2 Hours in Positano that Changed My Life

Not only was I satisfied for having tracked down the source of my curiosity, but the moment itself was just such a perfect snapshot of what I had imagined this place would be. I was so struck by the scene, that I quickly grabbed my camera and captured the moment so it would never fade from my memory.

Then something absolutely amazing happened that would alter the course of my life, from that moment on.

It was a cool morning in April of 2011 when I found myself wandering around this cliff side town of Positano, Italy. Truth be told, it wasn’t even on my list of “must see” places during this trip. We wouldn’t have been there at all if it wasn’t for my mother insisting that “we had to visit the Amalfi Coast before making our way to Pompeii.”

She knew. For those who have never been, Positano, Italy is one of several towns and cities that line Italy’s west coast near the Bay of Naples. Our tour bus journey from Naples to Positano was a winding path of roads that clung to the edge of rocky cliffs, weaving it’s way along the coastline.

On this chilly April morning the misty skies leant a surreal nature to the whole experience. After descending through what seemed like one impossible switchback after another (and witnessing some of the most miraculous mini-bus driving I have ever seen), we finally arrived in the heart of Positano. I stepped off the bus and fell in love with this unique Italian beauty.

Small shops, cafes and hotels line the cobblestone streets. Printed linens and lemons the size of small gourds hung from storefronts, and warm cappuccinos were being set down with biscotti’s atop outdoor tables. Arched pathways made of purple petunia flowers decorated our path as we set off to explore this cliffside wonder.

We shopped, tasted and drank in the postcard scenes all around us until finally we arrived at the stone wall overlooking the cobbler—and by then I was smitten. But I was also a little sad. Our morning was ticking away, managed by the tick-tock schedule of our Italian guide. After just two hours there, we boarded the bus again to make our way to Sorrento and Pompeii. Just as I had fallen in love, it was already time to leave.

That’s why the moment hit me so hard.

By this point in my life, I had already been in business for myself for 10 years. I had started with a flaming parachute leap from a dotcom startup in late 2000, and armed with just US$6,000 in savings and the equity I had built in my relationships over my career. From my living room—and with dogged determination—I found a way to survive for 10 more years, growing one client at a time.

But that was just it. After 10 years, I was still just “surviving” the creative agency I had always dreamed of building. I was able to support my wonderful family and my small staff, but we always operated one project to the next, navigating a predictably unpredictable cash flow. The hard truth was that my company really owned me. There was plenty of optimism but never any certainty (which meant profits were rare).

Eighteen months before I found myself here on the Amalfi coast, I was introduced to the Entrepreneurs’ Organization (EO). I had spent a year-and-a-half learning from the experiences of a group of peers I never knew I had, fellow business owners.

More than anything that I learned from the expert business resources I had access to, my thought process was mostly altered by the realization that my peers each had a different relationship to their business. Mine was very personal, while theirs seemed much more objective overall. I began to realize that the only business plan I had ever had was, “Just don’t go out of business”. It had been a long 10 years, never knowing what tomorrow would bring. I knew then that it didn’t have to keep being that way.

Back in Positano, I grabbed the handrail in front of me, looking out at the misty waters ahead. A vision suddenly came into sharp focus and I grinned as a powerful wave of emotion rolled over me. These moments in life are rare, and if you’re not paying attention, it’s easy to disregard them as some silly daydream. I knew enough to stop and say it out loud to someone who would hear my words for what they were. I turned to Lisa (pictured above) and said this:

“We are going to come back here in ten years and spend six weeks here over the summer, and at the end of those six weeks I want to be able turn to you and ask ‘do you want to spend another six weeks here?'”

I knew if I could afford to freely ask that question, I would have completely transformed my business from being one that was still surviving, to one that was finally thriving. So how has that moment shaped my life? It has been nearly six years since I made that commitment in Positano and today my life is right on course to fulfill my vision.

My firm, iluma Agency is growing aggressively and profitably, with a strong leadership team and incredible focus. We know what makes us tick, who we are, and how we add value. As a result, we’ve enjoyed being named to the Inc5000 list of America’s Fastest Growing Private Companies, for three years straight. I’ve also been serving as the president of the EO South Florida chapter that I joined just seven years ago, volunteering many hours each week, while developing critical leadership skills and experience. And just yesterday, I booked a flight for a week-long trip back to Italy  with Lisa. We’re going to spend three days in Positano and this time I’ll begin scouting out our perfect 2020 summer home just three years from now.

I can’t wait to send you that postcard.

Looking back on my life since that moment, here’s what I’ve realized. If you never create an inspiring vision for your future, then all of your daily choices will only be filled with repeated lessons from your past.

Imagining myself on that cliff—and asking my wife that one simple question—has shaped my response to countless decisions. In that moment, I had no idea how I would make it a reality. Every day since I’ve been presented with countless, seemingly inconsequential choices. Over time I’ve tried to guide my answer to each one by asking myself, “Does this get me back to Positano by 2020?” And every small choice has built upon the last one, until now when I look ahead—and what once seemed like a dream—now looks like a clear and predictable future.

So ask yourself: What’s your Positano?

Aaron Lee graduated from EO Accelerator and went on to become an EO member in 2011. He says, “One of the most meaningful discoveries I made in EO Accelerator was that I was not alone as an entrepreneur. EO Accelerator allowed me to accept my mistakes, fill my experience gaps with wisdom and create an inspiring vision for my business.” Learn more about this life-changing program for first-stage entrepreneurs, and hear from other participants.