What’s the Happiest Moment of Your Life?

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Whenever someone asks me to imagine the happiest moment of my life, I always think of the same story. It’s my old fall-back.

It was Halloween day, and I was a freshman in college. And it was still warm enough to sit outside on a bench and read. So I grabbed the book I was reading at the time—The Beautiful and Damned, I believe. And I sat on a bench to the edge of our freshman quad, and I read.

Shortly after, some of my friends came out to play football in the quad. It was all guys and one female friend, AJ. And they kept asking me to play. But I was invested in my book. How often do I ever sit outside and read? So I declined. Repeatedly. I was determined to have this little picturesque moment with my book.

And then, just a few minutes later, one of my friends—with impeccable aim, I might add—threw the football directly at my book and tore the page I was reading in two.

That was it. They’d finally bothered me enough to provoke action. So I threw down my book and stormed the field. And I just started tackling people. And everyone was laughing. And, finally, we played a game for maybe an hour. And then lay in the grass and just looked up at the sky.

And I remember thinking it was a pretty perfect day.

Not even six months later, AJ got in a sledding accident and passed away. So I always carry that memory close to my heart.

Whether it’s truly the happiest moment of my life or just a story I’ve repeated so many times that it’s become true, I don’t know. But it seems like a nice story. And a good day. And it always makes me smile to remember not to take myself so seriously.

I’ve had a lot of happy days in my life. I think about laughing so hard I can’t breathe—the kind of laughing that actually hurts.

Or adventures—spontaneous adventures. I think about a year and a half ago, when my sister was having a miscarriage over Labor Day Weekend in Charleston. We heard at maybe 1:30pm, and by 5pm, my parents, Garrett, and I were in the car driving down to South Carolina. It was an adventure, for sure. The whole weekend was an adventure. And it changed the energy around something so tragic. To be a time of support and love.

Gosh, I think of so many road trip adventures. When I was younger, it was the only way I traveled—well, that and sleeping in European airports. I couldn’t afford much else. So we drove. All across the country. And I always remembered thinking the trip itself was more fun than the destination.

I mean, I’d cycle through every emotion under the sun. And want to kill everyone in that car at least three times. But it was an adventure.

Happiness is such an interesting concept. Because implicit in each of these scenarios is myself. I see myself—my Aligned, Zany, Free, Unmistakable, Successful, Vulnerable self. I see adventure and limitlessness. I see uncontrollability. I see roaring laughter and eyes swelling with tears.

And I know that I am home. When I’m happy, I’m home. Because I can feel something—maybe pure life force—running through my veins. And I remember I’m alive. I remember who I am.

For me, those moments—or at least the one I call the ‘happiest moment of my life’—became a kind of gold standard. Something I could compare all things against. Do I feel as free in my job as I did that? If not, how can I change things to feel that? And do I feel as spontaneous as that moment? Well, what could I do to add in more spontaneity?

I think of how many moments in my life do make me feel that. How my job has changed radically over the last 10 years—evolving through iteration after iteration. I think of times when I booked a ticket to Ireland just one week before I left (and right in the middle of my last week of college ever). I think about surprising Garrett with a trip to Italy but having relatively no plan when we got there, and making him decide every activity. I think about jumping on Sacred Circle Mastermind Calls with no plan and watching the magic unfold. Or even creating the first Sacred Mastermind with no idea what was going to come forward.

I threw down the proverbial book and stormed the field. Not enough course or book or lesson. But putting myself right in the action, and seeing what I could do.

Happy moments always teach me about who I am. Because those are the moments that I can see myself so clearly. They’re where I witness myself externalized. And think, “Yeah, this is the life I want to live.”

What’s the happiest moment of your life?

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