.
Okay. So, because it's been three plus years ago, I was very successful in business.
I had a child who was in high school.
I was ready to kind of get back out into being seen, but really didn't know how to do that.
I really didn't date a lot in high school and in college.
And I'm a tall girl.
It's because I'm tall.
I'm intimidating.
I'm this.
I gave kind of all these excuses for why I didn't get asked out.
And so I just really just started seeing, okay,
what options are there? And so I took your introductory call and, or I guess it was your
introductory program, right? And every one of your points just hit home for exactly who I was,
how I operated, et cetera. And so, of course, I was like, okay, that's me. So she can help fix
me. And clearly it's something with me, right? And so I think it's so funny, Kara, because you're
Like, I'm a, I'm really tall.
That's the reason I don't get asked out.
And the funny thing is, like, I'm really, I'm five foot one.
And so maybe it's because I'm so short that I don't get asked out.
Like, we all say the dumbest shit to ourselves about why we're not lovable or why we're
not attractive or what's wrong with us.
And, you know, like what I wouldn't give to have two more inches on my thighs.
You know, so it's just so funny when women say things like that.
Not funny.
It's painful when we do that to ourselves.
But it's so ridiculous.
funny like it's a fucking lie basically completely complete it was lies that I told myself and then
going through the program and I know we'll talk a little bit more but these were lies that I told
myself you know to to to to understand right to understand why I wasn't getting asked out right
why why men weren't gravitating towards me my friends would say well you you're the whole package
you're the whole package and I'm like well I think I'm the whole package too but it wasn't at that
point in time it really wasn't translating and I think I you know I had been I I
I was in a marriage for about nine years, divorced when my daughter was younger.
I then went a couple years of, you know, hey, I'm just going to step back.
I was introduced to another gentleman.
We dated for seven years.
And so then fast forward, we broke up.
And then I got into kind of a little bit of a dating pool and trying to navigate that and was very insecure about it.
Just scared, frankly, scared.
And so that's what precipitated me contacting and seeing, you know, your.
program online and getting in contact with you? Yeah. I mean, it's crazy how women, I think that
we don't, the general public might see a woman who's an executive in a powerhouse and has
the designer bags or the lifestyle or a nice car and the clothes and all these things and a great
title and a great paycheck and not think for one second what might be going on behind closed doors,
like inside of yourself. Nobody would suspect that you would be insecure.
But this is, of course, the Ready for Love niche, super niche that we really work with women who have this kind of strange disconnect between how accomplished you are and successful you are on the outside and what things might look like.
And yet at the same time, we're all just this little girl on the inside who's still wounded and has baggage and fears and insecurities.
those things don't go away unless we actually work at it. You can you can't like succeed your way
out of that. Okay. So you so you found us online. You found the webinar. You did the webinar.
Then you did the breakthrough call and you signed up. Can you remember like a moment where
something clicked for you in the program or was there a specific tool or takeaway that really
shifted something for you? Well, I will start first in the call that the the initial call.
with you and I was kind of relaying where I was and I think I was whirling and different things and
you you really said you know this is solvable you don't have to live like this you don't have
to put up with this and so I do remember you know that was very pivotal pivotal for me because I was
reduced to tears and you were just like you this is this shouldn't be a part of this right so
that was the first pivotal point I think as I went through the program and you know you have to
put the work in. So, and you know, I was the first person, right? Oh, I'm busy with meetings.
I'm busy with this. And so finally I was like, I've really, I've made a commitment to this.
I'm making a commitment to myself. And I really had to work the program. And part of that
work in the program was, you know, attending the calls. I got a huge amount of benefit from
hearing other stories, right? Because a lot of times we've got a lot of similar characteristics.
but I do think a portion of the time was in the journaling and walking through the activities
to help peel back the onion of really where my probably insecurities, if I'm honest, lie.
And I can, you know, I can expand upon that.
I mean, there was, and it's just some little random things, right, that, you know, people said to me,
probably in my teenage years, and I do recall you saying, right, you know, you can hear things,
you can feel things and in your mind you tell yourself that over and over.
