From Corporate Grind to Global Freedom
I dropped out of college and started as a server at a retirement community in Colorado—what I thought would be a temporary gig turned into a nine-year journey that ended with me as a General Manager opening a new location in Naples, Florida.
I had everything most people strive for: steady income, leadership title, PTO, and time to travel with my family. But every time I returned from a trip, I felt like I was stepping back into a box I didn’t fit in anymore. While my family kept exploring, I returned to inboxes and routine. As 30 approached, that low hum of restlessness turned into a roar.
So I leapt out of the predictable and into something totally uncertain: the digital nomad life.
This blog isn’t just about what that means or how to do it—it’s about the messy, emotional, human parts of starting over.
What Is a Digital Nomad? (And What It Isn’t)
I casually surveyed about ten people who had been working remotely for the last 2–3 years, just trying to wrap my head around what it was like. Out of everyone I talked to, only one person—one—said their partner hated it. Everyone else told me they’d never go back to an office again.
That stuck with me. But here’s the thing—I still didn’t know if I wanted “in.”
Sure, it sounded amazing. Freedom, flexibility, morning coffee without a commute. But I was still clinging to the structure I’d known for years—corporate routines, HR policies, team meetings, clear lines of authority. I knew how to thrive in that world. I had climbed the ladder. I understood the rules. And even though it often left me unfulfilled at times, there was a strange comfort in it.
Letting go of that? Terrified me.
When I finally made the leap, I didn’t just step into remote work—I jumped into the trifecta of “what the hellephant did I just do!”
- I was entering a totally new industry.
- My brother was now my boss.
- And suddenly, “self-sufficient” took on a whole new meaning.
It’s easy to think you’re disciplined when someone’s watching. But what happens when no one’s tracking your hours? When your boss says, “Work whenever you want”? When your output isn’t tied to clock-ins but instead to whether a client’s digital marking succeeds or fails?
You don’t really know who you are as a worker until you’re thrown into the deep end with no life jacket and told to swim.
To quote Ted Chiang
“Anxiety is the dizziness of freedom.”
That was me.
And yet… even in the panic, even with the chaos, there was this spark of something new. I found myself waking up, sliding open the patio door, brewing my own coffee, standing barefoot at my desk, and thinking—this feels different.
Mornings didn’t feel robotic anymore. They felt like mine.
So what is a digital nomad?
It’s not just remote work with a passport.
It’s learning to manage yourself when there’s no blueprint.
It’s freedom, yes—but freedom that requires you to show up fully.
It’s scary.
It’s empowering.
And at first, I wasn’t sure I could do it. But I knew I had to try.
The Moment I Knew I Needed to Get Started
This wasn’t one of those impulsive “drop it all and start fresh” moments people joke about. This wasn’t typical Candace chaos. I was terrified.
My brother had floated the idea of me working for him years before—like 3 or 4 years ago. I had dipped my toes in on some small projects, tried to contribute, and absolutely fell flat on my face. So what did that do? Made me run back to my comfort of my office job. So, I stayed in my lane.
And then came Christmas of 2024. We were all together—me, Loren, Ma Ross—and she shared a medical update that was scary. Suddenly, I stopped asking others and started asking myself: Why the hell not?
No, I didn’t have it all figured out. I didn’t know the industry inside and out. But if there’s one thing I do know about myself, it’s that I figure things out when it counts. That’s always been my superpower.
Loren and I started having weekly meetings, walking through what this transition would actually look like. He was patient, detailed, and honest. But even with a plan forming, I couldn’t quiet the mental noise: Am I really about to give up my 401(k)? The office camaraderie? The health benefits? The comfort?
Even on the day I gave my notice, I almost backed out. I sat across from my boss at a Panera Bread—because nothing says “life-altering decision” like a You Pick Two—and when I finally said the words, “I think I’m giving my notice today,” my voice cracked.
I was that scared.
But you want to know what got me over the edge?
