https://youtu.be/pZfG4TJ0mWk

Many high-achieving women can lead teams, close deals, and build global careers — yet feel confused, frustrated, or discouraged when it comes to love.

Lynda Williams is the founder of the Evolved Woman Program, a relationship coach, and podcast host who helps ambitious women find love without compromising their success. After building a career across three continents in leadership and entrepreneurship, Lynda realized that the same traits driving her professional success were undermining her love life. Through deep inner work, she transformed her relationship patterns and now guides women worldwide through that same shift.

In this episode, we explore why professional success does not automatically translate into relationship fulfillment, and how the very mindset that fuels career achievement can quietly sabotage intimacy.

What you will learn from this episode:

  • Why do successful women feel confident at work but insecure in dating and relationships.
  • What the “success–love paradox” is and how it shows up in high-achieving women’s lives.
  • Why ambition is not a barrier to love — and how to use it as an asset instead.

“Many high-achieving women are incredibly successful on the outside but quietly struggling with self-worth.”

– Lynda Williams

Topics Covered:

02:34 – The success–love paradox for high-achieving women.

06:02 – Why professional confidence doesn’t translate to dating confidence.

09:54 – Doing the inner work to understand who you are and what you want.

12:25 – Why traditional dating strategies fail ambitious women.

16:38 – Self-awareness as the foundation of healthy relationships.

20:46 – Why relationships, not achievements, drive long-term happiness.

23:38 – How to balance ambition and love without sacrificing either.

Key Takeaways:

“The problem isn’t ambition — it’s the disconnect between how women show up at work and in relationships.” — Lynda Williams

“You don’t need to choose between career success and love. You can have both.” — Lynda Williams

Ways to Connect with Lynda Williams:

Ways to Connect with Sarah E. Brown:

 

Full Episode Transcript:

(AI helped us put this together, so if you see any weird grammar or missed words—just know we nailed it during the actual chat.)

Lynda Williams

The biggest challenge that I see is kind of what I call the success love paradox, and I see it play out a lot with my clients. You’ve got these amazing women who are total rock stars in their careers, but somehow they feel like they’re failing at dating 101. It’s like they’ve climbed the summit of Mount Career, only to look across at Mount Relationship looking completely incomparable. And they’re standing there thinking, wait, I’ve mastered boardrooms and business strategies and my career, but why can’t I figure this whole relationship thing out?

Sarah E. Brown 

Hello, everyone. Welcome to the KTS Success Factor podcast for women, where we talk about challenges senior female leaders face in being happy and successful at work. I’m your host, Dr. Sarah E. Brown. 

My guest today is Lynda Williams. She is founder of the Evolved Woman Program, a podcast host, and a relationship coach who specializes in helping high-achieving, ambitious women find love without compromising their success. After building success across three continents in leadership roles and entrepreneurship, Lynda discovered that the same mindset that advanced her career was quietly sabotaging her love life. 

Through her own journey of deep inner work, she finally attracted the loving, emotionally available partner she had been missing. Now, Lynda guides successful women worldwide through the same transformation, showing them that their ambition isn’t the barrier to love. It’s their greatest asset when they know how to leverage it. 

Welcome, Lynda. 

Lynda Williams

Thank you, Sarah. It’s great to be on your podcast. 

Sarah E. Brown 

Well, it’s great to talk about this. This is certainly a problem I had in my life. So tell me, how do women find you?

Lynda Williams

They find me through social media, a lot of referrals actually, showing up on podcasts like these, lots of different channels, a lot of referrals. Once I have my clients go through the program, they can’t wait to tell their friends and get them on it as well.

Sarah E. Brown 

So why is it that successful businesswomen have this problem with their love life?

Lynda Williams

Yeah, so the biggest challenge that I see is kind of what I call the success love paradox and I see it play out a lot with my clients. You know, you’ve got these amazing women who are total rock stars in their careers but somehow they feel like they’re failing at dating 101. It’s like they’ve climbed the summit of Mount Career, only to look across at Mount Relationship looking completely incomparable. 

