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Love, Happiness and Success with Dr. Lisa Marie Bobby

High Achiever? Why Everything Works Except Your Relationships | Hilary Silver | Love | E478

Love, Happiness and Success with Dr. Lisa Marie Bobby

YAP Media Network | Dr. Lisa Marie Bobby

Relationships, Society & Culture, Health & Fitness, Mental Health

4.7890 Ratings

🗓️ 13 October 2025

⏱️ 37 minutes

🧾️ Download transcript

Summary

Some women seem to have it all together. They’re confident, capable, and thriving in their careers. Yet when it comes to love… it’s like they’re playing a game with a whole different rulebook. I’ve talked with so many high-achieving women who can handle anything at work (big goals, big responsibilities, big wins) but still feel unsure or unseen when it comes to real connection. In this episode, I’m sitting down with Hilary Silver, clinical therapist, master coach, and host of the Ready for Love podcast. Hilary and I talk about why strong, successful women so often find themselves repeating the same relationship patterns. We get into how old habits of proving, pleasing, and perfecting the ones that helped you rise so high can quietly start working against you when it comes to love. Hilary shares the three roles she sees most often in high achievers: the Pleaser, the Perfectionist, and the Pusher. Each one starts as a way to stay safe, but over time it builds walls that make closeness harder. We talk about what it really takes to lower those defenses, feel solid in who you are, and let love in without losing yourself in the process. Episode Breakdown: 00:00 Why High-Achieving Women Struggle in Love 01:29 Hilary Silver’s Journey From Therapy to Coaching 08:08 The Hidden Wounds Behind High Achievement 11:08 Protection Prevents Connection: Pleaser, Perfectionist, Pusher 16:20 How Self-Protection Creates Relationship Difficulties 23:33 The Tree Metaphor for Personal Growth 26:08 Coaching vs. Therapy: Choosing the Right Path 31:08 Transformation Stories and Hope for Authentic Love Now, take a moment to reflect. When do you catch yourself working hard to prove your value in love? What parts of you stay tucked away because you’re afraid they won’t be accepted? And what might happen if you stopped trying to earn love and allowed yourself to receive it instead? I’d love to help you take the next step toward deeper, more authentic connection. You can schedule a free consultation with me or a member of my team. It’s a private, no-pressure space where you can share what’s been on your mind - whether that’s building self-worth, breaking old patterns, or learning how to open your heart again. We’ll help you find the right support so you can move forward feeling clear, encouraged, and hopeful. Come find me on Instagram, Facebook, or YouTube. I share stories, insights, and gentle reminders every week to help you stay grounded and connected as you grow. And if today’s topic brought up a question or an “aha” moment, I’d love to hear from you. Let’s keep talking about this - we’re all learning how to love better, together. xoxo, Dr. Lisa Marie BobbyGrowing Self

Transcript

Click on a timestamp to play from that location

0:00.0

98% of the women that we talk to when I ask them what they're most afraid of in being vulnerable

0:05.6

with a high quality person who's at their level is, I'm afraid that I'm going to let him see

0:12.0

who I am and he won't like what he sees and he'll leave. Then I'm not good enough.

0:16.6

So if you've ever wondered why women who seem like they have it all together, they are powerful, high achieving, ultra-competent in one part of their lives, typically their careers, in other parts of their lives, like their personal lives, their love lives are really struggling.

0:36.6

They are single and don't want to be. They're feeling stuck.

0:39.9

Feel like they're settling in love. This conversation is for you. Welcome back to love happiness and

0:47.3

success. I'm your host, Dr. Lisa Marie Bobby. And today I am joined by my pal Hillary Silver to talk about this weird paradox that can happen

0:58.4

with high achieving women and this trap that so many fall into. This belief that constant doing,

1:05.3

proving, achieving is going to earn them love in the same way it earned them success. Spoiler alert, it does not. And Hillary is

1:14.6

here to tell us why and what amazing women can do a little differently in order to get better

1:21.2

results in their personal lives. So, hello, Hillary. But let's just start with this. And maybe, I mean, if you could take us in a bit to your

1:30.2

origin story, like where you're coming from and how this particular type of earthling turned

1:37.9

into a passion project for you to help. Yeah. Well, I started as you in Denver with a therapy practice and I did that for

1:47.8

about 14 years and I really honed in on couples and relationships. I think because I had this weird

1:54.1

belief that if I could do couples therapy really well, then I was a really good therapist because

1:58.5

that's really hard work. It is so hard. It's the hardest.

2:02.5

So it was really good training. I got so much great experience from working with couples on the

2:08.4

most difficult life and relationship issues, right? Narcissism, infidelity, addictions, all the things.

2:15.2

But I really didn't enjoy it. I didn't. And so I really started to pull away from that

2:20.6

and focus on individuals who have relationship issues. And underneath all of that, what I was

2:26.1

enjoying the most was really about empowerment, relationship with self. And in the last probably five

2:31.8

years of my practice, I was really developing a curriculum without

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