After being questioned on why I chose the digital nomad life, I almost always get asked how?
As in, what do you do for work that allows you to live this lifestyle?
In the short version, I work in tech, and I work remotely. If you’re curious about how I got into that, my history, and my current status, read on.
What do you want to do when you grow up?
A long, long time ago, my Dad told me I should go to the local tech school in central WI. I could enroll in a two-year program, learn a trade, get a decent job, and then get my bachelor’s. I didn’t listen.
I thought I’d be better off at a university. I changed my mind about degrees a million times. The courses cost a ton, and I couldn’t figure out how they’d ever equip me with the skills to pay them back. It didn’t help that I preferred to party rather than worry about any of this.
It wasn’t a total loss, it’s where I had my first experience with computer science. Learning to code in C#. The course was brutal. I’d never done anything like it. Half the class was failing. I’d stay behind to ask questions. The professor would do his best to help, but at the end of the day, gave off vibes that I needed to accept my fate. Technology is not something everyone can understand. Because of the high fail rate, the professor said he’d weigh our grades against the highest score in the class for the final exam. I became determined. I studied my ass off and got something like a 78, which ended up being the highest score in the class & enough to pass.
Still, to this day, one of the best ways to get me to do something is to tell me I’m not capable. I am still deciding if that’s a good thing or a bad thing.
My half-assed attempts at a college degree in between partying went on for a couple of years. It wasn’t until my bestie finished their tech-school program that I realized I needed to get serious. She would be making twice as much money as I was. I’d been busting my butt working multiple jobs as a waitress, gas station attendant, bartender, and call center agent. I knew then and there that I did not want to continue as I was. Two plus years later, I finally decided to listen to my Dad.
Getting Serious about IT
I browsed through the tech school’s program catalog; phlebotomy, nursing, dental hygienist, agriculture, etc. I eventually landed on IT. My earlier experience stuck with me. Knowing it was challenging but I was capable would make it all the more rewarding to succeed.
Where other programs felt limited in growth, IT felt limitless. I could work with desktops, servers, networks, and programming languages. I could be a technician, an engineer, a developer, an architect. The only thing limiting me was myself.
I’d forgotten most of what I learned from my previous course. I naively considered myself computer savvy, which looking back, is a joke. I didn’t even know what an IP address was or the difference between CPU and memory. The courses were hard. I poured over the books, sentence by sentence & drew pictures until I grasped concepts. I gave myself neck problems and had dreams in binary.
The IT programs had a lot of overlapping courses that were prereqs for all associate degrees. It gave me a chance to see what piqued my interest the most. I decided to pursue the Network Specialist degree.
The network is how all computers talk to the internet and each other. It fascinated me. It was fun to map things out & felt like doing a puzzle. The program was intended to prepare you for the CCNA (Cisco Certified Network Associate) exam. When passed, would earn you a highly valued certificate in the industry.
I had finally decided I was going to be a Network Engineer and make my way up to Network Architect, the person responsible for designing the network.
My First IT Job
While still in school, I secured a job as a help desk tech at the call center I worked at. It wasn’t networking, but there was still a ton of overlap with what I was learning in school. Plus, they were flexible. I’d spend four hours in the morning working, then go to school for four, and then go back to work for four or whatever schedule they let me work out (these were the days before online schooling).
I would learn something at school (virtualization, switching, group policy, domains) and immediately look at how it was used at the call center. It was extremely helpful to see concepts learned at school applied in the real world.
I did everything from simple password resets & phone configs to cooling down an overheated server room with whatever fans we could find. As we tried to position them just right, a network engineer over the phone informed us of the rising temperature, decimals away from overheating, which would cause the switch to shut down. Outside the room, a director yelled at me that they would lose money if that happened. It’s the closest I hope I’ll ever come to having to diffuse a bomb, and still one of the most stressful things to happen on the job.
That same director once told me I’d never amount to anything in IT and should change my career choice because he was mad he forgot his password.
A Step Closer to Engineer Life
I moved on to another help desk role at a company in Wausau, WI, that provided managed services support. For my non-technical folks, that meant we supported IT for multiple businesses in the area. This was one of my favorite crews to work with. I’ve never laughed so hard or eaten so much ice cream on a job (despite the serious face below).
I eventually passed the CCNA & I was given the opportunity to work closer with the network and UC engineers. I remember realizing I knew nothing compared to these guys in those early days. It was difficult to apply what I had learned in school to the real world. Everything that I found confusing, I noted down and researched further when I had time.
I ended up moving out to California before I learned all I wanted, but I took with me enough knowledge to land my next job.
If you ever find yourself in the Central Wisconsin Airport, as of July 2023, it’s still my voice on the intercom system telling folks not to leave their bags unattended and to report suspicious activity.
Finally an Engineer
When I moved to San Diego, FINALLY, four years into my career, I landed a position as an engineer. I would be providing telephony and network support to the City of San Diego. I officially went from technician to engineer!
No more end-user support! Well, I still had to fix end-user phones, but no more fixing printing issues! (Unless it’s the network, which it always is until proven otherwise) But still, hallelujah!
Working for the city gave me a change to explore my new home more, with onsite visits to fire stations, libraries, lifeguard stations, and parks. It was always interesting. I had a great team that taught me a ton about cabling. They were always willing to lend their knowledge and were great mentors.
It was here my UC knowledge grew tenfold. I could change a name on a phone with my eyes closed, we must have got 30 of those requests a day. I learned how to create phone tree menus for libraries (Press 1 for this, 2 for that), set up call center agents, set up intercoms and paging, analog lines, and emergency lines. My role was definitely more UC Engineer than a Network Engineer at this point, I didn’t mind.
