Needing to bring in more money because writing about the locals and my life lived in Aspen wasn't enough, I stopped writing and started focusing on how to make more money.
I didn't realize it would become a six-year hiatus.
During that time, people kept telling me to write again. Complete strangers would send messages. Friends would ask what happened. Every once in a while something so bizarre would happen that it lingered in my mind, yet I resisted the calling.
One of those moments popped back into my head at 5:30 this morning, and I knew I had to write it down.
I was on the rooftop patio at Scarlett's (pre-pandemic, Catch Steak is there now) for a Kentucky Derby party with a friend. I was nursing a cold and wasn't drinking, which meant I had the rare opportunity to observe an Aspen party completely sober.
We struck up a conversation with a very animated guy. My friend was single, and I was thoroughly entertained watching the flirtation unfold as the three of us floated through the crowd meeting everyone in sight.
He was charming.
Until he shoved what looked like five sour gummy worms into his mouth at once, their day-glow blue and green bodies disappearing like a flock of startled birds. I'd seen robins in my garden eat with more finesse.
Then things got weird.
Which, if you stay at an Aspen party long enough, they usually do.
Announcing that he had to take a leak, he handed me a tiny glass bottle filled with white powder.
"Take care of this."
And off he stumbled toward the bathroom.
Being the only sober person there, my writer brain kicked in.
The underbelly of Aspen will take any excuse to celebrate, and if dressing up in oversized hats and seersucker suits helps disguise the darkness, all the better.
Just as I was thinking about slipping out, a big blonde woman appeared in front of me.
"HELLO!" she shouted.
Recognizing her, I matched her energy and shouted hello back, assuming we'd met before.
Apparently that opened the door.
"You're not listening!" she yelled.
I smiled politely.
"No, you're not FUCKING listening!"
Now she was inches from my face.
Instead of being alarmed, I found myself curious.
I knew she was a hairdresser who also claimed to be clairvoyant, so I decided to see where this was going.
Before I knew it, she wrapped me in a bear hug, spun me toward the sky and demanded,
"LOOK UP AND LISTEN TO WHAT THE UNIVERSE IS TELLING YOU!"
At this point I couldn't move even if I wanted to.
So I looked up.
And clear as day, one thought entered my mind.
START WRITING AGAIN, JILLIAN.
I remember thinking how funny it was that the Universe had chosen this particular messenger.
Still...
I didn't listen.
The block lasted another four years.
Ironically, it wasn't the desire to write that finally brought me back.
It was two people who fluttered into my life like little angels just as I was filling out applications to work for Aspen One and interviewing to become a concierge at a new resort.
I had convinced myself I wanted an admin job. A nice predictable job. One where I could wear a uniform, answer questions, stop thinking at an executive level, and finally stop worrying about money.
I was tired.
Mostly, I was tired of living in scarcity.
Instead, those little angels insisted it was time to build a new website and create an AI-driven event calendar for the valley.
And because I've learned that the best things in my life arrive disguised as detours, I said yes.
Now, with the launch of the newly redesigned Aspen Real Life, I've been writing fast and furiously.
The words are flowing again.
Which brings me back to the bottom line.
Every time I've chased money first, I've drifted away from myself.
Every time I've followed curiosity, connection, storytelling, and the people who light me up, the path has somehow appeared beneath my feet.
Maybe that's the lesson.
Maybe the bottom line isn't something to chase.
Maybe it's something that quietly follows when you finally start listening.
