Have you ever reached a milestone you thought would change everything — the new job, the house, the relationship — only to feel… underwhelmed?

It’s the moment you’re supposed to be celebrating. Everyone around you is proud. You tell yourself you’re proud too. And maybe you are, on the surface. But deep down, there’s a quiet disappointment: Why doesn’t this feel as good as I thought it would?

It’s the part no one talks about because it sounds ungrateful. But the truth is, you’re not ungrateful at all. You’re just realizing something most of us never stop to question: sometimes the dream doesn’t give us what we thought it would.

From “Show Me the Money” to “You Complete Me”

Have you ever seen the movie, Jerry Maguire? When we first meet Jerry, he’s not really chasing money for money’s sake. What he’s actually chasing is validation—the applause, the recognition, the proof that he’s worth something. Money and success were just the scoreboard he thought would finally make him feel enough.

But here’s the twist: no amount of contracts, deals, or dollar signs ever satisfied him. The more he won, the emptier he felt. Why? Because external success can only stroke your ego—it can’t soothe your soul.

It wasn’t until Dorothy and her son entered his life that Jerry finally got what he’d been craving all along. Their love, their belief in him, and the way they saw who he really was gave him the validation he had been chasing in all the wrong places. That famous moment—“You complete me”—wasn’t about Dorothy filling a void; it was about Jerry finally realizing that love, connection, and being truly seen were what he needed, not the money.

Aha Moment: What we often think we want (money, status, titles) is usually just a stand-in for what we really want (love, acceptance, security, worthiness). The trick is to stop chasing the scoreboard and start noticing the deeper need underneath it.

Why We Chase the Fantasy

There’s a reason this happens.

Looking outside of ourselves is easier. The fantasy gives us something we can point to, something other people will recognize as “success.” And deep down, part of us hopes that if the outside looks good, maybe the inside will catch up.

But the problem is this: no matter how much you achieve, buy, or collect, it won’t fix the emptiness if you never stop to ask what’s underneath it.

We chase the fantasy because it’s visible. But what we actually want is invisible.

My Condo Epiphany

When I bought my condo, I thought what I was chasing was independence — finally having my own rules, my own space, my own freedom.

But once I settled in, I realized it was so much more than that. It was a symbol of resilience, of responsibility, of becoming a woman who could depend on herself.

The condo wasn’t the victory. The feeling it gave me was.

And that’s the piece so many of us miss.

Even Pinterest Keeps Us Chasing

Think about it — this shows up in places as small as Pinterest.
We pin dream homes, perfect kitchens, stunning vacations. And sure, it’s fun to look at. But too often, pinning just keeps us stuck in “someday.” We collect images of a life we want instead of asking why we want it.
What if you paused before hitting save and asked: What’s the feeling behind this picture?
Maybe it’s not really about the marble countertops. Maybe it’s about wanting a space where people feel welcome. And if that’s true, you don’t have to wait for a remodel — you can start creating that feeling around your table tonight.

The Subtle Shift:

Here’s the shift that changes everything:

1. Name the fantasy. What’s the image you’re chasing?

2. Ask what it represents. What’s the feeling underneath it? Security? Freedom? Love? Confidence?

3. Find ways to embody that feeling now. Not when you’ve “made it,” but today.

This isn’t about lowering your standards. You can still want the house, the car, the career. But the point is, you don’t have to wait until those things arrive to live the way you want to feel.