The Myth of “I’ll Be Happy When”

The Finish Line That Keeps Moving

I work three different jobs. During the day, I’m a managed care pharmacist. On the side, I’m a licensed real estate agent in Washington. And in between all that, I run my own independent pharmacy consulting business.

Why take all that on? Honestly, it started with practical goals. I wanted to pay off my student loans. Save up for a house. Hitting the milestones that we’re told means we’ve “made it.”

For a long time, I believed this: Once I reach those goals, I’ll finally feel settled. I’ll feel like I’ve arrived.

But that belief doesn’t really hold up.

The “I’ll Be Happy When…” Trap

There’s this common idea that once we hit a big goal, get promoted, clear our debt, buy the house, we’ll finally feel happy and satisfied long-term.

But what usually happens?

We set a new goal.

I’ve experienced this myself. After years of juggling multiple income streams and being disciplined with money, I started reaching the targets I had set. And instead of feeling this deep, lasting satisfaction, I caught myself thinking, Okay… what’s next?

More savings. Another investment. Another achievement. Another target just a little further ahead.

It felt like I was always running, but never actually finishing.

Why This Is a Problem

This mindset can quietly take over your life.

When we attach our happiness to some future milestone, we put off enjoying the present. We tell ourselves we’ll relax later. We’ll enjoy life after we’ve earned it.

But “later” keeps moving. And while we’re chasing the next thing, life is happening right now, and we’re barely noticing it.

I’m not against ambition. Goals matter. Hard work matters. But there’s a difference between working toward something meaningful and constantly feeling like whatever you have isn’t enough.

What I’m Starting to Realize

I don’t have all the answers, but here’s what I’m learning:

First, you have to notice the pattern. Once I realized I was always chasing the next milestone, it gave me space to pause and ask: Do I really want this? Or am I just addicted to achieving things?

Life isn’t on hold. It’s not waiting for me to reach some number in my bank account. It’s happening in the everyday moments, the early mornings, the long days, the small wins. If I can’t appreciate those now, hitting another goal probably won’t magically fix that.

“Enough” isn’t a number. It’s a decision. There will always be more to earn and more to accomplish. At some point, I have to decide what’s enough for me instead of letting the world decide it for me.

Something to Think About

If you’re someone who’s always chasing the next big thing, always telling yourself you’ll be happy when, maybe it’s worth pausing for a second.

Not to give up on your goals. But to ask: Am I building a life I actually enjoy? Or am I just chasing a finish line that keeps moving?

Because if you can’t find some fulfillment along the way, reaching the goal probably won’t suddenly create it.

And the race? It doesn’t really end.