Why High Achievers Struggle in Love: Breaking Through Relationship Difficulties (with Hilary Silver)

Why High Achievers Struggle in Love: Breaking Through Relationship Difficulties (with Hilary Silver)

Lisa Marie Bobby, PhD, LMFT, BCC

Dr. Lisa Marie Bobby is a licensed psychologist, licensed marriage and family therapist, board-certified coach, AAMFT clinical supervisor, host of the Love, Happiness, and Success Podcast and founder of Growing Self.

Some high achievers seem to have it all together. They’re confident, capable, and thriving in their careers. They know how to set goals, lead with confidence, and make things happen. But when it comes to love, something feels off. Many women who can manage teams, solve complex problems, and handle anything life throws their way still face relationship difficulties that leave them feeling unseen, unsure, or unfulfilled.

If that sounds familiar, you are not alone.

In my latest episode of the Love, Happiness, and Success podcast, I sat down with Hilary Silver, clinical therapist, master coach, and host of the Ready for Love podcast, to unpack this paradox. We talked about why so many strong, successful women face relationship difficulties, and how habits that once helped them succeed — like proving, pleasing, and perfecting — can quietly create walls that keep real intimacy out.

This conversation is close to my heart, because I see this pattern so often in my practice. Many high achievers believe the same formula that brought them professional success — effort, excellence, and control — will also create emotional fulfillment. Love does not work that way. You cannot earn it through performance. Realizing this can feel confusing and deeply personal.

Why High Achievers Struggle in Relationships

Hilary calls it “protection prevents connection,” and it is such an important truth. Many high-achieving women grow up learning that being capable, helpful, or perfect earns them love and approval. Those patterns can start early in families where affection was tied to achievement, or where a “good girl” was praised for being self-sufficient and easy.

Over time, that conditioning turns into armor. In adulthood, it can show up as over-functioning, over-giving, or feeling like you always need to be the strong one. You might find yourself in relationships where you do most of the emotional work, or where you feel valued for what you do rather than who you are. These are some of the most common relationship difficulties for women who are otherwise thriving.

As Hilary shared, these behaviors often fall into three main roles:

• The Pleaser, who bends, accommodates, and gives endlessly in hopes of being loved in return.
• The Perfectionist, who stays behind a polished façade, afraid that if anyone sees the messier parts, they will leave.
• The Pusher, who keeps others at arm’s length and avoids vulnerability altogether.

Each role is rooted in self-protection. Yet all three can create the very loneliness and disconnection we are trying to avoid.

How Old Habits Create New Relationship Difficulties

If you are a high achiever, you are used to solving problems with effort. You study harder, work longer, do more. But relationships do not respond to hustle; they respond to openness, trust, and emotional safety.

When you are used to proving yourself, love can feel uncertain. You might catch yourself wondering, “If I stop trying so hard, will they still want me?” Or you may feel drawn to people who “need” you, mistaking their dependence for connection. These dynamics can feel comforting at first, until they become exhausting.

Real intimacy asks for something different. It asks you to drop the armor. To let someone see you, not just the version you have perfected. That can feel terrifying for someone who has built an identity on strength and success. But that vulnerability is where genuine love begins.

Growing Beyond Self-Protection as a High Achiever

One of my favorite parts of this episode is when Hilary talks about the “tree metaphor.” She explains that what looks like the problem — struggles with dating, one-sided relationships, feeling unseen — are just the leaves. The real work happens in the roots, where your beliefs about love and worthiness live.

Maybe somewhere deep down, there is an old belief whispering, “I’m not enough,” or “Love has to be earned.” Coaching helps you bring those hidden stories into the light so you can grow something stronger in their place — a sense of worth that does not depend on achievement or approval.

As Hilary said, “You are not paying for sessions; you are investing in who you want to become.” And when you do that inner work, everything else shifts — your energy, your boundaries, the kind of relationships you attract. For a high achiever facing relationship difficulties, this kind of growth is life changing.