And so what was a lie becomes then a truth.
And that was very pivotal for me, right?
And so I had to go back, figure out those lies that I was telling myself,
whether it was too tall, whether there were specific conversations that there was two
specific conversations, one that I had with someone that was, I didn't even know.
And they had said something to me that then impacted, you know, how I showed up.
you know, another was my, was my father. And, you know, I have always been very talkative, very
challenging. You know, we would, we, they used to use the term Bosti. We don't use Bosti. We use
driven now. But, you know, he relayed, right, in the heat of, I'm sure, you know, me challenging
and arguing with him that, you know, how are you going to find somebody that's going to put up
with that, right? And so, again, that's deep in my subconscious. So I had to work through
that. And I worked through that via the journaling. I worked through that on the calls. I worked through
that with, you know, with the one-on-one counseling. And it wasn't quick, right? You can't really
solve it quickly. I mean, I think at least I was working on this four to six months. And it was,
you know, only when I kind of opened up that portion, opened up bigger portions of the program,
things started to shift. You're starting to satisfy that inner child. You're starting to show up
differently. And it just takes time. And it took me whatever. And I guess that would have been 50 some
years to get there. Right. So clearly, you know, six months of the drop in the bucket to help me move
forward. Yeah. Well, you just said a lot of amazing things. And I'm going to go back just for the
listener's sake, because one of the things that we do so well is the reprogramming. So critical
key moments in our development. We experience micro traumas, as I call them. Like, were you, did you end up in the
hospital? No. Did anybody beat you in that moment? No. But those words of somebody that you seek
approval from, that you love, that you want adoration from, your dad, this figure. And for anybody
listening, there are many people in our lives like that when we're little. And he says to you,
without thinking of the long-term impact it may have on you, who's going to put up with you
if you're bossy, right, or you're a no at all or whatever? And it goes into your subconscious
and there it sits and it grows and it festers. And what our beliefs are are nothing more
than sentences or statements that we have told ourselves so many times that we come to believe
it. So there's a lot of shit in our subconscious that isn't true and a lot of things that don't
make sense. But if they're unexamined and unexplored and not challenged, they are actually
these things inside of our subconscious in charge of everything. All of that stuff is at the
wheel, whether we realize it or not. And that's why it's so important really for everybody to do
this work, not just for relationships, but for everything. And sometimes on my Facebook ads or
my Instagram ads or on my, all my social media, I get women saying things like,
blame the women. Why don't you just blame the women? Men are the ones that need to do the work
and blah, blah. I'm like, well, yeah, we all need to do this for ourselves. It's not about
he, she, or whatever. It's, if we want to really achieve our fullest potential and be the best
version of ourselves possible and have our own hands at the wheel so that we are self-determining
and self-defining and self-led. This work has to be done for all of us, no matter how successful
we are. And so that's why I love you and all of my clients so much, because despite how
successful you are, you're still willing to look within and see what things are holding you back.
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to mention you heard about cozy earth from me so in our program is 12 weeks eight or 12 weeks
depending on which version you sign up for but you really continued to do the work you stayed
committed and it took you like six months you're saying yes I think yes I yes and I will say you know
initially was I willing to look at it and determine that it was myself no of course I wanted
somebody else to tell me here's the here's the magic bullet here's why you're not dating right
and and that was where it was you know it was interesting then when you when when when
you know the program's like it's you and you're like wait a second this that's not what i wanted to hear
right i wanted some other magic bullet but but then when you you know but then it does make sense right
and then when you work the program and you go through the program and then you can kind of lay some
things to bed and again thank goodness you know i've talked to my daughter a lot about you know
portions of this program i've talked to friends because gosh knows i would like for them to heal wounds
way earlier right i mean thank goodness i had it you know in my 50s
right? And I didn't carry this throughout my whole life. So I encourage everyone to work on. And gosh
knows, I still have many things to work on as well. So it's not all. But you're right. Women often say,
where were you 20 years ago? I'm like, but you probably weren't ready for it by then.
You know, like we have to really be ready to accept that we are the problem. And again, that's
where I get a lot of blowback too is blame the women. But honestly, it is the most life-changing thing.
when we can just be willing to ask ourselves, how am I creating this? How am I contributing?