And they’re standing there thinking, wait, I’ve mastered boardrooms and business strategies and my career, but why can’t I figure this whole relationship thing out? And what is fascinating and it actually surprises quite a lot of people is that beneath those, you know, shiny LinkedIn profiles and sometimes swanky penthouse level offices, most of these high achieving women are actually dealing with low self-worth. 

And I know it sounds mad, but it’s like having a beautiful house you see that is perfectly staged on the outside, but the foundations are kind of rocky and no one can see that. They’ve built this amazing career and they have all this external success, but their internal foundation is shaky at best. And they’re actually looking for external validation. So that next promotion, the next bigger revenue target, another award. hoping that they’ll finally make themselves feel worthy. 

So it’s like trying to fill a leaky bucket, no matter how much water you pour in it, it never gets full. And the symptoms are quite consistent. These women constantly hear that they’re too intimidating, they’re too much, they’re too independent, they have to dumb themselves down for potential partners. And it’s like being penalized for the very qualities that they’ve worked so hard to make them successful. I mean, can you imagine a man ever being told that he’s too successful to find love? It’s absurd. 

And many find themselves caught in this washing machine cycle that, you know, they’re attracted to partners who initially seem to admire their ambition but eventually become a bit threatened by it. 

And it’s like dating someone who, I don’t know, who says they love your singing voice but then asks you to stop singing because it makes them feel bad about their own voice, right? And then we’ve got the compartmentalization. 

The women become great at shape-shifting. They’ve got their boardroom self, and then they’ve got their dating self. And these two people shall never meet. One client told me she literally changes her vocabulary and her posture when she goes out on dates. I mean, talk about exhausting. 

And the saddest part is, when they start believing that they have to choose between their career success or having a fulfilling relationship, but you can’t have both. And here’s what I’ve learned as well after working with many women over the years. We need to look at why we do what we do. So, why do we do what we do. And it’s like trying to navigate a map without figuring out where you are first. You need to know your starting point, understanding our motivations, why we chase certain achievements, why we choose certain partners. And that’s the foundation for building a life that feels meaningful both in and outside of the office.

Sarah E. Brown 

So there was a lot there. Let me unpack some of it. Do you believe that many men are intimidated by high-achieving women?

Lynda Williams

It comes down to a few things. Those that are too intimidating, too much. That doesn’t only just come from men, it comes from well-meaning friends and family. Oh, she’s so amazing, why is she still single? And coming to the conclusion that she has to dumb herself down, let the man take the lead. She’s too much. 

And sometimes it can be to do with that dance between masculine and feminine energy. You know, as women, we have to operate in a world built by men, which demands the masculine energy to have our share at the table. So the proactiveness, the decisiveness, that go, go, go. 

And when we’re constantly surviving and operating in these environments, it becomes our baseline, our go-to. So perhaps sometimes we kind of come across as intimidating if we’re always in masculine mode, but that doesn’t mean we have to dumb ourselves down or be less than or dumb our accomplishments down and sweep it under the carpet. 

So it’s an interesting dance out there in terms of celebrating our success, but also understanding how we show up in our personal and professional lives.

Sarah E. Brown 

OK, so that part I understand. Now go to the part about how often these women are suffering from low self-esteem. Does that have any bearing on their ability to attract a partner?

Lynda Williams

Well, interesting, yes, because if we are coming from a place of low self-worth, we naturally start to attract someone on our level of values, needs, wants. So when we have low self-esteem we start putting up with behavior that’s less than. 

We end up entertaining relationships for longer than we should and putting up with behavior that’s not in line with what we want, not in line with our values. And so our self-worth is congruent to what we really want in our overall relationship. So yes, it does have an impact on having a fulfilling relationship.

Sarah E. Brown 

Okay. All right. So how does a woman determine what she really needs in a relationship? It all starts with the self.

