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