15. Why “I’ll be happy when…” never works, and what to do instead

15.  Why “I’ll be happy when…” never works, and what to do instead

Welcome to the blog version of the Redefining Happiness Podcast. I’m Karen Castillo and in this post, we're diving into a mindset that many of us fall into without realizing it. It sounds like this:

“I’ll be happy when I lose the weight…”
“I’ll be happy when I finally get a break…”
“I’ll be happy when the house is done… or the job is better… or find the right partner…”

It’s that idea that happiness is always just over the next hill. That once we “arrive” at the next milestone, we’ll finally feel complete.

It’s the belief that fulfillment is waiting for us at some distant finish line. The belief that once we finally achieve something, we’ll feel happy, whole, and fulfilled for good

And if you’ve ever reached a long-awaited goal and still felt like something was missing, you know exactly what I mean.

Why Arrival Doesn’t Deliver

This mindset can feel motivating at first. It gives us something to aim for. And there’s nothing wrong with having goals. The problem starts when we tie our emotional well-being to those goals, expecting them to permanently change how we feel about our lives.

Because often, it doesn’t. Not for the way we thought it would.

You finally move into the new house, and then the to-do list starts. You land the promotion, and it comes with new pressure. You lose the weight, and then you wonder why you still don’t feel more confident.

It’s not that the goal was wrong. It’s that the emotional payoff we imagined doesn’t stick around the way we thought it would.

The Research: Why This Happens

There’s a well-known concept in positive psychology called the arrival fallacy, introduced by Dr. Tal Ben-Shahar.

He describes it as the illusion that happiness lies at the end of accomplishment. But what actually happens is that once we arrive, the positive feelings fade quickly, and we start chasing the next thing.

In his words,

“The arrival fallacy is the illusion that once we make it, once we attain our goal or reach our destination, we will reach lasting happiness.”

He explains that our brains are wired to pursue, not just to arrive. And when we believe happiness lives only in the destination, we overlook the value of the journey itself.

Think of the outcome as the trophy. You don’t train for and run a marathon just for the trophy. You do it for the experience, the health benefits, the challenge, the community. I’m really guessing here. I am so not a runner. But the metaphor stands. Focus on the process, and enjoy the outcome when it arrives, knowing it’s just one more experience in your life.

This idea’s been echoed in newer studies, including research by Matthew Killingsworth and Daniel Gilbert in 2010, which found that people are generally less happy when their minds are focused on the future instead of the present. Even when people were doing something they usually enjoyed, if their minds were somewhere else, especially thinking about the future, they felt less happy. So even while working toward something exciting, if our minds are always somewhere else, somewhere in the future, we miss the happiness that’s already available now.

Why We Believe the Myth Anyway

So why do we believe this myth? From the time we’re young, we’re taught to chase the next thing. We’re rewarded for achieving, and we’re often told that success equals happiness. We’re sold the idea that we’ll feel whole once we achieve the next thing. So it makes sense that we’d tie our well-being to external markers.

We’ve been taught to live on a timeline: graduate, get the job, get married, buy the house, climb the ladder. It’s easy to believe that each milestone will bring more happiness. After all, that’s what we’ve been told.

We also live in a culture that celebrates achievement, productivity, and the appearance of having it all together. But we’re rarely taught how to feel satisfied along the way.

Add to that the constant highlight reels we see on social media, and it’s no wonder we feel like happiness is always just one step away.

The Research: Why Arrival Doesn’t Deliver

There’s a well-documented tendency in psychology where we overestimate how happy something will make us, and for how long. It’s called affective forecasting, and it refers to the way we try to predict our future emotional states.

The problem is, we’re not very good at it.

When we imagine reaching a goal, like getting a promotion, buying a home, or hitting a milestone, we picture a big emotional payoff. And we believe that payoff is going to last. But in reality, the emotional high is usually smaller and shorter than we expected.

This happens because we tend to focus too much on the one thing we’re imagining, like finally getting that dream job or finding the right relationship, and we forget that the rest of life will still be happening around it. The stress, the routines, the responsibilities, they don’t go away just because one thing changes.

We also underestimate how quickly we adapt. Even the most exciting accomplishments eventually become part of our normal lives. That emotional spike fades, and we’re left wondering why it didn’t fix things the way we hoped it would.

So if you’ve ever reached a goal and felt a little disappointed, or like you should be happier than you are, there’s nothing wrong with you. You’re not ungrateful or hard to please. You’re human, and your brain just did what it’s wired to do. This is why so many of us experience a strange letdown after big life milestones. The wedding is over. The degree is earned. The weight is lost. But that feeling of fulfillment doesn’t stick around.

A New Way to Think About Arrival

So what do we do instead? To start, you can shift your attention from the outcome to the journey. Fall in love with the process.

What if we stopped asking, “How do I get there?”
And started asking, “How do I want to feel along the way?”

Real happiness isn’t something you arrive at. It’s something you build into your life now, through how you live, how you think, and what you prioritize.

Also, put your goal into perspective. Your goals can still matter. But let’s stop putting so much pressure on them to carry our happiness.

You can still want the job, the trip, the home, or the degree. But don’t put all your emotional weight on its arrival. Start building the emotional life you want now.

This is where real happiness lives. Not at the finish line, but in the life you’re living along the way.

When happiness becomes something we nurture in the present instead of something we postpone for later, we create a life that actually feels good while we’re living it, not just in memory, not just in theory, but day to day.

This Week’s Happiness Challenge: Catch the Arrival Thought

This week, I want you to notice whenever you say or think,

“I’ll be happy when…”

It might be about your job, your appearance, your family, or your goals.

When you catch it, pause and ask yourself:

• What am I hoping I’ll feel when I arrive?
• Is there a way I could bring that feeling into my life right now?

Maybe you’re craving peace. Could you build five minutes of stillness into your evening?
Maybe you want to feel proud. Could you acknowledge one thing you’ve done today that deserves your own approval?

You can a worksheet with an expanded version of this challenge in a simple journaling format to inside the FREE Resources Hub. 

Final Thoughts

There’s nothing wrong with working toward goals. But you deserve to feel content and fulfilled while you’re still on the way. There’s no one thing waiting for you in the future that is going to complete your life, no matter how amazing it is.

Happiness isn’t waiting at the finish line. It’s something you can practice and experience right now, by shifting the way you think, noticing what matters, and experiencing all of the steps along the way without impatience.

Thanks so much for spending this time with me.

If you know someone who’s stuck in “I’ll be happy when…” thinking, I’d love it if you shared this posy with them. And don’t forget to grab your free worksheet in the Podcast Resources Hub.

I’ll see you next time.

😚🎶🪕