Lynda Williams

There’s a lot of outdated advice out there. And a lot of the time we’re trying to solve a 2025 problem with 1950 solutions. And there’s a lot of advice out there, the dating advice that just wasn’t and isn’t designed for today’s modern, high achieving woman. You know, the place, small stuff, let him lead, don’t intimidate him, all that kind of stuff. 

And really starting with the self and doing that self-exploration of doing that inner work, understanding your self-worth, recognizing your patterns, figuring out what is it you actually want, not what your mom or your social community or work or Instagram influencers tell you what you want. It’s the foundation that everything else sits on. 

And what’s eye-opening is a lot of my clients have never actually sat down and thought deeply about what they actually want in a relationship. You know, quite often they’re pursuing someone who looks good on paper or, you know, to impress their friends, but not someone who truly resonates with their authentic self. So it’s doing that deep inner work first and building on that self-worth before they even entertain a partnership or a relationship.

Sarah E. Brown 

So the big problem that I work with with mid-career professional women is they don’t know what they want in a career. And it does take a lot of inner work to do it. So how do you guide a woman to start that journey of inner work to figure out what she really wants?

Lynda Williams

Yeah, so it’s really, we’ve got to understand where we are now in order to evolve and move forward. We’re all a product of our experience, so it’s looking backwards, looking at how past relationships and experiences have shaped us. What is our makeup? How have we shown up in previous relationships? What do we really want in life? Like, what do we find of value? And I’m talking about deep inner work. What are our motivations? What fills our cup? What do we really, really want in a relationship? 

And as I said, it goes down to doing that inner work, working on the frameworks, looking at peeling back those limiting beliefs on what they can and they can’t have. And doing that development work to really get them to a stage where they feel confident, they have self-awareness, they have a lot more self-love, so they can move forward with that awareness. So you’re talking about you doing the work with your clients on their career. It’s the same in their love life. It’s like, what floats your boat? What have your experiences been, the good, the bad, and the ugly? What triggers you? What is going to make you happy at the end of the day? And you, not anyone else, but you. 

So we look to the past in the first couple of modules on the Evolve Woman program, what has happened, why you may have stayed too long in a relationship, and really do that inner work of who we are and what are our values. So we fill that self-worth cup up with not the external validation, like, who are we? Like, who are we as human beings? What are our amazing attributes that we have to offer in our innate human self, not because, Oh, Hey, look at my LinkedIn profile. That’s very impressive. Who are we and what do we have to offer to the world? So that’s what we work on. We work on our own values of values that we want in a relationship, the value that we want and rather in a human being, what we are and what we’re not going to compromise on. 

And then we also work on a huge chunk about communications. I’m an ex-PR girl back in the day. So there’s two things I really believe in when it comes to meaningful relationships. First is self-awareness and improving the relationship you have with yourself. Understanding yourself inside and out. And number two, it’s communication. We need to be able to communicate in a healthy way. 

And that requires self-worth and confidence to communicate what we really want, to communicate our values, to communicate our needs, to communicate when, you know, something’s up in a relationship, to communicate that in a really healthy and nurturing way. So it’s a whole big process we go through. It’s not like, hey, here’s a dating strategy for high achieving women. It’s so much more than that. 

And there’s so many nuances that go hand in hand with being a high-achieving woman that we work around in the program.

Sarah E. Brown 

And what are the biggest mistakes that the women who work with you make before they start working with you? 

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Lynda Williams

Yeah, I would say. I said, you know, as before, like relying on outdated dating advice, number one. Number two, thinking that they have to fall for that either or. They can either have this amazing career and be successful or they have to give it up if they really want a deep and meaningful and loving relationship, right? It’s like saying you can have coffee or breakfast when in reality you can actually have both, right? I actually worked with a lawyer who actually turned down a partner position in her law firm because she was convinced that it was going to make her indatable. I mean, seriously. 