And it's like, somebody said that to me when I was like 25 years old and I was at first put off by it,
of course, thinking I didn't do anything wrong. But that question has stuck with me and is,
I don't even know who it was at the time anymore, but like it planted this seed for me that has
become a foundational part of the program. It's like it starts with you. It always does.
we can all get what we want when we're willing to see how we're getting in our own way.
And yeah, it sucks to like, it's the bitter pill, magic pill, right?
It's a bitter pill that it's you.
It's a bit of the magic pill.
Yeah.
So really peeling back the layers, reprogramming some of those deep, deep, subconscious beliefs
and identity forming moments for you.
So tell us where you're at now.
Sure.
I am in what is going on almost a three-year committed relationship with,
a with a great guy and so I just you know met him and I'd want to say because I talked earlier
about being nervous about dating right I really hadn't dated a lot the program helped me you know
learn to go on dates right go on dates just have fun meet a lot of people set up the set up your
profile right I had not set up my profile on different things so it's interesting because I was
meeting let's say more of the guys that I was dating casually unmatched he was the only
one that ended up translating through Bumble like nobody was coming through my Bumble and then
all said at one point you know again it's the universe it's you know God it's whoever like that you
want to believe put him in my life and um and so it's been it's been a very fun ride uh it has not
all been smooth right um he he is um financially you know more successful than I am and and
which I love right because I had usually been the more successful one in these other
He's not intimidated.
You know, I think I even said, we just talked about a lot of things and he's, and, and I said, well, most guys are intimidated by me and he just laughed.
And, and, and, and it was, it was, it was, it was lovely, right?
He laughed and he's like, well, I'm not intimidated by you, right?
And, and, and, um, yes, so it's very, very fun.
And, and we have a lot in common.
Um, now, has it all been easy?
It has not.
There have been bumps.
He's got stuff.
He was, he was more out of a divorce or more recently out of a divorce.
Or more recently out of a divorce.
and he's had to work through things as well.
I have tried to encourage him, you know, to get counseling.
I wish, you know, you did handle the men portion of it.
And so we have had a lot of discussions.
We communicate a lot, more communication than I've probably ever had in,
and probably all my relationships combined.
If I'm honest.
That's great.
Yeah, talk to things.
I mean, this is realistic.
This is realistic.
And what I love what you're saying is this is different in many ways than your past experiences.
In the past, you were dating down, you were dating men who were not your equal.
They were intimidated by you.
It caused all kinds of trouble.
Maybe how you were showing up wasn't fully expressed, especially if you think you're intimidating
or you're tall or whatever, you might make yourself smaller.
And that never works.
So he's a different kind of person than you've been with in the past.
And you're showing up differently.
it sounds like there's space for you to actually be your full self in this relationship.
And I always say it's not up to anybody else, whether you get to be yourself.
Only you can decide that.
But if you felt like you had that belief that you're intimidating, you would bite your tongue.
So the reality is relationships take work.
It's a lot of work.
It's playful work.
It's hard work.
It's growth work.
It's stretching you.
It's taking you to your next level always.
but the women who have graduated our program who are in successful long-term relationships
use their skills and tools that they learned in this program forever into the relationship.
Agree.
Agree completely.
Because there's tools that I learned some of the times I have to go back and watch some of the,
or listen to some of the videos.
I go back to some of my notes.
I mean, again, like I talk about, it's not, you know,
we've had multiple bumps and different things.
And the last bump that happened probably four or five months ago, I just didn't, and it was a multitude of things going on at work, things, the way I was showing up and our relationship was handled, you know, and I was like, I need to take a step back. I need to take a step back from everything. I am not in a great place. And how am I showing up? And it was interesting that, you know, it made him rethink some things.
because I was actually willing to
to take a step back from the relationship.
I said, this, this is critical to me.
I'm not, this is not how it's going to work for me.
And so, you know, to his credit and, you know,
other men would have probably just gone running off.
He came back and said, no, I want to talk through this.
I want to continue to talk through this.
