This is the most powerful insight I know: Our deepest insecurities surround our greatest gifts. The very qualities we’re most ashamed of are usually the keys to finding real love. These qualities are your Core Gifts. This episode will help you find them.

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Episode Table of Contents


Deeper Dating: How to Drop the Games of Seduction and Discover the Power of Intimacy
Deeper Dating: How to Drop the Games of Seduction and Discover the Power of Intimacy


In my decades of practice as a psychotherapist, this is the insight that has inspired me most: Our deepest insecurities surround our greatest gifts. Those gifts are the greatest, richest key to finding love and helping it grow and thrive. In this podcast, you’ll learn how to discover your own core gifts, so stay tuned to Deeper Dating.

In my decades of practice as a psychotherapist, this is the insight that has inspired me most:

Our deepest wounds surround our greatest gifts.


The Key To Finding Love: Your Core Gifts


Our deepest insecurities is the key to finding real love
Our deepest insecurities are the key to finding real love. Photographer: Maurice Williams | Source: Unsplash


I’ve found that the very qualities we’re most ashamed of, the ones we keep trying to reshape or hide, are in fact the key to finding real love. I call them Core Gifts, and I explore them in great detail in my book Deeper Dating: How to Drop the Games of Seduction and Discover the Power of Intimacy.

It’s so easy to get lost in the quest for self-improvement. Every billboard seduces us with the vision of a happier, more successful life. I’m suggesting an opposite road to happiness. If we can name our own awkward, ardent gifts, and extricate them from the shame and wounds that keep them buried, we’ll find ourselves on a bullet train to deep, surprising, life-changing intimacy.

The characteristics I find most inspiring

Over the years, I realized that the characteristics of my clients which I found most inspiring, most essentially them, were the ones which frequently caused them the most suffering.

Some clients would complain of feeling like they were “too much”; too intense, too angry, or too demanding. From my therapist’s chair, I would see a passion so powerful that it frightened people away.

Other clients said they felt that they felt like they were “not enough”; too weak, too quiet, too ineffective. I would find a quality of humility and grace in them which would not let them assert themselves as others did.

Clients would describe lives devastated by codependency, and I would see an immense generosity with no healthy limits.

Again and again, where my clients saw their deepest insecurities, I also saw their most defining gifts!

Understanding Our Deepest Struggles


Understanding our deepest insecurities is like viewing a tapestry from the back
Understanding our deepest insecurities is like viewing a tapestry from the back. Photographer: Diego | Source: Unsplash


Cervantes said that reading a translation is like viewing a tapestry from the back. That’s what it’s like when we try to understand our deepest struggles without honoring the gifts that fuel them.


When we understand our lives through the lens of our gifts it’s as if we step out from behind the tapestry and really see it for the first time. All of a sudden, things make sense. We see the real picture, the moving, human story of what matters most to us. We begin to understand that our biggest mistakes, our most self-sabotaging behaviors were simply convulsive, unskilled attempts to express the deepest parts of ourselves.

Susan’s Story: Her kindness became a curse

Susan came to therapy after her boyfriend of two years left her. She had put the whole of her heart and all her energies into her relationship, and when it ended, she felt utterly destroyed. “Why can’t I let go and move on like he did, or as my friends tell me I should?” she asked me on her first visit.

As she described her relationship history, I saw a consistent quality of kindness in her; a soft-heartedness which people kept taking advantage of. Susan appreciated these qualities in herself, but she also felt like they were a curse. (That very ambivalence is one of the main indicators of a core gift.) I sensed that a key to her healing lay precisely there.

Again and again, we worked at helping her reframe her sensitivity not as a weakness, but as a gift that she-as well as her former partners-didn’t know how to honor.

It sounds simple, but seeing these qualities as a gift was the foundation of new dating life for her. By seeing their worth, she could learn to understand, honor, and even treasure them.

The Gift Theory


The Gift Theory
The Gift Theory | Photographer: Rob Laughter | Source: Unsplash


When Susan looked at her life through the lens of her gift, she felt triumphant. “I was right all along!” she said. “Those things that bothered me about my boyfriends bothered me for a reason. I wasn’t crazy. I just didn’t honor my gift and I found men who were all too happy to agree with me.”

I’ve named the approach I used with Susan “Gift Theory.” The easiest way to explain Gift Theory is by starting with the image of a target. Every ring inward toward the center moves us closer to our most authentic self. In the center of the target, where the bull’s-eye is, lie our core gifts.

Gifts aren’t hall-passes to happiness

Core gifts are not the same as talents or skills. In fact, until we understand them, they often feel like shameful weaknesses, or as parts of ourselves too vulnerable to expose. Yet they are where our soul lives. They are like the bone marrow of our psyche, generating a living stream of impulses toward intimacy and authentic self-expression.

But gifts aren’t hall-passes to happiness. They get us into trouble again and again. We become most defensive-or most naïve-around them. They challenge us and the people we care about. They ask more of us than we want to give. And we can be devastated when we feel them betrayed or rejected.

Creating Safer Versions Of Ourselves

Since the heat of our core is so hard to handle, we protect ourselves by moving further out from the center. Each ring outward represents a more airbrushed version of ourselves. Each makes us feel safer, puts us at less risk of embarrassment, failure, and rejection. Yet, each ring outward also moves us one step further from our soul, our authenticity, and our sense of meaning. As we get further away from our core gifts, we feel more and more isolated. When we get too far, we experience a terrible sense of emptiness.

So, most of us set up shop at a point where we are close enough to be warmed by our gifts, but far enough away that we do not get burned by their fire. We create safer versions of ourselves to enable us to get through our lives without having to face the existential risk of our core.

Discover your own gifts

The Gift Theory model invites us to discover what our core gifts are (most of us don’t really know), to extricate these gifts from the wounds that keep them buried, and to express them with bravery, generosity, and discrimination in our dating life. When we do this, we find healthy love moving closer.

If you’re looking for love, try to discover your own gifts. They shine in your joys and strengths, but they also live-and hide-right in the heart of your greatest insecurities and heartbreaks. If you learn to lead with them in your dating life, you will find-almost without trying– that you’re experiencing mutual attractions with people who love and treasure the very gifts you’re discovering.

An Invitation From Ken

In future episodes, we’ll explore in much greater detail how to discover your own core gifts. In the meantime, I invite you to take two or three minutes to reflect on the following question:

Are there essential qualities in you which have sometimes felt more like a curse than a gift?

Perhaps you haven’t known how to handle them, or maybe you’ve had the painful experience of other people misunderstanding or taking advantage of them. Take a minute to begin to put words on these qualities. As you name them, you’ll learn to honor them, and you’ll come to understand your struggles, your intimacy journey and your life story in a new way.