It was imagining myself 20 years down the road. Still in the same job, still collecting PTO, still in my comfort, still wondering what could’ve been.
I knew I’d look back and think:
You didn’t even give it a chance. You let anxiety and insecurity decide your future.
You gave fear the steering wheel.
And that? That was scarier than failing.
How I Got Started (A Very Candace Tale)
If there’s any part of this journey that screams Candace, it’s this one.
I gave my company plenty of notice before leaving. They were a great organization—truly. I didn’t walk away because anything was wrong. I walked away because something inside me was missing. I wasn’t searching for a better company, I was searching for deeper fulfillment.
So, I had my last day at work… and literally two days later, I hopped on a plane to Portugal.
I landed in Lisbon, jet-lagged and dazed, and met up with Loren and his girlfriend, Gisele. Day one on the new job? Yeah, that was the day I landed. But Loren—being the world’s most compassionate (and possibly chaotic) boss—let me take a nap first. Now that’s what I call team building!
That afternoon, we walked the cobblestone streets of Lisbon, grabbed coffee at a cafe, cracked open laptops for a bit of work, then headed to a coworking spot by the port. We sat outside, sun on our faces, ocean breeze, surrounded by strangers buzzing with their own projects and conversations. We had a meeting right there, mid-chaos, and for the first time it actually sank in:
This is real. This is happening. And this is going to be good.
…Then came the hike.
Just a couple days later, we kicked off the Rota Vicentina—a trail along Portugal’s coast—during the worst weather Portugal had seen in over a century.
I’m talking sideways rain, gusts of wind strong enough to knock over a small adult, flooded trails, and mud for days.
And here I was: brand new job, brand new lifestyle, learning everything on the go… while freezing, soaked, hungry, and honestly, kinda grumpy. Loren and I were exhausted—mentally, physically, emotionally. There was no pause button, no “maybe let’s reschedule this whole figuring-out-my-career thing.”
I was stretched in every way possibly mentally – learning systems, processes, communication styles.Physically – hiking with a pack in what felt like hurricane conditions and socially – adjusting to a new dynamic, team, and rhythm of life
But here’s the truth:
I did it.
And more than that—I met every challenge with, “I’m not going to let this discourage me.”It wasn’t a fairytale kickoff. It was gritty and uncomfortable. But it was also beautiful, honest, and mine. And that’s when I really knew—I didn’t just survive the leap, I landed in exactly the right place.
Lessons I Learned the Hard Way
So here’s the thing. Even though I imagined my new life would be this dream loop of working, hiking, exploring cute towns and sipping cappuccinos in foreign cafés… that’s not the full story. Not even close.
After Portugal, I came back home—and the chaos? Oh, it definitely followed. It just changed outfits.
Suddenly, there was no timecard. No office chatter. No “good morning” banter by the coffee machine. My “office” was about ten steps from my bed. I didn’t have to get dressed for work (something I dreaded doing Monday-Friday). And I didn’t need to be asleep by 9PM or up by 5AM. The structure I’d spent nearly a decade mastering? Gone.
And while that freedom is what I had wanted, it was also completely disorienting.
So… what did I learn? Here’s the list I wish someone gave me on day one:
- Get a Routine (Seriously)
- You think you’ll float through the day doing a little of this, a little of that… but without a solid routine, it’s not productive. A routine keeps you anchored when everything else feels flexible.
- Set Working Hours (And Protect Them)
- It’s way too easy to come home from trivia on a Tuesday and “just check one email”… and suddenly you’re three tasks deep at midnight. Boundaries are not just helpful—they’re necessary.
- Stick to Your Own Deadlines
- When you’re your own taskmaster, it’s easy to push non-critical stuff back. Until it’s Friday and you’ve got 15 assignments staring you down. Future-you will be very mad at past-you.
- Get Social—On Purpose
- Without coworkers, you have to build your social circles. I joined flag football, trivia nights, kickball—you name it. Not just for fun, but for sanity. Community isn’t built accidentally when you’re remote. More on getting connected as a digital nomad.
