Chasing Success: How to Stop the Cycle and Find Fulfillment Now

Chasing Success: Why Fulfillment Isn’t Found in the Next Milestone

Learning to Redefine Success and Find Peace Where You Are

Lately, I’ve been thinking about how easy it is to chase what’s next —
the next milestone, the next title, the next achievement.
Believing that’s where security or fulfillment lives.

I’ll be totally honest: I’ve done this for most of my life. And recently, I saw just how sneaky that pattern can be.

The Endless Chase for “Enough”

When I was in my late twenties, I thought owning a home would finally make me feel safe and successful. After years of saving and striving, my husband and I bought land with a double-wide.

I remember thinking, “Okay, now I can finally exhale.”

But almost immediately, my mind moved the goal line.
“Once we build the house, then it will feel complete.”

Six years later, we built it.
And almost instantaneously, my thoughts found a new “next”: the decks, the garage, the bathhouse…

That’s when it hit me:
I wasn’t chasing a house — I was chasing a feeling.

And no amount of progress could deliver it, because I was measuring success by the wrong metric.

When Achievement Doesn’t Equal Fulfillment

A client of mine once said it even more clearly.

She’s a driven, high-achieving leader in New York — someone who, from the outside, had made it.
Big role. Big salary. Beautiful home. Loving partner. Adorable dog.

But inside, she felt exhausted and empty — saying yes to everything, hoping her team would finally see that she’d arrived.

Eventually, she burned out and had to step away.

Only then did she realize she’d built a version of success that left no room to actually enjoy her life.

The Real Reason We Keep Chasing

What I’ve learned — and what I help my clients see — is this:
The chase is never really about the next thing.

It’s about wanting to feel something deeper — safe, seen, at ease — and believing that doing more will finally deliver that feeling.

But it doesn’t.

Because fulfillment doesn’t live in the next milestone.
It lives in our capacity to be present where we already are.

A Reflection for You

So here’s something to ponder this week:

What are you chasing right now — and what do you hope it will make you feel?
And what would change if you stopped chasing that feeling, and started cultivating it right where you are?

With love,
Lindsay