Twenty years ago last week, I packed everything I owned into my car and left Florida.
I was 24 years old, chasing a massive dream of working behind the scenes in the music industry, and convinced my destiny was waiting for me in San Diego, CA. Fortunately, I didn’t have to make that 3,000-mile drive alone. My lifelong friend Jaime rode shotgun.
Back then, our road trip strategy consisted of blasting The Killers on repeat, checking the oil at every single gas station, and relying on a packet of printed MapQuest directions.
We made it safely and took a celebratory photo when we arrived in San Diego:
Looking back, it was a massive risk to drive across the country on the pure hope of a dream. But the risk paid off. Within a year, I landed that dream music industry gig and ended up thriving behind the scenes for 13 incredible years. I started as an Admin Assistant but quickly stepped up to build out and manage their backend logistics from scratch.
Fast forward 20 years: Jaime came back to visit me in San Diego recently. We captured a photo to commemorate the milestone visit.
Reminiscing made me realize that taking a blind leap for a dream isn’t all that different from starting a business.
Today, both Jaime and I are following our dreams of self-employment. As anyone who has taken that leap knows, in the beginning, you are fueled entirely by momentum.
But eventually, the initial excitement settles down, the cheerleaders go back to their own lives, and you’re left at your desk realizing you have to handle the daily upkeep all by yourself.
I’ve spoken to many solopreneurs in the past few months, and a common theme has emerged. They want to grow, but they are stuck in at least one of these cycles:
🎯 Messy Lead Generation: Struggling to consistently bring new people into their world.
👥 Inconsistent Pipeline Follow-Up: Letting valuable connections go cold because they lack the systems or the mental space to follow up.
📁 Total File Disorganization: Wasting precious hours every single week just searching for things.
If you want to know what that actually looks like in real life, I dare you to look at your computer’s Downloads folder right now. If it looks like a digital graveyard of unnamed PDFs and mystery screenshots, you are not alone.
But driving your business forward while navigating that kind of daily friction is like trying to read a map at 70 mph.
Being a solopreneur doesn’t have to mean driving solo. Even if you aren’t ready for a full-time co-pilot yet, you can still get some help clearing your view.
This is exactly why I created the Digital Foundation Reset.
This is my latest one-on-one package designed as a quick jumpstart to clear the structural roadblocks draining your mental space. I step in to clean up your Google Drive, establish clear naming conventions, and organize your files.
It’s a direct route to getting your time and sanity back so you can smoothly run the rest of your business with ease.
Ready to re-pave your path? Click the “RESET” button and let’s get you back on the road to your dreams!
What I’m Loving Lately
P.S. Want to hear the wildest part of the cross-country adventure from 20 years ago? Five days after arriving in San Diego, my car was stolen with every single possession I owned still inside. All that was left on the street was my floor lamp sitting next to a pile of broken glass. But that is a story for another day 🙃.