- Meal Prep Is Not Just for Gym People
- You think you’ll have time to cook fresh lunches… but Google meetings, assignments, and random deadlines say otherwise. Prep some basics on Sunday and thank yourself all week.
- Schedule Time to Move Your Body
- Without a traditional office, you don’t get those little breaks walking to a meeting or heading to lunch. I had to block time to go outside, stretch, breathe, exist outside my four walls.
This lifestyle is amazing, but it also demands that you create structure where none exists. No one tells you that freedom without direction can feel just as overwhelming as rigidity. Instead, love the process of learning and don’t only focus on “when I figure this out, I’m going to be so happy!”
Embracing the Beautiful Chaos
I’ve learned more about myself by getting comfortable with the uncomfortable than I ever did in a decade of compliance training.
This lifestyle? It’s not all cute cafés and passport stamps. It’s real. It’s raw. It’s vulnerable.
But it’s also so worth it.
I won’t sit here and pretend I’ve got it all figured out—I’m still learning how to structure my days, stick to routines, set boundaries, and hold myself accountable. I’m still following the very steps I outlined earlier: carving out a routine, sticking to working hours, prioritizing connection, blocking time to move, and yes—still learning how not to procrastinate all my Friday tasks.
But what I’ve come to love is the chaos of growth—the unpredictability, the freedom, the invitation to build a life on my own terms. Not mundane. Not overly structured. Just mine.
And in all of this, here’s what I’ve truly discovered about myself:
- I am far more resilient than I ever gave myself credit for.
- I am incredibly resourceful—even when I don’t have all the answers.
- I can contribute to organizations in meaningful ways, even in industries I’m still learning.
- I’m not afraid to fail forward, ask questions, be vulnerable, and admit, “Hey, I’m still figuring this out.”
Because here’s the truth: you don’t need to have everything perfect before you begin. You just need to begin.
And if I can do it—scared, uncertain, voice-cracking over soup and salad at a Panera—you probably can too.
FAQs: How to Start as a Digital Nomad (2025)
What inspired you to become a digital nomad?
I had a stable job, a leadership role, and PTO—but after each trip, I felt trapped in a life that no longer fit. The turning point came in 2025 when I realized staying in my comfort zone was scarier than trying something new.
How did you actually get started as a digital nomad?
I gave notice at my job, packed up, and flew to Portugal just two days later. I joined my brother’s remote team, learned on the go, and embraced the messy reality of starting fresh. More about starting as a digital nomad.
Was it hard to leave your job and routine behind?
Absolutely. Letting go of the structure, health benefits, and daily familiarity terrified me—but imagining 20 years of “what-ifs” was even scarier.
What’s the biggest challenge of starting this lifestyle?
Creating structure without external accountability. Remote work demands discipline, boundaries, and self-awareness—especially when no one is watching. More about the Pros and Cons of being a digital nomad.
What did your first few weeks look like as a digital nomad?
Chaotic. I landed in Lisbon and jumped into work mid-jet lag, hiked Portugal’s coast in a storm, and learned everything on the fly. It wasn’t perfect—but it was real.
What surprised you the most about remote life?
The emotional shift. Freedom is incredible, but without structure, it can feel overwhelming. It forced me to learn more about myself than any office ever did.
What tools or habits helped you adjust?
Routines saved me. I blocked work hours, prepped meals, stayed physically active, and intentionally built a social life with things like trivia and sports leagues.
How do you stay motivated without a traditional boss?
I focus on impact. Knowing my work affects real clients and real outcomes keeps me driven. Plus, I hold myself to high standards—even when no one’s tracking me.
Do you need everything figured out before you start?
Not at all. I didn’t have a roadmap—I just trusted that I’d figure it out. You don’t need perfection to begin, just the courage to try.
What advice would you give someone starting as a digital nomad in 2025?
Expect discomfort, embrace flexibility, and build your own structure. The chaos is real—but so is the growth. If it scares you and excites you, you’re on the right path.
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