And so now we are back at a, you know, even 10 times better place, right?
And so that's, I know.
And I, it's where at different points in time,
I would have probably been scared, right?
not going through this program.
I would have been scared that I would have lost and scared.
I'm like, you know what?
I am my own self.
I go on vacations by myself, right?
You know, and so it's, you have to be willing to step back from it.
If it's not, if it's not right and it's not serving you or if it's not serving, you know,
what you're looking for in the future, you have to be, you know, you have to be willing to do that, right?
And so that's where it was, you know, it did, I think he then reabend.
evaluated some things and was like, wait, wait, no, no, no. And that, yeah, I love this even more.
If you're telling me that it's perfect and there's been no bumps, then I'm like, well,
let's coming. Go have a fight on purpose. I would literally tell you, go, go pick a fight so you can,
because my whole philosophy is conflict brings you to deeper connection. And what most women will say
to me is I've never had a man fight for me or just really be my right or die. And what you're saying is
he fought for you and that and being willing to have the difficult conversations and being
willing to sit through the discomfort of all of that brought you to a whole new level of
intimacy and connection you can't get there without the challenges you can't that's why I'm
like go have a fight if you haven't had one yet go have a fight because you don't know what
you're capable of together and you don't know what each of you are capable of until you do
that. And life will throw different things at you. I mean, you know, he was more recently out of a
divorce than, you know, his mom was sick and she ended up passing last fall. And so there was all
these different, you know, you know, reasons, right? And I kept then as a previous people
pleaser, right, and extending more reasons and giving more, you know, leeway in different things.
And then I just got to a point. I was like, I can't do this. You know, he had stepped back a couple
of times. I think he had gotten scared at different points in time and he was, you know, needed to
step back. And then it was my time. And I was like, I got to step back. I've got to step back.
And it was, it was, he is the only man that has fought for me. I will, I had not looked at that way.
I think I intuitively knew that, but, you know, he would not let me go. And, and I was willing to
go. That's because you are showing up, you're the most authentic, transparent, you. You're worth fighting for.
All of you, we are all worth fighting for.
When you hold back, you don't give anybody an opportunity to give them something to grab on to.
When you filter yourself and only share the best parts of you and the curated parts that you only want them to see and you alter or edit yourself or shift and shape shift into somebody you think that they want you to be and don't give them a reason to leave, you're creating the very rejection.
You're trying to avoid.
But what I love the most about this whole thing, Kara, is.
is the biggest takeaway that women get out of our program.
It's why we exist.
And it is that you have this relationship with you
that you are never going to ever betray ever again.
And being willing to walk away from something that isn't right for you
is what I want for all women.
And you know that you got your own back.
And you know you're going to be okay no matter what.
And being willing to do that,
you often end up getting the thing that you want,
but you being willing to lose that so that you can get what you really need more than
anything, which is you, is the true gift.
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you can give yourself and your family. Agree completely. I'm proud of you for that.
Yes. Well, it was interesting, right? Because when I did that and then I sat back and go
gosh, why didn't I do it sooner?
But clearly the timing was supposed to be, you know, how the timing worked.
But, you know, he's come back and showing up in ways, like, more affectionate,
you know, all this kind of things that, again, were what I really wanted.
But it just kind of took me being finally, you know, saying, I'm going to, this is what I need.
This is what I need.
I've given a lot, you know, some excuses.
But this is what I need and everything is.
Well, here's a sound bite, you know, from the program, ask for what you need and you're likely to receive.
I mean, it's like not that, that, like, it's kind of crazy that women don't ask for what they need, but, and it's like revelation here.
But hello, ask for what you need.
And you're likely to receive it.
Exactly.
Exactly.
But I do.
And I look back on, you know, as talking through like the attachment types and all these kind of different things.
And I don't try to play, you know, counselor to, you know, some of my friends or even to some of his friends, right, where they're going through.
because I do think there's something about people in their 50s, right?
And all the stuff starts coming up, right?
Everything starts coming up.
But being able to start being true to yourself, you know,
would have loved to have it earlier, but glad we have it now
and really try to just help showcase it.