I worked for the City of San Diego for nearly two years. As I did, continued my studies, preparing for the next cert to get me closer to the architect role, the Cisco Certified Network Professional (CCNP).
First Taste of Remote Work
With that experience, I got my first remote job at another managed service company based out of Chicago with an office in San Diego. They mainly focused on supporting infrastructure devices. I did a little bit of everything with this job – UC, Security, Network.
Technically I was supposed to go into the office once or twice every couple of weeks, but hardly anybody else was there unless we coordinated. At this point, I’d had no goal to become a digital nomad and probably wasn’t even aware of the phrase. I did love working remotely, though. In 2019, the company granted me approval to go fully remote so I could move to OR. I’ve been working remotely since.
From Engineer to Leader
It was a crazy couple of years as an engineer. I became a jack of all trades, doing on-call rotations every three weeks for firewall support, 24-hour troubleshooting sessions for a global UC network, overnight upgrades, and whatever other random issues occurred.
I was fortunate to have an amazing team to turn to. If you didn’t know, IT people tend to have reps for being ‘prickly’ – but with this set of engineers, there was never any question too dumb. Every senior engineer was always willing and happy to give you a lesson on whatever, and that energy flowed through the team.
There were complex issues that we had to troubleshoot & always different. I sharpened my critical thinking skills and learned to be methodical with my troubleshooting, realizing if you understand how something works, you can more quickly understand why it didn’t work. Escalations to senior engineers usually included crude drawings and a list of things I’d gone through. Even if I couldn’t stick around for the solution, I always followed up. If I didn’t understand why something was done, I mapped it out until I did.
After two years, I was asked if I would like to take the Operations Manager position. I jumped at the chance. At the time, I thought it was a way to make a difference with the team and to continue my growth from engineer to architect someday. I soon realized leadership is a whole different beast.
Back to School
While in the manager position, I realized the industry was shifting. The skills I had learned to become a network & UC engineer, although still valuable, were changing through software and automation. I felt like I had two choices:
- Continue to earn my next certificate towards being an architect, Cisco Certified Internetwork Expert (CCIE) +/-18 months of studying followed by an in-person exam and lab.
- Get my Bachelor’s in Software Development, about two years of studying
I chose the 2nd. Getting my Bachelor’s degree was something I’ve always wanted to do. Plus, automating everything was a constant topic of conversation at work, and I was excited to learn the skills necessary to be a part of it.
The Leadership Detour
For close to 3 years, I was fully leadership oriented, managing a 24/7 team of twenty-plus people. Leadership could be incredibly fulfilling, helping with career growth, mentoring, and creating solutions. But it could also be draining. Layoffs, underperforming employees, budget cuts, client escalations. While I was busy working on my leadership skills, technology was continuing to evolve at a rapid pace. I had little time to keep up and couldn’t shake the nagging feeling that my dream of evolving beyond an engineer was getting further and further away.
It was also around this time that Bruno was diagnosed with cancer. I felt myself becoming angrier and less patient with the team. I no longer had the energy necessary to give the team the leadership they deserved. The nagging feeling continued to get louder and louder.
Back to Engineering
Fortunately, I had a director at the time who supported me in transitioning into a role that would allow me to be a lead and engineer. I’d be using skills I had as a network engineer, plus utilizing my recently acquired developer skills. It felt like a good compromise. My new team would consist of only two engineers.
It was going to take time to transition to the new position.
In the meantime, a new director came in. Bruno passed. I trained my replacement. I moved to my new position. Me and Trixie became full-time digital nomads.
And then, my new director cut my position, forcing me into a position that would have taken me on another detour away from growing my technical skills. I feared I would become comfortable in this position, furthering the gap between what I was doing and what I really wanted to do. Instead, I decided to take a bet on myself. I put in my notice and started focusing on finding a job as an engineer again.
A New Start
I’ll always be thankful for the opportunities this company has given me, especially being the place where I was able to start my digital nomad journey.
After nearly six years, the hardest part was definitely leaving behind the folks that I talked to every day and am lucky to call friends.
I just started my new role as a Principal AIOps Engineer and am excited to dive back in!
My Digital Nomad Office
I chose to buy a camper for two reasons. My senior pup, Trixie, needed a dedicated space, and I needed dedicated office space. I toured what felt like 1000 campers and didn’t find one with an office. It’s like people only pull these things around to have fun.
I decided the place in a camper where bunks normally are would make a perfect spot. I got to work tearing out the bunks in my camper and mounted two monitors to the wall as a workspace.
Network connectivity is provided by a cellular hotspot. A WeBoost cell signal booster is used when the signal is weak.
I’m incredibly grateful for remote work and try my best not to take it for granted. During my working hours, I need to be present and put forward my best effort. When I’m done, I need to recharge for the next day. Even pre-nomad life, I strongly believed in having a workspace you can be focused on and one you can walk away from.
In 169 square foot space, it’s only ever a few feet away, but it’s only used for work. I have a separate table I can use for eating, painting, or writing and not feel like I’m still in my office.
Final Remarks
If you’re still here, thank you for taking the time to read the story of how my career has progressed over the years. I could ramble on and on about all the amazing people and lessons, and experiences I’ve had over the years. While IT can be a challenging field, it is also a very rewarding field. I’m a true believer that a person can learn anything they set their mind to. If you’re considering a career in tech, I couldn’t recommend it enough, especially if you plan to go nomadic.
I love talking about this stuff. One of the most rewarding parts of leadership was helping people map out their career paths and seeing them succeed. If you want someone to kick the topic around with, feel free to hit me up on my contact page.