And another client nearly sold her thriving business because her so-called therapist suggested it was an obstacle to finding love. I mean, talk about throwing the baby out with the bathwater. So there’s this critical mistake out there where we don’t realize the inner work comes first. And so the approach dating, like, I don’t know, it’s just another project to manage. Yeah, right. I’ve got a bit of a gap in my diary for the next three months. Like, yeah, how about we try that dating lark, right? So tick. 

So it’s like if they, you know, create another spreadsheet or a strategy and they’ll find that person, but relationships don’t work like that, you know, and the inner work that understanding your self-worth, recognizing your patterns, finding out exactly who you are and what you want is the foundation. And what’s really eye-opening is that many of my clients have never actually sat down and thought about what they actually want? 

And I guess another mistake. One of the other mistakes is misidentifying the actual problem, I guess. So they assume that, as I said before, that their success is a relationship barrier and they’re going to have to do something about it, right? You know, their achievements, their intelligence, their ambition, that it’s somehow turning people off. 

And the issue isn’t what they’ve achieved, it’s this kind of disconnect between how they show up, as we were saying before, the energy, how they show up professionally and also personally. 

And what makes some of these mistakes tricky is how they kind of reinforce each other. Breaking free from these patterns is, first of all, recognizing them and understanding that authentic connection requires something different than their approach at work. It’s not less than, it’s just a different approach.

Sarah E. Brown 

So if you were going to give our listeners one free and actionable tip to do next week to start this inner work, what would it be?

Lynda Williams

Yeah, I mean, as I said before, you can start it today like self-awareness. is the foundation to do before anything else so before you can build a genuine connection with someone else you first need to establish real connection with yourself first so improve the relationship you have with yourself first of all and again as I said before think of it like trying to use google maps without allowing to locate where you are first right you can have the perfect dream partnership. 

You can have that dream perfect destination program, but if the system doesn’t recognize your starting point, those directions are useless, right? So self-awareness is that you are here, pin on the map of your relationship journey. So start with the self first.

Sarah E. Brown 

So I do have a question. Are successful business women, how likely are they to find a relationship with a man that has similar business achievements versus totally different aspirations?

Lynda Williams

It absolutely all boils down to what values that they want in a relationship, regardless of what they do at work. Do you want someone, you know, who looks good on paper, who is equal to you in terms of status, salary, all those things? 

Or what is it that you’re really looking for? Is it, do they have time for you? Are they kind? Are they loyal? Are they trustworthy? Do they have the same outlook and values in life? Do they have family values? like what what is important to you is is it that career job title and the same salary package as you or is it the inherent human values that you’re looking for and so that becomes secondary of whether they’re you know an equal career person to you or not and that’s what a lot of the peeling away does and everyone talks about Dating up, dating sideways, dating down, like women can only date sideways or date up. 

Men can date up, sideways and down. All this talks about status and career, but we’re not talking about being a bloomin’ awesome human being. Like my partner, he’s not an entrepreneur like me. He’s got a good job. You can almost say I’m dating down, right? But he is the most amazing, he’s my rock. He is the most supportive, loving, caring, funny. We have so many shared interests. 

For me, that’s way more important than having someone who’s also an entrepreneur. And you’ve got to also look at the time here, the competing of time. And, you know, there’s always going to be a push and pull when you’re free and the resources available to spend time together. 

So there’s lots of things that you need to weigh up. Spending a lot of time with someone isn’t that important to you. So if you’ve got someone who’s always on the road, who’s always on the flight like you are, it could become a bit of an issue. But if that’s not an issue, then fine. So it’s so nuanced and different for each individual, depending on what they really, really want.

Sarah E. Brown 

So Lynda, what is one question that I should have asked you that I didn’t, that would help the women listening to this take one small step to find the love life they’ve always wanted?

Lynda Williams

Yeah, I mean this might sound a bit morbid and I’ve had this analogy or whatever you want to call it with me for many years since I started doing my own legacy work and became a coach when I packed in my own entrepreneurship journey to help other women. But bear with me, it’s basically work from your deathbed backwards. I know it’s not the cheeriest starting point, but seriously, imagine yourself at the end of life, looking back at how you’ve spent your days. 

