why external success doesn’t bring happiness

The Endless Search for Reassurance: Why Worthiness Isn’t Found Out There by David Regan

We’re not living for happiness—we're living for reassurance. And because we don’t know it, we remain stuck, frustrated, and exhausted.

When we are living from ego—which is to say, when we are still carrying the belief that we are fundamentally unworthy—we spend our lives chasing one thing: reassurance.

This is not a conscious choice. It feels automatic, even necessary. As long as we remain uncertain about our inherent worthiness—our worthiness of love, joy, success, and the good things life offers—we live in a kind of existential fear. We may not name it that way, but it's always there, subtly shaping our decisions, our reactions, and our priorities. We’re constantly seeking something outside ourselves to tell us: You’re okay. You’re good enough. You matter.

In this state, outcomes become everything. Results feel like life-or-death matters—not because of what they are, but because of what they represent: our worth. We chase worthiness through accomplishments, beautiful partners, material success, approval, admiration. We set goals not just to grow, but to prove something—to quiet the doubt within. The ego turns our life into a scoreboard, where everything we acquire or achieve becomes a symbol of our worth. A promotion isn’t just a career milestone—it’s reassurance. We pursue the dream vacation, the attractive partner, the seven-figure bank account, the car we’ve always wanted— not simply to enjoy them, but to prove something to ourselves and to quiet the voice of doubt within. They’re all attempts to end the internal debate: Am I worthy?

But here’s the painful truth: external achievements can never resolve an internal belief. Ever.

No matter what we acquire, there is always someone with more—more beauty, more wealth, more charm, more success. The ego keeps us comparing, always looking sideways and ahead. There’s always someone funnier, someone more magnetic, someone with the “better” life. And the moment we notice it, the fragile reassurance we've built crumbles.

So we go back to chasing, back on the hamster wheel hustling for our worth.

We move on to the next goal, the next project, the next purchase, hoping that this time, the payoff will be permanent. We think, once I get that thing, I’ll finally feel safe, whole, complete. But even when we arrive—we retire early, take the luxury vacation, check all the boxes—our sense of safety is brief and we all to quickly feel an unsettling emptiness.

Why?

Because we’ve been trying to solve an internal wound with external solutions. And that never works.

What we’re really solving for isn’t joy—it’s reassurance.

We’ve been trying to silence the voice of unworthiness through performance and perfectionism. And in doing so, we’ve disconnected from the present moment and from ourselves. We’re not living our lives—we’re performing them. And we’re exhausted.

This is the root of so much modern suffering: we are not connecting to our joy, but chasing security. Not allowing presence, but grasping for proof.

And here’s what makes this even more frustrating: no one else can give us what we’re looking for. Not permanently. Because worth is not something to be earned. It is something to be remembered.

The belief that we are unworthy is not based on truth. It’s a misunderstanding—one born in childhood, forged in moments of pain, disappointment, unmet needs, and wounds we never fully processed. And because that belief lives in the subconscious, we rarely stop to question it. Instead, we chase things outside ourselves in hopes they’ll quiet the discomfort within.

But the healing begins when we realize: this is an inside job, that our discomfort is based on a belief we need to challenge.

No amount of external reassurance will ever satisfy an internal belief that you are not enough—we need to recognize the belief itself is false.

You don’t need to win anything, fix anything, or prove anything. You are already worthy—right now, exactly as you are. God did not make a mistake in giving you this life. The very fact that you’re here is all the proof you need. It’s time to drop the internal debate—it’s futile, unresolvable, and rooted in illusion. You have the power to choose differently. Choose to recognize your worth, claim it fully, and step into the happiness that’s been yours all along.

You don’t need a reason to feel worthy and the moment you stop trying to earn love, you make space to receive it.