Life on the Road

Inspired by Jack Kerouac’s On the Road, my early twenties were spent traversing America. From the endless daylight of Anchorage, Alaska, to the vibrant streets of New York City; from the serenity of South Lake Tahoe to the bustling scenes of San Francisco and Los Angeles; and from the historic vibes of Key West to the cultural mosaic of Tampa and Austin, Texas—each location not only enriched my life with new experiences but also shaped the person I am today.

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From Travelling Barista to Web Design IT Nomad

Before diving into the world of IT, I embraced the life of a traveling barista, moving from city to city, brewing coffee by day and building websites by night. This journey wasn’t just about making ends meet; it was about exploring the intersections of technology, creativity, and personal growth. My stint as a line cook at Jimmy Buffett’s Margaritaville in Key West—crafting over a thousand “Cheeseburgers in Paradise” every day—added another layer of adventure and resilience that would surprisingly serve me well in the tech world.

An Unexpected Turn in the Florida Keys

My journey eventually led me further along the Florida Keys to Hawk’s Cay Resort, a private 60-acre island located at mile marker 61 on the Overseas Highway. Arriving several years after Hurricane Andrew had devastated the area, I was introduced to a community rebounding from significant destruction. It was here, in this resilient community, that my unexpected but fulfilling career in IT began.

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From Barista to IT Director

At Hawk’s Cay, my tech skills listed on my resume caught the attention of my future mentor. Under his guidance, I transitioned from Assistant Director of IT to Director of Information Technology in two years, spearheading my first major project—migrating Citrix from NT4 to Windows 2000 using Citrix Presentation Server. This not only boosted the resort’s operational capabilities but also cemented my passion for remote access technologies.

My First Tech Space: A Converted Hotel Room

My initial steps into IT were taken in a converted hotel room at Hawk’s Cay, where my office space was the old bathroom—cramped, unconventional, but incredibly fitting for someone whose career trajectory had been anything but ordinary.

Embracing the Unconventional

Throughout my career, the lessons have been clear:

• Adaptability: Transitioning from a nomadic lifestyle and diverse roles like a line cook and web designer to IT leadership taught me the value of adaptability and quick learning.
• Resilience: Just like enduring 24-hour sunlight in Alaska, hurricane seasons in Florida, and the high-pressure kitchen at Margaritaville, professional life required resilience.
• Mentorship: The influence of a good mentor can change the trajectory of a career, offering insights that textbooks and formal education often cannot.

Connect and Share Your Journey

Feel free to connect with me on LinkedIn, send me a DM on my page at www.linkedin.com/in/boehmjesse, or email me at IAM@jesseboehm.com. Let’s share our experiences and insights to inspire and learn from each other. What was your first job in IT, and how did it shape your career? I’d love to hear about your entry into the field and the lessons you’ve carried with you.