You want to ask yourself, am I happy that I slaved away at work every day and I didn’t make time to develop a meaningful relationship? And was I happy that I didn’t make time to develop a meaningful relationship with myself? so that I could create a really beautiful, nourishing relationship with my partner. And it’s not just like philosophical mumbo jumbo. I mean, the research is pretty clear. 

If you look at that famous Harvard study that’s been running for donkey’s years, they found that the quality of our relationships is the strongest predicator of happiness and well-being, not career success, not wealth, not achievements, but relationships. And we’re humans that are wired for connections. It’s fundamental to our need for food and water. It’s literally in our DNA. 

And the loneliness pandemic, it’s become a serious health risk that it’s comparable to actually smoking 15 cigarettes a day. And that’s not exaggeration, that’s science. And it’s all coming out at the moment. So if your honest answer is that deathbed reflection is yes, actually, I do want to make time for an amazing partnership, then it is time to roll your sleeves up and do the work. And that starts with you. 

Not with downloading another dating app or scrolling Instagram late at night wondering why it hasn’t happened for you yet. It’s like preparing for a marathon, right? You wouldn’t show up on race day without training. You get your body ready, develop endurance, you know, practice your pace, all that stuff. And dating relationships does require a little bit of the same prep, but it’s the internal work rather than just getting out there and dating. 

And I had this client actually, a wonderful surgeon, who initially questioned whether finding love, you know, was it worth the effort, the heartbreak, giving her insane schedule, you know, what surgeons are like. And she did this deathbed perspective exercise with me and had this kind of moment of clarity. She realized that, you know, she was proud of all the lives she saved. That was meaningful work and an incredible legacy. 

But she also deeply wanted to share her life with someone. And she told me, I don’t want to be the doctor who saved everyone else whilst actually missing out on that. experience for myself. And that clarity became her kind of compass. She didn’t suddenly get more hours in a day, but she became more intentional about how she used the hours that she had. So a lot of it is about being intentional. Yeah, so yeah, my program is designed, you know, my Evolve for Women program, I designed it specifically for this journey. 

You know, I’ve walked the path myself. I’ve only ever been a coach for many years, but I’ve only ever coached on anything, you know, matters that I have walked the path on myself. You know, balancing that in my past life, balancing that significant professional success with creating a fulfilling relationship. So I teach all of this in my program, so I’m not just talking from a textbook or from theory. I’m the guide that’s already hiked the trail, so I can show you where the shortcuts are and which paths lead to dead ends. 

But the truth is you don’t have to choose between career success and a beautiful romantic connection. You can have both. And there’s that false choice out there that keeps too many brilliant women out there a little bit lonely despite their achievements. So yeah, I mean, what you need is an approach that, you know, you can have both, that honors both your amazing ambition and your, you know, your want for a connection. It’s okay to want a relationship. You’re not desperate. You’re not lonely. You haven’t left it too late. 

So if you’re willing to bring a little bit of dedication and intelligence to your love life that you bring to your career, then, you know, the proof’s in the pudding. 

And I’ve seen it happen with all of my clients. But it starts with taking that, I deserve happiness too, and giving your heart that attention as much as that mind of yours is at work. So I hope that makes sense.

Sarah E. Brown 

Well, ending on you can’t have both is a great way to end this conversation. Lynda, thank you so much for being with me. Thank you. It’s been a pleasure to be on your brilliant podcast. 

Thanks for listening to the KTS Success Factor podcast for women. If you like what you are hearing, please go to iTunes to subscribe, rate us and leave a review. And if you would like more information on how we can help women in your organization to thrive, then go to www.sarahebrown.com. You can sign up for our newsletter, read show notes and learn more about our podcast guests, read my blog, browse through the books, or contact us for a chat. Goodbye for now.

Sarah E. Brown
Sarah E. Brown