I showcase it to, you know, my daughter, to my friends because it is, it's critical.
And it's, you would think we would learn these things in school from our parents.
We don't.
We don't.
No, we don't.
That's why I'm here.
But what I love, like if we look back on our conversation, the things that you have, that we've
covered have been everything from changing inner core beliefs and dealing with micro traumas
all the way to your dating profile and how to date online. And hello, everybody, this is a online
app, dating app, love match. So if you think the app suck, I'm telling you, a lot of our clients
find their people online. It does exist and it does work when you know how to use it.
all the way to navigating difficult conversations with somebody that you're in a relationship with
and holding your space and not losing yourself. That's what ready for love is. It's all of it.
It is. Like, I just love what I do. I love that. And thank you so much for sharing all of this
with everybody. What are we celebrating? What major cool things are going on in your life right now?
What are you up to, you know, tell us? Yes. So, well, we've got all of
our kids in college so we're traveling and we're having fun and we're you know between work and
and and and travel it is a very full life right and it's just it is it's nice to have the time with
just the two of us and he lives he lives about four hours away from me in this fast in this fabulous
little town so we get to you know enjoy the big city life with me the smaller city life with him
with tons of his friends, but just traveling.
We were out on the Oregon Coast for two weeks back in September.
We've got a lot of other trips planned.
So it's just, it's having fun.
It's like this season of life, right?
Where, you know, we've, we've channeled our children.
We've gotten them into college and grad programs.
They're all happy, you know, and now it's time.
Yeah, it's our turn.
Now, and it is interesting because we have this conversation.
He's like, I wish I had met you 20 years ago, 25 years ago.
I was like, well, I wish that too, but I'm not sure we were ready for each other then.
I believe that 100%.
I love getting, I love like that we share, again, for the listeners, we text each other and
message each other about the newest five-star fabulous resorts that were, check this one out,
check this one out.
Here's where you need to go next.
So you guys have quite the lifestyle together and I'm so happy.
And, you know, again, like highlighting that like in ready for.
love, we celebrate breakups. You know, that sounds maybe weird for a love coaching kind of
company, but when women are not willing to settle for something, the old you might have
stayed and settled and made it work and put up with stuff, but the new you does not.
And that is a win to walk away even after six months, six years with something that no longer
is the thing, the right thing for you is a win when you look back on who you used to be and
what you might have put up with and settled for. So, you know, I, I just love that. All right,
well, I'm going to still say, you all had me write down my wish list. So what is, what is the
perfect, you know, partner for you. What do you want in this partner? And I had, you know,
I had looked at it a lot when I was in the program. And I just recently found the list again.
And he checked off like every single box. And so even writing those things down, even when you're
on the dating sites being ruthless, right?
You don't have time to waste.
And I know that was through a lot of the coaching that you all had, right?
You've got to be ruthless with it.
And you have to believe.
And so you have to go into it and believe and put that aura out.
I do think I probably had a closed, very closed aura.
And so trying to be open and being willing to share and share myself, that was some other
factors of the program that I've reflected upon that were pretty pivotal.
Yeah, it's not just the list.
paper, it's actually recognizing it in real life. That's different, right? The map is
not always the same as the actual terrain. And, you know, so you can have your list of must
haves and requirements and deal breakers and all of that. But when he's standing in front of
you, do you recognize, is this it? And not ignoring the red and the yellow flags and really trusting
your intuition and all of that is a big part of it. And I love that you went back and looked at your
list and there it is like everything you want it. There it is. We do the the woo-woo kind of part of the
program that's really connected to the laws of the universe and the law of attraction and the
law of vibration and the energy piece is huge because you attracted this person. You were
attracting the lower quality men before because that's where you were kind of revving your
frequency. When you up your frequency, you attract people who have a higher frequency as well.
And it starts with you. And you did that for yourself first. And here he comes knocking.
Here it comes. There he was. Yeah. Out of the blue. Yeah. Love it. Well, thank you so much for sharing your
story with everybody. And I can't wait to see where it goes and invite me to the wedding. I'm coming.
Thank you.
