I Stopped Telling Myself “I’ll Be Happy When…”

Kyle Crocco
5 min readAug 7, 2019
Enjoying the simple moments, while waiting for my burger at The Habit.

My whole life I’ve been waiting for the day when I would be happy all the time. I figured when I reached a few milestones, achieved a few goals, then boom, I would be sitting with a buddha smile on my face for the rest of my life.

Don’t get me wrong. I wasn’t spending all this time unhappy, writing poems and sad song lyrics. Okay, maybe I did that for a few of my teenage years but for the most part, I wasn’t unhappy. I had fairly normal ups and downs. I just thought the downs might end and it would be all ups after I had achieved my goals.

I was always telling myself, I’ll be happy when I

Publish a book.

Get a girlfriend.

Make more money.

Become super fit.

Finish grad school.

Except, I never was.

I would achieve a goal, be excited for a few days, weeks, or maybe even a few months (if it was a new relationship). Then the happiness would pass. Daily annoyances would return. I would have a normal face, not even a Mona Lisa smile gracing my lips. I was neither extremely happy, nor extremely unhappy, but wondering when I could finally just be good all the time.

Then I realized what I needed to do: Set a new goal, achieve it, and then I would be happy forever.

Kidding. Then I found out why achieving goals wasn’t getting me what I wanted.

Achieving goals won’t make you happy forever.

Achieving goals is great when it happens. I remember achieving one of my biggest life goals: having my first book published. There it was, my words in print, with a cool cover and everything, sitting on a bookstore shelf for someone to buy. I was an author. My dream come true. Cue walking off into the sunset and eternal bliss.

Except the bliss wasn’t eternal. In fact, I went in the opposite direction. I felt empty inside.

What was wrong with me?

The problem, according to Daniel Gilbert, author of Stumbling Upon Happiness, wasn’t me: it was habituation. Once you achieve a goal, you become accustomed to the new normal. You adjust to the circumstances — be it a new car, house, job, relationship, etc. — and no longer derive any more excitement from the change.

I thought the cause for my short-term happiness (and sequential emptiness) was I had chosen the wrong goal. This put me in a constant cycle of setting new goals, achieving them, and thinking this time the happiness would last forever.

But I was missing half of the equation.

We need joy — and happiness.

According to vulnerability researcher Brené Brown, there is a difference between joy and happiness. Happiness is about external circumstances — it’s the excitement of the new house, the new car, winning a race, or getting a promotion. We need this kind of excitement in our lives but the excitement will always be fleeting.

What we also need in our lives is joy. Joy is different than happiness. Joy is about the ordinary moments in our life: laughing with friends at dinner, watching a sunset, or reading a good book. It’s about appreciating and expressing gratitude for what you already have. It’s not as exciting as achieving a goal but it makes you feel warm inside.

When I stopped the cycle of expecting eternal happiness by achieving goals, I discovered the pleasures of ordinary joy. I saw good things happened every day. When I wrote them down in a daily gratitude journal, I recognized all the moments I had taken for granted, never realizing how special they were.

I understood the importance of simple pleasures—having a beer at the local microbrewery, rollerblading at the beach on a sunny afternoon, or sleeping in on a lazy Saturday. It helped me refocus on what brought real pleasure in my life and stopped me from believing “I’ll be happy when…”

It also made me realize where much of my joy was coming from.

We need quality relationships too.

One last critical component to both joy and happiness in life is having quality relationships. For me, when I achieved a big goal, I found it much more fun if I could share that success with someone. Getting published was a dream—but celebrating that accomplishment by using the advance money to party in downtown Baltimore with my friend Wayne was better.

And for the ordinary moments in life, the ones I cherished most were my connections with friends and family. Watching a movie was nice, but the conversation after watching a new release with my buddy Rachel was better. Playing video games was entertaining, but my Sundays playing the same games online with my brother were much more fun.

The importance of connection is all backed up by the Harvard Study of Human Development. After following a group of men and their families for 80 years, the study director Robert Waldinger said the biggest takeaway was this: quality relationships were the key to health and happiness. Those participants who had quality relationships (be it friends, family, or romantic) had more happiness, health, and success than those who did not.

When I stopped following the delusion of “I’ll be happy when…”, I started experiencing more lasting pleasure in my life. I recognized the importance of connection and realized the wonder of ordinary moments.

Don’t get me wrong. I’m not ecstatic every day. I don’t walk around with that buddha smile on my face. But when things turn sour, as they do when I go to the DMV, I know how to find my way back to joy and happiness: practice gratitude and focus on quality relationships.

Kyle Crocco spends his daylight hours enjoying the simple moments as Chief Creative at BigSpeak Speakers Bureau and his evening hours focused on the pleasure of creating music for Duh Professors. He regularly publishes content about business thought leaders and personal growth on Medium, Business 2 Community, and Born 2 Invest.

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Kyle Crocco

Kyle Crocco is the author of Heroes, Inc. and Heroes Wanted.